NP-MRD: Showing NP-Card for (3e)-hexadec-3-enoic acid (NP0150615)

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Record Information

Version

2.0

Created at

2022-09-02 06:46:59 UTC

Updated at

2022-09-02 06:46:59 UTC

NP-MRD ID

NP0150615

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3e)-hexadec-3-enoic acid

Description

(3E)-3-hexadecenoic acid, also known as 3-e-hexadecenoate or (3E)-3-hexadecensaeure, 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. (3e)-hexadec-3-enoic acid is found in Glycine max. (3e)-hexadec-3-enoic acid was first documented in 1964 (PMID: 14250500). Based on a literature review a small amount of articles have been published on (3E)-3-hexadecenoic acid (PMID: 1126340) (PMID: 16666505) (PMID: 5498662) (PMID: 6079772).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 48 47  0  0  0  0  0  0  0  0999 V2000
   -6.1681    0.0446   -0.5684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7314   -0.8924    0.4866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3382   -0.8587    0.9662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8184    0.3727    1.5860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6725    1.5434    0.7152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8192    1.5218   -0.4717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3610    1.2850   -0.2983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0209   -0.0527    0.2051 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5044   -0.1850    0.3323 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1326   -0.0230   -1.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6347   -0.1799   -0.8603 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0606   -1.5166   -0.3297 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5684   -1.5667   -0.2324 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3392   -0.5508   -0.5790 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8368   -0.6168   -0.4763 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2954    0.4376    0.4345 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4619    1.2043    0.9744 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6568    0.5553    0.6734 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9747   -0.5195   -1.1745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3743    0.3198   -1.2730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7417    0.9287   -0.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4585   -0.8163    1.3657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9004   -1.9384    0.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6865   -1.1683    0.0809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2247   -1.7194    1.6966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0428    0.2340    2.3846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6959    0.7310    2.3343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4078    2.4704    1.3705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7238    1.8620    0.4009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1551    0.7235   -1.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8862    2.5232   -1.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8084    1.5233   -1.2500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9622    2.0287    0.4769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3303   -0.8656   -0.5259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3823   -0.2868    1.2141 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7498   -1.1625    0.7943 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8276    0.6689    0.9639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9743    0.9490   -1.4961 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8062   -0.8230   -1.7346 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0827   -0.0903   -1.8848 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9680    0.6571   -0.2005 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7804   -2.2878   -1.0770 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6089   -1.8134    0.6251 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0446   -2.4686    0.1354 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8377    0.3390   -0.9438 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1754   -1.6240   -0.2221 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2546   -0.3641   -1.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0843    1.4677    0.5507 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  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 18  1  0
 16 17  2  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 12 43  1  0
 13 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 18 48  1  0
M  END


  Mrv1652309022208472D          

 18 17  0  0  0  0            999 V2000
    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
   16.1901    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9046    3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1901    2.7474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  9 10  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  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0150615

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCC\C=C\CC(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/h13-14H,2-12,15H2,1H3,(H,17,18)/b14-13+

> <INCHI_KEY>
PCBKWKNYISJGPJ-BUHFOSPRSA-N

> <FORMULA>
C16H30O2

> <MOLECULAR_WEIGHT>
254.414

> <EXACT_MASS>
254.224580206

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
33.73555317134827

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3E)-hexadec-3-enoic acid

> <ALOGPS_LOGP>
6.99

> <JCHEM_LOGP>
5.894661121

> <ALOGPS_LOGS>
-5.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.827479020877875

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
78.20019999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.20e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3E)-hexadec-3-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      10.216   7.438   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.550   6.668   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.884   7.438   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.217   6.668   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.551   7.438   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.885   6.668   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.218   7.438   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.552   6.668   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      20.886   7.438   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.219   6.668   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.553   7.438   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      24.887   6.668   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      26.220   7.438   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      27.554   6.668   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      28.888   7.438   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      30.222   6.668   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      31.555   7.438   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      30.222   5.128   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    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                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

View in JSmol

Synonyms

Value	Source
(3E)-3-Hexadecensaeure	ChEBI
3-e-Hexadecenoic acid	ChEBI
3E-Hexadecenoic acid	ChEBI
Acide (3E)-3-hexadecenoique	ChEBI
Delta(3)-Hexadecenoic acid	ChEBI
Delta(3)-trans-Hexadecenoic acid	ChEBI
trans-3-Hexadecenoic acid	ChEBI
trans-Delta(3)-Hexadecenoic acid	ChEBI
3-e-Hexadecenoate	Generator
3E-Hexadecenoate	Generator
delta(3)-Hexadecenoate	Generator
Δ(3)-hexadecenoate	Generator
Δ(3)-hexadecenoic acid	Generator
delta(3)-trans-Hexadecenoate	Generator
Δ(3)-trans-hexadecenoate	Generator
Δ(3)-trans-hexadecenoic acid	Generator
trans-3-Hexadecenoate	Generator
trans-delta(3)-Hexadecenoate	Generator
trans-Δ(3)-hexadecenoate	Generator
trans-Δ(3)-hexadecenoic acid	Generator
(3E)-3-Hexadecenoate	Generator
delta(3)-Hexadecenoic acid, (e)-isomer	MeSH
delta(3)-Hexadecenoic acid, (Z)-isomer	MeSH

Chemical Formula

C₁₆H₃₀O₂

Average Mass

254.4140 Da

Monoisotopic Mass

254.22458 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCC\C=C\CC(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/h13-14H,2-12,15H2,1H3,(H,17,18)/b14-13+

InChI Key

PCBKWKNYISJGPJ-BUHFOSPRSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Glycine max	LOTUS Database	35616633

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 (LMFA01030266 )

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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4471843

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5312418

PDB ID

Not Available

ChEBI ID

142241

Good Scents ID

rw1440211

References

General References

Harwood JL, James AT: Metabolism of trans-3-hexadecenoic acid in broad bean. Eur J Biochem. 1975 Jan 2;50(2):325-34. doi: 10.1111/j.1432-1033.1975.tb09807.x. [PubMed:1126340 ]
WEENINK RO, SHORLAND FB: THE ISOLATION OF TRANS-3-HEXADECENOIC ACID FROM THE LIPIDS OF RED-CLOVER (TRIFOLIUM PRATENSE) LEAVES. Biochim Biophys Acta. 1964 Oct 2;84:613-4. doi: 10.1016/0926-6542(64)90133-7. [PubMed:14250500 ]
Huner NP, Williams JP, Maissan EE, Myscich EG, Krol M, Laroche A, Singh J: Low Temperature-Induced Decrease in trans-Delta-Hexadecenoic Acid Content Is Correlated with Freezing Tolerance in Cereals. Plant Physiol. 1989 Jan;89(1):144-50. doi: 10.1104/pp.89.1.144. [PubMed:16666505 ]
Kliachko-Gurvich GL, Semenenko VE, Vereshchagin AG: [Content of trans-3-hexadecenoic acid in Chlorella cells]. Biokhimiia. 1970 Jul-Aug;35(4):808-14. [PubMed:5498662 ]
Bartels CT, James AT, Nichols BW: Metabolism of trans-3-hexadecenoic acid by Chlorella vulgaris and by lettuce leaf. Eur J Biochem. 1967 Dec;3(1):7-10. doi: 10.1111/j.1432-1033.1967.tb19492.x. [PubMed:6079772 ]
LOTUS database [Link]

Showing NP-Card for (3e)-hexadec-3-enoic acid (NP0150615)

MOL for NP0150615 ((3e)-hexadec-3-enoic acid)

3D MOL for NP0150615 ((3e)-hexadec-3-enoic acid)

3D SDF for NP0150615 ((3e)-hexadec-3-enoic acid)

3D-SDF for NP0150615 ((3e)-hexadec-3-enoic acid)

PDB for NP0150615 ((3e)-hexadec-3-enoic acid)

3D PDB for NP0150615 ((3e)-hexadec-3-enoic acid)

SMILES for NP0150615 ((3e)-hexadec-3-enoic acid)

INCHI for NP0150615 ((3e)-hexadec-3-enoic acid)

Structure for NP0150615 ((3e)-hexadec-3-enoic acid)

3D Structure for NP0150615 ((3e)-hexadec-3-enoic acid)