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Showing NP-Card for (1r,2s,5r)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one (NP0192106)

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Record Information
Version2.0
Created at2022-09-04 09:14:16 UTC
Updated at2022-09-04 09:14:16 UTC
NP-MRD IDNP0192106
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1r,2s,5r)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one
DescriptionSCHEMBL12687613 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,2s,5r)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one is found in Aloysia gratissima, Artemisia alba, Chamaemelum nobile, Dracocephalum nutans, Hyssopus officinalis, Kunzea salina, Melissa officinalis, Pityophthorus pityographus and Xylopia aromatica. Based on a literature review very few articles have been published on SCHEMBL12687613.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0192106 ((1r,2s,5r)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one)


  Mrv1652309042211142D          

 11 12  0  0  1  0            999 V2000
    2.5423    1.5837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1267    0.8710    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5362    0.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3612    0.1512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1206   -0.5580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2957   -0.5544    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2326    0.1301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3017    0.8745    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8862    0.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1594    0.5522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1561   -0.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  8  7  1  6  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
M  END
Download

3D MOL for NP0192106 ((1r,2s,5r)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one)

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
    2.9095   -2.0504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000   -1.5374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2500   -0.2384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3353   -0.1051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000    1.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0607    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0607    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1213   -1.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1213    1.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3191   -2.5635    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4060   -1.0761    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3965   -3.4600    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2395   -3.0146    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2395    2.5379    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9095    1.5737    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.5607    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3465    0.7725    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7440   -0.4105    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -2.5607    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1820   -2.1213    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3034   -0.1372    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0607   -2.1213    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1820    2.1213    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3034    0.1372    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0607    2.1213    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  6  9  1  0
  9 10  1  0
  9 11  1  0
  3  2  1  0
  9  8  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  6
  8 21  1  1
  7 19  1  0
  7 20  1  0
  6 18  1  6
  5 16  1  0
  5 17  1  0
 10 22  1  0
 10 23  1  0
 10 24  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
M  END
Download

3D SDF for NP0192106 ((1r,2s,5r)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one)


  Mrv1652309042211142D          

 11 12  0  0  1  0            999 V2000
    2.5423    1.5837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1267    0.8710    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5362    0.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3612    0.1512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1206   -0.5580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2957   -0.5544    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2326    0.1301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3017    0.8745    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8862    0.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1594    0.5522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1561   -0.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  8  7  1  6  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0192106

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@H]2C[C@H](CC1=O)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C10H16O/c1-6-8-4-7(5-9(6)11)10(8,2)3/h6-8H,4-5H2,1-3H3/t6-,7+,8+/m0/s1

> <INCHI_KEY>
MQPHVIPKLRXGDJ-XLPZGREQSA-N

> <FORMULA>
C10H16O

> <MOLECULAR_WEIGHT>
152.237

> <EXACT_MASS>
152.120115135

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
26.737960975372747

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,5R)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one

> <JCHEM_LOGP>
2.2839903843333342

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.416966553301062

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
44.53959999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,5R)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0192106 ((1r,2s,5r)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one)

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PDB for NP0192106 ((1r,2s,5r)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one)
HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       4.746   2.956   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.970   1.626   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.734   0.289   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.274   0.282   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.959  -1.042   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.419  -1.035   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.301   0.243   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.430   1.632   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.654   0.302   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.298   1.031   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.291  -0.415   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7    2    9                                                  
CONECT    9    8    6   10   11                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END

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3D PDB for NP0192106 ((1r,2s,5r)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one)
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SMILES for NP0192106 ((1r,2s,5r)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one)
C[C@H]1[C@H]2C[C@H](CC1=O)C2(C)C
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INCHI for NP0192106 ((1r,2s,5r)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one)
InChI=1S/C10H16O/c1-6-8-4-7(5-9(6)11)10(8,2)3/h6-8H,4-5H2,1-3H3/t6-,7+,8+/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC10H16O
Average Mass152.2370 Da
Monoisotopic Mass152.12012 Da
IUPAC Name(1R,2S,5R)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one
Traditional Name(1R,2S,5R)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one
CAS Registry NumberNot Available
SMILES
C[C@H]1[C@H]2C[C@H](CC1=O)C2(C)C
InChI Identifier
InChI=1S/C10H16O/c1-6-8-4-7(5-9(6)11)10(8,2)3/h6-8H,4-5H2,1-3H3/t6-,7+,8+/m0/s1
InChI KeyMQPHVIPKLRXGDJ-XLPZGREQSA-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
Aloysia gratissimaLOTUS Database
Artemisia albaLOTUS Database
Chamaemelum nobileLOTUS Database
Dracocephalum nutansLOTUS Database
Hyssopus officinalis L.LOTUS Database
Kunzea salinaLOTUS Database
Melissa officinalisLOTUS Database
Pityophthorus pityographusLOTUS Database
Xylopia aromaticaLOTUS 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
  • Pinane monoterpenoid
    • 

  • Bicyclic monoterpenoid
    • 

  • Cyclic ketone
    • 

  • Ketone
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • 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
logP2.28ChemAxon
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity44.54 m³·mol⁻¹ChemAxon
Polarizability26.74 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 ID61396605  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12311188  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]