NP-MRD: Showing NP-Card for (Z)-13-Oxo-9-octadecenoic acid (NP0337174)

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Record Information

Version

2.0

Created at

2024-09-11 09:38:54 UTC

Updated at

2024-09-11 09:38:54 UTC

NP-MRD ID

NP0337174

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(Z)-13-Oxo-9-octadecenoic acid

Description

(Z)-13-Oxo-9-octadecenoic acid 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 (Z)-13-Oxo-9-octadecenoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, (Z)-13-Oxo-9-octadecenoic acid has been detected, but not quantified in, cereals and cereal products. This could make (Z)-13-oxo-9-octadecenoic acid a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241216332D          

 21 20  0  0  0  0            999 V2000
   -6.4357   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7212   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0049   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2904   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5759   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8597   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1451   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4306   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4307   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1452   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8597   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5759   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2904   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0049   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7213   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4357   -0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8597    0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7213    0.6188    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  1  0  0  0  0
  6 20  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
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  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
 18 21  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0337174

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC(=O)CC\C=C\CCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H32O3/c1-2-3-11-14-17(19)15-12-9-7-5-4-6-8-10-13-16-18(20)21/h7,9H,2-6,8,10-16H2,1H3,(H,20,21)/b9-7+

> <INCHI_KEY>
LDYZTLZOFONHNA-VQHVLOKHSA-N

> <FORMULA>
C18H32O3

> <MOLECULAR_WEIGHT>
296.4449

> <EXACT_MASS>
296.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
37.42911143339464

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9E)-13-oxooctadec-9-enoic acid

> <ALOGPS_LOGP>
5.87

> <JCHEM_LOGP>
5.604580725666667

> <ALOGPS_LOGS>
-5.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.988167283904006

> <JCHEM_PKA_STRONGEST_BASIC>
-7.352649748556592

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
88.04359999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.64e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9E)-13-oxooctadec-9-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0     -12.013  -1.155   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -10.680  -0.385   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.342  -1.155   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.009  -0.385   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.675  -1.155   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.338  -0.385   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.004  -1.155   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.670  -0.385   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -1.155   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -0.385   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -1.155   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.671  -0.385   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.004  -1.155   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.338  -0.385   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.675  -1.155   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.009  -0.385   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.342  -1.155   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.680  -0.385   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      12.013  -1.155   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -5.338   1.155   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      10.680   1.155   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   20                                                  
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                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18                                                            
CONECT   20    6                                                            
CONECT   21   18                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

View in JSmol

Synonyms

Value	Source
(Z)-13-oxo-9-Octadecenoate	Generator
Diethyl 2,4-diacetyl-2-(hydroxymethyl)pentanedioate	HMDB
13-Keto-trans-9-octadecenoate	Generator

Chemical Formula

C₁₈H₃₂O₃

Average Mass

296.4449 Da

Monoisotopic Mass

296.23514 Da

IUPAC Name

(9E)-13-oxooctadec-9-enoic acid

Traditional Name

(9E)-13-oxooctadec-9-enoic acid

CAS Registry Number

Not Available

SMILES

CCCCCC(=O)CC\C=C\CCCCCCCC(O)=O

InChI Identifier

InChI=1S/C18H32O3/c1-2-3-11-14-17(19)15-12-9-7-5-4-6-8-10-13-16-18(20)21/h7,9H,2-6,8,10-16H2,1H3,(H,20,21)/b9-7+

InChI Key

LDYZTLZOFONHNA-VQHVLOKHSA-N

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 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
Fatty acid
Unsaturated fatty acid
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	5.87	ALOGPS
logP	5.6	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	4.99	ChemAxon
pKa (Strongest Basic)	-7.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	88.04 m³·mol⁻¹	ChemAxon
Polarizability	37.43 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

HMDB0029796

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB001004

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

44612156

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (Z)-13-Oxo-9-octadecenoic acid (NP0337174)

MOL for NP0337174 ((Z)-13-Oxo-9-octadecenoic acid)

3D MOL for NP0337174 ((Z)-13-Oxo-9-octadecenoic acid)

3D SDF for NP0337174 ((Z)-13-Oxo-9-octadecenoic acid)

3D-SDF for NP0337174 ((Z)-13-Oxo-9-octadecenoic acid)

PDB for NP0337174 ((Z)-13-Oxo-9-octadecenoic acid)

3D PDB for NP0337174 ((Z)-13-Oxo-9-octadecenoic acid)

SMILES for NP0337174 ((Z)-13-Oxo-9-octadecenoic acid)

INCHI for NP0337174 ((Z)-13-Oxo-9-octadecenoic acid)

Structure for NP0337174 ((Z)-13-Oxo-9-octadecenoic acid)

3D Structure for NP0337174 ((Z)-13-Oxo-9-octadecenoic acid)