MiMeDB: Showing metabocard for LPA(18:1(11Z)/0:0) (MMDBc0045101)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 13:32:41 UTC

Update Date

2022-09-01 00:58:12 UTC

Metabolite ID

MMDBc0045101

Metabolite Identification

Common Name

LPA(18:1(11Z)/0:0)

Description

LPA(18:1(11Z)/0:0) is a lysophosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. Lysophosphatidic acids can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) or C-2 (sn-2) position. Fatty acids containing 16 and 18 carbons are the most common.LPA(18:1(11Z)/0:0), in particular, consists of one 11Z-octadecenoyl chain. Lysophosphatidic acid is the simplest possible glycerophospholipid. It is the biosynthetic precursor of phosphatidic acid. Although it is present at very low levels only in animal tissues, it is extremely important biologically, influencing many biochemical processes.

Structure

MOL SDF PDB SMILES InChI

LPA(18:1(11Z)/0:0)
  Mrv1652303302022362D          

 29 28  0  0  1  0            999 V2000
    9.1943   -4.4806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0108   -3.6472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0277   -5.2971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8442   -4.4637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0193   -4.4722    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    8.3810   -4.0225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6710   -4.4426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9522   -4.0378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2421   -4.4579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6798   -5.2676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5233   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5233   -3.2816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8092   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0951   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3810   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6669   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9528   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2386   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5245   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1896   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9037   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6178   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4428   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1569   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8710   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5851   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2993   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0134   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7275   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  5  1  1  0  0  0  0
  5  2  1  0  0  0  0
  5  3  2  0  0  0  0
  5  4  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END

LPA(18:1(11Z)/0:0)
  Mrv1652303302022362D          

 29 28  0  0  1  0            999 V2000
    9.1943   -4.4806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0108   -3.6472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0277   -5.2971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8442   -4.4637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0193   -4.4722    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    8.3810   -4.0225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6710   -4.4426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9522   -4.0378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2421   -4.4579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6798   -5.2676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5233   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5233   -3.2816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8092   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0951   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3810   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6669   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9528   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2386   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5245   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1896   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9037   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6178   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4428   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1569   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8710   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5851   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2993   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0134   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7275   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  5  1  1  0  0  0  0
  5  2  1  0  0  0  0
  5  3  2  0  0  0  0
  5  4  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0045101

> <DATABASE_NAME>
MIME

> <SMILES>
CCCCCC\C=C/CCCCCCCCCC(=O)OCC(O)COP(O)(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H41O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(23)27-18-20(22)19-28-29(24,25)26/h7-8,20,22H,2-6,9-19H2,1H3,(H2,24,25,26)/b8-7-

> <INCHI_KEY>
LWSYATLSXCUNTB-FPLPWBNLSA-N

> <FORMULA>
C21H41O7P

> <MOLECULAR_WEIGHT>
436.526

> <EXACT_MASS>
436.258990658

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
49.89692549222893

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{2-hydroxy-3-[(11Z)-octadec-11-enoyloxy]propoxy}phosphonic acid

> <ALOGPS_LOGP>
4.68

> <JCHEM_LOGP>
5.485689521666666

> <ALOGPS_LOGS>
-5.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.531115837556447

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.505317785248875

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4039997949880556

> <JCHEM_POLAR_SURFACE_AREA>
113.29000000000002

> <JCHEM_REFRACTIVITY>
115.29899999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
21

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.71e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-3-[(11Z)-octadec-11-enoyloxy]propoxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 30-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: LPA(18:1(11Z)/0:0)                                
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-MAR-20         0                                  
HETATM    1  O   UNK     0      17.163  -8.364   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      18.687  -6.808   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      18.718  -9.888   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      20.243  -8.332   0.000  0.00  0.00           O+0
HETATM    5  P   UNK     0      18.703  -8.348   0.000  0.00  0.00           P+0
HETATM    6  C   UNK     0      15.645  -7.509   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.319  -8.293   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.977  -7.537   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      11.652  -8.321   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      14.336  -9.833   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      10.310  -7.566   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      10.310  -6.126   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.977  -8.337   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.644  -7.566   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.311  -8.337   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.978  -7.566   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.645  -8.337   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.312  -7.566   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.979  -8.337   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.354  -7.566   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.687  -8.337   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.020  -7.566   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.560  -7.566   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.893  -8.337   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -7.226  -7.566   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -8.559  -8.337   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -9.892  -7.566   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -11.225  -8.337   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -12.558  -7.566   0.000  0.00  0.00           C+0
CONECT    1    6    5                                                       
CONECT    2    5                                                            
CONECT    3    5                                                            
CONECT    4    5                                                            
CONECT    5    1    2    3    4                                             
CONECT    6    1    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8   11                                                       
CONECT   10    7                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   56    0
END

Synonyms

Not Available

Molecular Formula

C₂₁H₄₁O₇P

Average Mass

436.526

Monoisotopic Mass

436.258990658

IUPAC Name

{2-hydroxy-3-[(11Z)-octadec-11-enoyloxy]propoxy}phosphonic acid

Traditional Name

2-hydroxy-3-[(11Z)-octadec-11-enoyloxy]propoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

CCCCCC\C=C/CCCCCCCCCC(=O)OCC(O)COP(O)(O)=O

InChI Identifier

InChI=1S/C21H41O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(23)27-18-20(22)19-28-29(24,25)26/h7-8,20,22H,2-6,9-19H2,1H3,(H2,24,25,26)/b8-7-

InChI Key

LWSYATLSXCUNTB-FPLPWBNLSA-N

Chemical Taxonomy

Description

This compound 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
Monoalkyl 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
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0017 g/L	ALOGPS
logP	4.68	ALOGPS
logP	5.49	ChemAxon
logS	-5.4	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	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	21	ChemAxon
Refractivity	115.3 m³·mol⁻¹	ChemAxon
Polarizability	49.9 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ot-7951000000-54abd62e66f89f71433d	2018-04-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05n0-3675900000-f3bacae3283833f3d540	2018-04-05	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ap1-9784100000-1aaf1b3e82342760f1e5	2018-04-05	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0avi-9481000000-cb4eff0eab7ebafe55b1	2018-04-05	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01sr-4190400000-f15143287f0347257678	2018-04-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9050000000-4e38604d03bcf993e167	2018-04-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-9f122f85c789b5480dc5	2018-04-06	View Spectrum

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

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0009325	Glycerol 3-phosphate	LPA(18:1(11Z)/0:0)	1-acylglycerol-3-phosphate O-acyltransferase 6		VMH	30371894

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	Human feces; Human saliva	Unknown

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
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0187017

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

87977831

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

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 ]
Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]

Showing metabocard for LPA(18:1(11Z)/0:0) (MMDBc0045101)

MOL for #<Metabolite:0x00007fed15486e30>

3D MOL for #<Metabolite:0x00007fed15486e30>

3D SDF for #<Metabolite:0x00007fed15486e30>

3D-SDF for #<Metabolite:0x00007fed15486e30>

PDB for #<Metabolite:0x00007fed15486e30>

3D PDB for #<Metabolite:0x00007fed15486e30>

SMILES for #<Metabolite:0x00007fed15486e30>

INCHI for #<Metabolite:0x00007fed15486e30>

Structure for #<Metabolite:0x00007fed15486e30>

3D Structure for #<Metabolite:0x00007fed15486e30>