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Showing NP-Card for 10-HETE (NP0339025)

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Record Information
Version2.0
Created at2024-09-11 19:18:44 UTC
Updated at2024-09-11 19:18:44 UTC
NP-MRD IDNP0339025
Secondary Accession NumbersNone
Natural Product Identification
Common Name10-HETE
Description10-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. 10-HETE was first documented in 1995 (PMID: 7646075). Based on a literature review a small amount of articles have been published on 10-HETE (PMID: 9435160) (PMID: 8806734).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0339025 (10-HETE)


  Mrv2104 05262321502D          

 23 22  0  0  0  0            999 V2000
   18.2144  -13.2347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3894  -13.2347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9769  -12.5203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1519  -12.5203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7394  -11.8058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9144  -11.8058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5019  -11.0913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9144  -10.3768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5019   -9.6624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9144   -8.9479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7394   -8.9479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1519   -9.6624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1519   -8.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7394   -7.5190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9144   -7.5190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5019   -6.8045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6769   -6.8045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2644   -7.5190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4394   -7.5190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0269   -8.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2019   -8.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7894   -7.5190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7894   -8.9479    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
 11 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  2  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  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
M  END
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3D MOL for NP0339025 (10-HETE)

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3D SDF for NP0339025 (10-HETE)

  Mrv2104 05262321502D          

 23 22  0  0  0  0            999 V2000
   18.2144  -13.2347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3894  -13.2347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9769  -12.5203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1519  -12.5203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7394  -11.8058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9144  -11.8058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5019  -11.0913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9144  -10.3768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5019   -9.6624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9144   -8.9479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7394   -8.9479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1519   -9.6624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1519   -8.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7394   -7.5190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9144   -7.5190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5019   -6.8045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6769   -6.8045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2644   -7.5190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4394   -7.5190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0269   -8.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2019   -8.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7894   -7.5190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7894   -8.9479    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
 11 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  2  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  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0339025

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC\C=C/C\C=C/C(O)\C=C/C\C=C/CCCC(O)=O

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

> <INCHI_KEY>
ZUOCVLADVGGUGH-OVMCANAPNA-N

> <FORMULA>
C20H32O3

> <MOLECULAR_WEIGHT>
320.473

> <EXACT_MASS>
320.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
37.97651663821033

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z,8Z,11Z,14Z)-10-hydroxyicosa-5,8,11,14-tetraenoic acid

> <JCHEM_LOGP>
5.512267204

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.052211833402424

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.819771923097506

> <JCHEM_PKA_STRONGEST_BASIC>
-1.9011626266450274

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
101.31549999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(5Z,8Z,11Z,14Z)-10-hydroxyicosa-5,8,11,14-tetraenoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0339025 (10-HETE)
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PDB for NP0339025 (10-HETE)
HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0      34.000 -24.705   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      32.460 -24.705   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      31.690 -23.371   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      30.150 -23.371   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      29.380 -22.037   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      27.840 -22.037   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      27.070 -20.704   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      27.840 -19.370   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      27.070 -18.036   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      27.840 -16.703   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      29.380 -16.703   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      30.150 -18.036   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      30.150 -15.369   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      29.380 -14.035   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      27.840 -14.035   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      27.070 -12.702   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      25.530 -12.702   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      24.760 -14.035   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      23.220 -14.035   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      22.450 -15.369   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      20.910 -15.369   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      20.140 -14.035   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      20.140 -16.703   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   13                                                  
CONECT   12   11                                                            
CONECT   13   11   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                                                       
CONECT   21   20   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 NP0339025 (10-HETE)
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SMILES for NP0339025 (10-HETE)
CCCCC\C=C/C\C=C/C(O)\C=C/C\C=C/CCCC(O)=O
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INCHI for NP0339025 (10-HETE)
InChI=1/C20H32O3/c1-2-3-4-5-6-7-10-13-16-19(21)17-14-11-8-9-12-15-18-20(22)23/h6-9,13-14,16-17,19,21H,2-5,10-12,15,18H2,1H3,(H,22,23)/b7-6-,9-8-,16-13-,17-14-
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View in JSmol
SynonymsNot Available
Chemical FormulaC20H32O3
Average Mass320.4730 Da
Monoisotopic Mass320.23514 Da
IUPAC Name(5Z,8Z,11Z,14Z)-10-hydroxyicosa-5,8,11,14-tetraenoic acid
Traditional Name(5Z,8Z,11Z,14Z)-10-hydroxyicosa-5,8,11,14-tetraenoic acid
CAS Registry NumberNot Available
SMILES
CCCCC\C=C/C\C=C/C(O)\C=C/C\C=C/CCCC(O)=O
InChI Identifier
InChI=1/C20H32O3/c1-2-3-4-5-6-7-10-13-16-19(21)17-14-11-8-9-12-15-18-20(22)23/h6-9,13-14,16-17,19,21H,2-5,10-12,15,18H2,1H3,(H,22,23)/b7-6-,9-8-,16-13-,17-14-
InChI KeyZUOCVLADVGGUGH-OVMCANAPNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound 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
logP5.51ChemAxon
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
Polarizability37.98 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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
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  ] 
  2. Hornsten L, Bylund J, Oliw EH: Dexamethasone induces bisallylic hydroxylation of polyunsaturated fatty acids by rat liver microsomes. Arch Biochem Biophys. 1996 Aug 15;332(2):261-8. doi: 10.1006/abbi.1996.0341. [PubMed:8806734  ] 
  3. Brash AR, Boeglin WE, Capdevila JH, Yeola S, Blair IA: 7-HETE, 10-HETE, and 13-HETE are major products of NADPH-dependent arachidonic acid metabolism in rat liver microsomes: analysis of their stereochemistry, and the stereochemistry of their acid-catalyzed rearrangement. Arch Biochem Biophys. 1995 Aug 20;321(2):485-92. doi: 10.1006/abbi.1995.1421. [PubMed:7646075  ]