MiMeDB: Showing metabocard for 1-Hexadec-9-enoyl-sn-glycerol 3-phosphate (MMDBc0031546)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:38:36 UTC

Update Date

2022-08-31 18:12:57 UTC

Metabolite ID

MMDBc0031546

Metabolite Identification

Common Name

1-Hexadec-9-enoyl-sn-glycerol 3-phosphate

Description

1-hexadec-9-enoyl-sn-glycerol 3-phosphate belongs to the class of Lysophosphatidic Acids. These are glycerophosphates where the glycerol is esterified with one saturated fatty acid. (inferred from compound structure)

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 08141218042D          

 29 28  0  0  0  0            999 V2000
    2.0921    7.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921    6.9829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066    6.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066    5.7454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5211    5.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5211    4.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2368    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8092    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513    4.0954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9526    3.6829    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   14.6506    2.5559    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   13.8256    3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5237    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2381    3.2704    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    4.5079    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5211    2.8579    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  2  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  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
 18 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 15  1  0  0  0  0
 20 18  1  0  0  0  0
 21 19  2  0  0  0  0
 25 16  1  0  0  0  0
 25 19  1  0  0  0  0
 26 17  1  0  0  0  0
 27 22  1  0  0  0  0
 27 23  1  0  0  0  0
 27 24  2  0  0  0  0
 27 26  1  0  0  0  0
 28  7  1  0  0  0  0
 29  8  1  0  0  0  0
M  CHG  2  22  -1  23  -1
M  END


  Mrv0541 08141218042D          

 29 28  0  0  0  0            999 V2000
    2.0921    7.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921    6.9829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066    6.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066    5.7454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5211    5.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5211    4.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2368    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8092    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513    4.0954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9526    3.6829    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   14.6506    2.5559    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   13.8256    3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5237    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2381    3.2704    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    4.5079    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5211    2.8579    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  2  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  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
 18 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 15  1  0  0  0  0
 20 18  1  0  0  0  0
 21 19  2  0  0  0  0
 25 16  1  0  0  0  0
 25 19  1  0  0  0  0
 26 17  1  0  0  0  0
 27 22  1  0  0  0  0
 27 23  1  0  0  0  0
 27 24  2  0  0  0  0
 27 26  1  0  0  0  0
 28  7  1  0  0  0  0
 29  8  1  0  0  0  0
M  CHG  2  22  -1  23  -1
M  END
> <DATABASE_ID>
MMDBc0031546

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(CCCCCC)=C(\[H])CCCCCCCC(=O)OCC(O)COP([O-])([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H37O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(21)25-16-18(20)17-26-27(22,23)24/h7-8,18,20H,2-6,9-17H2,1H3,(H2,22,23,24)/p-2/b8-7+

> <INCHI_KEY>
GLGQZYWTNAOWHT-BQYQJAHWSA-L

> <FORMULA>
C19H35O7P

> <MOLECULAR_WEIGHT>
406.4508

> <EXACT_MASS>
406.212039986

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
45.31864335198387

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
-2

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-3-(phosphonatooxy)propyl (9E)-hexadec-9-enoate

> <ALOGPS_LOGP>
4.78

> <JCHEM_LOGP>
4.5965521916666665

> <ALOGPS_LOGS>
-4.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.531115837556444

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.505317785248875

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4039997949880556

> <JCHEM_POLAR_SURFACE_AREA>
118.95000000000002

> <JCHEM_REFRACTIVITY>
103.85359999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
19

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.41e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-3-(phosphonatooxy)propyl (9E)-hexadec-9-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 14-AUG-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-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  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O-1
HETATM   23  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O-1
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  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   27  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
HETATM   28  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   29  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   28                                                  
CONECT    8    7    9   29                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   19                                                       
CONECT   16   18   25                                                       
CONECT   17   18   26                                                       
CONECT   18   16   17   20                                                  
CONECT   19   15   21   25                                                  
CONECT   20   18                                                            
CONECT   21   19                                                            
CONECT   22   27                                                            
CONECT   23   27                                                            
CONECT   24   27                                                            
CONECT   25   16   19                                                       
CONECT   26   17   27                                                       
CONECT   27   22   23   24   26                                             
CONECT   28    7                                                            
CONECT   29    8                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   56    0
END

Synonyms

Value	Source
1-Hexadec-9-enoyl-sn-glycerol 3-phosphoric acid	Generator
2-Hydroxy-3-(phosphonatooxy)propyl (9E)-hexadec-9-enoic acid	Generator

Molecular Formula

C₁₉H₃₅O₇P

Average Mass

406.4508

Monoisotopic Mass

406.212039986

IUPAC Name

2-hydroxy-3-(phosphonatooxy)propyl (9E)-hexadec-9-enoate

Traditional Name

2-hydroxy-3-(phosphonatooxy)propyl (9E)-hexadec-9-enoate

CAS Registry Number

Not Available

SMILES

[H]\C(CCCCCC)=C(\[H])CCCCCCCC(=O)OCC(O)COP([O-])([O-])=O

InChI Identifier

InChI=1S/C19H37O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(21)25-16-18(20)17-26-27(22,23)24/h7-8,18,20H,2-6,9-17H2,1H3,(H2,22,23,24)/p-2/b8-7+

InChI Key

GLGQZYWTNAOWHT-BQYQJAHWSA-L

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-acylglycerol-3-phosphates. These are lysophosphatidic acids where the glycerol is esterified with a fatty acid at O-1 position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphates

Direct Parent

1-acylglycerol-3-phosphates

Alternative Parents

Substituents

1-acylglycerol-3-phosphate
Fatty acid ester
Fatty acyl
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Secondary alcohol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Organic anion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0084 g/L	ALOGPS
logP	4.78	ALOGPS
logP	4.6	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	1.51	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	118.95 Å²	ChemAxon
Rotatable Bond Count	19	ChemAxon
Refractivity	103.85 m³·mol⁻¹	ChemAxon
Polarizability	45.32 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

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

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

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
Bacteria	Proteobacteria	129	Human feces; Human sputum; Human ; Human unknown; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human feces; pleural fluid plaque; bal	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	265	Human feces; Human pleural fluid plaque; Human	Metabolic reconstruction
Bacteria	Actinobacteria	109	Human feces; Human pleural fluid plaque; Human dental plaque; Human sputum; Human ; Human nasopharyngeal swab	Metabolic reconstruction
Bacteria	Bacteroidetes	20	Human feces; Human	Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1	Human feces	Metabolic reconstruction
Bacteria	Fusobacteria	4	Human feces; Human	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

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

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]

Showing metabocard for 1-Hexadec-9-enoyl-sn-glycerol 3-phosphate (MMDBc0031546)

MOL for #<Metabolite:0x0000560be250c7d0>

3D MOL for #<Metabolite:0x0000560be250c7d0>

3D SDF for #<Metabolite:0x0000560be250c7d0>

3D-SDF for #<Metabolite:0x0000560be250c7d0>

PDB for #<Metabolite:0x0000560be250c7d0>

3D PDB for #<Metabolite:0x0000560be250c7d0>

SMILES for #<Metabolite:0x0000560be250c7d0>

INCHI for #<Metabolite:0x0000560be250c7d0>

Structure for #<Metabolite:0x0000560be250c7d0>

3D Structure for #<Metabolite:0x0000560be250c7d0>