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Showing NP-Card for 13-L-Hydroperoxylinoleic acid (NP0334103)

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Record Information
Version2.0
Created at2024-09-09 22:11:48 UTC
Updated at2024-09-09 22:11:49 UTC
NP-MRD IDNP0334103
Secondary Accession NumbersNone
Natural Product Identification
Common Name13-L-Hydroperoxylinoleic acid
Description13-L-Hydroperoxylinoleic acid (13(S)-HPODE) is one of the primary products of the major polyunsaturated fatty acids (linoleic acid and arachidonic acid) from the 15-1ipoxygenase pathway (EC: 1.13.11.31). 13(S)-HPODE is a rather unstable metabolite and is rapidly metabolized to more stable secondary products such as diverse forms of hydroxy fatty acids (via reduction of the hydroperoxy group), alkoxy radicals (via homolytic cleavage of the peroxy group), forms of dihydro(pero)xy fatty acids (via lipoxygenase-catalysed double and triple oxygenation), or epoxy leukotrienes (via a hydrogen abstraction from a doubly allylic methylene group and a homolytic cleavage of the hydroperoxy group). (PMID 9082450 ) [HMDB]
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0334103 (13-L-Hydroperoxylinoleic acid)


  Mrv2104 05252300442D          

 23 22  0  0  1  0            999 V2000
   -4.1467    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4322    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7177    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0033    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2888    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743    2.1434    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2888    0.9059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743    2.9684    0.0000 H   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 11  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  2  0  0  0  0
  8 10  1  0  0  0  0
  9 12  1  0  0  0  0
 10 13  1  0  0  0  0
 11 14  1  0  0  0  0
 12 15  2  0  0  0  0
 13 16  1  0  0  0  0
 17 14  1  0  0  0  0
 17 15  1  0  0  0  0
 16 18  1  0  0  0  0
 17 23  1  6  0  0  0
 17 22  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
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3D MOL for NP0334103 (13-L-Hydroperoxylinoleic acid)

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3D SDF for NP0334103 (13-L-Hydroperoxylinoleic acid)

  Mrv2104 05252300442D          

 23 22  0  0  1  0            999 V2000
   -4.1467    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4322    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7177    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0033    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2888    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743    2.1434    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2888    0.9059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743    2.9684    0.0000 H   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 11  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  2  0  0  0  0
  8 10  1  0  0  0  0
  9 12  1  0  0  0  0
 10 13  1  0  0  0  0
 11 14  1  0  0  0  0
 12 15  2  0  0  0  0
 13 16  1  0  0  0  0
 17 14  1  0  0  0  0
 17 15  1  0  0  0  0
 16 18  1  0  0  0  0
 17 23  1  6  0  0  0
 17 22  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334103

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@](CCCCC)(OO)\C=C\C=C\CCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H32O4/c1-2-3-11-14-17(22-21)15-12-9-7-5-4-6-8-10-13-16-18(19)20/h7,9,12,15,17,21H,2-6,8,10-11,13-14,16H2,1H3,(H,19,20)/b9-7+,15-12+/t17-/m0/s1

> <INCHI_KEY>
JDSRHVWSAMTSSN-WHLLTAFYSA-N

> <FORMULA>
C18H32O4

> <MOLECULAR_WEIGHT>
312.45

> <EXACT_MASS>
312.23005951

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
39.182523685717996

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9E,11E,13S)-13-hydroperoxyoctadeca-9,11-dienoic acid

> <JCHEM_LOGP>
5.640401104666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.712374089551586

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.988167201984285

> <JCHEM_PKA_STRONGEST_BASIC>
-4.236807609077442

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
91.38449999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(9E,11E,13S)-13-hydroperoxyoctadeca-9,11-dienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0334103 (13-L-Hydroperoxylinoleic acid)
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PDB for NP0334103 (13-L-Hydroperoxylinoleic acid)
HEADER    PROTEIN                                 25-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-MAY-23         0                                  
HETATM    1  C   UNK     0      -7.740   4.771   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.407   4.001   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.073   4.771   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.596   4.771   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.263   4.001   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.929   4.771   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.739   4.001   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.595   4.001   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.406   4.771   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.262   4.771   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.598   4.771   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.072   4.001   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      16.266   4.771   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      14.932   2.461   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.406   1.691   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.072   2.461   0.000  0.00  0.00           O+0
HETATM   23  H   UNK     0      -1.072   5.541   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2   11                                                       
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   12                                                       
CONECT   10    8   13                                                       
CONECT   11    3   14                                                       
CONECT   12    9   15                                                       
CONECT   13   10   16                                                       
CONECT   14   11   17                                                       
CONECT   15   12   17                                                       
CONECT   16   13   18                                                       
CONECT   17   14   15   23   22                                             
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   22                                                            
CONECT   22   17   21                                                       
CONECT   23   17                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   44    0
END

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3D PDB for NP0334103 (13-L-Hydroperoxylinoleic acid)
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SMILES for NP0334103 (13-L-Hydroperoxylinoleic acid)
[H][C@@](CCCCC)(OO)\C=C\C=C\CCCCCCCC(O)=O
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INCHI for NP0334103 (13-L-Hydroperoxylinoleic acid)
InChI=1S/C18H32O4/c1-2-3-11-14-17(22-21)15-12-9-7-5-4-6-8-10-13-16-18(19)20/h7,9,12,15,17,21H,2-6,8,10-11,13-14,16H2,1H3,(H,19,20)/b9-7+,15-12+/t17-/m0/s1
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SynonymsNot Available
Chemical FormulaC18H32O4
Average Mass312.4500 Da
Monoisotopic Mass312.23006 Da
IUPAC Name(9E,11E,13S)-13-hydroperoxyoctadeca-9,11-dienoic acid
Traditional Name(9E,11E,13S)-13-hydroperoxyoctadeca-9,11-dienoic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](CCCCC)(OO)\C=C\C=C\CCCCCCCC(O)=O
InChI Identifier
InChI=1S/C18H32O4/c1-2-3-11-14-17(22-21)15-12-9-7-5-4-6-8-10-13-16-18(19)20/h7,9,12,15,17,21H,2-6,8,10-11,13-14,16H2,1H3,(H,19,20)/b9-7+,15-12+/t17-/m0/s1
InChI KeyJDSRHVWSAMTSSN-WHLLTAFYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassLineolic acids and derivatives  
Direct ParentLineolic acids and derivatives  
Alternative Parents
Substituents
  • Octadecanoid
    • 

  • Long-chain fatty acid
    • 

  • Hydroperoxy fatty acid
    • 

  • Fatty acid
    • 

  • Unsaturated fatty acid
    • 

  • Allylic hydroperoxide
    • 

  • Hydroperoxide
    • 

  • Carboxylic acid derivative
    • 

  • Alkyl hydroperoxide
    • 

  • Carboxylic acid
    • 

  • Peroxol
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carbonyl group
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organic oxygen 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
logP5.64ChemAxon
pKa (Strongest Acidic)4.99ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity91.38 m³·mol⁻¹ChemAxon
Polarizability39.18 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
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 Compound49866404  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References