NP-MRD: Showing NP-Card for 5-Tetradecenoic acid (NP0086598)

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Record Information

Version

2.0

Created at

2022-05-11 16:25:35 UTC

Updated at

2022-05-11 16:25:35 UTC

NP-MRD ID

NP0086598

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-Tetradecenoic acid

Description

5-Tetradecenoic acid, also known as 5-tetradecenoate or physeterate, 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. 5-Tetradecenoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 5Z-Tetradecenoic acid is an intermediate of unsaturated fatty acid oxidation that is incorporated in triglycerides but not in phospholipids in tissues from patients with mitochondrial beta-oxidation defects, particularly in very long-chain acyl-CoA dehydrogenase deficiency (VLCADD1/ VLCADD2). 5-Tetradecenoic acid is found in Campylobacter jejuni. 5-Tetradecenoic acid was first documented in 1995 (PMID: 7586519). 5-Tetradecenoic acid, with regard to humans, has been linked to the inborn metabolic disorder very long chain acyl-coa dehydrogenase deficiency (PMID: 11486898).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 41  0  0  0  0  0  0  0  0999 V2000
   -6.0526    1.6895   -0.3401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9281    0.1979   -0.4249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5044   -0.2124   -0.6686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5619    0.2442    0.4274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1784   -0.2566    0.0181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1363    0.1208    1.0168 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1974   -0.3953    0.5829 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6277    0.1561   -0.7394 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9415   -0.3495   -1.1746 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7028   -1.2070   -0.4854 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9996   -1.6419   -1.0265 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2064   -1.3292   -0.2083 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5278    0.0869    0.0477 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6165    0.9103    0.8084 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5776    0.5867    1.4045 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9306    2.2904    0.9036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8749    1.9960    0.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0888    1.9658   -0.6558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3134    2.1277   -1.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5301   -0.2309   -1.2555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2540   -0.3083    0.5200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4578   -1.3368   -0.6874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1323    0.1456   -1.6435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5976    1.3518    0.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8568   -0.1135    1.4144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9591    0.2976   -0.9383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1756   -1.3526   -0.1184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3903   -0.2791    2.0276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1172    1.2407    1.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1002   -1.5024    0.5069 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9418   -0.0947    1.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6292    1.2739   -0.6633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0872   -0.1158   -1.5694 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3356   -0.0094   -2.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3222   -1.5720    0.4637 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1674   -1.1371   -2.0282 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9617   -2.7278   -1.3127 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0808   -1.7558   -0.8071 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1323   -1.9131    0.7529 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7956    0.5821   -0.9380 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5206    0.0862    0.6080 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8816    2.4912    1.1607 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 16  1  0
 14 15  2  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 16 42  1  0
M  END

  Mrv1652303192021432D          

 16 15  0  0  0  0            999 V2000
 9997.9490 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.6639 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3795 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0931 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.8088 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.5224 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.2381 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.9537 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.6673 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.2342 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.5192 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.8044 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.0895 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.3747 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.6597 9998.0698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.3747 9999.3071    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  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
  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>
NP0086598

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H26O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h9-10H,2-8,11-13H2,1H3,(H,15,16)/b10-9+

> <INCHI_KEY>
AFGUVBVUFZMJMX-MDZDMXLPSA-N

> <FORMULA>
C14H26O2

> <MOLECULAR_WEIGHT>
226.355

> <EXACT_MASS>
226.193280076

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
29.144877503130864

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5E)-tetradec-5-enoic acid

> <ALOGPS_LOGP>
5.77

> <JCHEM_LOGP>
5.005523791

> <ALOGPS_LOGS>
-5.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.885676019177561

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
68.9982

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.79e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
physeteric acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-MAR-20         0                                  
HETATM    1  C   UNK     0    8662.8388663.064   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8664.1738663.832   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8665.5088663.064   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8666.8408663.832   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8668.1768663.064   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8669.5088663.832   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8670.8448663.064   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8672.1808663.832   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8673.5128663.064   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8661.5048663.832   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8660.1698663.064   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8658.8358663.832   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8657.5008663.064   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8656.1668663.832   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0    8654.8318663.064   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0    8656.1668665.373   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
5-Tetradecenoate	Generator
Physeterate	HMDB
Physeteric acid	HMDB
Physoterate	HMDB
Physoteric acid	HMDB
(5E)-5-Tetradecenoic acid	HMDB
(e)-5-Tetradecenoic acid	HMDB
C14:1W9	HMDB
FA(14:1(5E))	HMDB
FA(14:1n9)	HMDB
trans-5-Tetradecenoic acid	HMDB
5-Tetradecenoic acid	HMDB

Chemical Formula

C₁₄H₂₆O₂

Average Mass

226.3550 Da

Monoisotopic Mass

226.19328 Da

IUPAC Name

(5E)-tetradec-5-enoic acid

Traditional Name

physeteric acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C14H26O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h9-10H,2-8,11-13H2,1H3,(H,15,16)/b10-9+

InChI Key

AFGUVBVUFZMJMX-MDZDMXLPSA-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
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
Campylobacter jejuni	LOTUS Database	35616633
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
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 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

Unsaturated fatty acids (LMFA01030913 )

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	5.01	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	4.89	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	11	ChemAxon
Refractivity	69 m³·mol⁻¹	ChemAxon
Polarizability	29.14 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

HMDB0000499

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022089

KNApSAcK ID

Not Available

Chemspider ID

4445867

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5485

PubChem Compound

5282740

PDB ID

Not Available

ChEBI ID

89393

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 ]
Onkenhout W, Venizelos V, Scholte HR, De Klerk JB, Poorthuis BJ: Intermediates of unsaturated fatty acid oxidation are incorporated in triglycerides but not in phospholipids in tissues from patients with mitochondrial beta-oxidation defects. J Inherit Metab Dis. 2001 Jun;24(3):337-44. doi: 10.1023/a:1010592232317. [PubMed:11486898 ]

Showing NP-Card for 5-Tetradecenoic acid (NP0086598)

MOL for NP0086598 (5-Tetradecenoic acid)

3D MOL for NP0086598 (5-Tetradecenoic acid)

3D SDF for NP0086598 (5-Tetradecenoic acid)

3D-SDF for NP0086598 (5-Tetradecenoic acid)

PDB for NP0086598 (5-Tetradecenoic acid)

3D PDB for NP0086598 (5-Tetradecenoic acid)

SMILES for NP0086598 (5-Tetradecenoic acid)

INCHI for NP0086598 (5-Tetradecenoic acid)

Structure for NP0086598 (5-Tetradecenoic acid)

3D Structure for NP0086598 (5-Tetradecenoic acid)