MiMeDB: Showing metabocard for 1-(9Z-Octadecenoyl)-glycerol (MMDBc0054111)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 22:53:47 UTC

Update Date

2024-04-30 20:51:22 UTC

Metabolite ID

MMDBc0054111

Metabolite Identification

Common Name

1-(9Z-Octadecenoyl)-glycerol

Description

1-(9Z-Octadecenoyl)-glycerol, also known as MG(18:1(9Z)/0:0/0:0), is a monoacylglyceride. A monoglyceride, more correctly known as a monoacylglycerol, is a glyceride consisting of one fatty acid chain covalently bonded to a glycerol molecule through an ester linkage. Monoacylglycerol can be broadly divided into two groups; 1-monoacylglycerols (or 3-monoacylglycerols) and 2-monoacylglycerols, depending on the position of the ester bond on the glycerol moiety. Normally the 1-/3-isomers are not distinguished from each other and are termed 'alpha-monoacylglycerols', while the 2-isomers are beta-monoacylglycerols. Monoacylglycerols are formed biochemically via release of a fatty acid from diacylglycerol by diacylglycerol lipase or hormone sensitive lipase. Monoacylglycerols are broken down by monoacylglycerol lipase. They tend to be minor components only of most plant and animal tissues, and indeed would not be expected to accumulate because their strong detergent properties would have a disruptive effect on membranes. 2-Monoacylglycerols are a major end product of the intestinal digestion of dietary fats in animals via the enzyme pancreatic lipase. They are taken up directly by the intestinal cells and converted to triacylglycerols via the monoacylglycerol pathway before being transported in lymph to the liver. Mono- and Diglycerides are commonly added to commercial food products in small quantities. They act as emulsifiers, helping to mix ingredients such as oil and water that would not otherwise blend well.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 08091208232D          

 27 26  0  0  0  0            999 V2000
   -0.4638    3.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2507    2.8066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2507    1.9816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9651    1.5691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9651    0.7441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6796    0.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6796   -0.4934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3941   -0.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3941   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1086   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8230   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9664   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6809   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3954   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1099   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6822   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2533   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9677   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8243   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3967   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9677   -0.9059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8243   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5388   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6796   -2.1434    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1086   -2.9684    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 20 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 17  1  0  0  0  0
 22 18  1  0  0  0  0
 23 20  1  0  0  0  0
 24 21  2  0  0  0  0
 25 19  1  0  0  0  0
 25 21  1  0  0  0  0
 26  9  1  0  0  0  0
 27 10  1  0  0  0  0
M  END


  Mrv0541 08091208232D          

 27 26  0  0  0  0            999 V2000
   -0.4638    3.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2507    2.8066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2507    1.9816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9651    1.5691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9651    0.7441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6796    0.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6796   -0.4934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3941   -0.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3941   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1086   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8230   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9664   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6809   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3954   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1099   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6822   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2533   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9677   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8243   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3967   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9677   -0.9059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8243   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5388   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6796   -2.1434    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1086   -2.9684    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 20 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 17  1  0  0  0  0
 22 18  1  0  0  0  0
 23 20  1  0  0  0  0
 24 21  2  0  0  0  0
 25 19  1  0  0  0  0
 25 21  1  0  0  0  0
 26  9  1  0  0  0  0
 27 10  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0054111

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(CCCCCCCC)=C(/[H])CCCCCCCC(=O)OCC(O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C21H40O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(24)25-19-20(23)18-22/h9-10,20,22-23H,2-8,11-19H2,1H3/b10-9-

> <INCHI_KEY>
RZRNAYUHWVFMIP-KTKRTIGZSA-N

> <FORMULA>
C21H40O4

> <MOLECULAR_WEIGHT>
356.5399

> <EXACT_MASS>
356.292659768

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
44.79172168213751

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,3-dihydroxypropyl (9Z)-octadec-9-enoate

> <ALOGPS_LOGP>
6.32

> <JCHEM_LOGP>
5.609255553000001

> <ALOGPS_LOGS>
-5.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.561713304317518

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.619245765321082

> <JCHEM_PKA_STRONGEST_BASIC>
-2.968684336972288

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
104.42609999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
19

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.51e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
oleoyl glycerol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-AUG-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-AUG-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   26  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   26                                                  
CONECT   10    9   11   27                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   21                                                       
CONECT   18   20   22                                                       
CONECT   19   20   25                                                       
CONECT   20   18   19   23                                                  
CONECT   21   17   24   25                                                  
CONECT   22   18                                                            
CONECT   23   20                                                            
CONECT   24   21                                                            
CONECT   25   19   21                                                       
CONECT   26    9                                                            
CONECT   27   10                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   52    0
END

Synonyms

Value	Source
1-(9Z-Octadecenoyl)-glycerol	ChEBI
1-(9Z-Octadecenoyl)-rac-glycerol	ChEBI
1-Monoolein	ChEBI
1-Monooleoyl-rac-glycerol	ChEBI
1-Monooleoylglycerol	ChEBI
1-Oleoyl-rac-glycerol	ChEBI
2,3-Dihydroxypropyl oleate	ChEBI
MG (18:1/0:0/0:0)	ChEBI
2,3-Dihydroxypropyl oleic acid	Generator
Glyceryl 1-oleic acid	Generator
1-(9Z)-Octadecenoylglycerol	ChEBI, HMDB
1-Oleoyl monoglyceride	MeSH, HMDB
1-Oleoyl-2-glycerol	MeSH, HMDB
Monoelaidin	MeSH, HMDB
Myverol 18-99	MeSH, HMDB
sn-1-O-(cis-9)Octadecenylglycerol	MeSH, HMDB
Glyceryl monooleate	MeSH, HMDB
Monolein	MeSH, HMDB
Glycerol monooleate	MeSH, HMDB
Glycerylmonooleate	MeSH, HMDB
mono-Oleoylglycerol	MeSH, HMDB
Oleic acid monoglyceride	MeSH, HMDB

Molecular Formula

C₂₁H₄₀O₄

Average Mass

356.5399

Monoisotopic Mass

356.292659768

IUPAC Name

2,3-dihydroxypropyl (9Z)-octadec-9-enoate

Traditional Name

oleoyl glycerol

CAS Registry Number

Not Available

SMILES

[H]\C(CCCCCCCC)=C(/[H])CCCCCCCC(=O)OCC(O)CO

InChI Identifier

InChI=1S/C21H40O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(24)25-19-20(23)18-22/h9-10,20,22-23H,2-8,11-19H2,1H3/b10-9-

InChI Key

RZRNAYUHWVFMIP-KTKRTIGZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-monoacylglycerols. These are monoacylglycerols containing a glycerol acylated at the 1-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerolipids

Sub Class

Monoradylglycerols

Direct Parent

1-monoacylglycerols

Alternative Parents

Substituents

1-acyl-sn-glycerol
Fatty acid ester
Fatty acyl
1,2-diol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Primary alcohol
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Alcohol
Organic oxide
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

1-monoglyceride (CHEBI:75342 )
Monoacylglycerols (LMGL01010005 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0015 g/L	ALOGPS
logP	6.32	ALOGPS
logP	5.61	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	13.62	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	19	ChemAxon
Refractivity	104.43 m³·mol⁻¹	ChemAxon
Polarizability	44.79 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0ufr-3941000000-863ed9a1a307beb4a1a8	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-01ot-8950000000-35c590cce9dff8869298	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0ufs-1900000000-ecd5f6a96f0e3005d450	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0f79-9561400000-65fdf1d5087668734b1e	2017-10-06	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0532-0069000000-8ebd454263638be9a356	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-06rt-0069000000-0ca2c02d94f2434099c9	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-001i-0094000000-ae9df2b39a5a3e609d9e	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-052b-0069000000-1b2499b87288e3a0cc7c	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-052b-0069000000-61627df65991c534b2fb	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0gb9-0013649000-09e4a7f8726d9fa56e6d	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-014i-0013549000-913cbee00d9ce0f8129d	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0002-0059000000-a485dc334652f9d25ebf	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-054k-0049000000-3cce669ed7aca2869e31	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0009000000-6278c7e8ab10862172da	2017-10-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0009000000-6278c7e8ab10862172da	2017-10-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0boi-0069000000-468bbe23a7c3125ab01c	2017-10-04	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0015647	1-(9Z-Octadecenoyl)-glycerol	(9Z)-octadecenoic acid	Monoacylglycerol lipase	Lipid (ester bond) hydrolysis	RHEA	34755880
MMDBr0015648	1-(9Z-Octadecenoyl)-glycerol	(9Z)-octadecenoic acid	Monoacylglycerol lipase	Lipid (ester bond) hydrolysis	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1
Bacteria	Actinobacteria	1	Human

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0094684

DrugBank ID

DB13171

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

CPD-11690

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5283468

PDB ID

Not Available

ChEBI ID

75342

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Ghosh S, Strum JC, Bell RM: Lipid biochemistry: functions of glycerolipids and sphingolipids in cellular signaling. FASEB J. 1997 Jan;11(1):45-50. doi: 10.1096/fasebj.11.1.9034165. [PubMed:9034165 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. doi: 10.1038/35036052. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. doi: 10.1194/jlr.R600022-JLR200. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. doi: 10.1194/jlr.R700005-JLR200. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 1-(9Z-Octadecenoyl)-glycerol (MMDBc0054111)

MOL for #<Metabolite:0x00007fa5091e6300>

3D MOL for #<Metabolite:0x00007fa5091e6300>

3D SDF for #<Metabolite:0x00007fa5091e6300>

3D-SDF for #<Metabolite:0x00007fa5091e6300>

PDB for #<Metabolite:0x00007fa5091e6300>

3D PDB for #<Metabolite:0x00007fa5091e6300>

SMILES for #<Metabolite:0x00007fa5091e6300>

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Structure for #<Metabolite:0x00007fa5091e6300>

3D Structure for #<Metabolite:0x00007fa5091e6300>