LIPID MAPS Lipid Chemistry Tutorial

Fatty Acyls (FA)

Glycerolipids (GL)

Glycerophospholipids (GP)

Sphingolipids (SP)

Sterol Lipids (ST)

Prenol Lipids (PR)

Eoin Fahy Ph.D.

San Diego Supercomputer Center
University of California, San Diego
Copyright/attribution notice: You are free to copy, distribute, adapt and transmit this tutorial or
individual slides (without alteration) for academic, non-profit and non-commercial purposes.
Attribution: Eoin Fahy (2010) “LIPID MAPS Lipid Chemistry Tutorial” www.lipidmaps.org

E.Fahy 2010 ©
LIPID MAPS Website
http://www.lipidmaps.org/
 Definition of a lipid*

Lipids may be broadly defined as hydrophobic or

amphiphilic small molecules that originate entirely or
in part from two distinct types of biochemical
subunits or "building blocks": ketoacyl and isoprene
groups. Using this approach, lipids may be divided
into eight categories : fatty acyls, glycerolipids,
,glycerophospholipids, sphingolipids, saccharolipids
and polyketides (derived from condensation of
ketoacyl subunits); and sterol lipids and prenol lipids
(derived from condensation of isoprene subunits).

* Fahy,E. et al, Journal of Lipid Research, Vol. 46, 839-862, May 2005

E. Fahy 2010 ©
Lipid classification: biosynthetic routes
1: Carbanion-based condensation

CATEGORIES
Fatty Acyls
Glycerolipids
Glycerophospholipids
Sphingolipids
Saccharolipids
Polyketides

E. Fahy 2010 ©
Lipid classification: biosynthetic routes
2: Carbocation-based condensation

CATEGORIES
Sterol lipids
Prenol lipids

E. Fahy 2010 ©
J. Lipid Res. Classification publications
Journal of Lipid Research, Vol. 46, 839-862, May 2005
Journal of Lipid Research, 50th anniversary edition, May 2009

E. Fahy 2010 ©
 LIPID MAPS Classification System
Categories and Examples
Category Abbreviation Example

Fatty acyls FA Dodecanoic acid

Glycerolipids GL 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-
glycerol
Glycerophospholipids GP 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-
glycero-3-phosphocholine
Sphingolipids SP N-(tetradecanoyl)-sphing-4-enine

Sterol lipids ST Cholest-5-en-3b-ol

Prenol lipids PR 2E,6E-farnesol

Saccharolipids SL UDP-3-O-(3R-hydroxy-tetradecanoyl)-aD-
N-acetylglucosamine
Polyketides PK Aflatoxin B1

E. Fahy 2010 ©
 LIPID MAPS: Compound ID
• LIPID MAPS compound ID
– LMGP01010005

1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine

• Database identifier
– Digits 1-2: Database: LM (LIPID MAPS)
– Digits 3-4: Category: GP (Glycerophospholipids)
– Digits 5-6: Class: 01 (Glycerophosphocholines)
– Digits 7-8: Subclass: 01 (Diacylglycerophosphocholines)
– Digits 9-?: Optional additional class levels (typically not required)
– Last 4 digits: Unique identifier within subclass: 0005

E. Fahy 2010 ©
 Consistent structure representation across classes

Fatty Acyls(FA)

Glycerolipids (GL)

Glycerophospholipids (GP)

Sphingolipids (SP)

Sterol Lipids (ST)

Prenol Lipids (PR)

E. Fahy 2010 ©
 Lipids per category in LMSD (10/21/10)
8000

7000

6000
Total: 22,500

5000

4000

3000

2000

1000

0
FA GL GP SP ST PR SL PK

E. Fahy 2010 ©
Populating LIPID MAPS structure database

Structures from core labs

and partners

New structures
identified by LIPID MAPS
experiments

LIPID
Computationally
generated structures
MAPS
structure
database
Public databases

Websites,
22,500 structures
Publications as of 10/21/10

E. Fahy 2010 ©
 LIPID MAPS Structure Database (LMSD)
http://www.lipidmaps.org/data/structure/

Online features:
Browse
Text search
Substructure search
Download structures E. Fahy 2010 ©
Querying Lipidomics Gateway website as well as
LIPID MAPS databases via “Quick search”

Small “footprint”
High visibility (on home page)
Multi-purpose

E. Fahy 2010 ©
Quick search query types Example
LIPID MAPS LM_ID LMFA03010003

Lipid classification term “Choline”, “prostaglandin”, “diterpene”

Lipid common/systematic “Linoleic”, “HETE”, ”, “PAF”, “PGE”,

“5Z,8Z,14Z-eicosatrienoic”,
name or synonym “PC(16:0/18:1(9Z))”
“MGDG “docosa”, “phytosphingosine”

Lipid molecular formula C12H24O2

InChI Key XEYBRNLFEZDVAW-ARSRFYASSA-N

Lipid standard (name or LMID) sterol

Gene/protein name/synonym FABP

Keywords on Lipidomics
Gateway website pages “Atherosclerosis”, “Dennis”, “homeostasis”
(personnel, publications, news,
updates, etc.)
E. Fahy 2010 ©
Use InChIKey to find structures differing only in stereochemistry,
double-bond geometry or isotopic labeling

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Use InChIKey (full or partial) to perform a Google structure search

European Bioinformatics
Inst.

LIPID MAPS

PubChem

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 Quick search summary report

Database hits
(lipid,gene,standards db’s
Classification system)

Text page hits

(LM information,
updates,references,etc.)

E. Fahy 2010 ©
 Online lipid structure-drawing tools
http://www.lipidmaps.org/tools/index.html

Online drawing tools for Structures viewable in Marvin,

various lipid categories JMol and Chemdraw format. May
be saved as Molfiles
(FA,GL,GP,SP,ST)

E. Fahy 2010 ©
Online generation of glycan structures in full chair conformation

http://www.lipidmaps.org/tools/index.html
Sugars
Glc
Gal
GlcNAc
GalNac
Xyl
Fuc
Man
NeuAc
NeuGc
KDN

Anomeric Carbon
a or b linkages may
be specified

E. Fahy 2010 ©
Lipid Proteome Database (LMPD)

E. Fahy 2010 ©
Search LMSD with ontology terms

e.g. find all lipids with 20

carbons, 3 double bonds, at
least 3 hydroxyl groups and
1 epoxy group

E. Fahy 2010 ©
 LIPID BIOSYNTHETIC NETWORKS

SPHINGOLIPIDS GLYCEROPHOSPHOLIPIDS GLYCEROLIPIDS

FATTY ACIDS
EICOSANOIDS STEROLS

Acetyl CoA

PRENOLS

Isopentenyl-PP E. Fahy 2010 ©

E. Fahy 2010 ©
Educating the public about lipids

E. Fahy 2010 ©
 Acknowledgement

I wish to thank Dr. Edward A. Dennis and the other co-authors of

the following 2 publications:[Fahy et al (2005) J Lipid Res, 46, 839-
61; Fahy et al (2009) J Lipid Res, 50, S9-14] for their input in the
development of the lipid classification scheme covered in this
tutorial. I am also grateful to Dr. Shankar Subramaniam and the
LIPID MAPS Bioinformatics core for their efforts in creation of an
online infrastructure of databases, tools, pathways and other
resources pertaining to lipidomics.

Eoin Fahy
September, 2010
U.C. San Diego

E. Fahy 2010 ©
Appendix: Lipid Classification System

See following slides

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 Lipid Classification

Category
Main class
Subclass
Level 4 class

E. Fahy 2010 ©
 Lipid Classification
Categories and Examples
Category Abbrev Example

Fatty Acyls FA dodecanoic acid

Glycerolipids GL 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-
glycerol
Glycerophospholipids GP 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-
glycero-3-phosphocholine
Sphingolipids SP N-(tetradecanoyl)-sphing-4-enine

Sterol Lipids ST cholest-5-en-3b -ol

Prenol Lipids PR 2E,6E-farnesol

Saccharolipids SL UDP-3-O-(3R-hydroxy-tetradecanoyl)-a D-N-

acetylglucosamine
Polyketides PK aflatoxin B1

E. Fahy 2010 ©
 Lipid Classification

Category
Main class
Subclass
Level 4 class

E. Fahy 2010 ©
 1: Fatty Acyls [FA] Main classes
http://www.lipidmaps.org/data/classification/LM_classification_exp.php?category=1

[+] Fatty Acids and Conjugates [FA01]

[+] Octadecanoids [FA02]
[+] Eicosanoids [FA03]
Docosanoids [FA04]
Fatty alcohols [FA05]
Fatty aldehydes [FA06]
[+] Fatty esters [FA07]
[+] Fatty amides [FA08]
Fatty nitriles [FA09]
Fatty ethers [FA010]
Hydrocarbons [FA11]
Oxygenated hydrocarbons [FA12]
[+] Fatty acyl glycosides [FA13]
Other [FA00]

E. Fahy 2010 ©
 2: Glycerolipids [GL] Main classes

http://www.lipidmaps.org/data/classification/LM_classification_exp.php?category=2

[+] Monoradylglycerols [GL01]

[+] Diradylglycerols [GL02]
[+] Triradylglycerols [GL03]
[+] Glycosylmonoradylglycerols [GL04]
[+] Glycosyldiradylglycerols [GL05]
Other Glycerolipids [GL00]

E. Fahy 2010 ©
 3: Glycerophospholipids [GP] Main classes
http://www.lipidmaps.org/data/classification/LM_classification_exp.php?category=3
[+] Glycerophosphocholines [GP01]
[+] Glycerophosphoethanolamines [GP02]
[+] Glycerophosphoserines [GP03]
[+] Glycerophosphoglycerols [GP04]
[+] Glycerophosphoglycerophosphates [GP05]
[+] Glycerophosphoinositols [GP06]
[+] Glycerophosphoinositol monophosphates [GP07]
[+] Glycerophosphoinositol bisphosphates [GP08]
[+] Glycerophosphoinositol trisphosphates [GP09]
[+] Glycerophosphates [GP10]
[+] Glyceropyrophosphates [GP11]
[+] Glycerophosphoglycerophosphoglycerols [GP12]
[+] CDP-Glycerols [GP13]
[+] Glycosylglycerophospholipids [GP14]
[+] Glycerophosphoinositolglycans [GP15]
[+] Glycerophosphonocholines [GP16]
[+] Glycerophosphonoethanolamines [GP17]
Di-glycerol tetraether phospholipids (caldarchaeols) [GP18]
Glycerol-nonitol tetraether phospholipids [GP19]
Oxidized glycerophospholipids [GP20]
Other Glycerophospholipids [GP00]
E. Fahy 2010 ©
 4: Sphingolipids [SP] Main classes
http://www.lipidmaps.org/data/classification/LM_classification_exp.php?category=4

[+] Sphingoid bases [SP01]

[+] Ceramides [SP02]
[+] Phosphosphingolipids [SP03]
Phosphonosphingolipids [SP04]
[+] Neutral glycosphingolipids [SP05]
[+] Acidic glycosphingolipids [SP06]
Basic glycosphingolipids [SP07]
Amphoteric glycosphingolipids [SP08]
Arsenosphingolipids [SP09]
Other Sphingolipids [SP00]

E. Fahy 2010 ©
 5: Sterol Lipids [ST] Main classes
http://www.lipidmaps.org/data/classification/LM_classification_exp.php?category=5

[+] Sterols [ST01]

[+] Steroids [ST02]
[+] Secosteroids [ST03]
[+] Bile acids and derivatives [ST04]
[+] Steroid conjugates [ST05]
Other Sterol Lipids [ST00]

E. Fahy 2010 ©
 6: Prenol Lipids [PR] Main classes
http://www.lipidmaps.org/data/classification/LM_classification_exp.php?category=6

[+] Isoprenoids [PR01]

[+] Quinones and hydroquinones [PR02]
[+] Polyprenols [PR03]
Hopanoids [PR04]
Other Prenol lipids [PR00]

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 7: Saccharolipids [SL] Main classes
http://www.lipidmaps.org/data/classification/LM_classification_exp.php?category=7

[+] Acylaminosugars [SL01]

Acylaminosugar glycans [SL02]
Acyltrehaloses [SL03]
Acyltrehalose glycans [SL04]
Other acyl sugars [SL05]
Other Saccharolipids [SL00]

E. Fahy 2010 ©
 8: Polyketides [PK] Main classes
http://www.lipidmaps.org/data/classification/LM_classification_exp.php?category=8

Linear polyketides [PK01]

Halogenated acetogenins [PK02]
Annonaceae acetogenins [PK03]
Macrolides and lactone polyketides [PK04]
Ansamycins and related polyketides [PK05]
Polyenes [PK06]
Linear tetracyclines [PK07]
Angucyclines [PK08]
Polyether antibiotics [PK09]
Aflatoxins and related substances [PK10]
Cytochalasins [PK11]
[+] Flavonoids [PK12]
[+] Aromatic polyketides [PK13]
Non-ribosomal peptide/polyketide hybrids [PK14]
Other Polyketides [PK00]

E. Fahy 2010 ©
 Lipid Classification

Category
Main class
Subclass
Level 4 class

E. Fahy 2010 ©
 1: Fatty Acyls [FA] Subclasses
http://www.lipidmaps.org/data/classification/LM_classification_exp.php?category=1

Fatty Acids and Conjugates [FA01]

Straight chain fatty acids [FA0101]
Methyl branched fatty acids [FA0102]
Unsaturated fatty acids [FA0103]
Hydroperoxy fatty acids [FA0104]
Hydroxy fatty acids [FA0105]
Oxo fatty acids [FA0106]
Epoxy fatty acids [FA0107]
Methoxy fatty acids [FA0108]
Halogenated fatty acids [FA0109]
Amino fatty acids [FA0110]
Cyano fatty acids [FA0111]
Nitro fatty acids [FA0112]
Thia fatty acids [FA0113]
Carbocyclic fatty acids [FA0114]
Heterocyclic fatty acids [FA0115]
Mycolic acids [FA0116]
Dicarboxylic acids [FA0117]

E. Fahy 2010 ©
 1: Fatty Acyls [FA] Subclasses
http://www.lipidmaps.org/data/classification/LM_classification_exp.php?category=1

Octadecanoids [FA02]
12-oxophytodienoic acid metabolites [FA0201]
jasmonic acids [FA0202]
Eicosanoids [FA03]
Prostaglandins [FA0301]
Leukotrienes [FA0302]
Thromboxanes [FA0303]
Lipoxins [FA0304]
Hydroxy/hydroperoxyeicosatrienoic acids [FA0305]
Hydroxy/hydroperoxyeicosatetraenoic acids [FA0306]
Hydroxy/hydroperoxyeicosapentaenoic acids [FA0307]
Epoxyeicosatrienoic acids [FA0308]
Hepoxilins [FA0309]
Levuglandins [FA0310]
Isoprostanes [FA0311]
Clavulones and derivatives [FA0312]
Other [FA0300]
Docosanoids [FA04]

E. Fahy 2010 ©
 1: Fatty Acyls [FA] Subclasses
http://www.lipidmaps.org/data/classification/LM_classification_exp.php?category=1

Fatty alcohols [FA05]

Fatty aldehydes [FA06]
Fatty esters [FA07]
Wax monoesters [FA0701]
Wax diesters [FA0702]
Cyano esters [FA0703]
Lactones [FA0704]
Fatty acyl CoAs [FA0705]
Fatty acyl ACPs [FA0706]
Fatty acyl carnitines [FA0707]
Fatty acyl adenylates [FA0708]
Fatty amides [FA08]
Primary amides [FA0801]
N-acyl amides [FA0802]
Fatty acyl homoserine lactones [FA0803]
N-acyl ethanolamides (endocannabinoids) [FA0804]

E. Fahy 2010 ©
 1: Fatty Acyls [FA] Subclasses
http://www.lipidmaps.org/data/classification/LM_classification_exp.php?category=1

Fatty nitriles [FA09]

Fatty ethers [FA010]
Hydrocarbons [FA11]
Oxygenated hydrocarbons [FA12]
Fatty acyl glycosides [FA13]
Fatty acyl glycosides of mono- and disaccharides [FA1301]
Sophorolipids [FA1302]
Rhamnolipids [FA1303]
Other Fatty acyl glycosides [FA1300]
Other Fatty Acyls [FA00]

E. Fahy 2010 ©
 2: Glycerolipids [GL] Subclasses
http://www.lipidmaps.org/data/classification/LM_classification_exp.php?category=2

Monoradylglycerols [GL01]
Monoacylglycerols [GL0101]
Monoalkylglycerols [GL0102]
Mono-(1Z-alkenyl)-glycerols [GL0103]
Monoacylglycerolglycosides [GL0104]
Monoalkylglycerolglycosides [GL0105]
Diradylglycerols [GL02]
Diacylglycerols [GL0201]
1-alkyl,2-acylglycerols [GL0202]
1-acyl,2-alkylglycerols [GL0207]
Dialkylglycerols [GL0203]
1Z-alkenylacylglycerols [GL0204]
Di-glycerol tetraethers [GL0205]
Di-glycerol tetraether glycans [GL0206]

E. Fahy 2010 ©
 2: Glycerolipids [GL] Subclasses
http://www.lipidmaps.org/data/classification/LM_classification_exp.php?category=2
Triradylglycerols [GL03]
Triacylglycerols [GL0301]
Alkyldiacylglycerols [GL0302]
Dialkylmonoacylglycerols [GL0303]
1Z-alkenyldiacylglycerols [GL0304]
Estolides [GL0305]

Glycosylmonoradylglycerols [GL04]
Glycosylmonoacylglycerols [GL0401]
Glycosylmonoalkylglycerols [GL0402]

Glycosyldiradylglycerols [GL05]
Glycosyldiacylglycerols [GL0501]
Glycosylalkylacylglycerols [GL0502]
Glycosyldialkylglycerols [GL0503]

Other Glycerolipids [GL00]

E. Fahy 2010 ©
 3: Glycerophospholipids [GP] Subclasses
http://www.lipidmaps.org/data/classification/LM_classification_exp.php?category=3

Glycerophosphocholines [GP01]
Diacylglycerophosphocholines [GP0101]
1-alkyl,2-acylglycerophosphocholines [GP0102]
1-acyl,2-alkylglycerophosphocholines [GP0108]
1Z-alkenyl,2-acylglycerophosphocholines [GP0103]
Dialkylglycerophosphocholines [GP0104]
Monoacylglycerophosphocholines [GP0105]
Monoalkyl glycerophosphocholines [GP0106]
1Z-alkenylglycerophosphocholines [GP0107]

Glycerophosphoethanolamines [GP02]
Diacylglycerophosphoethanolamines [GP0201]
1-alkyl,2-acylglycerophosphoethanolamines [GP0202]
1-acyl,2-alkylglycerophosphoethanolamines [GP0208]
1Z-alkenyl,2-acylglycerophosphoethanolamines [GP0203]
Dialkylglycerophosphoethanolamines [GP0204]
Monoacylglycerophosphoethanolamines [GP0205]
Monoalkyl glycerophosphoethanolamines [GP0206]
1Z-alkenylglycerophosphoethanolamines [GP0207]
E. Fahy 2010 ©
 3: Glycerophospholipids [GP] Subclasses
http://www.lipidmaps.org/data/classification/LM_classification_exp.php?category=3

Glycerophosphoserines [GP03]
Diacylglycerophosphoserines [GP0301]
1-alkyl,2-acylglycerophosphoserines [GP0302]
1Z-alkenyl,2-acylglycerophosphoserines [GP0303]
Dialkylglycerophosphoserines [GP0304]
Monoacylglycerophosphoserines [GP0305]
Monoalkyl glycerophosphoserines [GP0306]
1Z-alkenylglycerophosphoserines [GP0307]
Glycerophosphoglycerols [GP04]
Diacylglycerophosphoglycerols [GP0401]
1-alkyl,2-acylglycerophosphoglycerols [GP0402]
1Z-alkenyl,2-acylglycerophosphoglycerols [GP0403]
Dialkylglycerophosphoglycerols [GP0404]
Monoacylglycerophosphoglycerols [GP0405]
Monoalkyl glycerophosphoglycerols [GP0406]
1Z-alkenylglycerophosphoglycerols [GP0407]
Diacylglycerophosphodiradylglycerols [GP0408]
Diacylglycerophosphomonoradylglycerols [GP0409]
Monoacylglycerophosphomonoradylglycerols [GP0410]
E. Fahy 2010 ©
 3: Glycerophospholipids [GP] Subclasses
http://www.lipidmaps.org/data/classification/LM_classification_exp.php?category=3

Glycerophosphoglycerophosphates [GP05]
Diacylglycerophosphoglycerophosphates [GP0501]
1-alkyl,2-acylglycerophosphoglycerophosphates [GP0502]
1Z-alkenyl,2-acylglycerophosphoglycerophosphates [GP0503]
Dialkylglycerophosphoglycerophosphates [GP0504]
Monoacylglycerophosphoglycerophosphates [GP0505]
Monoalkyl glycerophosphoglycerophosphates [GP0506]
1Z-alkenylglycerophosphoglycerophosphates [GP0507]
Glycerophosphoinositols [GP06]
Diacylglycerophosphoinositols [GP0601]
1-alkyl,2-acylglycerophosphoinositols [GP0602]
1Z-alkenyl,2-acylglycerophosphoinositols [GP0603]
Dialkylglycerophosphoinositols [GP0604]
Monoacylglycerophosphoinositols [GP0605]
Monoalkyl glycerophosphoinositols [GP0606]
1Z-alkenylglycerophosphoinositols [GP0607]

E. Fahy 2010 ©
 3: Glycerophospholipids [GP] Subclasses
http://www.lipidmaps.org/data/classification/LM_classification_exp.php?category=3

Glycerophosphoinositol monophosphates [GP07]

Diacylglycerophosphoinositol monophosphates [GP0701]
1-alkyl,2-acylglycerophosphoinositol monophosphates [GP0702]
1Z-alkenyl,2-acylglycerophosphoinositol monophosphates [GP0703]
Dialkylglycerophosphoinositol monophosphates [GP0704]
Monoacylglycerophosphoinositol monophosphates [GP0705]
Monoalkyl glycerophosphoinositol monophosphates [GP0706]
1Z-alkenylglycerophosphoinositol monophosphates [GP0707]
Glycerophosphoinositol bisphosphates [GP08]
Diacylglycerophosphoinositol bisphosphates [GP0801]
1-alkyl,2-acylglycerophosphoinositol bisphosphates [GP0802]
1Z-alkenyl,2-acylglycerophosphoinositol bisphosphates [GP0803]
Monoacylglycerophosphoinositol bisphosphates [GP0804]
Monoalkyl glycerophosphoinositol bisphosphates [GP0805]
1Z-alkenylglycerophosphoinositol bisphosphates [GP0806]

E. Fahy 2010 ©
 3: Glycerophospholipids [GP] Subclasses
http://www.lipidmaps.org/data/classification/LM_classification_exp.php?category=3

Glycerophosphoinositol trisphosphates [GP09]

Diacylglycerophosphoinositol trisphosphates [GP0901]
1-alkyl,2-acylglycerophosphoinositol trisphosphates [GP0902]
1Z-alkenyl,2-acylglycerophosphoinositol trisphosphates [GP0903]
Monoacylglycerophosphoinositol trisphosphates [GP0904]
Monoalkyl glycerophosphoinositol trisphosphates [GP0905]
1Z-alkenylglycerophosphoinositol trisphosphates [GP0906]
Glycerophosphates [GP10]
Diacylglycerophosphates [GP1001]
1-alkyl,2-acylglycerophosphates [GP1002]
1Z-alkenyl,2-acylglycerophosphates [GP1003]
Dialkylglycerophosphates [GP1004]
Monoacylglycerophosphates [GP1005]
Monoalkyl glycerophosphates [GP1006]
1Z-alkenylglycerophosphates [GP1007]
Glyceropyrophosphates [GP11]
Diacylglyceropyrophosphates [GP1101]
Monoacylglyceropyrophosphates [GP1102]

E. Fahy 2010 ©
 3: Glycerophospholipids [GP] Subclasses
http://www.lipidmaps.org/data/classification/LM_classification_exp.php?category=3

Glycerophosphoglycerophosphoglycerols (Cardiolipins) [GP12]

Diacylglycerophosphoglycerophosphodiradylglycerols [GP1201]
Diacylglycerophosphoglycerophosphomonoradylglycerols [GP1202]
1-alkyl,2-acylglycerophosphoglycerophosphodiradylglycerols [GP1203]
1-alkyl,2-acylglycerophosphoglycerophosphomonoradylglycerols [GP1204]
1Z-alkenyl,2-acylglycerophosphoglycerophosphodiradylglycerols [GP1205]
1Z-alkenyl,2-acylglycerophosphoglycerophosphomonoradylglycerols [GP1206]
Dialkylglycerophosphoglycerophosphodiradylglycerols [GP1212]
Dialkylglycerophosphoglycerophosphomonoradylglycerols [GP1213]
Monoacylglycerophosphoglycerophosphomonoradylglycerols [GP1207]
Monoalkyl glycerophosphoglycerophosphodiradylglycerols [GP1208]
Monoalkyl glycerophosphoglycerophosphomonoradylglycerols [GP1209]
1Z-alkenylglycerophosphoglycerophosphodiradylglycerols [GP1210]
1Z-alkenylglycerophosphoglycerophosphomonoradylglycerols [GP1211]

E. Fahy 2010 ©
 3: Glycerophospholipids [GP] Subclasses
http://www.lipidmaps.org/data/classification/LM_classification_exp.php?category=3

CDP-Glycerols [GP13]
CDP-diacylglycerols [GP1301]
CDP-1-alkyl,2-acylglycerols [GP1302]
CDP-1Z-alkenyl,2-acylglycerols [GP1303]
CDP-Dialkylglycerols [GP1304]
CDP-Monoacylglycerols [GP1305]
CDP-Monoalkyl glycerols [GP1306]
CDP-1Z-alkenylglycerols [GP1307]

E. Fahy 2010 ©
 3: Glycerophospholipids [GP] Subclasses
http://www.lipidmaps.org/data/classification/LM_classification_exp.php?category=3

Glycosylglycerophospholipids [GP14]
Diacylglycosylglycerophospholipids [GP1401]
1-alkyl,2-acylglycosylglycerophospholipids [GP1402]
1Z-alkenyl,2-acylglycosylglycerophospholipids [GP1403]
Dialkylglycosylglycerophospholipids [GP1407]
Monoacylglycosylglycerophospholipids [GP1404]
Monoalkylglycosylglycerophospholipids [GP1405]
1Z-alkenylglycosylglycerophospholipids [GP1406]

Glycerophosphoinositolglycans [GP15]
Diacylglycerophosphoinositolglycans [GP1501]
1-alkyl,2-acylglycerophosphoinositolglycans [GP1502]
1Z-alkenyl,2-acylglycerophosphoinositolglycans [GP1503]
Monoacylglycerophosphoinositolglycans [GP1504]
Monoalkylglycerophosphoinositolglycans [GP1505]
1Z-alkenylglycerophosphoinositolglycans [GP1506]

E. Fahy 2010 ©
 3: Glycerophospholipids [GP] Subclasses
http://www.lipidmaps.org/data/classification/LM_classification_exp.php?category=3

Glycerophosphonocholines [GP16]
Diacylglycerophosphonocholines [GP1601]
1-alkyl,2-acylglycerophosphonocholines [GP1602]
1Z-alkenyl,2-acylglycerophosphonocholines [GP1603]
Dialkylglycerophosphonocholines [GP1604]
Monoacylglycerophosphonocholines [GP1605]
Monoalkyl glycerophosphonocholines [GP1606]
1Z-alkenylglycerophosphonocholines [GP1607]
Glycerophosphonoethanolamines [GP17]
Diacylglycerophosphonoethanolamines [GP1701]
1-alkyl,2-acylglycerophosphonoethanolamines [GP1702]
1Z-alkenyl,2-acylglycerophosphonoethanolamines [GP1703]
Dialkylglycerophosphonoethanolamines [GP1704]
Monoacylglycerophosphonoethanolamines [GP1705]
Monoalkyl glycerophosphonoethanolamines [GP1706]
1Z-alkenylglycerophosphonoethanolamines [GP1707]
Di-glycerol tetraether phospholipids (caldarchaeols) [GP18]
Glycerol-nonitol tetraether phospholipids [GP19]
Oxidized glycerophospholipids [GP20]
Other glycerophospholipids[GP00]
E. Fahy 2010 ©
 4: Sphingolipids [SP] Subclasses
http://www.lipidmaps.org/data/classification/LM_classification_exp.php?category=4
Sphingoid bases [SP01]
Sphing-4-enines (Sphingosines) [SP0101]
Sphinganines [SP0102]
4-Hydroxysphinganines (Phytosphingosines) [SP0103]
Sphingoid base homologs and variants [SP0104]
Sphingoid base 1-phosphates [SP0105]
Lysosphingomyelins and lysoglycosphingolipids [SP0106]
N-methylated sphingoid bases [SP0107]
Sphingoid base analogs [SP0108]
Ceramides [SP02]
N-acylsphingosines (ceramides) [SP0201]
N-acylsphinganines (dihydroceramides) [SP0202]
N-acyl-4-hydroxysphinganines (phytoceramides) [SP0203]
Acylceramides [SP0204]
Ceramide 1-phosphates [SP0205]
Phosphosphingolipids [SP03]
Ceramide phosphocholines (sphingomyelins) [SP0301]
Ceramide phosphoethanolamines [SP0302]
Ceramide phosphoinositols [SP0303]
Phosphonosphingolipids [SP04]
E. Fahy 2010 ©
 4: Sphingolipids [SP] Subclasses
http://www.lipidmaps.org/data/classification/LM_classification_exp.php?category=4
Neutral glycosphingolipids [SP05]
Simple Glc series (GlcCer, LacCer, etc) [SP0501]
GalNAcb1-3Gala1-4Galb1-4Glc- (Globo series) [SP0502]
GalNAcb1-4Galb1-4Glc- (Ganglio series) [SP0503]
Galb1-3GlcNAcb1-3Galb1-4Glc- (Lacto series) [SP0504]
Galb1-4GlcNAcb1-3Galb1-4Glc- (Neolacto series) [SP0505]
GalNAcb1-3Gala1-3Galb1-4Glc- (Isoglobo series) [SP0506]
GlcNAcb1-2Mana1-3Manb1-4Glc- (Mollu series) [SP0507]
GalNAcb1-4GlcNAcb1-3Manb1-4Glc- (Arthro series) [SP0508]
Gal- (Gala series) [SP0509]
Other [SP0510]
Acidic glycosphingolipids [SP06]
Gangliosides [SP0601]
Sulfoglycosphingolipids (sulfatides) [SP0602]
Glucuronosphingolipids [SP0603]
Phosphoglycosphingolipids [SP0604]
Other [SP0600]
Basic glycosphingolipids [SP07]
Amphoteric glycosphingolipids [SP08]
Arsenosphingolipids [SP09]
Other Sphingolipids [SP00] E. Fahy 2010 ©
 5: Sterol Lipids [ST] Subclasses
http://www.lipidmaps.org/data/classification/LM_classification_exp.php?category=5

Sterols [ST01]
Cholesterol and derivatives [ST0101]
Cholesteryl esters [ST0102]
Ergosterols and C24-methyl derivatives [ST0103]
Stigmasterols and C24-ethyl derivatives [ST0104]
C24-propyl sterols and derivatives [ST0105]
Gorgosterols and derivatives [ST0106]
Furostanols and derivatives [ST0107]
Spirostanols and derivatives [ST0108]
Furospirostanols and derivatives [ST0109]
Cycloartanols and derivatives [ST0110]
Calysterols and derivatives [ST0111]
Cardanolides and derivatives [ST0112]
Bufanolides and derivatives [ST0113]
Brassinolides and derivatives [ST0114]
Solanidines and alkaloid derivatives [ST0115]
E. Fahy 2010 ©
 5: Sterol Lipids [ST] Subclasses
http://www.lipidmaps.org/data/classification/LM_classification_exp.php?category=5

Steroids [ST02]
C18 steroids (estrogens) and derivatives [ST0201]
C19 steroids (androgens) and derivatives [ST0202]
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives [ST0203]
Secosteroids [ST03]
Vitamin D2 and derivatives [ST0301]
Vitamin D3 and derivatives [ST0302]
Vitamin D4 and derivatives [ST0303]
Vitamin D5 and derivatives [ST0304]
Vitamin D6 and derivatives [ST0305]
Vitamin D7 and derivatives [ST0306]

E. Fahy 2010 ©
 5: Sterol Lipids [ST] Subclasses
http://www.lipidmaps.org/data/classification/LM_classification_exp.php?category=5
Bile acids and derivatives [ST04]
C22 bile acids, alcohols, and derivatives [ST0405]
C23 bile acids, alcohols, and derivatives [ST0406]
C24 bile acids, alcohols, and derivatives [ST0401]
C25 bile acids, alcohols, and derivatives [ST0407]
C26 bile acids, alcohols, and derivatives [ST0402]
C27 bile acids, alcohols, and derivatives [ST0403]
C28 bile acids, alcohols, and derivatives [ST0404]
C29 bile acids, alcohols, and derivatives [ST0408]
Steroid conjugates [ST05]
Glucuronides [ST0501]
Sulfates [ST0502]
Glycine conjugates [ST0503]
Taurine conjugates [ST0504]
Other Sterol lipids [ST00]

E. Fahy 2010 ©
 6: Prenol Lipids [PR] Subclasses

http://www.lipidmaps.org/data/classification/LM_classification_exp.php?category=6

Isoprenoids [PR01]
C5 isoprenoids [PR0101]
[+] C10 isoprenoids (monoterpenes) [PR0102]
[+] C15 isoprenoids (sesquiterpenes) [PR0103]
[+] C20 isoprenoids (diterpenes) [PR0104]
[+] C25 isoprenoids (sesterterpenes) [PR0105]
[+] C30 isoprenoids (triterpenes) [PR0106]
C40 isoprenoids (tetraterpenes) [PR0107]
Polyterpenes [PR0108]
Retinoids [PR0109]
Quinones and hydroquinones [PR02]
Ubiquinones [PR0201]
Vitamin E [PR0202]
Vitamin K [PR0203]

E. Fahy 2010 ©
 6: Prenol Lipids [PR] Subclasses

http://www.lipidmaps.org/data/classification/LM_classification_exp.php?category=6

Polyprenols [PR03]
Bactoprenols [PR0301]
Bactoprenol monophosphates [PR0302]
Bactoprenol diphosphates [PR0303]
Phytoprenols [PR0304]
Phytoprenol monophosphates [PR0305]
Phytoprenol diphosphates [PR0306]
Dolichols [PR0307]
Dolichol monophosphates [PR0308]
Dolichol diphosphates [PR0309]
Hopanoids [PR04]
Other Prenol lipids [PR00]

E. Fahy 2010 ©
 7: Saccharolipids [SL] Subclasses

http://www.lipidmaps.org/data/classification/LM_classification_exp.php?category=7

Acylaminosugars [SL01]
Monoacylaminosugars [SL0101]
Diacylaminosugars [SL0102]
Triacylaminosugars [SL0103]
Tetraacylaminosugars [SL0104]
Pentaacylaminosugars [SL0105]
Hexaacylaminosugars [SL0106]
Heptaacylaminosugars [SL0107]
Acylaminosugar glycans [SL02]
Acyltrehaloses [SL03]
Acyltrehalose glycans [SL04]
Other [SL00]

E. Fahy 2010 ©
 8: Polyketides [PK] Subclasses

http://www.lipidmaps.org/data/classification/LM_classification_exp.php?category=8

Linear polyketides [PK01]

Halogenated acetogenins [PK02]
Annonaceae acetogenins [PK03]
Macrolides and lactone polyketides [PK04]
Ansamycins and related polyketides [PK05]
Polyenes [PK06]
Linear tetracyclines [PK07]
Angucyclines [PK08]
Polyether antibiotics [PK09]
Aflatoxins and related substances [PK10]
Cytochalasins [PK11]

E. Fahy 2010 ©
 8: Polyketides [PK] Subclasses

http://www.lipidmaps.org/data/classification/LM_classification_exp.php?category=8

Flavonoids [PK12]
Anthocyanidins [PK1201]
Flavans, Flavanols and Leucoanthocyanidins [PK1202]
Proanthocyanidins [PK1203]
Biflavonoids and polyflavonoids [PK1204]
Isoflavonoids [PK1205]
Rotenoid flavonoids [PK1206]
Pterocarpans [PK1207]
Isoflavans [PK1208]
Coumestan flavonoids [PK1209]
Neoflavonoids [PK1210]
Flavones and Flavonols [PK1211]
Chalcones and dihydrochalcones [PK1212]
Aurone flavonoids [PK1213]
Flavanones [PK1214]
Dihydroflavonols [PK1215]
Other Flavonoids [PK1216]

E. Fahy 2010 ©
 8: Polyketides [PK] Subclasses

http://www.lipidmaps.org/data/classification/LM_classification_exp.php?category=8

Aromatic polyketides [PK13]

Monocyclic aromatic polyketides [PK1301]
Naphthalenes and naphthoquinones [PK1302]
Benzoisochromanquinones [PK1303]
Anthracenes and phenanthrenes [PK1304]
Anthracyclinones [PK1305]
Dibenzofurans, griseofulvins, dibenzopyrans and xanthones [PK1306]
Diphenylmethanes, acylphloroglucinols and benzophenones [PK1307]
Depsides and depsidones [PK1308]
Diphenyl ethers, biphenyls, dibenzyls and stilbenes [PK1309]
Benzofuranoids [PK1310]
Benzopyranoids [PK1311]
Other aromatic polyketides [PK1312]
Non-ribosomal peptide/polyketide hybrids [PK14]
Other Polyketides [PK00]

E. Fahy 2010 ©
 Lipid Classification

Category
Main class
Subclass
Level 4 class

E. Fahy 2010 ©
 6: Prenol Lipids [PR] Level 4 classes
http://www.lipidmaps.org/data/classification/LM_classification_exp.php?category=6
Isoprenoids [PR01]
[+] C10 isoprenoids (monoterpenes) [PR0102]
Acyclic monoterpenoids [PR010201]
Irregular acyclic monoterpenoids [PR010202]
12 others…….
[+] C15 isoprenoids (sesquiterpenes) [PR0103]
Acyclic farnesane sesquiterpenoids [PR010301]
Furanoid farnesane sesquiterpenoids [PR010302]
87 others…….
[+] C20 isoprenoids (diterpenes) [PR0104]
Acyclic diterpenoids [PR010401]
Prenylbisabolane and cyclophytane diterpenoids [PR010402]
53 others…….
[+] C25 isoprenoids (sesterterpenes) [PR0105]
Acyclic sesterterpenoids [PR010501]
Cyclohexane sesterterpenoids [PR010502]
5 others…….
[+] C30 isoprenoids (triterpenes) [PR0106]
Acyclic triterpenoids [PR010601]
Cyclohexane triterpenoids [PR010602]
23 others…….
E. Fahy 2010 ©