MiMeDB: Showing metabocard for LysoPA(12:0(3-OH)/0:0) (MMDBc0056517)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-07-07 21:51:46 UTC

Update Date

2023-12-14 16:53:41 UTC

Metabolite ID

MMDBc0056517

Metabolite Identification

Common Name

LysoPA(12:0(3-OH)/0:0)

Description

LysoPA(12:0(3-OH)/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. LysoPA(12:0(3-OH)/0:0), in particular, consists of one 3-hydroxydodecanoyl chain. Lysophosphatidic acid is the simplest possible glycerophospholipid. It is the biosynthetic precursor of phosphatidic acid and is extremely important biologically, influencing many biochemical processes.

Structure

MOL SDF PDB SMILES InChI

LPA(12:0(3-OH)/0:0)
  Mrv1652308091922432D          

 24 23  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
    4.0951   -3.2816    0.0000 O   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
   -2.3319   -4.4662    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
 14 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  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0056517

> <DATABASE_NAME>
MIME

> <SMILES>
CCCCCCCCCC(O)CC(=O)OCC(O)COP(O)(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H31O8P/c1-2-3-4-5-6-7-8-9-13(16)10-15(18)22-11-14(17)12-23-24(19,20)21/h13-14,16-17H,2-12H2,1H3,(H2,19,20,21)

> <INCHI_KEY>
SATNERLJLZYTNU-UHFFFAOYSA-N

> <FORMULA>
C15H31O8P

> <MOLECULAR_WEIGHT>
370.379

> <EXACT_MASS>
370.175654956

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
39.36097679051597

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{2-hydroxy-3-[(3-hydroxydodecanoyl)oxy]propoxy}phosphonic acid

> <ALOGPS_LOGP>
1.41

> <JCHEM_LOGP>
1.9493881213333326

> <ALOGPS_LOGS>
-2.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.531115803204517

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.5053177522862358

> <JCHEM_PKA_STRONGEST_BASIC>
-2.798751555937584

> <JCHEM_POLAR_SURFACE_AREA>
133.52

> <JCHEM_REFRACTIVITY>
88.0919

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.37e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-3-[(3-hydroxydodecanoyl)oxy]propoxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-AUG-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: LPA(12:0(3-OH)/0:0)                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-AUG-19         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  O   UNK     0       7.644  -6.126   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.311  -8.337   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.978  -7.566   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.645  -8.337   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.312  -7.566   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.979  -8.337   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.354  -7.566   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.687  -8.337   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.020  -7.566   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.353  -8.337   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   16                                                  
CONECT   15   14                                                            
CONECT   16   14   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                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   46    0
END

Synonyms

Value	Source
{2-hydroxy-3-[(3-hydroxydodecanoyl)oxy]propoxy}phosphonate	Generator

Molecular Formula

C₁₅H₃₁O₈P

Average Mass

370.379

Monoisotopic Mass

370.175654956

IUPAC Name

{2-hydroxy-3-[(3-hydroxydodecanoyl)oxy]propoxy}phosphonic acid

Traditional Name

2-hydroxy-3-[(3-hydroxydodecanoyl)oxy]propoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCCCC(O)CC(=O)OCC(O)COP(O)(O)=O

InChI Identifier

InChI=1S/C15H31O8P/c1-2-3-4-5-6-7-8-9-13(16)10-15(18)22-11-14(17)12-23-24(19,20)21/h13-14,16-17H,2-12H2,1H3,(H2,19,20,21)

InChI Key

SATNERLJLZYTNU-UHFFFAOYSA-N

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
Beta-hydroxy acid
Fatty acid ester
Monoalkyl phosphate
Hydroxy acid
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Fatty acyl
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Carbonyl group
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	0.44 g/L	ALOGPS
logP	1.41	ALOGPS
logP	1.95	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	1.51	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.52 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	88.09 m³·mol⁻¹	ChemAxon
Polarizability	39.36 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

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-09	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

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

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

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

References

Synthesis Reference

Not Available

General References

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 LysoPA(12:0(3-OH)/0:0) (MMDBc0056517)

MOL for #<Metabolite:0x00007fecb645a100>

3D MOL for #<Metabolite:0x00007fecb645a100>

3D SDF for #<Metabolite:0x00007fecb645a100>

3D-SDF for #<Metabolite:0x00007fecb645a100>

PDB for #<Metabolite:0x00007fecb645a100>

3D PDB for #<Metabolite:0x00007fecb645a100>

SMILES for #<Metabolite:0x00007fecb645a100>

INCHI for #<Metabolite:0x00007fecb645a100>

Structure for #<Metabolite:0x00007fecb645a100>

3D Structure for #<Metabolite:0x00007fecb645a100>