NP-MRD: Showing NP-Card for 9-Hydroperoxyoctadecadienoic acid (NP0050308)

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Record Information

Version

2.0

Created at

2022-04-27 20:52:17 UTC

Updated at

2022-04-27 20:52:17 UTC

NP-MRD ID

NP0050308

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-Hydroperoxyoctadecadienoic acid

Description

(9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecadienoate, also known as (10E,12Z)-(9S)-9-hydroperoxyoctadeca-10,12-dienoic acid or 9(S)-HPOD, 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 (9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecadienoate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, (9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecadienoate has been detected, but not quantified in, several different foods, such as muscadine grapes, bamboo shoots, towel gourds, nectarines, and cardoons. 9-Hydroperoxyoctadecadienoic acid is found in Chlorella pyrenoidosa, Fusarium oxysporum, Mus musculus and Trypanosoma brucei. This could make (9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecadienoate a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv1533007131514022D          

 27 26  0  0  1  0            999 V2000
    1.5395    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1118   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263    0.4125    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
    6.5408   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2552    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5408   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3184    2.8875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3184    1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  8  6  2  0  0  0  0
  9  7  1  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  9  1  0  0  0  0
 13 10  1  0  0  0  0
 14 11  2  0  0  0  0
 15 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
 17 15  1  0  0  0  0
 18 16  1  0  0  0  0
 19 18  2  0  0  0  0
 20 18  1  0  0  0  0
 17 22  1  1  0  0  0
 22 21  1  0  0  0  0
 23  6  1  0  0  0  0
 24  8  1  0  0  0  0
 25 11  1  0  0  0  0
 26 14  1  0  0  0  0
 17 27  1  1  0  0  0
M  END


  Mrv1533007131514022D          

 27 26  0  0  1  0            999 V2000
    1.5395    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1118   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263    0.4125    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
    6.5408   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2552    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5408   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3184    2.8875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3184    1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  8  6  2  0  0  0  0
  9  7  1  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  9  1  0  0  0  0
 13 10  1  0  0  0  0
 14 11  2  0  0  0  0
 15 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
 17 15  1  0  0  0  0
 18 16  1  0  0  0  0
 19 18  2  0  0  0  0
 20 18  1  0  0  0  0
 17 22  1  1  0  0  0
 22 21  1  0  0  0  0
 23  6  1  0  0  0  0
 24  8  1  0  0  0  0
 25 11  1  0  0  0  0
 26 14  1  0  0  0  0
 17 27  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0050308

> <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)/b8-6-,14-11+/t17-/m1/s1

> <INCHI_KEY>
JGUNZIWGNMQSBM-UINYOVNOSA-N

> <FORMULA>
C18H32O4

> <MOLECULAR_WEIGHT>
312.45

> <EXACT_MASS>
312.23005951

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
38.05740226768299

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
5.74

> <JCHEM_LOGP>
5.640401104666667

> <ALOGPS_LOGS>
-4.92

> <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>
-4.236807609084804

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
91.38449999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.73e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-HpODE

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-JUL-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-JUL-15         0                                  
HETATM    1  C   UNK     0       2.874  10.010   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540   9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.540   7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.206   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.206   5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.127   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.875  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.127   3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.541   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.208   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.206   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.207  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.542  -0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.206   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.876   0.770   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      12.209  -0.000   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      13.543   0.770   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      12.209  -1.540   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.206  -2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       1.540  -1.540   0.000  0.00  0.00           O+0
HETATM   23  H   UNK     0      -2.461   5.390   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      -2.461   2.310   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0       1.540   3.080   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0      -1.127  -0.000   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.540   1.540   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    8   23                                                  
CONECT    7    9   10                                                       
CONECT    8    6   11   24                                                  
CONECT    9    7   12                                                       
CONECT   10    7   13                                                       
CONECT   11    8   14   25                                                  
CONECT   12    9   15                                                       
CONECT   13   10   16                                                       
CONECT   14   11   17   26                                                  
CONECT   15   12   17                                                       
CONECT   16   13   18                                                       
CONECT   17   14   15   22   27                                             
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
(10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoic acid	ChEBI
(9S,10E,12Z)-9-Hydroperoxy-10,12-octadecadienoic acid	ChEBI
9(S)-HPOD	ChEBI
(9S,10E,12Z)-9-Hydroperoxy-10,12-octadecadienoate	Kegg
(10E,12Z)-(9S)-9-Hydroperoxyoctadeca-10,12-dienoate	Generator
(9S,10E,12Z,15Z)-9-Hydroperoxy-10,12,15-octadecadienoic acid	Generator
9-Hydroperoxy-11,12-octadecadienoic acid	MeSH, HMDB
9-Hydroperoxy-11,12-octadecadienoic acid, (e,Z)-isomer	MeSH, HMDB
9-Hydroperoxy-11,12-octadecadienoic acid, (Z,e)-isomer	MeSH, HMDB
9-HPODE	MeSH, HMDB

Chemical Formula

C₁₈H₃₂O₄

Average Mass

312.4500 Da

Monoisotopic Mass

312.23006 Da

IUPAC Name

(9S,10E,12Z)-9-hydroperoxyoctadeca-10,12-dienoic acid

Traditional Name

9-HpODE

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)/b8-6-,14-11+/t17-/m1/s1

InChI Key

JGUNZIWGNMQSBM-UINYOVNOSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Chlorella pyrenoidosa	Plant	KNApSAcK
Fusarium oxysporum	Fungi	KNApSAcK
Mus musculus	LOTUS Database	35616633
Trypanosoma brucei	LOTUS Database	35616633

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Lineolic acids and derivatives

Direct Parent

Lineolic 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 Framework

Aliphatic acyclic compounds

External Descriptors

HPODE (CHEBI:34498 )
Other Octadecanoids (C14827 )
Other Octadecanoids (LMFA02000012 )

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	5.74	ALOGPS
logP	5.64	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	4.68	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	91.38 m³·mol⁻¹	ChemAxon
Polarizability	38.06 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

HMDB0062434

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB030133

KNApSAcK ID

C00000393

Chemspider ID

Not Available

KEGG Compound ID

C14827

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

34498

Good Scents ID

Not Available

References

General References

Showing NP-Card for 9-Hydroperoxyoctadecadienoic acid (NP0050308)

MOL for NP0050308 (9-Hydroperoxyoctadecadienoic acid)

3D MOL for NP0050308 (9-Hydroperoxyoctadecadienoic acid)

3D SDF for NP0050308 (9-Hydroperoxyoctadecadienoic acid)

3D-SDF for NP0050308 (9-Hydroperoxyoctadecadienoic acid)

PDB for NP0050308 (9-Hydroperoxyoctadecadienoic acid)

3D PDB for NP0050308 (9-Hydroperoxyoctadecadienoic acid)

SMILES for NP0050308 (9-Hydroperoxyoctadecadienoic acid)

INCHI for NP0050308 (9-Hydroperoxyoctadecadienoic acid)

Structure for NP0050308 (9-Hydroperoxyoctadecadienoic acid)

3D Structure for NP0050308 (9-Hydroperoxyoctadecadienoic acid)