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Showing NP-Card for (+)-Sabinone (NP0045571)

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Record Information
Version2.0
Created at2022-03-17 19:32:03 UTC
Updated at2022-03-17 19:32:03 UTC
NP-MRD IDNP0045571
Secondary Accession NumbersNone
Natural Product Identification
Common Name(+)-Sabinone
Description(+)-Sabinone, also known as (1S,5S)-sabinone, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. (+)-Sabinone is found in Chenopodium ambrosioides and Tanacetum vulgare . Thus, (+)-sabinone is considered to be an isoprenoid lipid molecule (+)-Sabinone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0045571 ((+)-Sabinone)

 
  Mrv0541 02241221082D          
 
 12 13  0  0  1  0            999 V2000
   13.6594  -10.6304    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.3768   -9.3857    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.3768  -10.2107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9455  -10.2107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6450  -11.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6594   -8.9733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9455   -9.3857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9205  -11.6491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3446  -11.6456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6594   -8.1446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2246   -8.9624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9148   -8.7580    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  1  5  1  6  0  0  0
  2  6  1  0  0  0  0
  4  7  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  1  0  0  0  0
  6 10  2  0  0  0  0
  7 11  2  0  0  0  0
  2  3  1  0  0  0  0
  6  7  1  0  0  0  0
  2 12  1  6  0  0  0
M  END
Download

3D MOL for NP0045571 ((+)-Sabinone)

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3D SDF for NP0045571 ((+)-Sabinone)
 
  Mrv0541 02241221082D          
 
 12 13  0  0  1  0            999 V2000
   13.6594  -10.6304    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.3768   -9.3857    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.3768  -10.2107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9455  -10.2107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6450  -11.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6594   -8.9733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9455   -9.3857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9205  -11.6491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3446  -11.6456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6594   -8.1446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2246   -8.9624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9148   -8.7580    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  1  5  1  6  0  0  0
  2  6  1  0  0  0  0
  4  7  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  1  0  0  0  0
  6 10  2  0  0  0  0
  7 11  2  0  0  0  0
  2  3  1  0  0  0  0
  6  7  1  0  0  0  0
  2 12  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0045571

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12C[C@]1(CC(=O)C2=C)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C10H14O/c1-6(2)10-4-8(10)7(3)9(11)5-10/h6,8H,3-5H2,1-2H3/t8-,10+/m1/s1

> <INCHI_KEY>
PBLWMCQDAGOTPV-SCZZXKLOSA-N

> <FORMULA>
C10H14O

> <MOLECULAR_WEIGHT>
150.2176

> <EXACT_MASS>
150.10446507

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
17.40042427389456

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,5S)-4-methylidene-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-one

> <ALOGPS_LOGP>
1.58

> <JCHEM_LOGP>
2.192311755333333

> <ALOGPS_LOGS>
-2.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-5.007121393695666

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
44.342999999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.83e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+)-sabinone

> <JCHEM_VEBER_RULE>
1

$$$$

Download
3D-SDF for NP0045571 ((+)-Sabinone)
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PDB for NP0045571 ((+)-Sabinone)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      25.498 -19.843   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      26.837 -17.520   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      26.837 -19.060   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      24.165 -19.060   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      25.471 -21.015   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      25.498 -16.750   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      24.165 -17.520   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      24.118 -21.745   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      26.777 -21.738   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      25.498 -15.203   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      22.819 -16.730   0.000  0.00  0.00           O+0
HETATM   12  H   UNK     0      27.841 -16.348   0.000  0.00  0.00           H+0
CONECT    1    2    3    4    5                                             
CONECT    2    1    6    3   12                                             
CONECT    3    1    2                                                       
CONECT    4    1    7                                                       
CONECT    5    1    8    9                                                  
CONECT    6    2   10    7                                                  
CONECT    7    4   11    6                                                  
CONECT    8    5                                                            
CONECT    9    5                                                            
CONECT   10    6                                                            
CONECT   11    7                                                            
CONECT   12    2                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

Download
3D PDB for NP0045571 ((+)-Sabinone)
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SMILES for NP0045571 ((+)-Sabinone)
[H][C@]12C[C@]1(CC(=O)C2=C)C(C)C
Download
INCHI for NP0045571 ((+)-Sabinone)
InChI=1S/C10H14O/c1-6(2)10-4-8(10)7(3)9(11)5-10/h6,8H,3-5H2,1-2H3/t8-,10+/m1/s1
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View in JSmol
Synonyms
ValueSource
(1S,5S)-SabinoneChEBI
Chemical FormulaC10H14O
Average Mass150.2176 Da
Monoisotopic Mass150.10447 Da
IUPAC Name(1S,5S)-4-methylidene-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-one
Traditional Name(+)-sabinone
CAS Registry Number67690-48-6
SMILES
[H][C@]12C[C@]1(CC(=O)C2=C)C(C)C
InChI Identifier
InChI=1S/C10H14O/c1-6(2)10-4-8(10)7(3)9(11)5-10/h6,8H,3-5H2,1-2H3/t8-,10+/m1/s1
InChI KeyPBLWMCQDAGOTPV-SCZZXKLOSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Dysphania ambrosioidesPlant
Salvia officinalisFooDB
Tanacetum vulgarePlant
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 ketone
    • 

  • Ketone
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • 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
logP1.58ALOGPS
logP2.19ChemAxon
logS-2.4ALOGPS
pKa (Strongest Basic)-5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity44.34 m³·mol⁻¹ChemAxon
Polarizability17.4 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 IDFDB001455  
KNApSAcK IDC00000828  
Chemspider IDNot Available
KEGG Compound IDC01868  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound439592  
PDB IDNot Available
ChEBI ID15403  
Good Scents IDNot Available
References
General ReferencesNot Available