NP-MRD: Showing NP-Card for 9S-Hydroxyarachidonic acid (NP0050329)

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Record Information

Version

2.0

Created at

2022-04-27 20:53:04 UTC

Updated at

2022-04-27 20:53:05 UTC

NP-MRD ID

NP0050329

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9S-Hydroxyarachidonic acid

Description

9(S)-HETE, also known as 9S-HETE, belongs to the class of organic compounds known as hydroxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroxyl group and four CC double bonds. Thus, 9(S)-hete is considered to be an eicosanoid. 9S-Hydroxyarachidonic acid is found in Polyneura latissima. Based on a literature review very few articles have been published on 9(S)-HETE.

Structure

MOL SDF PDB SMILES InChI

  Mrv1652304272222532D          

 23 22  0  0  1  0            999 V2000
   -2.3349    8.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0493    8.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0493    7.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7638    6.9020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7638    6.0770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4783    5.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4783    4.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7638    4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7638    3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0493    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349    3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    3.1895    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6204    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    3.6020    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  1  0  0  0  0
 13 14  2  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
 12 23  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0050329

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-10-13-16-19(21)17-14-11-9-12-15-18-20(22)23/h6-7,9-11,13-14,17,19,21H,2-5,8,12,15-16,18H2,1H3,(H,22,23)/b7-6-,11-9-,13-10-,17-14+/t19-/m0/s1

> <INCHI_KEY>
KATOYYZUTNAWSA-VBLHFSPLSA-N

> <FORMULA>
C20H32O3

> <MOLECULAR_WEIGHT>
320.473

> <EXACT_MASS>
320.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
38.365024162743886

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z,7E,9S,11Z,14Z)-9-hydroxyicosa-5,7,11,14-tetraenoic acid

> <ALOGPS_LOGP>
5.88

> <JCHEM_LOGP>
5.356359744

> <ALOGPS_LOGS>
-5.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.72081997446193

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.491227766154946

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6087138346993122

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
101.4695

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.63e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9(S)-hete

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-22         0                                  
HETATM    1  C   UNK     0      -4.358  15.964   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.692  15.194   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.692  13.654   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.026  12.884   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.026  11.344   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -8.359  10.574   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -8.359   9.034   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -7.026   8.264   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -7.026   6.724   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.692   5.954   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.358   6.724   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.025   5.954   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.025   4.414   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.691   3.644   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.691   2.104   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.357   1.334   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.977   1.334   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.311   2.104   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.977  -0.206   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -1.691   6.724   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   23                                                  
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                                                            
CONECT   23   12                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   44    0
END

View in JSmol

Synonyms

Value	Source
(5Z,7E,11Z,14Z)-(9S)-9-Hydroxyeicosa-5,7,11,14-tetraenoic acid	ChEBI
(5Z,7E,11Z,14Z)-(9S)-9-Hydroxyicosa-5,7,11,14-tetraenoic acid	ChEBI
(5Z,7E,9S,11Z,14Z)-9-Hydroxyeicosa-5,7,11,14-tetraenoic acid	ChEBI
(S)-(Z,e,Z,Z)-9-Hydroxyeicosa-5,7,11,14-tetraenoic acid	ChEBI
(S)-(Z,e,Z,Z)-9-Hydroxyicosa-5,7,11,14-tetraenoic acid	ChEBI
9(S)-Hydroxyeicosatetraenoic acid	ChEBI
9S-HETE	ChEBI
(5Z,7E,11Z,14Z)-(9S)-9-Hydroxyeicosa-5,7,11,14-tetraenoate	Generator
(5Z,7E,11Z,14Z)-(9S)-9-Hydroxyicosa-5,7,11,14-tetraenoate	Generator
(5Z,7E,9S,11Z,14Z)-9-Hydroxyeicosa-5,7,11,14-tetraenoate	Generator
(S)-(Z,e,Z,Z)-9-Hydroxyeicosa-5,7,11,14-tetraenoate	Generator
(S)-(Z,e,Z,Z)-9-Hydroxyicosa-5,7,11,14-tetraenoate	Generator
9(S)-Hydroxyeicosatetraenoate	Generator

Chemical Formula

C₂₀H₃₂O₃

Average Mass

320.4730 Da

Monoisotopic Mass

320.23514 Da

IUPAC Name

(5Z,7E,9S,11Z,14Z)-9-hydroxyicosa-5,7,11,14-tetraenoic acid

Traditional Name

9(S)-hete

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-10-13-16-19(21)17-14-11-9-12-15-18-20(22)23/h6-7,9-11,13-14,17,19,21H,2-5,8,12,15-16,18H2,1H3,(H,22,23)/b7-6-,11-9-,13-10-,17-14+/t19-/m0/s1

InChI Key

KATOYYZUTNAWSA-VBLHFSPLSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Polyneura latissima	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroxyl group and four CC double bonds.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Hydroxyeicosatetraenoic acids

Alternative Parents

Substituents

Hydroxyeicosatetraenoic acid
Long-chain fatty acid
Hydroxy fatty acid
Fatty acid
Unsaturated fatty acid
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

HETE (CHEBI:34495 )
Hydroxy/hydroperoxyeicosatetraenoic acids (C14779 )
Hydroxy/hydroperoxyeicosatetraenoic acids (LMFA03060027 )

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	5.88	ALOGPS
logP	5.36	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	4.49	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	101.47 m³·mol⁻¹	ChemAxon
Polarizability	38.37 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

C00000420

Chemspider ID

4446291

KEGG Compound ID

C14779

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5283167

PDB ID

Not Available

ChEBI ID

34495

Good Scents ID

Not Available

References

General References

Showing NP-Card for 9S-Hydroxyarachidonic acid (NP0050329)

MOL for NP0050329 (9S-Hydroxyarachidonic acid)

3D MOL for NP0050329 (9S-Hydroxyarachidonic acid)

3D SDF for NP0050329 (9S-Hydroxyarachidonic acid)

3D-SDF for NP0050329 (9S-Hydroxyarachidonic acid)

PDB for NP0050329 (9S-Hydroxyarachidonic acid)

3D PDB for NP0050329 (9S-Hydroxyarachidonic acid)

SMILES for NP0050329 (9S-Hydroxyarachidonic acid)

INCHI for NP0050329 (9S-Hydroxyarachidonic acid)

Structure for NP0050329 (9S-Hydroxyarachidonic acid)

3D Structure for NP0050329 (9S-Hydroxyarachidonic acid)