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Showing NP-Card for cis-3-Hexen-1-yl pyruvate (NP0046293)

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Record Information
Version2.0
Created at2022-03-17 19:55:42 UTC
Updated at2022-03-17 19:55:42 UTC
NP-MRD IDNP0046293
Secondary Accession NumbersNone
Natural Product Identification
Common Namecis-3-Hexen-1-yl pyruvate
DescriptionCis-3-Hexenyl pyruvate, also known as (Z)-hex-3-enyl pyruvate or fema 3934, belongs to the class of organic compounds known as alpha-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon. Cis-3-Hexenyl pyruvate is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, cis-3-Hexenyl pyruvate has been detected, but not quantified in, celery stalks and wild celeries. This could make cis-3-hexenyl pyruvate a potential biomarker for the consumption of these foods. Those are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon. Cis-3-hexenyl pyruvate belongs to alpha-keto acids and derivatives class of compounds. Cis-3-hexenyl pyruvate is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Cis-3-hexenyl pyruvate has a banana peel, cucumber skin, and green taste.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0046293 (cis-3-Hexen-1-yl pyruvate)


  Mrv0541 05061310202D          

 12 11  0  0  0  0            999 V2000
   -1.2375    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3349    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9520    1.9520    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
   -1.2375    0.7145    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
    1.6204    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9059    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6204   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9059    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1914    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  3  1  0  0  0  0
  5  4  2  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  2  1  0  0  0  0
  9  8  1  0  0  0  0
 10  8  2  0  0  0  0
 11  9  2  0  0  0  0
 12  7  1  0  0  0  0
 12  9  1  0  0  0  0
M  END
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3D MOL for NP0046293 (cis-3-Hexen-1-yl pyruvate)

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3D SDF for NP0046293 (cis-3-Hexen-1-yl pyruvate)

  Mrv0541 05061310202D          

 12 11  0  0  0  0            999 V2000
   -1.2375    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3349    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9520    1.9520    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
   -1.2375    0.7145    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
    1.6204    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9059    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6204   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9059    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1914    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  3  1  0  0  0  0
  5  4  2  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  2  1  0  0  0  0
  9  8  1  0  0  0  0
 10  8  2  0  0  0  0
 11  9  2  0  0  0  0
 12  7  1  0  0  0  0
 12  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046293

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC\C=C/CCOC(=O)C(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H14O3/c1-3-4-5-6-7-12-9(11)8(2)10/h4-5H,3,6-7H2,1-2H3/b5-4-

> <INCHI_KEY>
LKNXTZXOBHAYSR-PLNGDYQASA-N

> <FORMULA>
C9H14O3

> <MOLECULAR_WEIGHT>
170.2057

> <EXACT_MASS>
170.094294314

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
18.54023268444725

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3Z)-hex-3-en-1-yl 2-oxopropanoate

> <ALOGPS_LOGP>
1.92

> <JCHEM_LOGP>
2.296216030666666

> <ALOGPS_LOGS>
-2.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.90083076342382

> <JCHEM_PKA_STRONGEST_BASIC>
-7.734759804363135

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
46.95100000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.27e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3Z)-hex-3-en-1-yl 2-oxopropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0046293 (cis-3-Hexen-1-yl pyruvate)
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PDB for NP0046293 (cis-3-Hexen-1-yl pyruvate)
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      -2.310   5.954   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.358   2.104   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.310   4.414   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.644   3.644   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.644   2.104   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  C   UNK     0      -0.976   2.104   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.025   1.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.691   2.104   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.025  -0.206   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.691   3.644   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.357   1.334   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    8                                                            
CONECT    3    1    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6   12                                                       
CONECT    8    2    9   10                                                  
CONECT    9    8   11   12                                                  
CONECT   10    8                                                            
CONECT   11    9                                                            
CONECT   12    7    9                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

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3D PDB for NP0046293 (cis-3-Hexen-1-yl pyruvate)
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SMILES for NP0046293 (cis-3-Hexen-1-yl pyruvate)
CC\C=C/CCOC(=O)C(C)=O
Download
INCHI for NP0046293 (cis-3-Hexen-1-yl pyruvate)
InChI=1S/C9H14O3/c1-3-4-5-6-7-12-9(11)8(2)10/h4-5H,3,6-7H2,1-2H3/b5-4-
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Synonyms
ValueSource
cis-3-Hexenyl pyruvic acidGenerator
(Z)-3-Hexenyl pyruvateHMDB
(Z)-Hex-3-enyl pyruvateHMDB
2-oxo-3-Hexenyl ester(Z)-propanoic acidHMDB
cis-3-HexenylpyruvateHMDB
FEMA 3934HMDB
Propanoic acid, 2-oxo-, (3Z)-3-hexen-1-yl esterHMDB
Propanoic acid, 2-oxo-, (3Z)-3-hexenyl esterHMDB
Pyruvic acid, 3-hexenyl esterHMDB
(3Z)-Hex-3-en-1-yl 2-oxopropanoic acidGenerator
cis-3-Hexen-1-yl pyruvic acidGenerator
Chemical FormulaC9H14O3
Average Mass170.2057 Da
Monoisotopic Mass170.09429 Da
IUPAC Name(3Z)-hex-3-en-1-yl 2-oxopropanoate
Traditional Name(3Z)-hex-3-en-1-yl 2-oxopropanoate
CAS Registry Number68133-76-6
SMILES
CC\C=C/CCOC(=O)C(C)=O
InChI Identifier
InChI=1S/C9H14O3/c1-3-4-5-6-7-12-9(11)8(2)10/h4-5H,3,6-7H2,1-2H3/b5-4-
InChI KeyLKNXTZXOBHAYSR-PLNGDYQASA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
    • Harvey J. Gold, Charles W. Wilson III The Volatile Flavor Substances of Celery. Journal of Food S...
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassKeto acids and derivatives  
Sub ClassAlpha-keto acids and derivatives  
Direct ParentAlpha-keto acids and derivatives  
Alternative Parents
Substituents
  • Alpha-keto acid
    • 

  • Ketone
    • 

  • 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 DescriptorsNot Available
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
logP1.92ALOGPS
logP2.3ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)16.9ChemAxon
pKa (Strongest Basic)-7.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity46.95 m³·mol⁻¹ChemAxon
Polarizability18.54 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0038276  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003918  
KNApSAcK IDNot Available
Chemspider ID4515658  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5363291  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available