NP-MRD: Showing NP-Card for 13-Hydroperoxyoctadecadienoic acid (NP0050309)

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Record Information

Version

2.0

Created at

2022-04-27 20:52:18 UTC

Updated at

2022-04-27 20:52:18 UTC

NP-MRD ID

NP0050309

Secondary Accession Numbers

None

Natural Product Identification

Common Name

13-Hydroperoxyoctadecadienoic acid

Description

13-L-Hydroperoxylinoleic acid, also known as 13(S)-hpode or linoleic acid 13(S)-hydroperoxide, 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. 13-L-Hydroperoxylinoleic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 13-L-Hydroperoxylinoleic acid has been detected, but not quantified in, several different foods, such as chinese mustards, chives, peachs, dills, and mountain yams. 13-Hydroperoxyoctadecadienoic acid is found in Chlorella pyrenoidosa and Fusarium oxysporum. This could make 13-L-hydroperoxylinoleic acid a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305251817432D          

 22 21  0  0  0  0            999 V2000
 9990.2888 9987.3755    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9989.5754 9987.7878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9988.8600 9987.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9988.1446 9987.7878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9987.3202 9987.7878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9986.6056 9987.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9985.8908 9987.7878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9985.1762 9987.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9984.4616 9987.7878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9983.7470 9987.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9983.0322 9987.7878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9982.3176 9987.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9981.6030 9987.7878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9980.8864 9987.3755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9981.6030 9988.6126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.0042 9987.7878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.7196 9987.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.4330 9987.7878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.1484 9987.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.8637 9987.7878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.2888 9986.5512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.0042 9986.1376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 16  1  0  0  0  0
  1 21  1  6  0  0  0
  2  3  2  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  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  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
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050309

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC[C@H](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-IRQZEAMPSA-N

> <FORMULA>
C18H32O4

> <MOLECULAR_WEIGHT>
312.4443

> <EXACT_MASS>
312.230059512

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
37.13716024232122

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
5.76

> <JCHEM_LOGP>
5.640401104666667

> <ALOGPS_LOGS>
-4.98

> <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>
-4.2368076090774425

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
91.38449999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.28e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13-HpODE

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-MAY-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-MAY-18         0                                  
HETATM    1  C   UNK     0    8648.5398643.101   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8647.2078643.871   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8645.8728643.101   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8644.5378643.871   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8642.9988643.871   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8641.6648643.101   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8640.3308643.871   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8638.9968643.101   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8637.6628643.871   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8636.3288643.101   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8634.9938643.871   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8633.6608643.101   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8632.3268643.871   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0    8630.9888643.101   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0    8632.3268645.410   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0    8649.8748643.871   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8651.2108643.101   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8652.5428643.871   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8653.8778643.101   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8655.2128643.871   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0    8648.5398641.562   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0    8649.8748640.790   0.000  0.00  0.00           O+0
CONECT    1    2   16   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                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    1   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21    1   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   42    0
END

View in JSmol

Synonyms

Value	Source
(9Z,11E)-(13S)-13-Hydroperoxyoctadeca-9,11-dienoate	ChEBI
(9Z,11E)-(13S)-13-Hydroperoxyoctadeca-9,11-dienoic acid	ChEBI
13S-Hydroperoxy-9Z,11E-octadecadienoic acid	ChEBI
13(S)-HPODE	Kegg
13S-Hydroperoxy-9Z,11E-octadecadienoate	Generator
13-L-Hydroperoxylinoleate	Generator
(9Z,11E,13S)-13-Hydroperoxyoctadeca-9,11-dienoic acid	HMDB
(9Z,11E,13S)-13-Hydroperoxyoctadeca-9,11-dienoate	HMDB
(13S,9Z,11E)-13-Hydroperoxy-9,11-octadecadienoate	HMDB
(13S,9Z,11E)-13-Hydroperoxy-9,11-octadecadienoic acid	HMDB
13(S)-Hydroperoxy-9Z,11E-octadecadienoate	HMDB
13(S)-Hydroperoxy-9Z,11E-octadecadienoic acid	HMDB
13(S)-Hydroperoxylinoleic acid	HMDB
13-HPOD	HMDB
13-Hpode	HMDB
13-L-Hydroperoxy-9-cis,11-trans-octadecadienoate	HMDB
13-L-Hydroperoxy-9-cis,11-trans-octadecadienoic acid	HMDB
13-L-Hydroperoxy-cis-9,trans-11-octadecadienoate	HMDB
13-L-Hydroperoxy-cis-9,trans-11-octadecadienoic acid	HMDB
Hpode	HMDB
Linoleic acid 13(S)-hydroperoxide	HMDB
13-Hydroperoxy-9,11-octadecadienoic acid	HMDB
13-Hydroperoxy-9,11-octadecadienoic acid, (Z,e)-isomer	HMDB

Chemical Formula

C₁₈H₃₂O₄

Average Mass

312.4443 Da

Monoisotopic Mass

312.23006 Da

IUPAC Name

(9Z,11E,13S)-13-hydroperoxyoctadeca-9,11-dienoic acid

Traditional Name

13-HpODE

CAS Registry Number

Not Available

SMILES

CCCCC[C@H](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-IRQZEAMPSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Chlorella pyrenoidosa	Plant	KNApSAcK
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Fusarium oxysporum	Fungi	KNApSAcK
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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:15655 )
Hydroperoxy fatty acids (C04717 )
Other Octadecanoids (LMFA02000034 )

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	5.76	ALOGPS
logP	5.64	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	4.99	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	37.14 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