Np mrd loader

Showing NP-Card for 2,7,7-trimethylcyclohepta-2,4-dien-1-one (NP0330829)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version1.0
Created at2022-09-12 16:34:21 UTC
Updated at2022-09-12 16:34:21 UTC
NP-MRD IDNP0330829
Secondary Accession NumbersNone
Natural Product Identification
Common Name2,7,7-trimethylcyclohepta-2,4-dien-1-one
Description2,7,7-Trimethylcyclohepta-2,4-dienone belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety. 2,7,7-trimethylcyclohepta-2,4-dien-1-one is found in Artemisia judaica. It was first documented in 2010 (PMID: 21049987). Based on a literature review a significant number of articles have been published on 2,7,7-trimethylcyclohepta-2,4-dienone (PMID: 31514359) (PMID: 28953273) (PMID: 27746930) (PMID: 25553053) (PMID: 24988224) (PMID: 23173924).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0330829 (2,7,7-trimethylcyclohepta-2,4-dien-1-one)


  Mrv1652309122218342D          

 11 11  0  0  0  0            999 V2000
    2.5878    0.0174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7834    0.2009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2691   -0.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4441   -0.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0703    0.2009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1133    1.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8566    1.3632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3422    2.0082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3709    2.0082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5999    1.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2449    1.5196    0.0000 O   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
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  2  0  0  0  0
M  END
Download

3D MOL for NP0330829 (2,7,7-trimethylcyclohepta-2,4-dien-1-one)

     RDKit          3D

 25 25  0  0  0  0  0  0  0  0999 V2000
    3.0045   -0.5366   -0.2003 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6504    0.0295   -0.1597 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5377    1.3544   -0.3376 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3071    2.1365   -0.3386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8580    1.8699    0.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1637    0.6589    1.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9108   -0.5543    0.1700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6059   -1.7795    0.7776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5369   -0.2730   -1.1814 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5194   -0.8862    0.0707 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8820   -2.0799    0.1886 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2505   -0.8926   -1.2337 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7184    0.2821    0.0125 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1523   -1.3266    0.5532 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4583    1.9090   -0.4995 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3339    3.0910   -0.8917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6516    2.6057    0.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1978    0.6351    1.3974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4784    0.5757    1.9094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3816   -1.8518    1.8697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1753   -2.7023    0.3268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6900   -1.7132    0.6674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0714   -0.8658   -1.9916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6305   -0.4923   -1.0647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4626    0.8063   -1.4223 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
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 11  2  0
 10  2  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  4 16  1  0
  5 17  1  0
  6 18  1  0
  6 19  1  0
  8 20  1  0
  8 21  1  0
  8 22  1  0
  9 23  1  0
  9 24  1  0
  9 25  1  0
M  END
Download

3D SDF for NP0330829 (2,7,7-trimethylcyclohepta-2,4-dien-1-one)


  Mrv1652309122218342D          

 11 11  0  0  0  0            999 V2000
    2.5878    0.0174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7834    0.2009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2691   -0.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4441   -0.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0703    0.2009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1133    1.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8566    1.3632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3422    2.0082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3709    2.0082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5999    1.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2449    1.5196    0.0000 O   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
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0330829

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC=CCC(C)(C)C1=O

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

> <INCHI_KEY>
OPQCAZJRIRHZQK-UHFFFAOYSA-N

> <FORMULA>
C10H14O

> <MOLECULAR_WEIGHT>
150.221

> <EXACT_MASS>
150.104465071

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
17.271173316407896

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,7,7-trimethylcyclohepta-2,4-dien-1-one

> <JCHEM_LOGP>
3.0632158323333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.671831111292769

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
48.4909

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2,7,7-trimethylcyclohepta-2,4-dien-1-one

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0330829 (2,7,7-trimethylcyclohepta-2,4-dien-1-one)

Download
PDB for NP0330829 (2,7,7-trimethylcyclohepta-2,4-dien-1-one)
HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       4.830   0.032   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.329   0.375   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.369  -0.829   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.829  -0.829   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.131   0.375   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.211   1.876   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.599   2.545   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.639   3.749   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.559   3.749   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.986   1.876   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.190   2.837   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7    2   11                                                  
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

Download
3D PDB for NP0330829 (2,7,7-trimethylcyclohepta-2,4-dien-1-one)
Download
SMILES for NP0330829 (2,7,7-trimethylcyclohepta-2,4-dien-1-one)
CC1=CC=CCC(C)(C)C1=O
Download
INCHI for NP0330829 (2,7,7-trimethylcyclohepta-2,4-dien-1-one)
InChI=1S/C10H14O/c1-8-6-4-5-7-10(2,3)9(8)11/h4-6H,7H2,1-3H3
Download
View in JSmol
SynonymsNot Available
Chemical FormulaC10H14O
Average Mass150.2210 Da
Monoisotopic Mass150.10447 Da
IUPAC Name2,7,7-trimethylcyclohepta-2,4-dien-1-one
Traditional Name2,7,7-trimethylcyclohepta-2,4-dien-1-one
CAS Registry NumberNot Available
SMILES
CC1=CC=CCC(C)(C)C1=O
InChI Identifier
InChI=1S/C10H14O/c1-8-6-4-5-7-10(2,3)9(8)11/h4-6H,7H2,1-3H3
InChI KeyOPQCAZJRIRHZQK-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 judaicaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbonyl compounds  
Direct ParentCyclic ketones  
Alternative Parents
Substituents
  • Cyclic ketone
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic 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
logP3.06ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity48.49 m³·mol⁻¹ChemAxon
Polarizability17.27 ųChemAxon
Number of Rings1ChemAxon
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 ID60824963  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound85794676  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Huynh TH, Chen PC, Yang SN, Lin FY, Su TP, Chen LY, Peng BR, Hu CC, Chen YY, Wen ZH, Wu TY, Sung PJ: New 1,4-Dienonesteroids from the Octocoral Dendronephthya sp. Mar Drugs. 2019 Sep 11;17(9). pii: md17090530. doi: 10.3390/md17090530. [PubMed:31514359  ] 
  2. Marciniak H, Hristova S, Deneva V, Kamounah FS, Hansen PE, Lochbrunner S, Antonov L: Dynamics of excited state proton transfer in nitro substituted 10-hydroxybenzo[h]quinolines. Phys Chem Chem Phys. 2017 Oct 11;19(39):26621-26629. doi: 10.1039/c7cp04476c. [PubMed:28953273  ] 
  3. Bauri AK, Foro S, Do NQ: Crystal structure of an aryl cyclo-hexyl nona-noid, an anti-proliferative mol-ecule isolated from the spice Myristica malabarica. Acta Crystallogr E Crystallogr Commun. 2016 Sep 5;72(Pt 10):1408-1411. doi: 10.1107/S2056989016013797. eCollection 2016 Oct 1. [PubMed:27746930  ] 
  4. Ghichi N, Benboudiaf A, Merazig H: Crystal structure of (Z)-3-benz-yloxy-6-[(2-hy-droxy-anilino)methyl-idene]cyclo-hexa-2,4-dien-1-one. Acta Crystallogr Sect E Struct Rep Online. 2014 Nov 26;70(Pt 12):o1292. doi: 10.1107/S1600536814024568. eCollection 2014 Dec 1. [PubMed:25553053  ] 
  5. Koch R, Blanch RJ, Wentrup C: Ketene-ketene interconversion. 6-Carbonylcyclohexa-2,4-dienone-hepta-1,2,4,6-tetraene-1,7-dione-6-oxocyclohexa-2 ,4-dienylidene and Wolff rearrangement to fulven-6-one. J Org Chem. 2014 Aug 1;79(15):6978-86. doi: 10.1021/jo5011087. Epub 2014 Jul 11. [PubMed:24988224  ] 
  6. Hosseinzadeh M, Hadi AH, Mohamad J, Khalilzadeh MA, Cheahd SC, Fadaeinasab M: Flavonoids and linderone from Lindera oxyphylla and their bioactivities. Comb Chem High Throughput Screen. 2013 Feb;16(2):160-6. [PubMed:23173924  ] 
  7. Maji B, Lakhdar S, Mayr H: Nucleophilicity parameters of enamides and their implications for organocatalytic transformations. Chemistry. 2012 Apr 27;18(18):5732-40. doi: 10.1002/chem.201103519. Epub 2012 Mar 27. [PubMed:22461320  ] 
  8. Jaworska M, Hrynczyszyn PB, Welniak M, Wojtczak A, Nowicka K, Krasinski G, Kassassir H, Ciesielski W, Potrzebowski MJ: Solid state NMR spectroscopy as a precise tool for assigning the tautomeric form and proton position in the intramolecular bridges of o-hydroxy Schiff bases. J Phys Chem A. 2010 Dec 2;114(47):12522-30. doi: 10.1021/jp108104g. Epub 2010 Nov 4. [PubMed:21049987  ] 
  9. Greenman L, Mazziotti DA: Energy barriers of vinylidene carbene reactions from the anti-hermitian contracted Schrodinger equation. J Phys Chem A. 2010 Jan 14;114(1):583-8. doi: 10.1021/jp907890d. [PubMed:20055521  ] 
  10. Xin M, Bugg TD: Biomimetic formation of 2-tropolones by dioxygenase-catalysed ring expansion of substituted 2,4-cyclohexadienones. Chembiochem. 2010 Jan 25;11(2):272-6. doi: 10.1002/cbic.200900631. [PubMed:20013980  ] 
  11. LOTUS database [Link]