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Showing NP-Card for (-)-trans-Carveol (NP0048146)

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Record Information
Version2.0
Created at2022-03-17 20:51:50 UTC
Updated at2022-03-17 20:51:50 UTC
NP-MRD IDNP0048146
Secondary Accession NumbersNone
Natural Product Identification
Common Name(-)-trans-Carveol
Description(-)-Trans-Carveol, also known as (1S,5R)-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, (-)-trans-carveol is considered to be an isoprenoid lipid molecule (-)-trans-Carveol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (-)-trans-Carveol exists in all living organisms, ranging from bacteria to humans (-)-trans-Carveol is a caraway and solvent tasting compound. Outside of the human body, (-)-trans-Carveol has been detected, but not quantified in, several different foods, such as caraway, citrus, dills, and spearmints. (-)-trans-Carveol is found in Achillea grandifolia, Aegle marmelos, Agastache rugosa, Agathosma betulina, Aloysia citrodora, Anthemis aciphylla, Artemisia herba-alba, Artemisia sericea, Artemisia vulgaris, Baccharis dracunculifolia, Bellis perennis, Boltonia asteroides, Calyptranthes spruceana, Cistus incanus, Citrus aurantiifolia, Citrus reticulata, Cymbopogon martinii, Echinophora tournefortii, Foeniculum vulgare, Grindelia hirsutula, Hedychium spicatum, Helianthus annuus, Homo sapiens, Juniperus jaliscana, Kippistia suaedifolia, Laser trilobum, Lavandula stoechas, Malva sylvestris, Mentha arvensis, Micromeria cristata, Micromeria sinaica, Mikania cordifolia, Myrtus communis, Pectis elongata, Piper nigrum, Pistacia atlantica, Renealmia floribunda, Rhodiola rosea, Rhododendron groenlandicum, Teucrium polium, Thapsia maxima, Thuja occidentalis, Xylopia aromatica and Zingiber mioga. This could make (-)-trans-carveol a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0048146 ((-)-trans-Carveol)


  Mrv1652306131900232D          

 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  1  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  1  1  0  0  0
  8  5  1  0  0  0  0
M  END
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3D MOL for NP0048146 ((-)-trans-Carveol)

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3D SDF for NP0048146 ((-)-trans-Carveol)

  Mrv1652306131900232D          

 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  1  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  1  1  0  0  0
  8  5  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048146

> <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-ZJUUUORDSA-N

> <FORMULA>
C10H16O

> <MOLECULAR_WEIGHT>
152.2334

> <EXACT_MASS>
152.120115134

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
17.995093355874936

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,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>
47.9958

> <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 NP0048146 ((-)-trans-Carveol)
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PDB for NP0048146 ((-)-trans-Carveol)
HEADER    PROTEIN                                 13-JUN-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-JUN-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 NP0048146 ((-)-trans-Carveol)
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SMILES for NP0048146 ((-)-trans-Carveol)
CC(=C)[C@@H]1CC=C(C)[C@@H](O)C1
Download
INCHI for NP0048146 ((-)-trans-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,6S)-trans-CarveolChEBI
(1S,5R)-CarveolChEBI
CarveolHMDB
(-)-(4R,6S)-CarveolHMDB
(1S,5R)-2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-olHMDB
(e)-CarveolHMDB
(±)-trans-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(1S,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-ol
Traditional Name(-)-trans-carveol
CAS Registry Number1197-07-5
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-ZJUUUORDSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Achillea grandifoliaLOTUS Database
Aegle marmelosLOTUS Database
Agastache rugosaLOTUS Database
Agathosma betulinaLOTUS Database
Aloysia citrodoraLOTUS Database
Anethum graveolensFooDB
Anthemis aciphyllaLOTUS Database
Artemisia herba-albaLOTUS Database
Artemisia sericeaLOTUS Database
Artemisia vulgarisLOTUS Database
Baccharis dracunculifoliaLOTUS Database
Bellis perennisLOTUS Database
Boltonia asteroidesLOTUS Database
Calyptranthes spruceanaLOTUS Database
Carum carviFooDB
Cistus incanusLOTUS Database
Citrus aurantiifoliaLOTUS Database
Citrus reticulataLOTUS Database
Cymbopogon martiniiLOTUS Database
Echinophora tournefortiiLOTUS Database
Foeniculum vulgareLOTUS Database
Grindelia hirsutulaLOTUS Database
Hedychium spicatumLOTUS Database
Helianthus annuusLOTUS Database
Homo sapiensLOTUS Database
Juniperus jaliscanaLOTUS Database
Kippistia suaedifoliaLOTUS Database
Laser trilobumLOTUS Database
Lavandula stoechasLOTUS Database
Malva sylvestrisLOTUS Database
Mentha arvensisLOTUS Database
Mentha spicataFooDB
Micromeria cristataLOTUS Database
Micromeria sinaicaLOTUS Database
Mikania cordifoliaLOTUS Database
Myrtus communisLOTUS Database
Pectis elongataLOTUS Database
Piper nigrumLOTUS Database
Pistacia atlanticaLOTUS Database
Renealmia floribundaLOTUS Database
Rhodiola roseaLOTUS Database
Rhododendron groenlandicumLOTUS Database
Teucrium poliumLOTUS Database
Thapsia maximaLOTUS Database
Thuja occidentalisLOTUS Database
Xylopia aromaticaLOTUS Database
Zingiber miogaLOTUS 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 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0003450  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB013717  
KNApSAcK IDC00000814  
Chemspider ID85031  
KEGG Compound IDC00964  
BioCyc IDNot Available
BiGG ID36494  
Wikipedia LinkCarveol  
METLIN ID6934  
PubChem Compound94221  
PDB IDNot Available
ChEBI ID15389  
Good Scents IDNot Available
References
General ReferencesNot Available