Showing metabocard for sulcatone (MMDBc0033171)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 04:37:36 UTC
Update Date2024-09-29 04:45:43 UTC
Metabolite IDMMDBc0033171
Metabolite Identification
Common Namesulcatone
DescriptionSulcatone, also known as methylheptenone or fema 2707, belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. Sulcatone is a very hydrophobic methylketone, practically insoluble in water, and relatively neutral. It exists as a clear, colorless liquid. Sulcatone can be found in all eukaryotes, ranging from yeast to plants to humans. Sulcatone has a musty, apple green-bean, and pear-like taste. and a citrus-like lemongrass odor. It is a volatile oil component of citronella oil, lemon-grass oil and palmarosa oil. Sulcatone is naturally found in bay leaf, blackberry fruit, sour cherries, cloves, ginger and lavender. In insects and animals, it has a role as an alarm or attractant pheromone. In fact, sulcatone is one of a number of mosquito attractants, especially for those species such as Aedes aegypti with the odor receptor gene Or4 (PMID:25391959 ). Sulcatone is secreted by humans in their sweat and is a compound frequently found in human body odors (but in few other mammals). Sulcoatone is used as a pheromone by ferrets, european badgers, red foxes, treefrogs, bedbugs, wasps and butterflies. Sulcatone is one of several ketones found in Cannabis sativa (PMID:6991645 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f923a618c48>


  Mrv1652303202019012D          

  9  8  0  0  0  0            999 V2000
   -3.1527    2.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4382    2.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7237    2.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0093    2.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2948    2.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4197    2.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1341    2.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4382    3.2705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4197    3.2705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  8  1  0  0  0  0
  6  9  2  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f923a618c48>

HMDB0035915
     RDKit          3D
Sulcatone
 23 22  0  0  0  0  0  0  0  0999 V2000
    3.7656   -0.4153    0.8095 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5305   -0.7652    0.0544 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4988   -1.8196   -0.5400 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4135    0.2158    0.0851 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2260   -0.2635   -0.7194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8668    0.7558   -0.6562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0216    0.3834   -0.1461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2200   -0.9921    0.3426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1214    1.3739   -0.0719 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7283   -0.8469    1.8506 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6608   -0.8736    0.3046 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8961    0.6706    0.9422 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8009    1.1659   -0.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0804    0.2872    1.1455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1148   -1.2575   -0.4312 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5498   -0.2945   -1.7849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6909    1.7689   -1.0267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4484   -1.2834    1.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1833   -1.7276   -0.5122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2398   -1.0998    0.7658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1965    1.8385    0.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9469    2.2392   -0.7710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1001    0.9396   -0.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  3
  7  8  1  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  4 13  1  0
  4 14  1  0
  5 15  1  0
  5 16  1  0
  6 17  1  0
  8 18  1  0
  8 19  1  0
  8 20  1  0
  9 21  1  0
  9 22  1  0
  9 23  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007f923a618c48>


  Mrv1652303202019012D          

  9  8  0  0  0  0            999 V2000
   -3.1527    2.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4382    2.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7237    2.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0093    2.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2948    2.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4197    2.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1341    2.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4382    3.2705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4197    3.2705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  8  1  0  0  0  0
  6  9  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033171

> <DATABASE_NAME>
MIME

> <SMILES>
CC(C)=CCCC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H14O/c1-7(2)5-4-6-8(3)9/h5H,4,6H2,1-3H3

> <INCHI_KEY>
UHEPJGULSIKKTP-UHFFFAOYSA-N

> <FORMULA>
C8H14O

> <MOLECULAR_WEIGHT>
126.1962

> <EXACT_MASS>
126.10446507

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
15.532670844876723

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-methylhept-5-en-2-one

> <ALOGPS_LOGP>
2.01

> <JCHEM_LOGP>
2.021961265333334

> <ALOGPS_LOGS>
-1.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.59876414991478

> <JCHEM_PKA_STRONGEST_BASIC>
-7.277827114901278

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
40.0233

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.54e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-methyl-5-hepten-2-one

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for #<Metabolite:0x00007f923a618c48>

HMDB0035915
     RDKit          3D
Sulcatone
 23 22  0  0  0  0  0  0  0  0999 V2000
    3.7656   -0.4153    0.8095 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5305   -0.7652    0.0544 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4988   -1.8196   -0.5400 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4135    0.2158    0.0851 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2260   -0.2635   -0.7194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8668    0.7558   -0.6562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0216    0.3834   -0.1461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2200   -0.9921    0.3426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1214    1.3739   -0.0719 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7283   -0.8469    1.8506 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6608   -0.8736    0.3046 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8961    0.6706    0.9422 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8009    1.1659   -0.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0804    0.2872    1.1455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1148   -1.2575   -0.4312 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5498   -0.2945   -1.7849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6909    1.7689   -1.0267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4484   -1.2834    1.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1833   -1.7276   -0.5122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2398   -1.0998    0.7658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1965    1.8385    0.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9469    2.2392   -0.7710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1001    0.9396   -0.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  3
  7  8  1  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  4 13  1  0
  4 14  1  0
  5 15  1  0
  5 16  1  0
  6 17  1  0
  8 18  1  0
  8 19  1  0
  8 20  1  0
  9 21  1  0
  9 22  1  0
  9 23  1  0
M  END
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PDB for #<Metabolite:0x00007f923a618c48>

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0      -5.885   3.795   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.551   4.565   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.218   3.795   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.884   4.565   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.550   3.795   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.783   4.565   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.117   3.795   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.551   6.105   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.783   6.105   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6                                                            
CONECT    8    2                                                            
CONECT    9    6                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for #<Metabolite:0x00007f923a618c48>

COMPND    HMDB0035915
HETATM    1  C1  UNL     1       3.766  -0.415   0.810  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.530  -0.765   0.054  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.499  -1.820  -0.540  1.00  0.00           O  
HETATM    4  C3  UNL     1       1.413   0.216   0.085  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.226  -0.264  -0.719  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.867   0.756  -0.656  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.022   0.383  -0.146  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.220  -0.992   0.343  1.00  0.00           C  
HETATM    9  C8  UNL     1      -3.121   1.374  -0.072  1.00  0.00           C  
HETATM   10  H1  UNL     1       3.728  -0.847   1.851  1.00  0.00           H  
HETATM   11  H2  UNL     1       4.661  -0.874   0.305  1.00  0.00           H  
HETATM   12  H3  UNL     1       3.896   0.671   0.942  1.00  0.00           H  
HETATM   13  H4  UNL     1       1.801   1.166  -0.288  1.00  0.00           H  
HETATM   14  H5  UNL     1       1.080   0.287   1.145  1.00  0.00           H  
HETATM   15  H6  UNL     1      -0.115  -1.257  -0.431  1.00  0.00           H  
HETATM   16  H7  UNL     1       0.550  -0.294  -1.785  1.00  0.00           H  
HETATM   17  H8  UNL     1      -0.691   1.769  -1.027  1.00  0.00           H  
HETATM   18  H9  UNL     1      -1.448  -1.283   1.113  1.00  0.00           H  
HETATM   19  H10 UNL     1      -2.183  -1.728  -0.512  1.00  0.00           H  
HETATM   20  H11 UNL     1      -3.240  -1.100   0.766  1.00  0.00           H  
HETATM   21  H12 UNL     1      -3.197   1.839   0.944  1.00  0.00           H  
HETATM   22  H13 UNL     1      -2.947   2.239  -0.771  1.00  0.00           H  
HETATM   23  H14 UNL     1      -4.100   0.940  -0.372  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3    3    4
CONECT    4    5   13   14
CONECT    5    6   15   16
CONECT    6    7    7   17
CONECT    7    8    9
CONECT    8   18   19   20
CONECT    9   21   22   23
END
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SMILES for #<Metabolite:0x00007f923a618c48>

CC(C)=CCCC(C)=O
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INCHI for #<Metabolite:0x00007f923a618c48>

InChI=1S/C8H14O/c1-7(2)5-4-6-8(3)9/h5H,4,6H2,1-3H3
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Synonyms
ValueSource
6-Methyl-5-hepten-2-oneChEBI
6-Methylhept-5-en-2-oneChEBI
MethylheptenoneKegg
2-Methyl-2-hepten-6-oneHMDB
2-Methyl-6-heptenoneHMDB
2-Methyl-6-oxo-2-hepteneHMDB
2-Methylhept-2-en-6-oneHMDB
2-oxo-6-Methylhept-5-eneHMDB
6-Methyl hept-5-en-2-oneHMDB
6-Methyl-5-heptene-2-oneHMDB
6-Methylheptan-5-ene-2-oneHMDB
FEMA 2707HMDB
PrenylacetoneHMDB
6-Methylhept-5-ene-2-oneHMDB
SulcatoneMeSH
Molecular FormulaC8H14O
Average Mass126.1962
Monoisotopic Mass126.10446507
IUPAC Name6-methylhept-5-en-2-one
Traditional Name6-methyl-5-hepten-2-one
CAS Registry Number110-93-0
SMILES
CC(C)=CCCC(C)=O
InChI Identifier
InChI=1S/C8H14O/c1-7(2)5-4-6-8(3)9/h5H,4,6H2,1-3H3
InChI KeyUHEPJGULSIKKTP-UHFFFAOYSA-N