Showing metabocard for D-Carvone (MMDBc0047677)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 15:37:24 UTC
Update Date2024-04-30 20:28:40 UTC
Metabolite IDMMDBc0047677
Metabolite Identification
Common NameD-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
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fa4ac781e70>


  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 #<Metabolite:0x00007fa4ac781e70>

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 #<Metabolite:0x00007fa4ac781e70>


  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>
MMDBc0047677

> <DATABASE_NAME>
MIME

> <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 #<Metabolite:0x00007fa4ac781e70>

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 #<Metabolite:0x00007fa4ac781e70>

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
Download

3D PDB for #<Metabolite:0x00007fa4ac781e70>

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
Download

SMILES for #<Metabolite:0x00007fa4ac781e70>

CC(=C)[C@H]1CC=C(C)C(=O)C1
Download

INCHI for #<Metabolite:0x00007fa4ac781e70>

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
Download
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
Molecular FormulaC10H14O
Average Mass150.2176
Monoisotopic Mass150.10446507
IUPAC Name(5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one
Traditional Namecarvone, (+)-
CAS Registry NumberNot Available
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