NP-MRD: Showing NP-Card for (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate (NP0334292)

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Record Information

Version

2.0

Created at

2024-09-09 23:01:48 UTC

Updated at

2024-09-09 23:01:48 UTC

NP-MRD ID

NP0334292

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate

Description

(9S,10e,12z)-9-hydroperoxy-10,12-octadecadienoate, also known as 9(S)-hydroperoxy-10(E),12(z)-octadecadienoic acid or 9(S)-hpod(1-), belongs to lineolic acids and derivatives class of compounds. Those 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 (9s,10e,12z)-9-hydroperoxy-10,12-octadecadienoate is practically insoluble (in water) and a weakly acidic compound (based on its pKa). (9S,10e,12z)-9-hydroperoxy-10,12-octadecadienoate can be found in a number of food items such as mexican groundcherry, brazil nut, coconut, and winter savory, which makes (9s,10e,12z)-9-hydroperoxy-10,12-octadecadienoate a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05252301342D          

 27 26  0  0  1  0            999 V2000
   -4.8459    1.0914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3058    0.4677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4957    0.6236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9556   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1455    0.1559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6054   -0.4677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9052    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7953   -0.3118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3651    1.5591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7153    1.0914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2552   -0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5550    1.4032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2554    0.4677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5550   -0.7796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2849    0.6236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0655    0.6236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6056    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4158    0.1559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3356   -0.7796    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    2.1752   -0.4677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6351    0.1559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8754   -1.2473    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5252    0.4677    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5252   -1.7150    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0950   -1.4032    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0149   -0.1559    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  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6 23  1  0  0  0  0
  6  8  2  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
  8 24  1  0  0  0  0
  8 11  1  0  0  0  0
  9 12  1  0  0  0  0
 10 13  1  0  0  0  0
 11 25  1  0  0  0  0
 11 14  2  0  0  0  0
 12 15  1  0  0  0  0
 13 16  1  0  0  0  0
 14 26  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 27  1  1  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  CHG  1  20  -1
M  END


  Mrv2104 05252301342D          

 27 26  0  0  1  0            999 V2000
   -4.8459    1.0914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3058    0.4677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4957    0.6236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9556   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1455    0.1559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6054   -0.4677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9052    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7953   -0.3118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3651    1.5591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7153    1.0914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2552   -0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5550    1.4032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2554    0.4677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5550   -0.7796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2849    0.6236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0655    0.6236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6056    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4158    0.1559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3356   -0.7796    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    2.1752   -0.4677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6351    0.1559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8754   -1.2473    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5252    0.4677    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5252   -1.7150    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0950   -1.4032    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0149   -0.1559    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  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6 23  1  0  0  0  0
  6  8  2  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
  8 24  1  0  0  0  0
  8 11  1  0  0  0  0
  9 12  1  0  0  0  0
 10 13  1  0  0  0  0
 11 25  1  0  0  0  0
 11 14  2  0  0  0  0
 12 15  1  0  0  0  0
 13 16  1  0  0  0  0
 14 26  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 27  1  1  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  CHG  1  20  -1
M  END
> <DATABASE_ID>
NP0334292

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H32O4/c1-2-3-4-5-6-8-11-14-17(22-21)15-12-9-7-10-13-16-18(19)20/h6,8,11,14,17,21H,2-5,7,9-10,12-13,15-16H2,1H3,(H,19,20)/p-1/b8-6+,14-11-/t17-/m1/s1

> <INCHI_KEY>
JGUNZIWGNMQSBM-FGHHIYCJSA-M

> <FORMULA>
C18H31O4

> <MOLECULAR_WEIGHT>
311.443

> <EXACT_MASS>
311.222783058

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
37.52206863264482

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9S,10Z,12E)-9-hydroperoxyoctadeca-10,12-dienoate

> <JCHEM_LOGP>
5.640401104666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.712374047588172

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.676745143435034

> <JCHEM_PKA_STRONGEST_BASIC>
-4.236807609084803

> <JCHEM_POLAR_SURFACE_AREA>
69.59

> <JCHEM_REFRACTIVITY>
102.22159999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(9S,10Z,12E)-9-hydroperoxyoctadeca-10,12-dienoate

> <JCHEM_VEBER_RULE>
0

$$$$

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      -9.046   2.037   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.038   0.873   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.525   1.164   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.517  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.005   0.291   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.997  -0.873   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.556   1.746   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.484  -0.582   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.548   2.910   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.069   2.037   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.476  -1.746   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.036   2.619   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.077   0.873   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.036  -1.455   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.532   1.164   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.589   1.164   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.597   0.000   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.109   0.291   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.093  -1.455   0.000  0.00  0.00           O-1
HETATM   21  O   UNK     0       4.060  -0.873   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       3.052   0.291   0.000  0.00  0.00           O+0
HETATM   23  H   UNK     0      -3.501  -2.328   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      -0.980   0.873   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0      -0.980  -3.201   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0       2.044  -2.619   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.028  -0.291   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   23    8                                                  
CONECT    7    9   10                                                       
CONECT    8    6   24   11                                                  
CONECT    9    7   12                                                       
CONECT   10    7   13                                                       
CONECT   11    8   25   14                                                  
CONECT   12    9   15                                                       
CONECT   13   10   16                                                       
CONECT   14   11   26   17                                                  
CONECT   15   12   17                                                       
CONECT   16   13   18                                                       
CONECT   17   14   15   27   22                                             
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   22                                                            
CONECT   22   17   21                                                       
CONECT   23    6                                                            
CONECT   24    8                                                            
CONECT   25   11                                                            
CONECT   26   14                                                            
CONECT   27   17                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   52    0
END

View in JSmol

Synonyms

Value	Source
(9S,10E,12Z)-9-Hydroperoxy-10,12-octadecadienoic acid	Generator

Chemical Formula

C₁₈H₃₁O₄

Average Mass

311.4430 Da

Monoisotopic Mass

311.22278 Da

IUPAC Name

(9S,10Z,12E)-9-hydroperoxyoctadeca-10,12-dienoate

Traditional Name

(9S,10Z,12E)-9-hydroperoxyoctadeca-10,12-dienoate

CAS Registry Number

Not Available

SMILES

[H]\C(CCCCC)=C(\[H])/C(/[H])=C(/[H])[C@]([H])(CCCCCCCC([O-])=O)OO

InChI Identifier

InChI=1S/C18H32O4/c1-2-3-4-5-6-8-11-14-17(22-21)15-12-9-7-10-13-16-18(19)20/h6,8,11,14,17,21H,2-5,7,9-10,12-13,15-16H2,1H3,(H,19,20)/p-1/b8-6+,14-11-/t17-/m1/s1

InChI Key

JGUNZIWGNMQSBM-FGHHIYCJSA-M

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroperoxy fatty acids. These are fatty acids containing a hydroperoxide group attached to the chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Hydroperoxy fatty acids

Alternative Parents

Substituents

Hydroperoxy fatty acid
Allylic hydroperoxide
Hydroperoxide
Alkyl hydroperoxide
Peroxol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organic anion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

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	5.64	ChemAxon
pKa (Strongest Acidic)	4.68	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	69.59 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	102.22 m³·mol⁻¹	ChemAxon
Polarizability	37.52 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate (NP0334292)

MOL for NP0334292 ((9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate)

3D MOL for NP0334292 ((9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate)

3D SDF for NP0334292 ((9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate)

3D-SDF for NP0334292 ((9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate)

PDB for NP0334292 ((9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate)

3D PDB for NP0334292 ((9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate)

SMILES for NP0334292 ((9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate)

INCHI for NP0334292 ((9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate)

Structure for NP0334292 ((9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate)

3D Structure for NP0334292 ((9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate)