NP-MRD: Showing NP-Card for Avenoleic acid (NP0045502)

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Record Information

Version

2.0

Created at

2022-03-17 19:21:03 UTC

Updated at

2022-03-17 19:21:03 UTC

NP-MRD ID

NP0045502

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Avenoleic acid

Description

Avenoleic acid, also known as avenoleate, 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. Avenoleic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Avenoleic acid has been detected, but not quantified in, cereals and cereal products and oats. Avenoleic acid is found in Avena sativa and Secale cereale. This could make avenoleic acid a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061304572D          

 21 20  0  0  0  0            999 V2000
    1.0121   -2.4037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7420   -1.6242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2526    1.3381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9825    2.1177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1724    2.2736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9825   -0.0651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6323    1.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7927   -0.2210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8222    1.8058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3328    0.4027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2821    1.1822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1429    0.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2821   -1.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5521    0.4027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6830    0.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0121   -0.2210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4931    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2019   -0.0651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0332    1.3381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7632   -0.0651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12 10  2  0  0  0  0
 13 11  1  0  0  0  0
 14  2  1  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 17  1  0  0  0  0
 20 18  2  0  0  0  0
 21 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045502

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC(O)C\C=C/C\C=C/CCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H32O3/c1-2-14-17(19)15-12-10-8-6-4-3-5-7-9-11-13-16-18(20)21/h4,6,10,12,17,19H,2-3,5,7-9,11,13-16H2,1H3,(H,20,21)/b6-4-,12-10-

> <INCHI_KEY>
MZQXAWAWDWCIKG-OHPMOLHNSA-N

> <FORMULA>
C18H32O3

> <MOLECULAR_WEIGHT>
296.4449

> <EXACT_MASS>
296.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
35.976936532645155

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9Z,12Z)-15-hydroxyoctadeca-9,12-dienoic acid

> <ALOGPS_LOGP>
5.77

> <JCHEM_LOGP>
5.035158267333332

> <ALOGPS_LOGS>
-4.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.444729922541228

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.9881675116975455

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2920753596742043

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
90.18829999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.20e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9Z,12Z)-15-hydroxyoctadeca-9,12-dienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       1.889  -4.487   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.385  -3.032   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.938   2.498   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.434   3.953   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.930   1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.922   4.244   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.434  -0.122   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.914   3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.946  -0.413   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.401   3.371   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.955   0.752   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.393   2.207   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.467   0.461   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.393  -1.868   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.897   0.752   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.475   1.625   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.889  -0.413   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.987   1.334   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.377  -0.122   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      14.995   2.498   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      14.491  -0.122   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1   14                                                       
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   12                                                       
CONECT   11    9   13                                                       
CONECT   12   10   15                                                       
CONECT   13   11   16                                                       
CONECT   14    2   17                                                       
CONECT   15   12   17                                                       
CONECT   16   13   18                                                       
CONECT   17   14   15   19                                                  
CONECT   18   16   20   21                                                  
CONECT   19   17                                                            
CONECT   20   18                                                            
CONECT   21   18                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

View in JSmol

Synonyms

Value	Source
Avenoleate	Generator
15-Hydroxylinoleic acid	HMDB
15R-Hydroxylinoleic acid	HMDB
15-Hydroxy-9Z,12Z-octadecadienoate	Generator

Chemical Formula

C₁₈H₃₂O₃

Average Mass

296.4449 Da

Monoisotopic Mass

296.23514 Da

IUPAC Name

(9Z,12Z)-15-hydroxyoctadeca-9,12-dienoic acid

Traditional Name

(9Z,12Z)-15-hydroxyoctadeca-9,12-dienoic acid

CAS Registry Number

177931-23-6

SMILES

CCCC(O)C\C=C/C\C=C/CCCCCCCC(O)=O

InChI Identifier

InChI=1S/C18H32O3/c1-2-14-17(19)15-12-10-8-6-4-3-5-7-9-11-13-16-18(20)21/h4,6,10,12,17,19H,2-3,5,7-9,11,13-16H2,1H3,(H,20,21)/b6-4-,12-10-

InChI Key

MZQXAWAWDWCIKG-OHPMOLHNSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Avena sativa	LOTUS Database	35616633
Avena sativa L.	FooDB	KNAPSACK
Secale cereale	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
Hydroxy fatty acid
Fatty acid
Unsaturated fatty acid
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
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	5.77	ALOGPS
logP	5.04	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	4.99	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	90.19 m³·mol⁻¹	ChemAxon
Polarizability	35.98 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0029978

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB001265

KNApSAcK ID

C00000445

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

75536015

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Avenoleic acid (NP0045502)

MOL for NP0045502 (Avenoleic acid)

3D MOL for NP0045502 (Avenoleic acid)

3D SDF for NP0045502 (Avenoleic acid)

3D-SDF for NP0045502 (Avenoleic acid)

PDB for NP0045502 (Avenoleic acid)

3D PDB for NP0045502 (Avenoleic acid)

SMILES for NP0045502 (Avenoleic acid)

INCHI for NP0045502 (Avenoleic acid)

Structure for NP0045502 (Avenoleic acid)

3D Structure for NP0045502 (Avenoleic acid)