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Showing NP-Card for camphorquinone (NP0308901)

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Record Information
Version2.0
Created at2022-09-11 03:02:53 UTC
Updated at2022-09-11 03:02:53 UTC
NP-MRD IDNP0308901
Secondary Accession NumbersNone
Natural Product Identification
Common Namecamphorquinone
DescriptionBornane-2,3-dione, also known as camphoquinone or 2,3-bornanedione, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Thus, bornane-2,3-dione is considered to be an isoprenoid lipid molecule. camphorquinone is found in Artemisia carvifolia. camphorquinone was first documented in 2014 (PMID: 24430338). Bornane-2,3-dione is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0308901 (camphorquinone)


  Mrv1652310031710412D          

 12 13  0  0  0  0            999 V2000
    0.2085    0.3661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9988    0.1293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2085   -0.1075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2050    0.9543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4906    0.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4906   -0.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2050   -0.6957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2050   -1.5207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9195   -0.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6340   -0.6957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9195    0.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6340    0.9543    0.0000 O   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
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  2  0  0  0  0
M  END
Download

3D MOL for NP0308901 (camphorquinone)

     RDKit          3D

 26 27  0  0  0  0  0  0  0  0999 V2000
   -1.4376   -0.8664    1.0904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7294   -0.1285    0.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4211   -0.1502   -1.3127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5122    1.3010    0.5240 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3888    1.8760   -0.5002 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2641    0.6827   -0.9056 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7392   -0.4818   -0.0837 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0522   -1.8080   -0.5908 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1469   -0.2106    1.3254 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9739   -0.7946    2.0463 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3283    0.9578    1.7240 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3033    1.5624    2.8054 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6082   -1.9323    0.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3732   -0.3838    1.3773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7571   -0.8516    1.9882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4643    0.1724   -1.1644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9433    0.5741   -1.9940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4306   -1.1627   -1.7005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4165    1.8191    0.7540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0936    2.3209   -1.3747 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0243    2.6933   -0.0529 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2867    0.8893   -0.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2360    0.4971   -1.9822 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2441   -2.2509   -1.2343 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2520   -2.5618    0.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9475   -1.7630   -1.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  6
  7  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
  7  2  1  0
 11  4  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  3 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  1
  5 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  8 24  1  0
  8 25  1  0
  8 26  1  0
M  END
Download

3D SDF for NP0308901 (camphorquinone)


  Mrv1652310031710412D          

 12 13  0  0  0  0            999 V2000
    0.2085    0.3661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9988    0.1293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2085   -0.1075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2050    0.9543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4906    0.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4906   -0.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2050   -0.6957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2050   -1.5207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9195   -0.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6340   -0.6957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9195    0.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6340    0.9543    0.0000 O   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
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0308901

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)C2CCC1(C)C(=O)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H14O2/c1-9(2)6-4-5-10(9,3)8(12)7(6)11/h6H,4-5H2,1-3H3

> <INCHI_KEY>
VNQXSTWCDUXYEZ-UHFFFAOYSA-N

> <FORMULA>
C10H14O2

> <MOLECULAR_WEIGHT>
166.22

> <EXACT_MASS>
166.099379691

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
17.897135307124206

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione

> <ALOGPS_LOGP>
2.57

> <JCHEM_LOGP>
2.6536037746666667

> <ALOGPS_LOGS>
-2.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.887274943649484

> <JCHEM_PKA_STRONGEST_BASIC>
-8.81404562506879

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
45.26290000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.49e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
camphorquinone

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0308901 (camphorquinone)

Download
PDB for NP0308901 (camphorquinone)
HEADER    PROTEIN                                 03-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-OCT-17         0                                  
HETATM    1  C   UNK     0       0.389   0.683   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.864   0.241   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.389  -0.201   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.249   1.781   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.916   1.011   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.916  -0.529   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.249  -1.299   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.249  -2.839   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.583  -0.529   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.917  -1.299   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.583   1.011   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.917   1.781   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    7                                             
CONECT    3    2                                                            
CONECT    4    2    5   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    2    8    9                                             
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    4   12                                                  
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

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3D PDB for NP0308901 (camphorquinone)
Download
SMILES for NP0308901 (camphorquinone)
CC1(C)C2CCC1(C)C(=O)C2=O
Download
INCHI for NP0308901 (camphorquinone)
InChI=1S/C10H14O2/c1-9(2)6-4-5-10(9,3)8(12)7(6)11/h6H,4-5H2,1-3H3
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View in JSmol
Synonyms
ValueSource
2,3-BornanedioneChEBI
CamphoquinoneChEBI
Camphor quinoneChEBI
CamphoroquinoneChEBI
CamphorquinoneChEBI
Chemical FormulaC10H14O2
Average Mass166.2200 Da
Monoisotopic Mass166.09938 Da
IUPAC Name1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione
Traditional Namecamphorquinone
CAS Registry NumberNot Available
SMILES
CC1(C)C2CCC1(C)C(=O)C2=O
InChI Identifier
InChI=1S/C10H14O2/c1-9(2)6-4-5-10(9,3)8(12)7(6)11/h6H,4-5H2,1-3H3
InChI KeyVNQXSTWCDUXYEZ-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
Artemisia carvifoliaLOTUS 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
    • 

  • Bornane monoterpenoid
    • 

  • 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
logP2.57ALOGPS
logP2.65ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)17.89ChemAxon
pKa (Strongest Basic)-8.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity45.26 m³·mol⁻¹ChemAxon
Polarizability17.9 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
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 IDC14515  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound25208  
PDB IDNot Available
ChEBI ID34607  
Good Scents IDNot Available
References
General References
  1. Wessels M, Leyhausen G, Volk J, Geurtsen W: Oxidative stress is responsible for genotoxicity of camphorquinone in primary human gingival fibroblasts. Clin Oral Investig. 2014 Jul;18(6):1705-10. doi: 10.1007/s00784-013-1178-x. Epub  2014 Jan 16. [PubMed:24430338  ] 
  2. LOTUS database [Link]