NP-MRD: Showing NP-Card for (Z,Z)-5,8-Tetradecadienoic acid (NP0334652)

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Record Information

Version

2.0

Created at

2024-09-10 19:19:18 UTC

Updated at

2024-09-10 19:19:18 UTC

NP-MRD ID

NP0334652

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(Z,Z)-5,8-Tetradecadienoic acid

Description

Goshuyic acid, also known as goshuyate or fa(14:2(5Z,8Z)), belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. A straight-chain, diunsaturated, 14-carbon long-chain fatty acid with cis-double bonds at positions C-5 and C-8. Goshuyic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Goshuyic acid has been detected, but not quantified in, fats and oils. (Z,Z)-5,8-Tetradecadienoic acid was first documented in 1995 (PMID: 7586519). This could make goshuyic acid a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI

      
  Mrv1652305261800062D          

 16 15  0  0  0  0            999 V2000
10012.586610013.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.302310012.7142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.018110013.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.843710013.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10015.558510012.7142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10016.273310013.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10016.988110012.7142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10017.703110013.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10018.417910012.7142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.761710013.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.046110012.7142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.330610013.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.616910012.7142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.901410013.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.187710012.7142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10008.901410013.9515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 10  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  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
  7  8  1  0  0  0  0
  8  9  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
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0334652

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H24O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h6-7,9-10H,2-5,8,11-13H2,1H3,(H,15,16)/b7-6-,10-9-

> <INCHI_KEY>
HXHZGHRLVRFQDR-HZJYTTRNSA-N

> <FORMULA>
C14H24O2

> <MOLECULAR_WEIGHT>
224.3392

> <EXACT_MASS>
224.177630012

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
27.525730404385264

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z,8Z)-tetradeca-5,8-dienoic acid

> <ALOGPS_LOGP>
5.35

> <JCHEM_LOGP>
4.643602134333333

> <ALOGPS_LOGS>
-4.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.819771840522258

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
70.1148

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.20e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5Z,8Z)-tetradeca-5,8-dienoic acid

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 26-MAY-18   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-18         0                                  
HETATM    1  C   UNK     0    8690.1628691.168   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8691.4988690.400   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8692.8348691.168   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8694.3758691.168   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8695.7098690.400   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8697.0438691.168   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8698.3788690.400   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8699.7128691.168   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8701.0478690.400   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8688.6228691.168   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8687.2868690.400   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8685.9508691.168   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8684.6188690.400   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8683.2838691.168   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0    8681.9508690.400   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0    8683.2838692.709   0.000  0.00  0.00           O+0
CONECT    1    2   10                                                       
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                                                            
CONECT   10    1   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

View in JSmol

Synonyms

Value	Source
(Z,Z)-5,8-Tetradecadienoic acid	ChEBI
(Z,Z)-Tetradeca-5,8-dienoic acid	ChEBI
(cis,cis-delta(5),delta(8))-Tetradecanoate	Generator
(cis,cis-Δ(5),δ(8))-tetradecanoate	Generator
(cis,cis-Δ(5),δ(8))-tetradecanoic acid	Generator
(cis-delta(5),cis-delta(8))-Tetradecanoate	Generator
(cis-Δ(5),cis-δ(8))-tetradecanoate	Generator
(cis-Δ(5),cis-δ(8))-tetradecanoic acid	Generator
(Z,Z)-5,8-Tetradecadienoate	Generator
(Z,Z)-Tetradeca-5,8-dienoate	Generator
Goshuyate	Generator
5,8-Tetradecadienoate	HMDB
(cis,cis-Δ5,δ8)-tetradecanoic acid	HMDB
(cis-Δ5,cis-δ8)-tetradecanoic acid	HMDB
(cis,cis-delta5,delta8)-Tetradecanoic acid	HMDB
(cis-delta5,cis-delta8)-Tetradecanoic acid	HMDB
(5Z,8Z)-5,8-Tetradecadienoic acid	HMDB
cis,cis-Tetradeca-5,8-dienoic acid	HMDB
5,8-Tetradecadienoic acid	HMDB
FA(14:2(5Z,8Z))	HMDB

Chemical Formula

C₁₄H₂₄O₂

Average Mass

224.3392 Da

Monoisotopic Mass

224.17763 Da

IUPAC Name

(5Z,8Z)-tetradeca-5,8-dienoic acid

Traditional Name

(5Z,8Z)-tetradeca-5,8-dienoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C14H24O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h6-7,9-10H,2-5,8,11-13H2,1H3,(H,15,16)/b7-6-,10-9-

InChI Key

HXHZGHRLVRFQDR-HZJYTTRNSA-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 long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-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:70719 )
polyunsaturated fatty acid (CHEBI:70719 )
Unsaturated fatty acids (LMFA01030257 )

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	5.35	ALOGPS
logP	4.64	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	4.82	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	70.11 m³·mol⁻¹	ChemAxon
Polarizability	27.53 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000560

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB018642

KNApSAcK ID

Not Available

Chemspider ID

4471834

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5544

PubChem Compound

5312409

PDB ID

Not Available

ChEBI ID

70719

Good Scents ID

Not Available

References

General References

Onkenhout W, Venizelos V, van der Poel PF, van den Heuvel MP, Poorthuis BJ: Identification and quantification of intermediates of unsaturated fatty acid metabolism in plasma of patients with fatty acid oxidation disorders. Clin Chem. 1995 Oct;41(10):1467-74. [PubMed:7586519 ]

Showing NP-Card for (Z,Z)-5,8-Tetradecadienoic acid (NP0334652)

MOL for NP0334652 ((Z,Z)-5,8-Tetradecadienoic acid)

3D MOL for NP0334652 ((Z,Z)-5,8-Tetradecadienoic acid)

3D SDF for NP0334652 ((Z,Z)-5,8-Tetradecadienoic acid)

3D-SDF for NP0334652 ((Z,Z)-5,8-Tetradecadienoic acid)

PDB for NP0334652 ((Z,Z)-5,8-Tetradecadienoic acid)

3D PDB for NP0334652 ((Z,Z)-5,8-Tetradecadienoic acid)

SMILES for NP0334652 ((Z,Z)-5,8-Tetradecadienoic acid)

INCHI for NP0334652 ((Z,Z)-5,8-Tetradecadienoic acid)

Structure for NP0334652 ((Z,Z)-5,8-Tetradecadienoic acid)

3D Structure for NP0334652 ((Z,Z)-5,8-Tetradecadienoic acid)