NP-MRD: Showing NP-Card for (2r)-2-hydroxy-3-[(5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoyloxy]propoxyphosphonic acid (NP0307160)

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Record Information

Version

2.0

Created at

2022-09-11 00:06:07 UTC

Updated at

2022-09-11 00:06:07 UTC

NP-MRD ID

NP0307160

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r)-2-hydroxy-3-[(5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoyloxy]propoxyphosphonic acid

Description

1-Arachidonoyl-sn-glycerol 3-phosphate, also known as lpa(20:4(5Z,8Z,11Z,14Z)/0:0) Or 1-arachidonoyl lpa, 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. (2r)-2-hydroxy-3-[(5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoyloxy]propoxyphosphonic acid is found in Trypanosoma brucei. 1-Arachidonoyl-sn-glycerol 3-phosphate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1572008171514002D          

 40 39  0  0  1  0            999 V2000
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M  END

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  Mrv1572008171514002D          

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 10  9  2  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  2  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  2  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 22 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 19  1  0  0  0  0
 22 24  1  1  0  0  0
 25 23  2  0  0  0  0
 29 20  1  0  0  0  0
 29 23  1  0  0  0  0
 30 21  1  0  0  0  0
 31 26  1  0  0  0  0
 31 27  1  0  0  0  0
 31 28  2  0  0  0  0
 31 30  1  0  0  0  0
 32  6  1  0  0  0  0
 33  7  1  0  0  0  0
 34  9  1  0  0  0  0
 35 10  1  0  0  0  0
 36 12  1  0  0  0  0
 37 13  1  0  0  0  0
 38 15  1  0  0  0  0
 39 16  1  0  0  0  0
 22 40  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0307160

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(CCCCC)=C(/[H])C\C([H])=C(\[H])C\C([H])=C(\[H])C\C([H])=C(\[H])CCCC(=O)OC[C@@]([H])(O)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)29-20-22(24)21-30-31(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)/b7-6-,10-9-,13-12-,16-15-/t22-/m1/s1

> <INCHI_KEY>
XBFQFMCUPHZKTI-NZRYSPDRSA-N

> <FORMULA>
C23H39O7P

> <MOLECULAR_WEIGHT>
458.532

> <EXACT_MASS>
458.243340594

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
49.473273911139316

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(2R)-2-hydroxy-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propoxy]phosphonic acid

> <ALOGPS_LOGP>
5.01

> <JCHEM_LOGP>
5.289061881666667

> <ALOGPS_LOGS>
-5.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.531115837543949

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.5053177852360151

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4039997956636006

> <JCHEM_POLAR_SURFACE_AREA>
113.29000000000002

> <JCHEM_REFRACTIVITY>
127.85079999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
20

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.17e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-hydroxy-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propoxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-AUG-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-AUG-15         0                                  
HETATM    1  C   UNK     0      -4.620  16.004   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.390  14.670   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.620  13.337   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.390  12.003   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.620  10.669   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.390   9.336   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.620   8.002   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.080   8.002   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.310   6.668   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.080   5.335   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.620   5.335   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.390   4.001   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.620   2.667   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.080   2.667   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.310   1.334   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   2.667   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.770   4.001   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   5.335   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.850   4.001   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.160   2.667   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.540   5.335   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.850   1.334   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       2.310   6.668   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      10.010   1.334   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       8.470  -0.206   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       8.470   2.874   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       2.310   4.001   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       6.930   1.334   0.000  0.00  0.00           O+0
HETATM   31  P   UNK     0       8.470   1.334   0.000  0.00  0.00           P+0
HETATM   32  H   UNK     0      -6.930   9.336   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0      -5.390   6.668   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.770   6.668   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.310   4.001   0.000  0.00  0.00           H+0
HETATM   36  H   UNK     0      -6.930   4.001   0.000  0.00  0.00           H+0
HETATM   37  H   UNK     0      -5.390   1.334   0.000  0.00  0.00           H+0
HETATM   38  H   UNK     0      -3.080   0.000   0.000  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   40  H   UNK     0       5.390   4.001   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   32                                                  
CONECT    7    6    8   33                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   34                                                  
CONECT   10    9   11   35                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   36                                                  
CONECT   13   12   14   37                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   38                                                  
CONECT   16   15   17   39                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   23                                                       
CONECT   20   22   29                                                       
CONECT   21   22   30                                                       
CONECT   22   20   21   24   40                                             
CONECT   23   19   25   29                                                  
CONECT   24   22                                                            
CONECT   25   23                                                            
CONECT   26   31                                                            
CONECT   27   31                                                            
CONECT   28   31                                                            
CONECT   29   20   23                                                       
CONECT   30   21   31                                                       
CONECT   31   26   27   28   30                                             
CONECT   32    6                                                            
CONECT   33    7                                                            
CONECT   34    9                                                            
CONECT   35   10                                                            
CONECT   36   12                                                            
CONECT   37   13                                                            
CONECT   38   15                                                            
CONECT   39   16                                                            
CONECT   40   22                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   78    0
END

View in JSmol

Synonyms

Value	Source
1-(5Z,8Z,11Z,14Z)-Eicosatetraenoyl-sn-glycero-3-phosphate	ChEBI
1-(5Z,8Z,11Z,14Z)-Icosatetraenoyl-sn-glycero-3-phosphate	ChEBI
1-(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-sn-glycero-3-phosphate	ChEBI
1-Arachidonoyl lpa	ChEBI
1-Arachidonoyl lysophosphatidic acid	ChEBI
LPA(20:4(5Z,8Z,11Z,14Z)/0:0)	ChEBI
Lysophosphatidic acid (20:4(5Z,8Z,11Z,14Z)/0:0)	ChEBI
PA(20:4(5Z,8Z,11Z,14Z)/0:0)	ChEBI
PA(20:4/0:0)	ChEBI
1-(5Z,8Z,11Z,14Z)-Eicosatetraenoyl-sn-glycero-3-phosphoric acid	Generator
1-(5Z,8Z,11Z,14Z)-Icosatetraenoyl-sn-glycero-3-phosphoric acid	Generator
1-(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-sn-glycero-3-phosphoric acid	Generator
1-Arachidonoyl lysophosphatidate	Generator
Lysophosphatidate (20:4(5Z,8Z,11Z,14Z)/0:0)	Generator
1-Arachidonoyl-sn-glycerol 3-phosphoric acid	Generator

Chemical Formula

C₂₃H₃₉O₇P

Average Mass

458.5320 Da

Monoisotopic Mass

458.24334 Da

IUPAC Name

[(2R)-2-hydroxy-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propoxy]phosphonic acid

Traditional Name

(2R)-2-hydroxy-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

[H]\C(CCCCC)=C(/[H])C\C([H])=C(\[H])C\C([H])=C(\[H])C\C([H])=C(\[H])CCCC(=O)OC[C@@]([H])(O)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)29-20-22(24)21-30-31(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)/b7-6-,10-9-,13-12-,16-15-/t22-/m1/s1

InChI Key

XBFQFMCUPHZKTI-NZRYSPDRSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Trypanosoma brucei	LOTUS Database	35616633

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

1-acyl-sn-glycerol 3-phosphate (CHEBI:73792 )
Monoacylglycerophosphates (LMGP10050013 )

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	5.01	ALOGPS
logP	5.29	ChemAxon
logS	-5.2	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	20	ChemAxon
Refractivity	127.85 m³·mol⁻¹	ChemAxon
Polarizability	49.47 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

HMDB0062312

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

42607498

PDB ID

Not Available

ChEBI ID

73792

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r)-2-hydroxy-3-[(5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoyloxy]propoxyphosphonic acid (NP0307160)

MOL for NP0307160 ((2r)-2-hydroxy-3-[(5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoyloxy]propoxyphosphonic acid)

3D MOL for NP0307160 ((2r)-2-hydroxy-3-[(5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoyloxy]propoxyphosphonic acid)

3D SDF for NP0307160 ((2r)-2-hydroxy-3-[(5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoyloxy]propoxyphosphonic acid)

3D-SDF for NP0307160 ((2r)-2-hydroxy-3-[(5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoyloxy]propoxyphosphonic acid)

PDB for NP0307160 ((2r)-2-hydroxy-3-[(5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoyloxy]propoxyphosphonic acid)

3D PDB for NP0307160 ((2r)-2-hydroxy-3-[(5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoyloxy]propoxyphosphonic acid)

SMILES for NP0307160 ((2r)-2-hydroxy-3-[(5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoyloxy]propoxyphosphonic acid)

INCHI for NP0307160 ((2r)-2-hydroxy-3-[(5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoyloxy]propoxyphosphonic acid)

Structure for NP0307160 ((2r)-2-hydroxy-3-[(5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoyloxy]propoxyphosphonic acid)

3D Structure for NP0307160 ((2r)-2-hydroxy-3-[(5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoyloxy]propoxyphosphonic acid)