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Showing NP-Card for 2-Octenoic acid (NP0001017)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-19 23:58:40 UTC
NP-MRD IDNP0001017
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-Octenoic acid
Description2-Octenoic acid, also known as 2-octenoate, 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. 2-Octenoic acid has 8 carbon atoms. 2-Octenoic acid is also known as an olefinic fatty acid carrying a double bond at position 2. It can exist in two isomeric forms, the cis and the trans form, with the trans or 2-E form being more abundant. 2-Octenoic acid is a relatively hydrophobic molecule with a water solubility of approximately 1 g/L. The 2E-isomer has a musty, sour, cheesy aroma and a fatty or waxy taste. 2-Octenoic acid is found in the human body and is naturally produced by hepatic microsomal oxidation of aliphatic aldehydes. 2-Octenoic acid has been detected in human urine and plasma (PMID 1883862 , 8087979 , 4086594 , 1417834 , 6480773 ). 2-Octenoic acid has also been identified as a potential pheromone excreted by the male abdominal glands of the cockroach Leucophaea maderae (PMID: 17200891 ). Outside the human body 2-Octenoic acid has been detected in coffee, cranberries, mushrooms, black tea and strawberries. It is also used as a food flavourant for baked goods and candies.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001017 (2-Octenoic acid)

      
  Mrv1652305261923552D          

 10  9  0  0  0  0            999 V2000
   14.0174   -9.4264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7319   -8.1891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7319   -9.0140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2712   -9.4264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9855   -9.0140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4462   -9.4264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7000   -9.4264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4144   -9.0139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1289   -9.4264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8434   -9.0138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  2  3  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  3  1  0  0  0  0
  5  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
M  END
Download

3D MOL for NP0001017 (2-Octenoic acid)

HMDB0000392
     RDKit          3D
2-Octenoic acid
 24 23  0  0  0  0  0  0  0  0999 V2000
   -3.6450   -0.2655    0.7427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5677   -0.3197   -0.3075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2924    0.2561    0.3040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1726    0.2361   -0.6822 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0815    0.8213   -0.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4889    0.0577    1.1223 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6385   -0.5515    1.2484 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6978   -0.5840    0.2770 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7697   -1.2341    0.5664 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7218    0.0051   -0.9613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2330    0.6725    0.5974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2784   -1.1683    0.6330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1714   -0.2826    1.7306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3946   -1.3790   -0.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8841    0.2664   -1.1916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0438   -0.4643    1.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4825    1.2686    0.6834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0063   -0.7961   -1.0272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4624    0.8283   -1.5746 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7880    0.9629   -0.8554 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7634    1.8450    0.3484 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7430    0.0172    1.9441 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7697   -1.0813    2.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1719    0.8893   -1.1698 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  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  4 18  1  0
  4 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
 10 24  1  0
M  END
Download

3D SDF for NP0001017 (2-Octenoic acid)

      
  Mrv1652305261923552D          

 10  9  0  0  0  0            999 V2000
   14.0174   -9.4264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7319   -8.1891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7319   -9.0140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2712   -9.4264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9855   -9.0140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4462   -9.4264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7000   -9.4264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4144   -9.0139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1289   -9.4264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8434   -9.0138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  2  3  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  3  1  0  0  0  0
  5  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
M  END
> <DATABASE_ID>
NP0001017

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H14O2/c1-2-3-4-5-6-7-8(9)10/h6-7H,2-5H2,1H3,(H,9,10)/b7-6-

> <INCHI_KEY>
CWMPPVPFLSZGCY-SREVYHEPSA-N

> <FORMULA>
C8H14O2

> <MOLECULAR_WEIGHT>
142.1956

> <EXACT_MASS>
142.099379692

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
16.18621755375797

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z)-oct-2-enoic acid

> <ALOGPS_LOGP>
3.01

> <JCHEM_LOGP>
2.6978569473333334

> <ALOGPS_LOGS>
-2.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.252182202336849

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
41.368900000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.44e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cis-2-octenoic acid

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0001017 (2-Octenoic acid)

HMDB0000392
     RDKit          3D
2-Octenoic acid
 24 23  0  0  0  0  0  0  0  0999 V2000
   -3.6450   -0.2655    0.7427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5677   -0.3197   -0.3075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2924    0.2561    0.3040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1726    0.2361   -0.6822 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0815    0.8213   -0.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4889    0.0577    1.1223 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6385   -0.5515    1.2484 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6978   -0.5840    0.2770 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7697   -1.2341    0.5664 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7218    0.0051   -0.9613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2330    0.6725    0.5974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2784   -1.1683    0.6330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1714   -0.2826    1.7306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3946   -1.3790   -0.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8841    0.2664   -1.1916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0438   -0.4643    1.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4825    1.2686    0.6834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0063   -0.7961   -1.0272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4624    0.8283   -1.5746 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7880    0.9629   -0.8554 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7634    1.8450    0.3484 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7430    0.0172    1.9441 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7697   -1.0813    2.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1719    0.8893   -1.1698 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  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  4 18  1  0
  4 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
 10 24  1  0
M  END
Download

PDB for NP0001017 (2-Octenoic acid)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  O   UNK     0      26.166 -17.596   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      27.500 -15.286   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      27.500 -16.826   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      30.373 -17.596   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      31.706 -16.826   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      28.833 -17.596   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      33.040 -17.596   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      34.374 -16.826   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      35.707 -17.596   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      37.041 -16.826   0.000  0.00  0.00           C+0
CONECT    1    3                                                            
CONECT    2    3                                                            
CONECT    3    1    2    6                                                  
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4    3                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for NP0001017 (2-Octenoic acid)

COMPND    HMDB0000392
HETATM    1  C1  UNL     1      -3.645  -0.265   0.743  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.568  -0.320  -0.307  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.292   0.256   0.304  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.173   0.236  -0.682  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.082   0.821  -0.047  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.489   0.058   1.122  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.639  -0.552   1.248  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.698  -0.584   0.277  1.00  0.00           C  
HETATM    9  O1  UNL     1       4.770  -1.234   0.566  1.00  0.00           O  
HETATM   10  O2  UNL     1       3.722   0.005  -0.961  1.00  0.00           O  
HETATM   11  H1  UNL     1      -4.233   0.672   0.597  1.00  0.00           H  
HETATM   12  H2  UNL     1      -4.278  -1.168   0.633  1.00  0.00           H  
HETATM   13  H3  UNL     1      -3.171  -0.283   1.731  1.00  0.00           H  
HETATM   14  H4  UNL     1      -2.395  -1.379  -0.588  1.00  0.00           H  
HETATM   15  H5  UNL     1      -2.884   0.266  -1.192  1.00  0.00           H  
HETATM   16  H6  UNL     1      -1.044  -0.464   1.135  1.00  0.00           H  
HETATM   17  H7  UNL     1      -1.482   1.269   0.683  1.00  0.00           H  
HETATM   18  H8  UNL     1      -0.006  -0.796  -1.027  1.00  0.00           H  
HETATM   19  H9  UNL     1      -0.462   0.828  -1.575  1.00  0.00           H  
HETATM   20  H10 UNL     1       1.788   0.963  -0.855  1.00  0.00           H  
HETATM   21  H11 UNL     1       0.763   1.845   0.348  1.00  0.00           H  
HETATM   22  H12 UNL     1       0.743   0.017   1.944  1.00  0.00           H  
HETATM   23  H13 UNL     1       2.770  -1.081   2.209  1.00  0.00           H  
HETATM   24  H14 UNL     1       4.172   0.889  -1.170  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3   14   15
CONECT    3    4   16   17
CONECT    4    5   18   19
CONECT    5    6   20   21
CONECT    6    7    7   22
CONECT    7    8   23
CONECT    8    9    9   10
CONECT   10   24
END
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SMILES for NP0001017 (2-Octenoic acid)

CCCCC\C=C/C(O)=O
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INCHI for NP0001017 (2-Octenoic acid)

InChI=1S/C8H14O2/c1-2-3-4-5-6-7-8(9)10/h6-7H,2-5H2,1H3,(H,9,10)/b7-6-
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View in JSmol
Synonyms
ValueSource
2-OctenoateGenerator
cis-2-Octenoic acidHMDB
(Z)-2-Octenoic acidHMDB
2-Octenic acidHMDB
2Z-OctenoateHMDB
2Z-Octenoic acidHMDB
Oct-2-enoateHMDB
Oct-2-enoic acidHMDB
trans-2-OctenoateHMDB
2-Octenoic acidHMDB
Chemical FormulaC8H14O2
Average Mass142.1956 Da
Monoisotopic Mass142.09938 Da
IUPAC Name(2Z)-oct-2-enoic acid
Traditional Namecis-2-octenoic acid
CAS Registry Number1577-96-4
SMILES
CCCCC\C=C/C(O)=O
InChI Identifier
InChI=1S/C8H14O2/c1-2-3-4-5-6-7-8(9)10/h6-7H,2-5H2,1H3,(H,9,10)/b7-6-
InChI KeyCWMPPVPFLSZGCY-SREVYHEPSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
Catalpa ovata G.DON.KNApSAcK Database
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Deschampsia antarcticaLOTUS Database
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Osyris albaLOTUS Database
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-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 FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point5 - 6 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility797.6 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.74 g/LALOGPS
logP3.01ALOGPS
logP2.7ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)5.25ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity41.37 m³·mol⁻¹ChemAxon
Polarizability16.19 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000392
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022010
KNApSAcK IDC00031683
Chemspider ID4445840
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID4146
PubChem Compound5282713
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDrw1621221
References
General References
  1. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
  2. Watanabe K, Matsunaga T, Narimatsu S, Yamamoto I, Yoshimura H: Mouse hepatic microsomal oxidation of aliphatic aldehydes (C8 to C11) to carboxylic acids. Biochem Biophys Res Commun. 1992 Oct 15;188(1):114-9. [PubMed:1417834 ]
  3. Libert R, Draye JP, Van Hoof F, Schanck A, Soumillion JP, de Hoffmann E: Study of reactions induced by hydroxylamine treatment of esters of organic acids and of 3-ketoacids: application to the study of urines from patients under valproate therapy. Biol Mass Spectrom. 1991 Feb;20(2):75-86. [PubMed:1883862 ]
  4. Yanagisawa I, Yamane M, Urayama T: Simultaneous separation and sensitive determination of free fatty acids in blood plasma by high-performance liquid chromatography. J Chromatogr. 1985 Dec 13;345(2):229-40. [PubMed:4086594 ]
  5. Tsuchiya H, Hayashi T, Sato M, Tatsumi M, Takagi N: Simultaneous separation and sensitive determination of free fatty acids in blood plasma by high-performance liquid chromatography. J Chromatogr. 1984 Jul 13;309(1):43-52. [PubMed:6480773 ]
  6. Farine JP, Sirugue D, Abed-Vieillard D, Everaerts C, Le Quere JL, Bonnard O, Brossut R: The male abdominal glands of Leucophaea maderae: chemical identification of the volatile secretion and sex pheromone function. J Chem Ecol. 2007 Feb;33(2):405-15. doi: 10.1007/s10886-006-9224-7. Epub 2007 Jan 3. [PubMed:17200891 ]