Showing NP-Card for 13-Hydroxyarachidonic acid (NP0050333)

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Record Information
Version2.0
Created at2022-04-27 20:53:19 UTC
Updated at2022-04-27 20:53:19 UTC
NP-MRD IDNP0050333
Secondary Accession NumbersNone
Natural Product Identification
Common Name13-Hydroxyarachidonic acid
Description13R-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, 13R-hete is considered to be an eicosanoid. 13-Hydroxyarachidonic acid is found in Lithothamnion corallioides. 13-Hydroxyarachidonic acid was first documented in 1998 (PMID: 9435160). Based on a literature review very few articles have been published on 13r-hete.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0050333 (13-Hydroxyarachidonic acid)

  Mrv1652304272222532D          

 23 22  0  0  1  0            999 V2000
    5.6645   -3.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355   -3.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355   -3.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5211   -2.6368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066   -3.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921   -2.6368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921   -1.8118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066   -1.3993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066   -0.5743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921   -0.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3776   -0.5743    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6632   -0.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0513   -0.5743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0513   -1.3993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7658   -1.8118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7658   -2.6368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4802   -3.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4802   -3.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3776   -1.3993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934   -3.8743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789   -5.1118    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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  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  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
 12 20  1  6  0  0  0
  1 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
M  END
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3D MOL for NP0050333 (13-Hydroxyarachidonic acid)

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3D SDF for NP0050333 (13-Hydroxyarachidonic acid)
  Mrv1652304272222532D          

 23 22  0  0  1  0            999 V2000
    5.6645   -3.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355   -3.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355   -3.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5211   -2.6368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066   -3.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921   -2.6368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921   -1.8118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066   -1.3993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066   -0.5743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921   -0.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3776   -0.5743    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6632   -0.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0513   -0.5743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0513   -1.3993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7658   -1.8118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7658   -2.6368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4802   -3.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4802   -3.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3776   -1.3993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934   -3.8743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789   -5.1118    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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  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  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
 12 20  1  6  0  0  0
  1 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050333

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O3/c1-2-3-4-10-13-16-19(21)17-14-11-8-6-5-7-9-12-15-18-20(22)23/h6-9,13-14,16-17,19,21H,2-5,10-12,15,18H2,1H3,(H,22,23)/b8-6-,9-7-,16-13-,17-14-/t19-/m1/s1

> <INCHI_KEY>
SAKQICHVWOJSNI-PRVIWIHFSA-N

> <FORMULA>
C20H32O3

> <MOLECULAR_WEIGHT>
320.473

> <EXACT_MASS>
320.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
38.09968086142246

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z,8Z,11Z,13R,14Z)-13-hydroxyicosa-5,8,11,14-tetraenoic acid

> <ALOGPS_LOGP>
5.82

> <JCHEM_LOGP>
5.512267204

> <ALOGPS_LOGS>
-5.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.98210110956119

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.8197719174678

> <JCHEM_PKA_STRONGEST_BASIC>
-1.931829051623477

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
101.31549999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.65e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5Z,8Z,11Z,13R,14Z)-13-hydroxyicosa-5,8,11,14-tetraenoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0050333 (13-Hydroxyarachidonic acid)
Download
PDB for NP0050333 (13-Hydroxyarachidonic acid)
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      10.574  -7.232   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.240  -8.002   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.906  -7.232   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.906  -5.692   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.573  -4.922   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.239  -5.692   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.905  -4.922   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.905  -3.382   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.239  -2.612   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.239  -1.072   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.905  -0.302   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.572  -1.072   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.238  -0.302   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.096  -1.072   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.096  -2.612   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.429  -3.382   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.429  -4.922   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.763  -5.692   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.763  -7.232   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.572  -2.612   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      11.907  -8.002   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      13.241  -7.232   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      11.907  -9.542   0.000  0.00  0.00           O+0
CONECT    1    2   21                                                       
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   20                                                  
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                                                            
CONECT   20   12                                                            
CONECT   21    1   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   44    0
END

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3D PDB for NP0050333 (13-Hydroxyarachidonic acid)
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SMILES for NP0050333 (13-Hydroxyarachidonic acid)
CCCCC\C=C/[C@@H](O)\C=C/C\C=C/C\C=C/CCCC(O)=O
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INCHI for NP0050333 (13-Hydroxyarachidonic acid)
InChI=1S/C20H32O3/c1-2-3-4-10-13-16-19(21)17-14-11-8-6-5-7-9-12-15-18-20(22)23/h6-9,13-14,16-17,19,21H,2-5,10-12,15,18H2,1H3,(H,22,23)/b8-6-,9-7-,16-13-,17-14-/t19-/m1/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC20H32O3
Average Mass320.4730 Da
Monoisotopic Mass320.23514 Da
IUPAC Name(5Z,8Z,11Z,13R,14Z)-13-hydroxyicosa-5,8,11,14-tetraenoic acid
Traditional Name(5Z,8Z,11Z,13R,14Z)-13-hydroxyicosa-5,8,11,14-tetraenoic acid
CAS Registry NumberNot Available
SMILES
CCCCC\C=C/[C@@H](O)\C=C/C\C=C/C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O3/c1-2-3-4-10-13-16-19(21)17-14-11-8-6-5-7-9-12-15-18-20(22)23/h6-9,13-14,16-17,19,21H,2-5,10-12,15,18H2,1H3,(H,22,23)/b8-6-,9-7-,16-13-,17-14-/t19-/m1/s1
InChI KeySAKQICHVWOJSNI-PRVIWIHFSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Lithothamnion corallioides--
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.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassEicosanoids  
Direct ParentHydroxyeicosatetraenoic 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 FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.82ALOGPS
logP5.51ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)4.82ChemAxon
pKa (Strongest Basic)-1.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity101.32 m³·mol⁻¹ChemAxon
Polarizability38.1 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID103882429  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound101939320  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Bylund J, Kunz T, Valmsen K, Oliw EH: Cytochromes P450 with bisallylic hydroxylation activity on arachidonic and linoleic acids studied with human recombinant enzymes and with human and rat liver microsomes. J Pharmacol Exp Ther. 1998 Jan;284(1):51-60. [PubMed:9435160  ]