NP-MRD: Showing NP-Card for Hexadecenic acid (NP0046524)

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Record Information

Version

2.0

Created at

2022-03-17 20:04:40 UTC

Updated at

2022-03-17 20:04:40 UTC

NP-MRD ID

NP0046524

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Hexadecenic acid

Description

Trans-Hexa-dec-2-enoic acid 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. Trans-Hexa-dec-2-enoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Trans-Hexa-dec-2-enoic acid exists in all eukaryotes, ranging from yeast to humans. Within humans, trans-hexa-dec-2-enoic acid participates in a number of enzymatic reactions. In particular, trans-hexa-dec-2-enoic acid can be biosynthesized from (R)-3-hydroxy-hexadecanoic acid; which is catalyzed by the enzyme fatty acid synthase. Dyhydrase domain. In addition, trans-hexa-dec-2-enoic acid can be converted into palmitic acid through the action of the enzyme fatty acid synthase. Enoyl reductase domain. Hexadecenic acid is found in Althaea officinalis, Arbacia punctulata, Asclepias syriaca, Cystoclonium purpureum, Erylus formosus, Euphausia superba, Fagopyrum esculentum, Ganoderma applanatum, Hibiscus syriacus, Hoya multiflora, Hoya pottsii and Lumbricus terrestris. In humans, trans-hexa-dec-2-enoic acid is involved in fatty acid biosynthesis.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652307301920022D          

 20 19  0  0  0  0            999 V2000
    4.7586    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4730    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9020    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6164    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3309    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0454    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7599    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4743    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1888    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9033    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6177    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3322    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0467    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7612    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4756    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4756    4.8099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1901    3.5724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0467    4.8099    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.7612    2.7474    0.0000 H   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
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  2  0  0  0  0
 16 15  1  0  0  0  0
 17 16  2  0  0  0  0
 18 16  1  0  0  0  0
 19 14  1  0  0  0  0
 20 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046524

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(CCCCCCCCCCCCC)=C(\[H])C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h14-15H,2-13H2,1H3,(H,17,18)/b15-14+

> <INCHI_KEY>
ZVRMGCSSSYZGSM-CCEZHUSRSA-N

> <FORMULA>
C16H30O2

> <MOLECULAR_WEIGHT>
254.4082

> <EXACT_MASS>
254.224580204

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
33.74415362299203

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-hexadec-2-enoic acid

> <JCHEM_LOGP>
6.254406267333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.0255044264493

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
78.17689999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
hexadecenoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 30-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUL-19         0                                  
HETATM    1  C   UNK     0       8.883   6.668   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.216   7.438   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.550   6.668   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.884   7.438   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.217   6.668   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.551   7.438   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      16.885   6.668   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.218   7.438   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      19.552   6.668   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.886   7.438   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      22.219   6.668   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.553   7.438   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      24.887   6.668   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      26.221   7.438   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      27.554   6.668   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      28.888   7.438   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      28.888   8.978   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      30.222   6.668   0.000  0.00  0.00           O+0
HETATM   19  H   UNK     0      26.221   8.978   0.000  0.00  0.00           H+0
HETATM   20  H   UNK     0      27.554   5.128   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
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   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   14                                                            
CONECT   20   15                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   38    0
END

View in JSmol

Synonyms

Value	Source
trans-Hexa-dec-2-enoate	Generator
(2E)-Hexadecenoic acid	ChEBI
(e)-2-Hexadecenoic acid	ChEBI
2-Palmitoleic acid	ChEBI
2-trans-Hexadecenoic acid	ChEBI
Gaidic acid	ChEBI
t-16:1D2	ChEBI
t-2-Hexadecenoic acid	ChEBI
trans-2-Hexadecenoic acid	ChEBI
trans-Delta(2)-Hexadecenoic acid	ChEBI
trans-Hexadec-2-enoic acid	ChEBI
(2E)-Hexadecenoate	Generator
(e)-2-Hexadecenoate	Generator
2-Palmitoleate	Generator
2-trans-Hexadecenoate	Generator
Gaidate	Generator
t-2-Hexadecenoate	Generator
trans-2-Hexadecenoate	Generator
trans-delta(2)-Hexadecenoate	Generator
trans-δ(2)-hexadecenoate	Generator
trans-δ(2)-hexadecenoic acid	Generator
trans-Hexadec-2-enoate	Generator
Hexadecenoic acid, (e)-isomer	MeSH, HMDB
cis-Hexadecenoic acid	MeSH, HMDB
Hexadecenoic acid	MeSH, HMDB
Hexadecenoic acid, (Z)-isomer	MeSH, HMDB
trans-Hexadecenoic acid	MeSH, HMDB

Chemical Formula

C₁₆H₃₀O₂

Average Mass

254.4082 Da

Monoisotopic Mass

254.22458 Da

IUPAC Name

(2E)-hexadec-2-enoic acid

Traditional Name

hexadecenoic acid

CAS Registry Number

Not Available

SMILES

[H]\C(CCCCCCCCCCCCC)=C(\[H])C(O)=O

InChI Identifier

InChI=1S/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h14-15H,2-13H2,1H3,(H,17,18)/b15-14+

InChI Key

ZVRMGCSSSYZGSM-CCEZHUSRSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Althaea officinalis	LOTUS Database	35616633
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Arbacia punctulata	LOTUS Database	35616633
Asclepias syriaca	LOTUS Database	35616633
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Carum carvi	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Cystoclonium purpureum	LOTUS Database	35616633
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Erylus formosus	LOTUS Database	35616633
Euphausia superba	LOTUS Database	35616633
Fagopyrum esculentum	LOTUS Database	35616633
Gallus gallus	FooDB	FooDB
Ganoderma applanatum	LOTUS Database	35616633
Hibiscus syriacus	LOTUS Database	35616633
Hoya multiflora	LOTUS Database	35616633
Hoya pottsii	LOTUS Database	35616633
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Lumbricus terrestris	LOTUS Database	35616633
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

alpha,beta-unsaturated monocarboxylic acid (CHEBI:37252 )
hexadecenoic acid (CHEBI:37252 )
Unsaturated fatty acids (LMFA01030054 )

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	6.25	ChemAxon
pKa (Strongest Acidic)	5.03	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	13	ChemAxon
Refractivity	78.18 m³·mol⁻¹	ChemAxon
Polarizability	33.74 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

HMDB0010735

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB004789

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

5282743

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Hexadecenic acid (NP0046524)

MOL for NP0046524 (Hexadecenic acid)

3D MOL for NP0046524 (Hexadecenic acid)

3D SDF for NP0046524 (Hexadecenic acid)

3D-SDF for NP0046524 (Hexadecenic acid)

PDB for NP0046524 (Hexadecenic acid)

3D PDB for NP0046524 (Hexadecenic acid)

SMILES for NP0046524 (Hexadecenic acid)

INCHI for NP0046524 (Hexadecenic acid)

Structure for NP0046524 (Hexadecenic acid)

3D Structure for NP0046524 (Hexadecenic acid)