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Showing metabocard for (S)-Carvone (HMDB0004487)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-08-13 19:43:36 UTC
Update Date2023-02-21 17:17:03 UTC
HMDB IDHMDB0004487
Secondary Accession Numbers
  • HMDB0061788
  • HMDB04487
  • HMDB61788
Metabolite Identification
Common Name(S)-Carvone
DescriptionCarvone, with R and S isomers, also known as carvol or limonen-6-one, belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. p-Menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m-menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Carvone is a neutral compound. Carvone is a naturally occurring organic compound found in many essential oils but is most abundant in the oils from caraway seeds (Carum carvi), spearmint (Mentha spicata), and dill (PMID:27427817 ). Carvone is occasionally found as a component of biological fluids in normal individuals. Both carvones (R, S) are used in the food and flavor industry (http//doi:10.1016/j.foodchem.2005.01.003). R-carvone is also used in air freshening products and in essential oils used in aromatherapy and alternative medicine. Caraway was used for medicinal purposes by the ancient Romans, but carvone was probably not isolated as a pure compound until Varrentrapp obtained it in 1841 (PMID:5556886  , 2477620 ). Carvone may help in the management of diseases (PMID:30374904 ) and had been considered as an adjuvant for treatment of cancer patients (PMID:30087792 ) and patients with epilepsy (PMID:31239862 ). It also has been successfully used as a biopesticide (PMID:30250476 ).
Structure
Data?1676999823
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0004487 ((S)-Carvone)

  Mrv1652305261923502D          

 11 11  0  0  0  0            999 V2000
10001.095610000.4119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.8103 9999.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.095610001.2359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.239610000.4119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2396 9998.7640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.668910000.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.954410000.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9544 9999.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6689 9998.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3834 9999.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.383410000.0009    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  6  7  1  0  0  0  0
  6 11  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11  1  1  1  0  0  0
  7  4  2  0  0  0  0
  8  5  1  0  0  0  0
M  END
Download

3D MOL for HMDB0004487 ((S)-Carvone)

HMDB0004487
     RDKit          3D
(S)-Carvone
 25 25  0  0  0  0  0  0  0  0999 V2000
   -2.7049   -0.5982    0.9268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0677    0.1712    0.0702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8218    0.9028   -0.9724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6034    0.3137    0.1370 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0001   -0.5310    1.2342 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4782   -0.4208    1.1853 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1535   -0.1014    0.0929 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6429   -0.0115    0.1273 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4423    0.1605   -1.1360 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0243    0.6501   -2.1337 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0079   -0.1659   -1.1926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1748   -1.1437    1.6988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7852   -0.7291    0.9096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2617    1.7812   -1.3572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0422    0.1982   -1.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7562    1.2765   -0.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2715    1.3508    0.2965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2723   -1.6053    1.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3516   -0.1349    2.1968 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0724   -0.6064    2.0798 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8988    0.9814   -0.3271 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0871   -0.8100   -0.4793 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9810   -0.0072    1.1809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5002    0.3334   -2.0491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1588   -1.2542   -1.2983 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
 11  4  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  1
  5 18  1  0
  5 19  1  0
  6 20  1  0
  8 21  1  0
  8 22  1  0
  8 23  1  0
 11 24  1  0
 11 25  1  0
M  END
Download

3D SDF for HMDB0004487 ((S)-Carvone)

  Mrv1652305261923502D          

 11 11  0  0  0  0            999 V2000
10001.095610000.4119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.8103 9999.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.095610001.2359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.239610000.4119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2396 9998.7640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.668910000.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.954410000.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9544 9999.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6689 9998.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3834 9999.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.383410000.0009    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  6  7  1  0  0  0  0
  6 11  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11  1  1  1  0  0  0
  7  4  2  0  0  0  0
  8  5  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004487

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=C)[C@H]1CC=C(C)C(=O)C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9H,1,5-6H2,2-3H3/t9-/m0/s1

> <INCHI_KEY>
ULDHMXUKGWMISQ-VIFPVBQESA-N

> <FORMULA>
C10H14O

> <MOLECULAR_WEIGHT>
150.2176

> <EXACT_MASS>
150.10446507

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
17.648982205751555

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one

> <ALOGPS_LOGP>
2.77

> <JCHEM_LOGP>
2.552529290333333

> <ALOGPS_LOGS>
-2.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.655503656223822

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
47.1735

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.16e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
carvone, (+)-

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0004487 ((S)-Carvone)

HMDB0004487
     RDKit          3D
(S)-Carvone
 25 25  0  0  0  0  0  0  0  0999 V2000
   -2.7049   -0.5982    0.9268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0677    0.1712    0.0702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8218    0.9028   -0.9724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6034    0.3137    0.1370 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0001   -0.5310    1.2342 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4782   -0.4208    1.1853 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1535   -0.1014    0.0929 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6429   -0.0115    0.1273 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4423    0.1605   -1.1360 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0243    0.6501   -2.1337 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0079   -0.1659   -1.1926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1748   -1.1437    1.6988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7852   -0.7291    0.9096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2617    1.7812   -1.3572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0422    0.1982   -1.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7562    1.2765   -0.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2715    1.3508    0.2965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2723   -1.6053    1.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3516   -0.1349    2.1968 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0724   -0.6064    2.0798 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8988    0.9814   -0.3271 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0871   -0.8100   -0.4793 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9810   -0.0072    1.1809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5002    0.3334   -2.0491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1588   -1.2542   -1.2983 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
 11  4  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  1
  5 18  1  0
  5 19  1  0
  6 20  1  0
  8 21  1  0
  8 22  1  0
  8 23  1  0
 11 24  1  0
 11 25  1  0
M  END
Download

PDB for HMDB0004487 ((S)-Carvone)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0    8668.7128667.436   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8670.0468666.666   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8668.7128668.974   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8663.3818667.436   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    8663.3818664.359   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8666.0498667.438   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8664.7158666.668   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8664.7158665.128   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8666.0498664.358   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8667.3828665.128   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8667.3828666.668   0.000  0.00  0.00           C+0
CONECT    1    2    3   11                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    7                                                            
CONECT    5    8                                                            
CONECT    6    7   11                                                       
CONECT    7    6    8    4                                                  
CONECT    8    7    9    5                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11    6   10    1                                                  
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for HMDB0004487 ((S)-Carvone)

COMPND    HMDB0004487
HETATM    1  C1  UNL     1      -2.705  -0.598   0.927  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.068   0.171   0.070  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.822   0.903  -0.972  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.603   0.314   0.137  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.000  -0.531   1.234  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.478  -0.421   1.185  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.153  -0.101   0.093  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.643  -0.012   0.127  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.442   0.161  -1.136  1.00  0.00           C  
HETATM   10  O1  UNL     1       2.024   0.650  -2.134  1.00  0.00           O  
HETATM   11  C10 UNL     1      -0.008  -0.166  -1.193  1.00  0.00           C  
HETATM   12  H1  UNL     1      -2.175  -1.144   1.699  1.00  0.00           H  
HETATM   13  H2  UNL     1      -3.785  -0.729   0.910  1.00  0.00           H  
HETATM   14  H3  UNL     1      -2.262   1.781  -1.357  1.00  0.00           H  
HETATM   15  H4  UNL     1      -3.042   0.198  -1.805  1.00  0.00           H  
HETATM   16  H5  UNL     1      -3.756   1.276  -0.513  1.00  0.00           H  
HETATM   17  H6  UNL     1      -0.272   1.351   0.297  1.00  0.00           H  
HETATM   18  H7  UNL     1      -0.272  -1.605   1.128  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.352  -0.135   2.197  1.00  0.00           H  
HETATM   20  H9  UNL     1       2.072  -0.606   2.080  1.00  0.00           H  
HETATM   21  H10 UNL     1       3.899   0.981  -0.327  1.00  0.00           H  
HETATM   22  H11 UNL     1       4.087  -0.810  -0.479  1.00  0.00           H  
HETATM   23  H12 UNL     1       3.981  -0.007   1.181  1.00  0.00           H  
HETATM   24  H13 UNL     1      -0.500   0.333  -2.049  1.00  0.00           H  
HETATM   25  H14 UNL     1      -0.159  -1.254  -1.298  1.00  0.00           H  
CONECT    1    2    2   12   13
CONECT    2    3    4
CONECT    3   14   15   16
CONECT    4    5   11   17
CONECT    5    6   18   19
CONECT    6    7    7   20
CONECT    7    8    9
CONECT    8   21   22   23
CONECT    9   10   10   11
CONECT   11   24   25
END
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SMILES for HMDB0004487 ((S)-Carvone)

CC(=C)[C@H]1CC=C(C)C(=O)C1
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INCHI for HMDB0004487 ((S)-Carvone)

InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9H,1,5-6H2,2-3H3/t9-/m0/s1
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View in JSmolView Stereo Labels
Synonyms
ValueSource
(+)-(4S)-CarvoneChEBI
(+)-(S)-CarvoneChEBI
(5S)-2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-oneChEBI
(S)-(+)-CarvoneChEBI
(S)-(+)-p-Mentha-6,8-dien-2-oneChEBI
(S)-2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-oneChEBI
(S)-2-Methyl-5-(1-methylvinyl)cyclohex-2-en-1-oneChEBI
(S)-5-Isopropenyl-2-methylcyclohex-2-en-1-oneChEBI
CarvolChEBI
CarvoneChEBI
D-(+)-CarvoneChEBI
D-CarvoneChEBI
(+)-CarvoneKegg
2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-oneHMDB
D-p-Mentha-6,8(9)-dien-2-oneHMDB
(S)-CarvoneChEBI
Chemical FormulaC10H14O
Average Molecular Weight150.2176
Monoisotopic Molecular Weight150.10446507
IUPAC Name(5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one
Traditional Namecarvone, (+)-
CAS Registry Number2244-16-8
SMILES
CC(=C)[C@H]1CC=C(C)C(=O)C1
InChI Identifier
InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9H,1,5-6H2,2-3H3/t9-/m0/s1
InChI KeyULDHMXUKGWMISQ-VIFPVBQESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentMenthane monoterpenoids
Alternative Parents
Substituents
  • P-menthane monoterpenoid
  • Monocyclic monoterpenoid
  • Cyclohexenone
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationSource
ProcessNot Available
Role
Biological roleIndustrial application
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point< 15 °CNot Available
Boiling Point231.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1300 mg/L at 18 °CNot Available
LogP1.267Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBreast cancer details
Associated Disorders and Diseases
Disease References
Perillyl alcohol administration for cancer treatment
  1. Silva CL, Passos M, Camara JS: Solid phase microextraction, mass spectrometry and metabolomic approaches for detection of potential urinary cancer biomarkers--a powerful strategy for breast cancer diagnosis. Talanta. 2012 Jan 30;89:360-8. doi: 10.1016/j.talanta.2011.12.041. Epub 2011 Dec 22. [PubMed:22284503 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB013718
KNApSAcK IDC00010891
Chemspider ID15855
KEGG Compound IDC11383
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16724
PDB IDNot Available
ChEBI ID15399
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1007121
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References