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Showing NP-Card for 5-(1-Methylethyl)bicyclo[3.1.0]hexan-2-one (NP0084390)

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Record Information
Version2.0
Created at2022-04-29 05:07:55 UTC
Updated at2022-04-29 05:07:56 UTC
NP-MRD IDNP0084390
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-(1-Methylethyl)bicyclo[3.1.0]hexan-2-one
Description5-Isopropylbicyclo[3.1.0]Hexan-2-one, also known as 5-(1-methylethyl)-bicyclo(3.1.0)Hexan-2-one or sabina ketone, belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. 5-Isopropylbicyclo[3.1.0]Hexan-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 5-Isopropylbicyclo[3.1.0]Hexan-2-one has been detected, but not quantified in, herbs and spices and root vegetables. 5-(1-Methylethyl)bicyclo[3.1.0]hexan-2-one is found in Artemisia salsoloides, Artemisia sp., Atalantia guillauminii, Cyperus rotundus, Daucus carota , Lavandula angustifolia , Lavandula dentata , Mandragora autumnalis , Tanacetum vulgare , Teucrium polium and Zanthoxylum simulans. This could make 5-isopropylbicyclo[3.1.0]Hexan-2-one a potential biomarker for the consumption of these foods.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0084390 (5-(1-Methylethyl)bicyclo[3.1.0]hexan-2-one)


  Mrv0541 05061308192D          

 10 11  0  0  0  0            999 V2000
    0.3019    2.1386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6073    2.7198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7275    0.8862    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
    0.7434    0.8862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1224    2.0524    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
    2.2425    0.2188    0.0000 C   0  0  0  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
    2.4975   -0.5659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  6  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  5  1  0  0  0  0
  8  3  1  0  0  0  0
  8  7  1  0  0  0  0
  9  4  1  0  0  0  0
  9  5  1  0  0  0  0
  9  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  2  0  0  0  0
M  END
Download

3D MOL for NP0084390 (5-(1-Methylethyl)bicyclo[3.1.0]hexan-2-one)

     RDKit          3D

 24 25  0  0  0  0  0  0  0  0999 V2000
    1.6034   -0.2191   -1.5582 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2504   -0.5451   -0.1256 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2086    0.2076    0.7879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1360   -0.1504    0.2403 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7030    1.0534   -0.4639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2064    0.8906   -0.5028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4854   -0.4573    0.0535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5782   -0.9613    0.1606 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2233   -1.1192    0.4694 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5518   -0.4440    1.6441 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5960   -0.6617   -1.7854 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8751   -0.7305   -2.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6813    0.8601   -1.7380 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4698   -1.6230    0.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2357   -0.1615    0.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8072    0.1045    1.8301 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2011    1.2996    0.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3766    1.9540    0.0775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3433    1.0240   -1.5135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5950    0.8964   -1.5423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6399    1.7016    0.1158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1183   -2.1982    0.3215 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0943   -1.0828    2.2547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0657    0.3624    2.1829 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  4  2  1  0
  4 10  1  1
 10  9  1  0
  9  7  1  0
  7  8  2  0
  7  6  1  0
  6  5  1  0
  9  4  1  0
  5  4  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
  3 17  1  0
 10 23  1  0
 10 24  1  0
  9 22  1  1
  6 20  1  0
  6 21  1  0
  5 18  1  0
  5 19  1  0
M  END
Download

3D SDF for NP0084390 (5-(1-Methylethyl)bicyclo[3.1.0]hexan-2-one)


  Mrv0541 05061308192D          

 10 11  0  0  0  0            999 V2000
    0.3019    2.1386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6073    2.7198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7275    0.8862    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
    0.7434    0.8862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1224    2.0524    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
    2.2425    0.2188    0.0000 C   0  0  0  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
    2.4975   -0.5659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  6  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  5  1  0  0  0  0
  8  3  1  0  0  0  0
  8  7  1  0  0  0  0
  9  4  1  0  0  0  0
  9  5  1  0  0  0  0
  9  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0084390

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C12CC1C(=O)CC2

> <INCHI_IDENTIFIER>
InChI=1S/C9H14O/c1-6(2)9-4-3-8(10)7(9)5-9/h6-7H,3-5H2,1-2H3

> <INCHI_KEY>
MDDYCNAAAZKNAJ-UHFFFAOYSA-N

> <FORMULA>
C9H14O

> <MOLECULAR_WEIGHT>
138.2069

> <EXACT_MASS>
138.10446507

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
16.064459696363546

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-(propan-2-yl)bicyclo[3.1.0]hexan-2-one

> <ALOGPS_LOGP>
1.53

> <JCHEM_LOGP>
1.9969712880000001

> <ALOGPS_LOGS>
-1.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.903360239817477

> <JCHEM_PKA_STRONGEST_BASIC>
-7.422305654380924

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
39.991

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.11e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sabinaketone

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0084390 (5-(1-Methylethyl)bicyclo[3.1.0]hexan-2-one)

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PDB for NP0084390 (5-(1-Methylethyl)bicyclo[3.1.0]hexan-2-one)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       0.564   3.992   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.000   5.077   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   2.900   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.388   1.654   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.095   3.831   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.721   0.884   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.186   0.408   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.721   2.424   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.662  -1.056   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    6                                                            
CONECT    3    4    8                                                       
CONECT    4    3    9                                                       
CONECT    5    7    9                                                       
CONECT    6    1    2    9                                                  
CONECT    7    5    8    9                                                  
CONECT    8    3    7   10                                                  
CONECT    9    4    5    6    7                                             
CONECT   10    8                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   22    0
END

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3D PDB for NP0084390 (5-(1-Methylethyl)bicyclo[3.1.0]hexan-2-one)
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SMILES for NP0084390 (5-(1-Methylethyl)bicyclo[3.1.0]hexan-2-one)
CC(C)C12CC1C(=O)CC2
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INCHI for NP0084390 (5-(1-Methylethyl)bicyclo[3.1.0]hexan-2-one)
InChI=1S/C9H14O/c1-6(2)9-4-3-8(10)7(9)5-9/h6-7H,3-5H2,1-2H3
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View in JSmol
Synonyms
ValueSource
5-(1-Methylethyl)-bicyclo(3.1.0)hexan-2-oneHMDB
5-(1-Methylethyl)-bicyclo[3.1.0]hexan-2-oneHMDB
5-(1-Methylethyl)bicyclo[3.1.0]hexan-2-one, 9ciHMDB
5-Isopropyl-bicyclo[3.1.0]hexan-2-oneHMDB
5-Isopropylbicyclo(3.1.0)hexan-2-oneHMDB
Sabina ketoneHMDB
SabinaketoneHMDB
Sabine ketoneHMDB
Chemical FormulaC9H14O
Average Mass138.2069 Da
Monoisotopic Mass138.10447 Da
IUPAC Name5-(propan-2-yl)bicyclo[3.1.0]hexan-2-one
Traditional Namesabinaketone
CAS Registry NumberNot Available
SMILES
CC(C)C12CC1C(=O)CC2
InChI Identifier
InChI=1S/C9H14O/c1-6(2)9-4-3-8(10)7(9)5-9/h6-7H,3-5H2,1-2H3
InChI KeyMDDYCNAAAZKNAJ-UHFFFAOYSA-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
Artemisia salsoloidesLOTUS Database
Artemisia sp.Plant
Atalantia guillauminiiPlant
Cyperus rotundusLOTUS Database
Daucus carotaPlant
Lavandula angustifoliaPlant
Lavandula dentataPlant
Mandragora autumnalisPlant
Tanacetum vulgarePlant
Teucrium poliumLOTUS Database
Zanthoxylum simulansLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ketones. These are organic compounds  in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbonyl compounds  
Direct ParentKetones  
Alternative Parents
Substituents
  • Ketone
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • 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
logP1.53ALOGPS
logP2ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)19.9ChemAxon
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity39.99 m³·mol⁻¹ChemAxon
Polarizability16.06 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0035229  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB013884  
KNApSAcK IDNot Available
Chemspider ID83758  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound92784  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available