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Showing NP-Card for cis-3-Hexenyl butyrate (NP0047631)

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Record Information
Version2.0
Created at2022-03-17 20:43:22 UTC
Updated at2022-03-17 20:43:22 UTC
NP-MRD IDNP0047631
Secondary Accession NumbersNone
Natural Product Identification
Common Namecis-3-Hexenyl butyrate
DescriptionCis-3-Hexenyl butyrate, also known as (Z)-3-hexen-1-yl butanoate or (Z)-hex-3-enyl butyrate, belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Cis-3-Hexenyl butyrate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Cis-3-Hexenyl butyrate is an apple, buttery, and fresh tasting compound. Outside of the human body, cis-3-Hexenyl butyrate is found, on average, in the highest concentration within safflowers. Cis-3-Hexenyl butyrate has also been detected, but not quantified in, several different foods, such as cauliflowers, citrus, fruits, and tea. cis-3-Hexenyl butyrate is found in Acca sellowiana, Bistorta manshuriensis and Medicago sativa . This could make cis-3-hexenyl butyrate a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047631 (cis-3-Hexenyl butyrate)


  Mrv0541 05061307052D          

 12 11  0  0  0  0            999 V2000
    6.2388   -0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5243   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5243    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    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
    3.3809    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  5  2  0  0  0  0
  7  6  1  0  0  0  0
  8  4  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11 10  2  0  0  0  0
 12  9  1  0  0  0  0
 12 10  1  0  0  0  0
M  END
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3D MOL for NP0047631 (cis-3-Hexenyl butyrate)

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3D SDF for NP0047631 (cis-3-Hexenyl butyrate)

  Mrv0541 05061307052D          

 12 11  0  0  0  0            999 V2000
    6.2388   -0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5243   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5243    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    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
    3.3809    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  5  2  0  0  0  0
  7  6  1  0  0  0  0
  8  4  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11 10  2  0  0  0  0
 12  9  1  0  0  0  0
 12 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047631

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC(=O)OCC\C=C/CC

> <INCHI_IDENTIFIER>
InChI=1S/C10H18O2/c1-3-5-6-7-9-12-10(11)8-4-2/h5-6H,3-4,7-9H2,1-2H3/b6-5-

> <INCHI_KEY>
ZCHOPXVYTWUHDS-WAYWQWQTSA-N

> <FORMULA>
C10H18O2

> <MOLECULAR_WEIGHT>
170.2487

> <EXACT_MASS>
170.13067982

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
20.27500156860728

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3Z)-hex-3-en-1-yl butanoate

> <ALOGPS_LOGP>
3.18

> <JCHEM_LOGP>
2.918767541666666

> <ALOGPS_LOGS>
-2.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.033293900568625

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
50.83290000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.81e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3Z)-hex-3-en-1-yl butanoate

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0047631 (cis-3-Hexenyl butyrate)
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PDB for NP0047631 (cis-3-Hexenyl butyrate)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      11.646  -0.976   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.357   1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.312  -0.206   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.312   1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.978   2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.645   1.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.311   2.104   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.644   3.644   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       4.977   1.334   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    5                                                       
CONECT    4    2    8                                                       
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    9                                                       
CONECT    8    4   10                                                       
CONECT    9    7   12                                                       
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12    9   10                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

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3D PDB for NP0047631 (cis-3-Hexenyl butyrate)
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SMILES for NP0047631 (cis-3-Hexenyl butyrate)
CCCC(=O)OCC\C=C/CC
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INCHI for NP0047631 (cis-3-Hexenyl butyrate)
InChI=1S/C10H18O2/c1-3-5-6-7-9-12-10(11)8-4-2/h5-6H,3-4,7-9H2,1-2H3/b6-5-
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View in JSmol
Synonyms
ValueSource
cis-3-Hexenyl butyric acidGenerator
(3Z)-3-Hexenyl butyrateHMDB
(Z)-3-Hexen-1-ol, butanoateHMDB
(Z)-3-Hexen-1-yl butanoateHMDB
(Z)-3-Hexenyl butanoateHMDB
(Z)-3-Hexenyl butyrateHMDB
(Z)-Hex-3-enyl butanoateHMDB
(Z)-Hex-3-enyl butyrateHMDB
3(Z)-Hexenyl butanoateHMDB
3-Hexenyl butyrateHMDB
3-Hexenyl ester(Z)-butanoic acidHMDB
3-Hexenyl ester(Z)-butyric acidHMDB
beta,gamma-Hexenyl butyrateHMDB
Butanoate(Z)-3-hexen-1-olHMDB
Butanoic acid, (3Z)-3-hexen-1-yl esterHMDB
Butanoic acid, (3Z)-3-hexenyl esterHMDB
Butanoic acid, (Z)-3-hexenyl esterHMDB
cis-3-Hexen-1-yl butyrateHMDB
cis-3-Hexenyl butanoateHMDB
cis-3-Hexenyl N-butyrateHMDB
cis-Butyric acid, 3-hexenyl esterHMDB
cis-Hex-3-enyl butanoateHMDB
cis-Hex-3-enyl butyrateHMDB
FEMA 3402HMDB
Hex-3(Z)-enyl butanoateHMDB
Hexenyl butanoate (3Z)HMDB
Is-3-hexenyl N-butyrateHMDB
3Z-Hexenyl butyric acidGenerator
Chemical FormulaC10H18O2
Average Mass170.2487 Da
Monoisotopic Mass170.13068 Da
IUPAC Name(3Z)-hex-3-en-1-yl butanoate
Traditional Name(3Z)-hex-3-en-1-yl butanoate
CAS Registry Number16491-36-4
SMILES
CCCC(=O)OCC\C=C/CC
InChI Identifier
InChI=1S/C10H18O2/c1-3-5-6-7-9-12-10(11)8-4-2/h5-6H,3-4,7-9H2,1-2H3/b6-5-
InChI KeyZCHOPXVYTWUHDS-WAYWQWQTSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Acca sellowianaLOTUS Database
Bistorta manshuriensisLOTUS Database
Brassica oleracea var. botrytisFooDB
    • L. Valettea X. Fernandez, S. Poulain, A.-M. Loiseau, L. Lizzani-Cuvelier, R. Levieil, L. Restier....
Carthamus tinctoriusFooDB
Medicago sativaPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassFatty acid esters  
Direct ParentFatty acid esters  
Alternative Parents
Substituents
  • Fatty acid ester
    • 

  • Carboxylic acid ester
    • 

  • Monocarboxylic acid or derivatives
    • 

  • 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
logP3.18ALOGPS
logP2.92ChemAxon
logS-2.8ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity50.83 m³·mol⁻¹ChemAxon
Polarizability20.28 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0033377  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011407  
KNApSAcK IDNot Available
Chemspider ID4509328  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5352438  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References