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Showing NP-Card for (1r,3r)-1-isopropyl-4-methylbicyclo[3.1.0]hexan-3-ol (NP0274090)

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Record Information
Version2.0
Created at2022-09-08 21:20:50 UTC
Updated at2022-09-08 21:20:50 UTC
NP-MRD IDNP0274090
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1r,3r)-1-isopropyl-4-methylbicyclo[3.1.0]hexan-3-ol
DescriptionCis-Thujanol belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. (1r,3r)-1-isopropyl-4-methylbicyclo[3.1.0]hexan-3-ol is found in Alpinia zerumbet, Clinopodium grandiflorum, Origanum onites and Origanum vulgare. Cis-Thujanol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0274090 ((1r,3r)-1-isopropyl-4-methylbicyclo[3.1.0]hexan-3-ol)


  Mrv0541 02241221212D          

 11 12  0  0  1  0            999 V2000
    2.4975    2.3383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2425    1.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7275    0.8862    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2425    0.2188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4579    0.4737    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4579    1.2987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7434    0.8862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1224   -0.2800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3019   -0.3662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6073   -0.9474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5525    0.8862    0.0000 O   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
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  6  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  3 11  1  6  0  0  0
M  END
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3D MOL for NP0274090 ((1r,3r)-1-isopropyl-4-methylbicyclo[3.1.0]hexan-3-ol)

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3D SDF for NP0274090 ((1r,3r)-1-isopropyl-4-methylbicyclo[3.1.0]hexan-3-ol)

  Mrv0541 02241221212D          

 11 12  0  0  1  0            999 V2000
    2.4975    2.3383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2425    1.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7275    0.8862    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2425    0.2188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4579    0.4737    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4579    1.2987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7434    0.8862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1224   -0.2800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3019   -0.3662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6073   -0.9474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5525    0.8862    0.0000 O   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
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  6  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  3 11  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0274090

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@]12CC1C(C)[C@H](O)C2

> <INCHI_IDENTIFIER>
InChI=1S/C10H18O/c1-6(2)10-4-8(10)7(3)9(11)5-10/h6-9,11H,4-5H2,1-3H3/t7?,8?,9-,10-/m1/s1

> <INCHI_KEY>
DZVXRFMREAADPP-YDYPAMBWSA-N

> <FORMULA>
C10H18O

> <MOLECULAR_WEIGHT>
154.2493

> <EXACT_MASS>
154.135765198

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
18.71959848854658

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,3R)-4-methyl-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-ol

> <ALOGPS_LOGP>
1.59

> <JCHEM_LOGP>
1.8984761306666673

> <ALOGPS_LOGS>
-2.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.66465984866217

> <JCHEM_PKA_STRONGEST_BASIC>
-1.1958777821951667

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
45.4648

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.59e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3R)-1-isopropyl-4-methylbicyclo[3.1.0]hexan-3-ol

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0274090 ((1r,3r)-1-isopropyl-4-methylbicyclo[3.1.0]hexan-3-ol)
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PDB for NP0274090 ((1r,3r)-1-isopropyl-4-methylbicyclo[3.1.0]hexan-3-ol)
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       4.662   4.365   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.186   2.900   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.091   1.654   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.186   0.408   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.721   0.884   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.721   2.424   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.388   1.654   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.095  -0.523   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.564  -0.684   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.000  -1.768   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.631   1.654   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7    8                                             
CONECT    6    5    2    7                                                  
CONECT    7    6    5                                                       
CONECT    8    5    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    3                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END

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3D PDB for NP0274090 ((1r,3r)-1-isopropyl-4-methylbicyclo[3.1.0]hexan-3-ol)
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SMILES for NP0274090 ((1r,3r)-1-isopropyl-4-methylbicyclo[3.1.0]hexan-3-ol)
CC(C)[C@]12CC1C(C)[C@H](O)C2
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INCHI for NP0274090 ((1r,3r)-1-isopropyl-4-methylbicyclo[3.1.0]hexan-3-ol)
InChI=1S/C10H18O/c1-6(2)10-4-8(10)7(3)9(11)5-10/h6-9,11H,4-5H2,1-3H3/t7?,8?,9-,10-/m1/s1
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SynonymsNot Available
Chemical FormulaC10H18O
Average Mass154.2493 Da
Monoisotopic Mass154.13577 Da
IUPAC Name(1R,3R)-4-methyl-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-ol
Traditional Name(1R,3R)-1-isopropyl-4-methylbicyclo[3.1.0]hexan-3-ol
CAS Registry NumberNot Available
SMILES
CC(C)[C@]12CC1C(C)[C@H](O)C2
InChI Identifier
InChI=1S/C10H18O/c1-6(2)10-4-8(10)7(3)9(11)5-10/h6-9,11H,4-5H2,1-3H3/t7?,8?,9-,10-/m1/s1
InChI KeyDZVXRFMREAADPP-YDYPAMBWSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Alpinia zerumbetLOTUS Database
Clinopodium grandiflorumLOTUS Database
Origanum onitesLOTUS Database
Origanum vulgareLOTUS 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
  • Bicyclic monoterpenoid
    • 

  • Thujane monoterpenoid
    • 

  • Cyclic alcohol
    • 

  • Secondary alcohol
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
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
logP1.59ALOGPS
logP1.9ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)18.66ChemAxon
pKa (Strongest Basic)-1.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity45.46 m³·mol⁻¹ChemAxon
Polarizability18.72 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB006372  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3034320  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]