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Showing metabocard for (R)-Carvone (HMDB0035089)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 20:01:58 UTC
Update Date2022-03-07 02:54:21 UTC
HMDB IDHMDB0035089
Secondary Accession Numbers
  • HMDB35089
Metabolite Identification
Common Name(R)-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 a volatile terpenoid found in cannabis plants (PMID:6991645 ). 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0035089 ((R)-Carvone)

  Mrv1652303202019012D          

 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  1  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  6  0  0  0
  7  4  2  0  0  0  0
  8  5  1  0  0  0  0
M  END
Download

3D MOL for HMDB0035089 ((R)-Carvone)

HMDB0035089
     RDKit          3D
(R)-Carvone
 25 25  0  0  0  0  0  0  0  0999 V2000
   -2.5641    0.6527    1.4129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0477   -0.1250    0.4759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9289   -1.2229   -0.0654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6707    0.0444   -0.0405 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1595   -1.1914    0.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5665   -0.9284   -0.1885 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1384    0.2505   -0.1750 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5604    0.4032   -0.5449 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3710    1.4225    0.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8693    2.5548    0.1409 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0254    1.1992    0.6754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5616    0.4866    1.7506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9827    1.4711    1.8510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8333   -0.7531   -0.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1628   -1.8949    0.8065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3963   -1.8476   -0.8020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7114    0.3152   -1.1187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0932   -1.5319    1.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2078   -2.0178   -0.4839 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1944   -1.7749   -0.4844 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0860    1.0978    0.1656 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0526   -0.5820   -0.5251 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6161    0.8570   -1.5437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5880    2.1360    0.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0269    0.9791    1.7659 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  6
  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 HMDB0035089 ((R)-Carvone)

  Mrv1652303202019012D          

 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  1  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  6  0  0  0
  7  4  2  0  0  0  0
  8  5  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035089

> <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-/m1/s1

> <INCHI_KEY>
ULDHMXUKGWMISQ-SECBINFHSA-N

> <FORMULA>
C10H14O

> <MOLECULAR_WEIGHT>
150.2176

> <EXACT_MASS>
150.10446507

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
17.648483865240138

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5R)-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>
47.173500000000004

> <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 HMDB0035089 ((R)-Carvone)

HMDB0035089
     RDKit          3D
(R)-Carvone
 25 25  0  0  0  0  0  0  0  0999 V2000
   -2.5641    0.6527    1.4129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0477   -0.1250    0.4759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9289   -1.2229   -0.0654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6707    0.0444   -0.0405 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1595   -1.1914    0.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5665   -0.9284   -0.1885 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1384    0.2505   -0.1750 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5604    0.4032   -0.5449 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3710    1.4225    0.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8693    2.5548    0.1409 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0254    1.1992    0.6754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5616    0.4866    1.7506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9827    1.4711    1.8510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8333   -0.7531   -0.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1628   -1.8949    0.8065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3963   -1.8476   -0.8020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7114    0.3152   -1.1187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0932   -1.5319    1.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2078   -2.0178   -0.4839 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1944   -1.7749   -0.4844 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0860    1.0978    0.1656 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0526   -0.5820   -0.5251 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6161    0.8570   -1.5437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5880    2.1360    0.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0269    0.9791    1.7659 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  6
  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 HMDB0035089 ((R)-Carvone)

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    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 HMDB0035089 ((R)-Carvone)

COMPND    HMDB0035089
HETATM    1  C1  UNL     1      -2.564   0.653   1.413  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.048  -0.125   0.476  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.929  -1.223  -0.065  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.671   0.044  -0.041  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.159  -1.191   0.161  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.567  -0.928  -0.188  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.138   0.251  -0.175  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.560   0.403  -0.545  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.371   1.422   0.207  1.00  0.00           C  
HETATM   10  O1  UNL     1       1.869   2.555   0.141  1.00  0.00           O  
HETATM   11  C10 UNL     1      -0.025   1.199   0.675  1.00  0.00           C  
HETATM   12  H1  UNL     1      -3.562   0.487   1.751  1.00  0.00           H  
HETATM   13  H2  UNL     1      -1.983   1.471   1.851  1.00  0.00           H  
HETATM   14  H3  UNL     1      -3.833  -0.753  -0.481  1.00  0.00           H  
HETATM   15  H4  UNL     1      -3.163  -1.895   0.807  1.00  0.00           H  
HETATM   16  H5  UNL     1      -2.396  -1.848  -0.802  1.00  0.00           H  
HETATM   17  H6  UNL     1      -0.711   0.315  -1.119  1.00  0.00           H  
HETATM   18  H7  UNL     1       0.093  -1.532   1.195  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.208  -2.018  -0.484  1.00  0.00           H  
HETATM   20  H9  UNL     1       2.194  -1.775  -0.484  1.00  0.00           H  
HETATM   21  H10 UNL     1       4.086   1.098   0.166  1.00  0.00           H  
HETATM   22  H11 UNL     1       4.053  -0.582  -0.525  1.00  0.00           H  
HETATM   23  H12 UNL     1       3.616   0.857  -1.544  1.00  0.00           H  
HETATM   24  H13 UNL     1      -0.588   2.136   0.530  1.00  0.00           H  
HETATM   25  H14 UNL     1      -0.027   0.979   1.766  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 HMDB0035089 ((R)-Carvone)

CC(=C)[C@@H]1CC=C(C)C(=O)C1
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INCHI for HMDB0035089 ((R)-Carvone)

InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9H,1,5-6H2,2-3H3/t9-/m1/s1
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View in JSmolView Stereo Labels
Synonyms
Chemical FormulaC10H14O
Average Molecular Weight150.2176
Monoisotopic Molecular Weight150.10446507
IUPAC Name(5R)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one
Traditional Name(-)-carvone
CAS Registry Number6485-40-1
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-/m1/s1
InChI KeyULDHMXUKGWMISQ-SECBINFHSA-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 locationRoute of exposureSource
Process
Naturally occurring process
Role
Biological roleIndustrial application
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point< 15 °CNot Available
Boiling Point227.00 to 230.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1.31 mg/mL at 25 °CNot Available
LogP2.71Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB013718
KNApSAcK IDC00000807
Chemspider ID388655
KEGG Compound IDC01767
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound439570
PDB IDNot Available
ChEBI ID15400
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1002741
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References