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Showing NP-Card for (1r,5s)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one (NP0263485)

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Record Information
Version2.0
Created at2022-09-08 06:41:03 UTC
Updated at2022-09-08 06:41:03 UTC
NP-MRD IDNP0263485
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1r,5s)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one
DescriptionVERBENONE 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,5s)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one is found in Annona squamosa, Artemisia judaica, Artemisia sericea, Artemisia thuscula, Asarum canadense, Athamanta macedonica, Blepharocalyx tweediei, Boswellia serrata, Brassica nigra, Cleonia lusitanica, Cryptomeria japonica, Curcuma pierreana, Echinophora tenuifolia, Etlingera elatior, Eucalyptus approximans, Eucalyptus bridgesiana, Eucalyptus saligna, Gossypium hirsutum, Gutierrezia sarothrae, Helianthus annuus, Helichrysum taenari, Hyssopus seravschanicus, Juniperus durangensis, Kunzea salina, Micromeria biflora, Mikania cordifolia, Myrtus communis, Pityophthorus pityographus, Polygala senega, Renealmia floribunda, Rhanterium epapposum, Salvia cuspidata, Salvia vermifolia, Santolina chamaecyparissus, Satureja montana, Swertia japonica, Teucrium polium, Tithonia diversifolia, Umbellularia californica, Vitex negundo, Xylopia aethiopica and Xylopia aromatica. Based on a literature review very few articles have been published on VERBENONE.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0263485 ((1r,5s)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one)


  Mrv1652309082208412D          

 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  0  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
    2.1206   -0.5580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5301   -1.2742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2957   -0.5544    0.0000 C   0  0  2  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  2  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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  6  0  0  0
  8  7  1  1  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 NP0263485 ((1r,5s)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one)

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
    2.2500    2.3597    0.0000 C   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
    2.2500   -0.2384    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   -2.8365    0.0000 O   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
    3.0000    3.6587    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5490    1.6097    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9510    3.1097    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7500   -0.2384    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  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  8  2  1  0
  9  6  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  6 16  1  6
  7 17  1  0
  7 18  1  0
  8 19  1  1
 10 20  1  0
 10 21  1  0
 10 22  1  0
 11 23  1  0
 11 24  1  0
 11 25  1  0
M  END
Download

3D SDF for NP0263485 ((1r,5s)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one)


  Mrv1652309082208412D          

 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  0  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
    2.1206   -0.5580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5301   -1.2742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2957   -0.5544    0.0000 C   0  0  2  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  2  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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  6  0  0  0
  8  7  1  1  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>
NP0263485

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H14O/c1-6-4-9(11)8-5-7(6)10(8,2)3/h4,7-8H,5H2,1-3H3/t7-,8-/m0/s1

> <INCHI_KEY>
DCSCXTJOXBUFGB-YUMQZZPRSA-N

> <FORMULA>
C10H14O

> <MOLECULAR_WEIGHT>
150.221

> <EXACT_MASS>
150.104465071

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
41.63706671518356

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,5S)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one

> <JCHEM_LOGP>
2.2381560493333343

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.843767813525115

> <JCHEM_PKA_STRONGEST_BASIC>
-4.725266923599422

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
45.366299999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,5S)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0263485 ((1r,5s)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one)

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PDB for NP0263485 ((1r,5s)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one)
HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-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  C   UNK     0       3.959  -1.042   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.723  -2.378   0.000  0.00  0.00           O+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                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    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 NP0263485 ((1r,5s)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one)
Download
SMILES for NP0263485 ((1r,5s)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one)
CC1=CC(=O)[C@@H]2C[C@@H]1C2(C)C
Download
INCHI for NP0263485 ((1r,5s)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one)
InChI=1S/C10H14O/c1-6-4-9(11)8-5-7(6)10(8,2)3/h4,7-8H,5H2,1-3H3/t7-,8-/m0/s1
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View in JSmol
Synonyms
ValueSource
Verbenone, (+-)-isomerMeSH
Verbenone, (1R)-isomerMeSH
Verbenone, (1S)-isomerMeSH
Chemical FormulaC10H14O
Average Mass150.2210 Da
Monoisotopic Mass150.10447 Da
IUPAC Name(1R,5S)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one
Traditional Name(1R,5S)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one
CAS Registry NumberNot Available
SMILES
CC1=CC(=O)[C@@H]2C[C@@H]1C2(C)C
InChI Identifier
InChI=1S/C10H14O/c1-6-4-9(11)8-5-7(6)10(8,2)3/h4,7-8H,5H2,1-3H3/t7-,8-/m0/s1
InChI KeyDCSCXTJOXBUFGB-YUMQZZPRSA-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
Annona squamosaLOTUS Database
Artemisia judaicaLOTUS Database
Artemisia sericeaLOTUS Database
Artemisia thusculaLOTUS Database
Asarum canadenseLOTUS Database
Athamanta macedonicaLOTUS Database
Blepharocalyx tweedieiLOTUS Database
Boswellia serrataLOTUS Database
Brassica nigraLOTUS Database
Cleonia lusitanicaLOTUS Database
Cryptomeria japonicaLOTUS Database
Curcuma pierreanaLOTUS Database
Echinophora tenuifoliaLOTUS Database
Etlingera elatiorLOTUS Database
Eucalyptus approximansLOTUS Database
Eucalyptus bridgesianaLOTUS Database
Eucalyptus salignaLOTUS Database
Gossypium hirsutumLOTUS Database
Gutierrezia sarothraeLOTUS Database
Helianthus annuusLOTUS Database
Helichrysum taenariLOTUS Database
Hyssopus seravschanicusLOTUS Database
Juniperus durangensisLOTUS Database
Kunzea salinaLOTUS Database
Micromeria bifloraLOTUS Database
Mikania cordifoliaLOTUS Database
Myrtus communisLOTUS Database
Pityophthorus pityographusLOTUS Database
Polygala senegaLOTUS Database
Renealmia floribundaLOTUS Database
Rhanterium epapposumLOTUS Database
Salvia cuspidataLOTUS Database
Salvia vermifoliaLOTUS Database
Santolina chamaecyparissusLOTUS Database
Satureja montanaLOTUS Database
Swertia japonicaLOTUS Database
Teucrium poliumLOTUS Database
Tithonia diversifoliaLOTUS Database
Umbellularia californicaLOTUS Database
Vitex negundoLOTUS Database
Xylopia aethiopicaLOTUS 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
    • 

  • Cyclohexenone
    • 

  • 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
logP2.24ChemAxon
pKa (Strongest Acidic)19.84ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity45.37 m³·mol⁻¹ChemAxon
Polarizability41.64 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 IDC00003067  
Chemspider ID19958095  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6973628  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]