NP-MRD: Showing NP-Card for 14,15-Dehydrocrepenynic acid (NP0081306)

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Record Information

Version

2.0

Created at

2022-04-29 02:15:45 UTC

Updated at

2022-04-29 02:15:45 UTC

NP-MRD ID

NP0081306

Secondary Accession Numbers

None

Natural Product Identification

Common Name

14,15-Dehydrocrepenynic acid

Description

Cis-9-dodecenoic acid, also known as 12:1, N-3 cis or (Z)-dodec-9-enoic acid, 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. 14,15-Dehydrocrepenynic acid is found in Afzelia cuanzesis, Agave decipiens and Daucus carota subsp. Sativus . 14,15-Dehydrocrepenynic acid was first documented in 1991 (PMID: 16668490). Based on a literature review very few articles have been published on cis-9-dodecenoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 35  0  0  0  0  0  0  0  0999 V2000
   -4.4223    2.0275    0.1936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7004    1.0863    1.1665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0707   -0.2803    0.7835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1953   -1.1799    0.4196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7475   -0.9224    0.3550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2183   -1.1291   -1.0668 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2541   -0.8369   -1.0593 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0547   -1.7107   -0.1410 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5133   -1.3578   -0.2275 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8362    0.0566    0.1529 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3503    0.2668    0.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6961    1.6572    0.4018 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7775    1.9905    1.6335 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9290    2.5864   -0.5943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3031    1.5767   -0.8125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4786    2.0516    0.5381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9458    3.0299    0.2012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0114    1.3169    2.2138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6476    1.3595    1.1023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1526   -0.5841    0.7975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5061   -2.2104    0.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3771    0.0090    0.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2736   -1.7554    0.9776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3642   -2.2113   -1.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7854   -0.4857   -1.7408 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4378    0.2314   -0.7631 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6217   -0.9372   -2.0933 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8692   -2.7765   -0.3727 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7210   -1.5761    0.9278 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9097   -1.5467   -1.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1106   -2.0275    0.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5077    0.2883    1.1666 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3422    0.7698   -0.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6902    0.0901   -0.9973 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8549   -0.4275    0.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7238    3.5609   -0.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  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 14  1  0
 12 13  2  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  2 19  1  0
  3 20  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 14 36  1  0
M  END

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       2.929   4.771   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.263   4.001   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.596   4.771   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.264   4.771   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      10.931   4.771   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.598   4.771   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      16.266   4.771   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      14.932   2.461   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.929   6.311   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.595   7.081   0.000  0.00  0.00           C+0
CONECT    1    2   13                                                       
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   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    1   14                                                       
CONECT   14   13                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

View in JSmol

Synonyms

Value	Source
(Z)-9-Dodecenoic acid	ChEBI
(Z)-Dodec-9-enoic acid	ChEBI
12:1, N-3 cis	ChEBI
9Z-Dodecenoic acid	ChEBI
9Z-Dodecensaeure	ChEBI
C12:1, N-3 cis	ChEBI
cis-Dodec-9-enoic acid	ChEBI
Dodec-9C-enoic acid	ChEBI
Dodec-9C-ensaeure	ChEBI
Lauroleic acid	ChEBI
(Z)-9-Dodecenoate	Generator
(Z)-Dodec-9-enoate	Generator
9Z-Dodecenoate	Generator
cis-Dodec-9-enoate	Generator
Dodec-9C-enoate	Generator
Lauroleate	Generator
cis-9-Dodecenoate	Generator

Chemical Formula

C₁₂H₂₂O₂

Average Mass

198.3060 Da

Monoisotopic Mass

198.16198 Da

IUPAC Name

(9Z)-dodec-9-enoic acid

Traditional Name

lauroleic acid

CAS Registry Number

Not Available

SMILES

CC\C=C/CCCCCCCC(O)=O

InChI Identifier

InChI=1S/C12H22O2/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h3-4H,2,5-11H2,1H3,(H,13,14)/b4-3-

InChI Key

FKLSONDBCYHMOQ-ARJAWSKDSA-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
Afzelia cuanzesis	Plant	KNApSAcK
Agave decipiens	LOTUS Database	35616633
Daucus carota ssp. sativus	Plant	KNApSAcK

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

9-dodecenoic acid (CHEBI:38377 )
Unsaturated fatty acids (LMFA01030229 )

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	4.7	ALOGPS
logP	4.12	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	4.99	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	9	ChemAxon
Refractivity	59.8 m³·mol⁻¹	ChemAxon
Polarizability	24.63 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4471806

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5312381

PDB ID

Not Available

ChEBI ID

38377

Good Scents ID

Not Available

References

General References

Gardner HW, Weisleder D, Plattner RD: Hydroperoxide Lyase and Other Hydroperoxide-Metabolizing Activity in Tissues of Soybean, Glycine max. Plant Physiol. 1991 Nov;97(3):1059-72. doi: 10.1104/pp.97.3.1059. [PubMed:16668490 ]

Showing NP-Card for 14,15-Dehydrocrepenynic acid (NP0081306)

MOL for NP0081306 (14,15-Dehydrocrepenynic acid)

3D MOL for NP0081306 (14,15-Dehydrocrepenynic acid)

3D SDF for NP0081306 (14,15-Dehydrocrepenynic acid)

3D-SDF for NP0081306 (14,15-Dehydrocrepenynic acid)

PDB for NP0081306 (14,15-Dehydrocrepenynic acid)

3D PDB for NP0081306 (14,15-Dehydrocrepenynic acid)

SMILES for NP0081306 (14,15-Dehydrocrepenynic acid)

INCHI for NP0081306 (14,15-Dehydrocrepenynic acid)

Structure for NP0081306 (14,15-Dehydrocrepenynic acid)

3D Structure for NP0081306 (14,15-Dehydrocrepenynic acid)