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Showing NP-Card for carane (NP0213635)

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Record Information
Version2.0
Created at2022-09-05 12:40:53 UTC
Updated at2022-09-05 12:40:53 UTC
NP-MRD IDNP0213635
Secondary Accession NumbersNone
Natural Product Identification
Common Namecarane
DescriptionCis-Carane belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Thus, cis-carane is considered to be an isoprenoid lipid molecule. Cis-Carane is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. carane is found in Aucoumea klaineana and Chrysopogon zizanioides. carane was first documented in 1981 (PMID: 7229954). A carbobicyclic compound that is bicycloheptane substituted by methyl groups at positions 3, 7 and 7 (PMID: 17192005) (PMID: 1492839) (PMID: 8083817) (PMID: 14664397) (PMID: 15525450) (PMID: 21441619).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0213635 (carane)

carane
  Mrv1652304022019362D          

 10 11  0  0  0  0            999 V2000
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0387    1.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0387    0.7643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  6  8  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
M  END
Download

3D MOL for NP0213635 (carane)

     RDKit          3D

 28 29  0  0  0  0  0  0  0  0999 V2000
    3.2336    0.3574    0.2486 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8567    0.0259   -0.2090 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5030   -1.4232   -0.1374 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0042   -1.5518   -0.0717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7175   -0.4751   -0.8340 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3733    0.9145   -0.3313 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7873    0.7748    0.5937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7071    0.3975   -0.0958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8033    0.9666   -1.0042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2182   -0.0303    1.2468 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4926    1.3776   -0.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3403    0.4532    1.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9388   -0.3459   -0.2065 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7786    0.3272   -1.2950 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9363   -1.9995   -0.9883 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9563   -1.8909    0.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2686   -2.5179   -0.5102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2697   -1.5897    0.9998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7759   -0.5753   -1.9169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2242    1.7191   -1.1101 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2088    1.7497    0.9407 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5594    0.2025    1.5124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5287    0.8580   -2.0754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7923    0.5678   -0.7538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7745    2.0789   -0.8149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2838    0.2829    1.4246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2272   -1.1392    1.3794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6314    0.4853    2.0340 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
  7  2  1  0
  8  5  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  6
  3 15  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  6
  6 20  1  6
  7 21  1  0
  7 22  1  0
  9 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 10 28  1  0
M  END
Download

3D SDF for NP0213635 (carane)

carane
  Mrv1652304022019362D          

 10 11  0  0  0  0            999 V2000
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0387    1.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0387    0.7643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  6  8  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0213635

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCC2C(C1)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C10H18/c1-7-4-5-8-9(6-7)10(8,2)3/h7-9H,4-6H2,1-3H3

> <INCHI_KEY>
BWRHOYDPVJPXMF-UHFFFAOYSA-N

> <FORMULA>
C10H18

> <MOLECULAR_WEIGHT>
138.254

> <EXACT_MASS>
138.14085058

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
17.989229463750736

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,7,7-trimethylbicyclo[4.1.0]heptane

> <ALOGPS_LOGP>
4.02

> <JCHEM_LOGP>
3.207240927666667

> <ALOGPS_LOGS>
-4.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
43.872299999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.89e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
carane

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0213635 (carane)

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PDB for NP0213635 (carane)
HEADER    PROTEIN                                 02-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: carane                                            
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-APR-20         0                                  
HETATM    1  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.072   3.193   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.072   1.427   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    2                                                       
CONECT    8    6    5    9   10                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   22    0
END

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3D PDB for NP0213635 (carane)
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SMILES for NP0213635 (carane)
CC1CCC2C(C1)C2(C)C
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INCHI for NP0213635 (carane)
InChI=1S/C10H18/c1-7-4-5-8-9(6-7)10(8,2)3/h7-9H,4-6H2,1-3H3
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View in JSmol
Synonyms
ValueSource
Carane, (1S-(1alpha,3alpha,6alpha))-isomerHMDB
Carane, (1alpha,3beta,6alpha)-isomerHMDB
Carane, (1S-(1alpha,3beta,6alpha))-isomerHMDB
Carane, (1alpha,3alpha,6alpha)-isomerHMDB
(-)-cis-CaraneHMDB
Chemical FormulaC10H18
Average Mass138.2540 Da
Monoisotopic Mass138.14085 Da
IUPAC Name3,7,7-trimethylbicyclo[4.1.0]heptane
Traditional Namecarane
CAS Registry NumberNot Available
SMILES
CC1CCC2C(C1)C2(C)C
InChI Identifier
InChI=1S/C10H18/c1-7-4-5-8-9(6-7)10(8,2)3/h7-9H,4-6H2,1-3H3
InChI KeyBWRHOYDPVJPXMF-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Aucoumea klaineanaLOTUS Database
Vetiveria zizanioidesLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassMonoterpenoids  
Direct ParentBicyclic monoterpenoids  
Alternative Parents
Substituents
  • Carane monoterpenoid
    • 

  • Bicyclic monoterpenoid
    • 

  • Polycyclic hydrocarbon
    • 

  • Saturated hydrocarbon
    • 

  • Hydrocarbon
    • 

  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic 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
logP4.02ALOGPS
logP3.21ChemAxon
logS-4.6ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity43.87 m³·mol⁻¹ChemAxon
Polarizability17.99 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0061796  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound79043  
PDB IDNot Available
ChEBI ID35663  
Good Scents IDNot Available
References
General References
  1. Ishida T, Asakawa Y, Takemoto T, Aratani T: Terpenoids biotransformation in mammals III: Biotransformation of alpha-pinene, beta-pinene, pinane, 3-carene, carane, myrcene, and p-cymene in rabbits. J Pharm Sci. 1981 Apr;70(4):406-15. doi: 10.1002/jps.2600700417. [PubMed:7229954  ] 
  2. Ishida T: Biotransformation of terpenoids by mammals, microorganisms, and plant-cultured cells. Chem Biodivers. 2005 May;2(5):569-90. doi: 10.1002/cbdv.200590038. [PubMed:17192005  ] 
  3. Czarnecki R, Czerwinska K, Grochowska K, Grochowski J, Librowski T, Serda P: Molecular structure and antiaggregating activity of the potent local anaesthetic (-)-4-[2-hydroxy-3-(N-isopropylamino)-propoxyimino]-cis-carane . Arzneimittelforschung. 1992 Nov;42(11):1279-83. [PubMed:1492839  ] 
  4. Librowski T, Nalepa I, Czarnecki R, Vetulani J: The effect of (-)-4-(2-hydroxy-3(N-isopropylamino)-propoxyimino)-cis-carane on basal and forskolin-stimulated accumulation of cyclic AMP in the cerebral cortical slices of the rat. J Pharm Pharmacol. 1994 May;46(5):393-4. doi: 10.1111/j.2042-7158.1994.tb03823.x. [PubMed:8083817  ] 
  5. Dang HS, Roberts BP, Tocher DA: Thiol-catalysed radical-chain redox rearrangement reactions of benzylidene acetals derived from terpenoid diols. Org Biomol Chem. 2003 Nov 21;1(22):4073-84. doi: 10.1039/b309060b. [PubMed:14664397  ] 
  6. Librowski T, Vetulani J, Nalepa I: Carane derivative stereoisomers of different local anaesthetic and antiplatelet activity similarly potentiate forskolin-stimulated cyclic AMP response and bind to beta-adrenoceptors in the rat brain cortex. J Pharm Pharmacol. 2004 Nov;56(11):1429-34. doi: 10.1211/0022357044742. [PubMed:15525450  ] 
  7. Moniczewski A, Librowski T, Lochynski S, Strub D: Evaluation of the irritating influence of carane derivatives and their antioxidant properties in a deoxyribose degradation test. Pharmacol Rep. 2011;63(1):120-9. doi: 10.1016/s1734-1140(11)70406-6. [PubMed:21441619  ] 
  8. LOTUS database [Link]