NP-MRD: Showing NP-Card for (2'E,4'Z,8E)-Colneleic acid (NP0046089)

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Record Information

Version

2.0

Created at

2022-03-17 19:48:12 UTC

Updated at

2022-03-17 19:48:12 UTC

NP-MRD ID

NP0046089

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2'E,4'Z,8E)-Colneleic acid

Description

(2'E,4'Z,8E)-Colneleic acid, also known as 9-oxa-8t10t12c-18:3 Or colneleinsaeure, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms (2'E,4'Z,8E)-Colneleic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, (2'E,4'Z,8E)-Colneleic acid has been detected, but not quantified in, alcoholic beverages and potato. This could make (2'e,4'z,8E)-colneleic acid a potential biomarker for the consumption of these foods. (2'E,4'Z,8E)-Colneleic acid was first documented in 1974 (PMID: 4209994). A long-chain, divinyl ether fatty acid composed of 8-nonenoic acid having the E- hydrogen at position 9 substituted by a (1E,3Z)-nona-1,3,-dien-1-yloxy group (PMID: 10072406) (PMID: 11696374) (PMID: 15670154).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061305392D          

 21 20  0  0  0  0            999 V2000
   -1.2888    3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2888    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401    0.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401    0.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546   -0.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    0.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836   -0.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    0.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    0.0809    0.0000 O   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
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  6  1  0  0  0  0
 10  7  2  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  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  2  0  0  0  0
 17 14  2  0  0  0  0
 18 15  1  0  0  0  0
 19 18  2  0  0  0  0
 20 18  1  0  0  0  0
 21 16  1  0  0  0  0
 21 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046089

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC\C=C/C=C/O\C=C\CCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H30O3/c1-2-3-4-5-7-10-13-16-21-17-14-11-8-6-9-12-15-18(19)20/h7,10,13-14,16-17H,2-6,8-9,11-12,15H2,1H3,(H,19,20)/b10-7-,16-13+,17-14+

> <INCHI_KEY>
HHZKKFXQEIBVEV-CXXUKANQSA-N

> <FORMULA>
C18H30O3

> <MOLECULAR_WEIGHT>
294.429

> <EXACT_MASS>
294.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
35.4452035677402

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(8E)-9-[(1E,3Z)-nona-1,3-dien-1-yloxy]non-8-enoic acid

> <ALOGPS_LOGP>
6.43

> <JCHEM_LOGP>
5.559828782666667

> <ALOGPS_LOGS>
-5.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.766695739610842

> <JCHEM_PKA_STRONGEST_BASIC>
-5.148207564902848

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
89.73789999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.33e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
colneleic 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      -2.406   6.311   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.406   4.771   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.072   4.001   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.072   2.461   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.262   1.691   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.262   0.151   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.595  -0.619   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.929   0.151   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.930   2.461   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.598   4.771   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.263  -0.619   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.596   1.691   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      16.266   4.771   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      14.932   2.461   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.596   0.151   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    7                                                       
CONECT    6    8    9                                                       
CONECT    7    5   10                                                       
CONECT    8    6   11                                                       
CONECT    9    6   12                                                       
CONECT   10    7   13                                                       
CONECT   11    8   14                                                       
CONECT   12    9   15                                                       
CONECT   13   10   16                                                       
CONECT   14   11   17                                                       
CONECT   15   12   18                                                       
CONECT   16   13   21                                                       
CONECT   17   14   21                                                       
CONECT   18   15   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   16   17                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

View in JSmol

Synonyms

Value	Source
(8E,1'e,3'z)-9-(1',3'-Nonadienyloxy)-8-nonenoic acid	ChEBI
9-Oxa-8t10t12c-18:3	ChEBI
9-Oxa-8t10t12c-C18:3	ChEBI
Colneleinsaeure	ChEBI
(8E)-9-[(1E,3Z)-Nona-1,3-dien-1-yloxy]non-8-enoate	Kegg
(8E,1'e,3'z)-9-(1',3'-Nonadienyloxy)-8-nonenoate	Generator
(8E)-9-[(1E,3Z)-Nona-1,3-dien-1-yloxy]non-8-enoic acid	Generator
(2'e,4'z,8E)-Colneleate	Generator
9-(1,3-Nonadienyloxy)-(e,e,Z)-8-nonenoic acid	HMDB
9-(Nona-1',3'-dienoxy)non-8-enoic acid	HMDB
Colneleic acid	HMDB
Colneleate	Generator

Chemical Formula

C₁₈H₃₀O₃

Average Mass

294.4290 Da

Monoisotopic Mass

294.21949 Da

IUPAC Name

(8E)-9-[(1E,3Z)-nona-1,3-dien-1-yloxy]non-8-enoic acid

Traditional Name

colneleic acid

CAS Registry Number

52761-34-9

SMILES

CCCCC\C=C/C=C/O\C=C\CCCCCCC(O)=O

InChI Identifier

InChI=1S/C18H30O3/c1-2-3-4-5-7-10-13-16-21-17-14-11-8-6-9-12-15-18(19)20/h7,10,13-14,16-17H,2-6,8-9,11-12,15H2,1H3,(H,19,20)/b10-7-,16-13+,17-14+

InChI Key

HHZKKFXQEIBVEV-CXXUKANQSA-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
Solanum tuberosum	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-chain fatty acids

Alternative Parents

Substituents

Medium-chain fatty acid
Unsaturated fatty acid
Straight chain fatty acid
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

long-chain fatty acid (CHEBI:60956 )
straight-chain fatty acid (CHEBI:60956 )
divinyl ether fatty acid (CHEBI:60956 )
Fatty ethers (LMFA10000001 )

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	6.43	ALOGPS
logP	5.56	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	4.77	ChemAxon
pKa (Strongest Basic)	-5.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	89.74 m³·mol⁻¹	ChemAxon
Polarizability	35.45 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

HMDB0030995

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002983

KNApSAcK ID

C00000449

Chemspider ID

Not Available

KEGG Compound ID

C19827

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6441681

PDB ID

Not Available

ChEBI ID

60956

Good Scents ID

Not Available

References

General References

Weber H, Chetelat A, Caldelari D, Farmer EE: Divinyl ether fatty acid synthesis in late blight-diseased potato leaves. Plant Cell. 1999 Mar;11(3):485-94. doi: 10.1105/tpc.11.3.485. [PubMed:10072406 ]
Stumpe M, Kandzia R, Gobel C, Rosahl S, Feussner I: A pathogen-inducible divinyl ether synthase (CYP74D) from elicitor-treated potato suspension cells. FEBS Lett. 2001 Nov 2;507(3):371-6. doi: 10.1016/s0014-5793(01)03019-8. [PubMed:11696374 ]
Hamberg M: Hidden stereospecificity in the biosynthesis of divinyl ether fatty acids. FEBS J. 2005 Feb;272(3):736-43. doi: 10.1111/j.1742-4658.2004.04510.x. [PubMed:15670154 ]
Galliard T, Wardale DA, Mathew JA: The enzymic and non-enzymic degradation of colneleic acid, an unsaturated fatty acid ether intermediate in the lipoxygenase pathway of linoleic acid oxidation in potato (Solanum tuberosum) tubers. Biochem J. 1974 Jan;138(1):23-31. doi: 10.1042/bj1380023. [PubMed:4209994 ]

Showing NP-Card for (2'E,4'Z,8E)-Colneleic acid (NP0046089)

MOL for NP0046089 ((2'E,4'Z,8E)-Colneleic acid)

3D MOL for NP0046089 ((2'E,4'Z,8E)-Colneleic acid)

3D SDF for NP0046089 ((2'E,4'Z,8E)-Colneleic acid)

3D-SDF for NP0046089 ((2'E,4'Z,8E)-Colneleic acid)

PDB for NP0046089 ((2'E,4'Z,8E)-Colneleic acid)

3D PDB for NP0046089 ((2'E,4'Z,8E)-Colneleic acid)

SMILES for NP0046089 ((2'E,4'Z,8E)-Colneleic acid)

INCHI for NP0046089 ((2'E,4'Z,8E)-Colneleic acid)

Structure for NP0046089 ((2'E,4'Z,8E)-Colneleic acid)

3D Structure for NP0046089 ((2'E,4'Z,8E)-Colneleic acid)