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Showing NP-Card for 1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-ol (NP0214609)

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Record Information
Version2.0
Created at2022-09-05 13:57:25 UTC
Updated at2022-09-05 13:57:25 UTC
NP-MRD IDNP0214609
Secondary Accession NumbersNone
Natural Product Identification
Common Name1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-ol
DescriptionSabinol belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. 1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-ol is found in Anethum graveolens, Cannabis sativa, Hyptis spicigera, Citrus aurantiifolia, Citrus aurantium, Clinopodium grandiflorum, Echinophora tenuifolia, Helianthus annuus, Larix occidentalis, Rhanterium epapposum and Salvia absconditiflora. Sabinol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0214609 (1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-ol)


  Mrv1533004201505142D          

 11 12  0  0  0  0            999 V2000
    1.6073    1.7724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1224    1.1050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3019    1.1912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4579    0.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2425    0.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7275   -0.0612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5525   -0.0612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2425   -0.7286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4975   -1.5133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4579   -0.4737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7434   -0.0612    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
  2  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
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
M  END
Download

3D MOL for NP0214609 (1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-ol)

     RDKit          3D

 27 28  0  0  0  0  0  0  0  0999 V2000
    2.8022    1.4979    1.0119 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8252    0.7015    0.6006 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9568   -0.2079   -0.5709 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8624   -1.2203   -0.2565 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5674   -0.7343   -0.8273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3065   -0.1523    0.2338 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6902    0.3502   -0.0996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8092    0.8948   -1.4766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6361   -0.8413    0.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0641   -0.7309    1.6119 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4980    0.5805    1.2015 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7676    1.5387    0.5179 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6544    2.1375    1.8671 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3018    0.3056   -1.4795 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0072   -1.7616   -1.0933 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1866   -0.4982   -1.8290 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5822   -1.8387   -0.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9432    1.1377    0.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6674    1.6257   -1.4837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9398    1.4354   -1.8457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1237    0.1056   -2.2190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1924   -1.7462   -0.3719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5995   -0.6289   -0.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7645   -1.0472    1.1690 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5965   -1.6245    1.7098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9454   -0.7457    2.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0737    1.4669    1.7322 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  9  1  0
  6  7  1  6
  6 10  1  0
 10 11  1  0
 11  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  1  0
  3  5  1  0
 11  6  1  0
  5  6  1  0
  8 19  1  0
  8 20  1  0
  8 21  1  0
  7 18  1  0
  9 22  1  0
  9 23  1  0
  9 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  1
  1 12  1  0
  1 13  1  0
  3 14  1  6
  4 15  1  0
  5 16  1  0
  5 17  1  0
M  END
Download

3D SDF for NP0214609 (1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-ol)


  Mrv1533004201505142D          

 11 12  0  0  0  0            999 V2000
    1.6073    1.7724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1224    1.1050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3019    1.1912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4579    0.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2425    0.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7275   -0.0612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5525   -0.0612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2425   -0.7286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4975   -1.5133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4579   -0.4737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7434   -0.0612    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
  2  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
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0214609

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C12CC1C(=C)C(O)C2

> <INCHI_IDENTIFIER>
InChI=1S/C10H16O/c1-6(2)10-4-8(10)7(3)9(11)5-10/h6,8-9,11H,3-5H2,1-2H3

> <INCHI_KEY>
MDFQXBNVOAKNAY-UHFFFAOYSA-N

> <FORMULA>
C10H16O

> <MOLECULAR_WEIGHT>
152.237

> <EXACT_MASS>
152.120115135

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
18.084450526033237

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
1.90

> <JCHEM_LOGP>
1.628784049666666

> <ALOGPS_LOGS>
-1.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.87382847462683

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5417874251982244

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
45.165299999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.73e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-ol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0214609 (1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-ol)

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PDB for NP0214609 (1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-ol)
HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0       3.000   3.308   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.095   2.063   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.563   2.224   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.721   0.656   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.186   1.132   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.091  -0.114   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.631  -0.114   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.186  -1.360   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.662  -2.825   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.721  -0.884   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.388  -0.114   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   10   11                                             
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    4   11                                                  
CONECT   11   10    4                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END

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3D PDB for NP0214609 (1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-ol)
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SMILES for NP0214609 (1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-ol)
CC(C)C12CC1C(=C)C(O)C2
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INCHI for NP0214609 (1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-ol)
InChI=1S/C10H16O/c1-6(2)10-4-8(10)7(3)9(11)5-10/h6,8-9,11H,3-5H2,1-2H3
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View in JSmol
Synonyms
ValueSource
Sabinol, (1alpha,3alpha,5alpha)-isomerMeSH
Sabinol, (1alpha,3beta,5alpha)-isomerMeSH
Chemical FormulaC10H16O
Average Mass152.2370 Da
Monoisotopic Mass152.12012 Da
IUPAC Name4-methylidene-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-ol
Traditional Name1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-ol
CAS Registry NumberNot Available
SMILES
CC(C)C12CC1C(=C)C(O)C2
InChI Identifier
InChI=1S/C10H16O/c1-6(2)10-4-8(10)7(3)9(11)5-10/h6,8-9,11H,3-5H2,1-2H3
InChI KeyMDFQXBNVOAKNAY-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
Anethum graveolensLOTUS Database
Cannabis sativaLOTUS Database
Cantinoa americanaLOTUS Database
Citrus aurantiifoliaLOTUS Database
Citrus aurantiumLOTUS Database
Clinopodium grandiflorumLOTUS Database
Echinophora tenuifoliaLOTUS Database
Helianthus annuusLOTUS Database
Larix occidentalisLOTUS Database
Rhanterium epapposumLOTUS Database
Salvia absconditifloraLOTUS 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 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
logP1.9ALOGPS
logP1.63ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)17.87ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity45.17 m³·mol⁻¹ChemAxon
Polarizability18.08 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 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 Compound564260  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]