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Showing NP-Card for 3-hexenoic acid (NP0246671)

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Record Information
Version1.0
Created at2022-09-07 08:13:14 UTC
Updated at2022-09-07 08:13:14 UTC
NP-MRD IDNP0246671
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-hexenoic acid
Description3-Hexenoic acid, also known as hex-3-ensaeure or hydrosorbic 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. 3-hexenoic acid is found in Arctium lappa. It was first documented in 1978 (PMID: 348363). 3-Hexenoic acid is a weakly acidic compound (based on its pKa) (PMID: 11504038) (PMID: 14558774) (PMID: 22224297) (PMID: 4013523).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0246671 (3-hexenoic acid)


  Mrv1533004171518272D          

  8  7  0  0  0  0            999 V2000
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  4  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
M  END
Download

3D MOL for NP0246671 (3-hexenoic acid)

     RDKit          3D

 18 17  0  0  0  0  0  0  0  0999 V2000
   -2.6289    0.2098    0.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7751   -0.9803    0.5110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3336   -0.7712    0.2573 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1114    0.3556   -0.2275 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4711    0.7707   -0.5502 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5567   -0.1663   -0.3226 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4978   -1.3347    0.1316 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8679    0.2766   -0.6502 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6841   -0.0174    0.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5353    0.4431   -0.9074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3501    1.1157    0.7328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9588   -1.2987    1.5717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0904   -1.8458   -0.1069 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3246   -1.5769    0.4862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6769    1.1180   -0.4243 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4510    1.0407   -1.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7599    1.7380   -0.0474 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9926    0.9231   -1.4155 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  8  1  0
  6  7  2  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  2 13  1  0
  3 14  1  0
  4 15  1  0
  5 16  1  0
  5 17  1  0
  8 18  1  0
M  END
Download

3D SDF for NP0246671 (3-hexenoic acid)


  Mrv1533004171518272D          

  8  7  0  0  0  0            999 V2000
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  4  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0246671

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC=CCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H10O2/c1-2-3-4-5-6(7)8/h3-4H,2,5H2,1H3,(H,7,8)

> <INCHI_KEY>
XXHDAWYDNSXJQM-UHFFFAOYSA-N

> <FORMULA>
C6H10O2

> <MOLECULAR_WEIGHT>
114.144

> <EXACT_MASS>
114.068079562

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
12.57994073855005

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
hex-3-enoic acid

> <ALOGPS_LOGP>
1.42

> <JCHEM_LOGP>
1.4489744709999999

> <ALOGPS_LOGS>
-0.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.927641530394589

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
32.190200000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.38e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hexenoic acid

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0246671 (3-hexenoic acid)

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PDB for NP0246671 (3-hexenoic acid)
HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -3.080  -2.667   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -3.080   0.000   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    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END

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3D PDB for NP0246671 (3-hexenoic acid)
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SMILES for NP0246671 (3-hexenoic acid)
CCC=CCC(O)=O
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INCHI for NP0246671 (3-hexenoic acid)
InChI=1S/C6H10O2/c1-2-3-4-5-6(7)8/h3-4H,2,5H2,1H3,(H,7,8)
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View in JSmol
Synonyms
ValueSource
3-Hexenoic acidsChEBI
beta,gamma-Hexenoic acidChEBI
Beta.gamma-hexensaeureChEBI
Hex-3-en-carbonsaeureChEBI
Hex-3-enoic acidsChEBI
Hex-3-ensaeureChEBI
Hydrosorbic acidChEBI
b,g-HexenoateGenerator
b,g-Hexenoic acidGenerator
beta,gamma-HexenoateGenerator
Β,γ-hexenoateGenerator
Β,γ-hexenoic acidGenerator
HydrosorbateGenerator
3-HexenoateGenerator
Hex-3-enoateGenerator
Chemical FormulaC6H10O2
Average Mass114.1440 Da
Monoisotopic Mass114.06808 Da
IUPAC Namehex-3-enoic acid
Traditional Name3-hexenoic acid
CAS Registry NumberNot Available
SMILES
CCC=CCC(O)=O
InChI Identifier
InChI=1S/C6H10O2/c1-2-3-4-5-6(7)8/h3-4H,2,5H2,1H3,(H,7,8)
InChI KeyXXHDAWYDNSXJQM-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Arctium lappaLOTUS Database
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
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.42ALOGPS
logP1.45ChemAxon
logS-0.68ALOGPS
pKa (Strongest Acidic)4.93ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity32.19 m³·mol⁻¹ChemAxon
Polarizability12.58 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound20200  
PDB IDNot Available
ChEBI ID49283  
Good Scents IDNot Available
References
General References
  1. Clarke SR, Dani FR, Jones GR, Morgan ED, Schmidt JO: (Z)-3-hexenyl (R)-3-hydroxybutanoate: a male specific compound in three North American decorator wasps Eucerceris rubripes, E. conata and E. tricolor. J Chem Ecol. 2001 Jul;27(7):1437-47. doi: 10.1023/a:1010373427774. [PubMed:11504038  ] 
  2. Dregus M, Engel KH: Volatile constituents of uncooked rhubarb (Rheum rhabarbarum L.) stalks. J Agric Food Chem. 2003 Oct 22;51(22):6530-6. doi: 10.1021/jf030399l. [PubMed:14558774  ] 
  3. Froissard D, Fons F, Bessiere JM, Buatois B, Rapior S: Volatiles of French ferns and "fougere" scent in perfumery. Nat Prod Commun. 2011 Nov;6(11):1723-6. [PubMed:22224297  ] 
  4. Roberts JL, Schwartz MM, Lewis EJ: Hereditary C2 deficiency and systemic lupus erythematosus associated with severe glomerulonephritis. Clin Exp Immunol. 1978 Feb;31(2):328-38. [PubMed:348363  ] 
  5. Idstein H, Bauer C, Schreier P: [Volatile acids in tropical fruits: cherimoya (Annona cherimolia, Mill.), guava (psidium guajava, L.), mango (Mangifera indica, L., var. Alphonso), papaya (Carica papaya, L.)]. Z Lebensm Unters Forsch. 1985 May;180(5):394-7. doi: 10.1007/BF01027773. [PubMed:4013523  ] 
  6. LOTUS database [Link]