NP-MRD: Showing NP-Card for 1-Lyso-2-arachidonoyl-phosphatidate (NP0339019)

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Record Information

Version

2.0

Created at

2024-09-11 19:16:43 UTC

Updated at

2024-09-11 19:16:44 UTC

NP-MRD ID

NP0339019

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-Lyso-2-arachidonoyl-phosphatidate

Description

1-Lyso-2-arachidonoyl-phosphatidate 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. 1-Lyso-2-arachidonoyl-phosphatidate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02251208062D          

 31 30  0  0  1  0            999 V2000
   10.2226  -17.9955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0476  -17.9955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4601  -17.2809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2851  -17.2809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6976  -16.5663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5226  -16.5663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9351  -15.8524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5232  -15.1378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6982  -15.1372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2857  -14.4226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6976  -13.7080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5226  -13.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9344  -12.9928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5219  -12.2782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6969  -12.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2851  -11.5630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6969  -10.8484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5219  -10.8465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9338  -10.1320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7576  -10.1308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1713  -10.8440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1695   -9.4162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9945   -9.4155    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.4064   -8.7008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9934   -7.9866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4075  -10.1297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9954  -10.8445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4085  -11.5586    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   15.6944  -11.9717    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   17.1227  -11.1456    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   16.8215  -12.2728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  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  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 26  1  0  0  0  0
 24 25  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
 28 30  1  0  0  0  0
 28 31  2  0  0  0  0
M  CHG  2  29  -1  30  -1
M  END


  Mrv0541 02251208062D          

 31 30  0  0  1  0            999 V2000
   10.2226  -17.9955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0476  -17.9955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4601  -17.2809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2851  -17.2809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6976  -16.5663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5226  -16.5663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9351  -15.8524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5232  -15.1378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6982  -15.1372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2857  -14.4226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6976  -13.7080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5226  -13.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9344  -12.9928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5219  -12.2782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6969  -12.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2851  -11.5630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6969  -10.8484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5219  -10.8465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9338  -10.1320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7576  -10.1308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1713  -10.8440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1695   -9.4162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9945   -9.4155    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.4064   -8.7008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9934   -7.9866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4075  -10.1297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9954  -10.8445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4085  -11.5586    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   15.6944  -11.9717    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   17.1227  -11.1456    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   16.8215  -12.2728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  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  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 26  1  0  0  0  0
 24 25  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
 28 30  1  0  0  0  0
 28 31  2  0  0  0  0
M  CHG  2  29  -1  30  -1
M  END
> <DATABASE_ID>
NP0339019

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)O[C@H](CO)COP([O-])([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H39O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(25)30-22(20-24)21-29-31(26,27)28/h6-7,9-10,12-13,15-16,22,24H,2-5,8,11,14,17-21H2,1H3,(H2,26,27,28)/p-2/b7-6-,10-9-,13-12-,16-15-/t22-/m1/s1

> <INCHI_KEY>
BDCFJMBXZCIVRH-NZRYSPDRSA-L

> <FORMULA>
C23H37O7P

> <MOLECULAR_WEIGHT>
456.5094

> <EXACT_MASS>
456.22769005

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
49.07428356144413

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
-2

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R)-1-hydroxy-3-(phosphonatooxy)propan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate

> <ALOGPS_LOGP>
5.57

> <JCHEM_LOGP>
5.289061881666667

> <ALOGPS_LOGS>
-5.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.345670791975907

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.3198427008627798

> <JCHEM_PKA_STRONGEST_BASIC>
-2.983758076417394

> <JCHEM_POLAR_SURFACE_AREA>
118.95000000000002

> <JCHEM_REFRACTIVITY>
125.60739999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
20

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.45e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-1-hydroxy-3-(phosphonatooxy)propan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-FEB-12         0                                  
HETATM    1  C   UNK     0      19.082 -33.592   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.622 -33.592   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      21.392 -32.258   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      22.932 -32.258   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      23.702 -30.924   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      25.242 -30.924   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      26.012 -29.591   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      25.243 -28.257   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      23.703 -28.256   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.933 -26.922   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.702 -25.588   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      25.242 -25.587   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      26.011 -24.253   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      25.241 -22.919   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      23.701 -22.917   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      22.932 -21.584   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      23.701 -20.250   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      25.241 -20.247   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      26.010 -18.913   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      27.548 -18.911   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      28.320 -20.242   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      28.316 -17.577   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      29.856 -17.576   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      30.625 -16.241   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      29.854 -14.908   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      30.627 -18.909   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      29.858 -20.243   0.000  0.00  0.00           O+0
HETATM   28  P   UNK     0      30.629 -21.576   0.000  0.00  0.00           P+0
HETATM   29  O   UNK     0      29.296 -22.347   0.000  0.00  0.00           O-1
HETATM   30  O   UNK     0      31.962 -20.805   0.000  0.00  0.00           O-1
HETATM   31  O   UNK     0      31.400 -22.909   0.000  0.00  0.00           O+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                                                       
CONECT   10    9   11                                                       
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   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30   31                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   28                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   60    0
END

View in JSmol

Synonyms

Value	Source
2-(5Z,8Z,11Z,14Z)-Icosatetraenoyl-sn-glycero-3-phosphate(2-)	ChEBI
2-(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-sn-glycero-3-phosphate	ChEBI
2-(5Z,8Z,11Z,14Z)-Icosatetraenoyl-sn-glycero-3-phosphoric acid(2-)	Generator
2-(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-sn-glycero-3-phosphoric acid	Generator
1-Lyso-2-arachidonoyl-phosphatidic acid	Generator
2-(5Z,8Z,11Z,14Z)-Eicosatetraenoyl-sn-glycero-3-phosphate	ChEBI
2-(5Z,8Z,11Z,14Z)-Eicosatetraenoyl-sn-glycero-3-phosphoric acid	Generator
1-lyso-2-all-cis-5,8,11,14-Eicosatetraenoyl-sn-glycero-3-phosphatidic acid	HMDB
2-all-cis-5,8,11,14-Eicosatetraenoyl-lysophosphatidic acid	HMDB
2-Arachidonoyl-lysophosphatidic acid	HMDB
2-Arachidonoyl-sn-glycero-3-phosphate	HMDB
L-beta-Arachidonoyl-alpha-lysophosphatidic acid	HMDB

Chemical Formula

C₂₃H₃₇O₇P

Average Mass

456.5094 Da

Monoisotopic Mass

456.22769 Da

IUPAC Name

(2R)-1-hydroxy-3-(phosphonatooxy)propan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate

Traditional Name

(2R)-1-hydroxy-3-(phosphonatooxy)propan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate

CAS Registry Number

Not Available

SMILES

CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)O[C@H](CO)COP([O-])([O-])=O

InChI Identifier

InChI=1S/C23H39O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(25)30-22(20-24)21-29-31(26,27)28/h6-7,9-10,12-13,15-16,22,24H,2-5,8,11,14,17-21H2,1H3,(H2,26,27,28)/p-2/b7-6-,10-9-,13-12-,16-15-/t22-/m1/s1

InChI Key

BDCFJMBXZCIVRH-NZRYSPDRSA-L

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2-acyl-sn-glycero-3-phosphate(2-) (CHEBI:78209 )

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	5.57	ALOGPS
logP	5.29	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	1.32	ChemAxon
pKa (Strongest Basic)	-3	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	20	ChemAxon
Refractivity	125.61 m³·mol⁻¹	ChemAxon
Polarizability	49.07 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

FDB029101

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

53481443

PDB ID

Not Available

ChEBI ID

78209

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 1-Lyso-2-arachidonoyl-phosphatidate (NP0339019)

MOL for NP0339019 (1-Lyso-2-arachidonoyl-phosphatidate)

3D MOL for NP0339019 (1-Lyso-2-arachidonoyl-phosphatidate)

3D SDF for NP0339019 (1-Lyso-2-arachidonoyl-phosphatidate)

3D-SDF for NP0339019 (1-Lyso-2-arachidonoyl-phosphatidate)

PDB for NP0339019 (1-Lyso-2-arachidonoyl-phosphatidate)

3D PDB for NP0339019 (1-Lyso-2-arachidonoyl-phosphatidate)

SMILES for NP0339019 (1-Lyso-2-arachidonoyl-phosphatidate)

INCHI for NP0339019 (1-Lyso-2-arachidonoyl-phosphatidate)

Structure for NP0339019 (1-Lyso-2-arachidonoyl-phosphatidate)

3D Structure for NP0339019 (1-Lyso-2-arachidonoyl-phosphatidate)