NP-MRD: Showing NP-Card for LPA(0:0/18:1(9Z)) (NP0334215)

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Record Information

Version

2.0

Created at

2024-09-09 22:40:43 UTC

Updated at

2024-09-09 22:40:44 UTC

NP-MRD ID

NP0334215

Secondary Accession Numbers

None

Natural Product Identification

Common Name

LPA(0:0/18:1(9Z))

Description

LPA(0:0/18:1(9Z)) 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. 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. In particular, lysophosphatidic acid is an intercellular lipid mediator with growth factor-like activities, and is rapidly produced and released from activated platelets to influence target cells. 1-Palmitoyl lysophosphatidic acid is the major component of lysophosphatidic acid (LPA) in plasma, and is in a reduced ratio in individuals with gynecological cancers (PMID 11585410 ). LPA is a pluripotent lipid mediator controlling growth, motility, and differentiation, that has a strong influence on the chemotaxis and ultrastructure of human neutrophils (PMID 7416233 ). In serum and plasma, LPA is mainly converted from lysophospholipids, whereas in platelets and some cancer cells it is converted from phosphatidic acid. In each pathway, at least two phospholipase activities are required: Phospholipase A1 (PLA1)/PLA2 plus lysophospholipase D (lysoPLD) activities are involved in the first pathway and phospholipase D (PLD) plus PLA1/PLA2 activities are involved in the second pathway. (PMID 15271293 ) [HMDB]

Structure

MOL SDF PDB SMILES InChI


  Mrv1572004261609052D          

 32 31  0  0  1  0            999 V2000
   -2.0660   -4.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2864   -4.4782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6628   -3.9381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1168   -4.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7404   -3.6680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5200   -3.9381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1436   -3.3980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9232   -3.6680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5468   -3.1279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3264   -3.3980    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
    5.7296   -3.1279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3532   -2.5878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1327   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7564   -2.3178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5359   -2.5878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1596   -2.0477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4982   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9660   -1.5077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3423   -2.0477    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.9391   -2.3178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8746   -3.3980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0950   -3.1279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9928   -0.6975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9092   -1.8613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8291   -0.6140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7455   -1.7777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5628   -1.7777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3692   -1.2376    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.3909   -2.3178    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4823   -4.2081    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1219   -2.3178    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 21  2  0  0  0  0
 27 19  1  0  0  0  0
 20 28  1  6  0  0  0
 28 21  1  0  0  0  0
 29 24  1  0  0  0  0
 29 25  1  0  0  0  0
 29 26  2  0  0  0  0
 29 27  1  0  0  0  0
 30  9  1  0  0  0  0
 31 10  1  0  0  0  0
 20 32  1  6  0  0  0
M  END


  Mrv1572004261609052D          

 32 31  0  0  1  0            999 V2000
   -2.0660   -4.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2864   -4.4782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6628   -3.9381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1168   -4.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7404   -3.6680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5200   -3.9381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1436   -3.3980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9232   -3.6680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5468   -3.1279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3264   -3.3980    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
    5.7296   -3.1279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3532   -2.5878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1327   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7564   -2.3178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5359   -2.5878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1596   -2.0477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4982   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9660   -1.5077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3423   -2.0477    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.9391   -2.3178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8746   -3.3980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0950   -3.1279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9928   -0.6975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9092   -1.8613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8291   -0.6140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7455   -1.7777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5628   -1.7777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3692   -1.2376    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.3909   -2.3178    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4823   -4.2081    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1219   -2.3178    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 21  2  0  0  0  0
 27 19  1  0  0  0  0
 20 28  1  6  0  0  0
 28 21  1  0  0  0  0
 29 24  1  0  0  0  0
 29 25  1  0  0  0  0
 29 26  2  0  0  0  0
 29 27  1  0  0  0  0
 30  9  1  0  0  0  0
 31 10  1  0  0  0  0
 20 32  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0334215

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(CCCCCCCC)=C(\[H])CCCCCCCC(=O)O[C@]([H])(CO)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)28-20(18-22)19-27-29(24,25)26/h9-10,20,22H,2-8,11-19H2,1H3,(H2,24,25,26)/b10-9+/t20-/m1/s1

> <INCHI_KEY>
ZOOLJLSXNRZLDH-SQUSKLHYSA-N

> <FORMULA>
C21H41O7P

> <MOLECULAR_WEIGHT>
436.526

> <EXACT_MASS>
436.258990658

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
50.18250369044186

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(2R)-3-hydroxy-2-[(9E)-octadec-9-enoyloxy]propoxy]phosphonic acid

> <ALOGPS_LOGP>
4.70

> <JCHEM_LOGP>
5.485689521666666

> <ALOGPS_LOGS>
-5.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.345670795497991

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.3198427043855556

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9837580757427844

> <JCHEM_POLAR_SURFACE_AREA>
113.29000000000002

> <JCHEM_REFRACTIVITY>
115.29899999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
21

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.74e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-3-hydroxy-2-[(9E)-octadec-9-enoyloxy]propoxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-16         0                                  
HETATM    1  C   UNK     0      -3.856  -7.855   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.401  -8.359   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.237  -7.351   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.218  -7.855   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.382  -6.847   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.837  -7.351   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -6.343   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.457  -6.847   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.621  -5.839   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.076  -6.343   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.240  -5.335   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.695  -5.839   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.859  -4.831   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.314  -5.335   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.479  -4.327   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.934  -4.831   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.098  -3.822   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      21.463  -5.335   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      22.336  -2.814   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      21.172  -3.822   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      18.553  -4.327   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      20.299  -6.343   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      18.844  -5.839   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      26.120  -1.302   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      25.964  -3.474   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      23.948  -1.146   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      23.792  -3.318   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      19.717  -3.318   0.000  0.00  0.00           O+0
HETATM   29  P   UNK     0      24.956  -2.310   0.000  0.00  0.00           P+0
HETATM   30  H   UNK     0       6.330  -4.327   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       8.367  -7.855   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0      22.628  -4.327   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   30                                                  
CONECT   10    9   11   31                                                  
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   27                                                       
CONECT   20   18   19   28   32                                             
CONECT   21   17   23   28                                                  
CONECT   22   18                                                            
CONECT   23   21                                                            
CONECT   24   29                                                            
CONECT   25   29                                                            
CONECT   26   29                                                            
CONECT   27   19   29                                                       
CONECT   28   20   21                                                       
CONECT   29   24   25   26   27                                             
CONECT   30    9                                                            
CONECT   31   10                                                            
CONECT   32   20                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   62    0
END

View in JSmol

Synonyms

Value	Source
[(2R)-3-Hydroxy-2-[(9E)-octadec-9-enoyloxy]propoxy]phosphonate	Generator

Chemical Formula

C₂₁H₄₁O₇P

Average Mass

436.5260 Da

Monoisotopic Mass

436.25899 Da

IUPAC Name

[(2R)-3-hydroxy-2-[(9E)-octadec-9-enoyloxy]propoxy]phosphonic acid

Traditional Name

(2R)-3-hydroxy-2-[(9E)-octadec-9-enoyloxy]propoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

[H]\C(CCCCCCCC)=C(\[H])CCCCCCCC(=O)O[C@]([H])(CO)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)28-20(18-22)19-27-29(24,25)26/h9-10,20,22H,2-8,11-19H2,1H3,(H2,24,25,26)/b10-9+/t20-/m1/s1

InChI Key

ZOOLJLSXNRZLDH-SQUSKLHYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-acylglycerol-3-phosphates. These are lysophosphatidic acids where the glycerol is esterified with a fatty acid at O-2 position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphates

Direct Parent

2-acylglycerol-3-phosphates

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.7	ALOGPS
logP	5.49	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	1.32	ChemAxon
pKa (Strongest Basic)	-3	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	50.18 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

General References

Showing NP-Card for LPA(0:0/18:1(9Z)) (NP0334215)

MOL for NP0334215 (LPA(0:0/18:1(9Z)))

3D MOL for NP0334215 (LPA(0:0/18:1(9Z)))

3D SDF for NP0334215 (LPA(0:0/18:1(9Z)))

3D-SDF for NP0334215 (LPA(0:0/18:1(9Z)))

PDB for NP0334215 (LPA(0:0/18:1(9Z)))

3D PDB for NP0334215 (LPA(0:0/18:1(9Z)))

SMILES for NP0334215 (LPA(0:0/18:1(9Z)))

INCHI for NP0334215 (LPA(0:0/18:1(9Z)))

Structure for NP0334215 (LPA(0:0/18:1(9Z)))

3D Structure for NP0334215 (LPA(0:0/18:1(9Z)))