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Showing metabocard for cis-3-Hexenyl pyruvate (HMDB0038276)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:33:38 UTC
Update Date2023-02-21 17:26:27 UTC
HMDB IDHMDB0038276
Secondary Accession Numbers
  • HMDB38276
Metabolite Identification
Common Namecis-3-Hexenyl 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 has been detected, but not quantified in, celery stalks (Apium graveolens var. dulce) and wild celeries (Apium graveolens). This could make cis-3-hexenyl pyruvate a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on cis-3-Hexenyl pyruvate.
Structure
Data?1677000387
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0038276 (cis-3-Hexenyl 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
Download

3D MOL for HMDB0038276 (cis-3-Hexenyl pyruvate)

HMDB0038276
     RDKit          3D
cis-3-Hexenyl pyruvate
 26 25  0  0  0  0  0  0  0  0999 V2000
   -3.7973   -0.2553    0.0019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2431   -0.9094   -1.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8350   -0.9064   -1.5183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7647   -0.4198   -0.9767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7121    0.3428    0.2657 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1770   -0.3661    1.2951 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4889   -0.5384    0.8695 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4031    0.4289    0.5329 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0390    1.6250    0.6111 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7558    0.1445    0.0954 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6694    1.2563   -0.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1894   -1.0452   -0.0060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9573   -0.4096   -0.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7307    0.8462   -0.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5560   -0.6806    0.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7753   -0.4280   -2.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6667   -1.9854   -1.2889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5572   -1.4657   -2.5048 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2352   -0.5831   -1.4878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6681    0.4843    0.7463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1851    1.3264    0.0928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2565   -1.3676    1.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0866    0.2393    2.2278 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4060    0.9020   -0.9942 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1718    1.6640    0.6726 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0829    2.1009   -0.7012 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  2  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  2 17  1  0
  3 18  1  0
  4 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
 11 24  1  0
 11 25  1  0
 11 26  1  0
M  END
Download

3D SDF for HMDB0038276 (cis-3-Hexenyl 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>
HMDB0038276

> <DATABASE_NAME>
hmdb

> <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

$$$$
Download

3D-SDF for HMDB0038276 (cis-3-Hexenyl pyruvate)

HMDB0038276
     RDKit          3D
cis-3-Hexenyl pyruvate
 26 25  0  0  0  0  0  0  0  0999 V2000
   -3.7973   -0.2553    0.0019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2431   -0.9094   -1.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8350   -0.9064   -1.5183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7647   -0.4198   -0.9767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7121    0.3428    0.2657 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1770   -0.3661    1.2951 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4889   -0.5384    0.8695 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4031    0.4289    0.5329 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0390    1.6250    0.6111 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7558    0.1445    0.0954 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6694    1.2563   -0.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1894   -1.0452   -0.0060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9573   -0.4096   -0.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7307    0.8462   -0.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5560   -0.6806    0.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7753   -0.4280   -2.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6667   -1.9854   -1.2889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5572   -1.4657   -2.5048 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2352   -0.5831   -1.4878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6681    0.4843    0.7463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1851    1.3264    0.0928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2565   -1.3676    1.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0866    0.2393    2.2278 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4060    0.9020   -0.9942 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1718    1.6640    0.6726 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0829    2.1009   -0.7012 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  2  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  2 17  1  0
  3 18  1  0
  4 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
 11 24  1  0
 11 25  1  0
 11 26  1  0
M  END
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PDB for HMDB0038276 (cis-3-Hexenyl 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 HMDB0038276 (cis-3-Hexenyl pyruvate)

COMPND    HMDB0038276
HETATM    1  C1  UNL     1      -3.797  -0.255   0.002  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.243  -0.909  -1.184  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.835  -0.906  -1.518  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.765  -0.420  -0.977  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.712   0.343   0.266  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.177  -0.366   1.295  1.00  0.00           C  
HETATM    7  O1  UNL     1       1.489  -0.538   0.870  1.00  0.00           O  
HETATM    8  C7  UNL     1       2.403   0.429   0.533  1.00  0.00           C  
HETATM    9  O2  UNL     1       2.039   1.625   0.611  1.00  0.00           O  
HETATM   10  C8  UNL     1       3.756   0.144   0.095  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.669   1.256  -0.246  1.00  0.00           C  
HETATM   12  O3  UNL     1       4.189  -1.045  -0.006  1.00  0.00           O  
HETATM   13  H1  UNL     1      -4.957  -0.410  -0.014  1.00  0.00           H  
HETATM   14  H2  UNL     1      -3.731   0.846  -0.050  1.00  0.00           H  
HETATM   15  H3  UNL     1      -3.556  -0.681   0.989  1.00  0.00           H  
HETATM   16  H4  UNL     1      -3.775  -0.428  -2.087  1.00  0.00           H  
HETATM   17  H5  UNL     1      -3.667  -1.985  -1.289  1.00  0.00           H  
HETATM   18  H6  UNL     1      -1.557  -1.466  -2.505  1.00  0.00           H  
HETATM   19  H7  UNL     1       0.235  -0.583  -1.488  1.00  0.00           H  
HETATM   20  H8  UNL     1      -1.668   0.484   0.746  1.00  0.00           H  
HETATM   21  H9  UNL     1      -0.185   1.326   0.093  1.00  0.00           H  
HETATM   22  H10 UNL     1      -0.256  -1.368   1.495  1.00  0.00           H  
HETATM   23  H11 UNL     1       0.087   0.239   2.228  1.00  0.00           H  
HETATM   24  H12 UNL     1       5.406   0.902  -0.994  1.00  0.00           H  
HETATM   25  H13 UNL     1       5.172   1.664   0.673  1.00  0.00           H  
HETATM   26  H14 UNL     1       4.083   2.101  -0.701  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3   16   17
CONECT    3    4    4   18
CONECT    4    5   19
CONECT    5    6   20   21
CONECT    6    7   22   23
CONECT    7    8
CONECT    8    9    9   10
CONECT   10   11   12   12
CONECT   11   24   25   26
END
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SMILES for HMDB0038276 (cis-3-Hexenyl pyruvate)

CC\C=C/CCOC(=O)C(C)=O
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INCHI for HMDB0038276 (cis-3-Hexenyl 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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View in JSmolView Stereo Labels
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 acidHMDB
cis-3-Hexen-1-yl pyruvic acidGenerator
Chemical FormulaC9H14O3
Average Molecular Weight170.2057
Monoisotopic Molecular Weight170.094294314
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
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
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point75.00 to 77.00 °C. @ 5.00 mm HgThe Good Scents Company Information System
Water Solubility4917 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.848 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1005191
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .