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Showing NP-Card for trans-1-Carveol (NP0046526)

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Record Information
Version2.0
Created at2022-03-17 20:04:42 UTC
Updated at2022-03-17 20:04:42 UTC
NP-MRD IDNP0046526
Secondary Accession NumbersNone
Natural Product Identification
Common Nametrans-1-Carveol
Description(+)-Trans-Carveol, also known as (1R,5S)-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. It is a substrate for cytochrome P450 2C9 and cytochrome P450 2C19 (+)-trans-Carveol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (+)-trans-Carveol has been detected, but not quantified in, caraway. trans-1-Carveol is found in Anethum graveolens and Mentha aquatica. This could make (+)-trans-carveol a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0046526 (trans-1-Carveol)


  Mrv1652307201902242D          

 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  2  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  1  6  0  0  0
  8  5  1  0  0  0  0
M  END
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3D MOL for NP0046526 (trans-1-Carveol)

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3D SDF for NP0046526 (trans-1-Carveol)

  Mrv1652307201902242D          

 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  2  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  1  6  0  0  0
  8  5  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046526

> <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+/m0/s1

> <INCHI_KEY>
BAVONGHXFVOKBV-VHSXEESVSA-N

> <FORMULA>
C10H16O

> <MOLECULAR_WEIGHT>
152.2334

> <EXACT_MASS>
152.120115134

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
18.071609543885224

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,5S)-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>
(+)-trans-carveol

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0046526 (trans-1-Carveol)
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PDB for NP0046526 (trans-1-Carveol)
HEADER    PROTEIN                                 20-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUL-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 NP0046526 (trans-1-Carveol)
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SMILES for NP0046526 (trans-1-Carveol)
CC(=C)[C@H]1CC=C(C)[C@H](O)C1
Download
INCHI for NP0046526 (trans-1-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+/m0/s1
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View in JSmol
Synonyms
ValueSource
(1R,5S)-CarveolChEBI
(4S,6R)-trans-CarveolChEBI
(1R,5S)-2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-olHMDB
(e)-CarveolHMDB
(±)-trans-carveolHMDB
CarveolHMDB
trans-(+)-CarveolHMDB
trans-5-(1-Methylethenyl)-2-methyl-2-cyclohexenolHMDB
trans-CarveolHMDB
trans-Mentha-1,8-dien-6-olHMDB
(+)-trans-CarveolHMDB
Chemical FormulaC10H16O
Average Mass152.2334 Da
Monoisotopic Mass152.12012 Da
IUPAC Name(1R,5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-ol
Traditional Name(+)-trans-carveol
CAS Registry NumberNot Available
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+/m0/s1
InChI KeyBAVONGHXFVOKBV-VHSXEESVSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anethum graveolensLOTUS Database
Carum carviFooDB
Mentha aquaticaLOTUS 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
Polarizability18.07 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0059608  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB004802  
KNApSAcK IDC00010883  
Chemspider IDNot Available
KEGG Compound IDC11409  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound443178  
PDB IDNot Available
ChEBI ID15388  
Good Scents IDNot Available
References
General References