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Showing NP-Card for cis-2-Carveol (NP0046523)

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Record Information
Version2.0
Created at2022-03-17 20:04:39 UTC
Updated at2022-03-17 20:04:39 UTC
NP-MRD IDNP0046523
Secondary Accession NumbersNone
Natural Product Identification
Common Namecis-2-Carveol
Description(-)-Cis-Carveol 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. Thus, (-)-cis-carveol is considered to be an isoprenoid lipid molecule (-)-cis-Carveol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (-)-cis-Carveol is a spearmint tasting compound. Outside of the human body, (-)-cis-Carveol has been detected, but not quantified in, citrus. This could make (-)-cis-carveol a potential biomarker for the consumption of these foods. cis-2-Carveol is found in Achillea millefolium, Aegle marmelos, Agastache rugosa, Agathosma betulina, Aloysia citrodora, Anthemis aciphylla, Artemisia herba-alba, Artemisia judaica, Artemisia sericea, Baccharis dracunculifolia, Bellis perennis, Cantinoa mutabilis, Citrus aurantiifolia, Cymbopogon martinii, Cyperus rotundus, Diplotaenia cachrydifolia, Grindelia hirsutula, Laser trilobum, Lepechinia floribunda, Mentha arvensis, Mentha spicata, Micromeria sinaica, Myrcianthes fragrans, Origanum syriacum, Piper nigrum, Salvia cuspidata, Stoebe vulgaris, Thapsia villosa and Xylopia aromatica. The (1R,5R)-stereoisomer of carveol.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0046523 (cis-2-Carveol)


  Mrv0541 02241217232D          

 11 11  0  0  1  0            999 V2000
    2.5006   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    0.2063    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0717    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006    1.4438    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2151    1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006    0.6188    0.0000 C   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
  4  2  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
  4 11  1  0  0  0  0
M  END
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3D MOL for NP0046523 (cis-2-Carveol)

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3D SDF for NP0046523 (cis-2-Carveol)

  Mrv0541 02241217232D          

 11 11  0  0  1  0            999 V2000
    2.5006   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    0.2063    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0717    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006    1.4438    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2151    1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006    0.6188    0.0000 C   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
  4  2  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
  4 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046523

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9-11H,1,5-6H2,2-3H3/t9-,10-/m1/s1

> <INCHI_KEY>
BAVONGHXFVOKBV-NXEZZACHSA-N

> <FORMULA>
C10H16O

> <MOLECULAR_WEIGHT>
152.2334

> <EXACT_MASS>
152.120115134

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
18.390495237035452

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-ol

> <ALOGPS_LOGP>
2.41

> <JCHEM_LOGP>
1.9890015846666664

> <ALOGPS_LOGS>
-1.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.207236734718403

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3959546522341704

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
47.995799999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.82e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-cis-carveol

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0046523 (cis-2-Carveol)
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PDB for NP0046523 (cis-2-Carveol)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       4.668  -1.925   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.334  -1.155   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.001  -1.925   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.334   0.385   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.001   1.155   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.001   2.695   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.334   3.465   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.334   5.005   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.668   2.695   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.002   3.465   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.668   1.155   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    4                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for NP0046523 (cis-2-Carveol)
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SMILES for NP0046523 (cis-2-Carveol)
CC(=C)[C@@H]1CC=C(C)[C@H](O)C1
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INCHI for NP0046523 (cis-2-Carveol)
InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9-11H,1,5-6H2,2-3H3/t9-,10-/m1/s1
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View in JSmol
Synonyms
ValueSource
(-)-(4R,6R)-cis-CarveolChEBI
(-)-cis-p-Mentha-1,8-dien-6-olHMDB
(1R)-cis-CarveolHMDB
(1R,5R)-(-)-cis-CarveolHMDB
(1R-cis)-2-Methyl-5-(1-methylvinyl)cyclohex-2-en-1-olHMDB
(1R-cis)-2-Methyl-5-isopropenyl-2-cyclohexen-1-olHMDB
(4R,6R)-p-Mentha-1,8-dien-6-olHMDB
2-Methyl-5-(1-methylethenyl)-(1R,5R)-2-cyclohexen-1-olHMDB
2-Methyl-5-(1-methylethenyl)-(1R-cis)-2-cyclohexen-1-olHMDB
cis-(-)-CarveolHMDB
Chemical FormulaC10H16O
Average Mass152.2334 Da
Monoisotopic Mass152.12012 Da
IUPAC Name(1R,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-ol
Traditional Name(-)-cis-carveol
CAS Registry Number2102-59-2
SMILES
CC(=C)[C@@H]1CC=C(C)[C@H](O)C1
InChI Identifier
InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9-11H,1,5-6H2,2-3H3/t9-,10-/m1/s1
InChI KeyBAVONGHXFVOKBV-NXEZZACHSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Achillea millefoliumLOTUS Database
Aegle marmelosLOTUS Database
Agastache rugosaLOTUS Database
Agathosma betulinaLOTUS Database
Aloysia citrodoraLOTUS Database
Anthemis aciphyllaLOTUS Database
Artemisia herba-albaLOTUS Database
Artemisia judaicaLOTUS Database
Artemisia sericeaLOTUS Database
Baccharis dracunculifoliaLOTUS Database
Bellis perennisLOTUS Database
Cantinoa mutabilisLOTUS Database
Carum carviFooDB
Citrus aurantiifoliaLOTUS Database
Cymbopogon martiniiLOTUS Database
Cyperus rotundusLOTUS Database
Diplotaenia cachrydifoliaLOTUS Database
Grindelia hirsutulaLOTUS Database
Laser trilobumLOTUS Database
Lepechinia floribundaLOTUS Database
Mentha arvensisLOTUS Database
Mentha spicataLOTUS Database
Micromeria sinaicaLOTUS Database
Myrcianthes fragransLOTUS Database
Origanum syriacumLOTUS Database
Piper nigrumLOTUS Database
Salvia cuspidataLOTUS Database
Stoebe vulgarisLOTUS Database
Thapsia villosaLOTUS Database
Xylopia aromaticaLOTUS Database
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
    • 

  • Secondary alcohol
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.41ALOGPS
logP1.99ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)18.21ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity48 m³·mol⁻¹ChemAxon
Polarizability18.39 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0036082  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014918  
KNApSAcK IDC00029971  
Chemspider ID292842  
KEGG Compound IDC11395  
BioCyc IDCPD-10050  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound330573  
PDB IDNot Available
ChEBI ID227  
Good Scents IDNot Available
References
General References