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Showing NP-Card for 1,4-dimethyl-2,3-dihydro-1h-azulen-6-one (NP0142330)

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Record Information
Version2.0
Created at2022-09-01 20:51:32 UTC
Updated at2022-09-01 20:51:32 UTC
NP-MRD IDNP0142330
Secondary Accession NumbersNone
Natural Product Identification
Common Name1,4-dimethyl-2,3-dihydro-1h-azulen-6-one
Description(R)-11,12,13-Trinor-1(5),6,9-guaiatrien-8-one belongs to the class of organic compounds known as tropones. Tropones are compounds containing a tropone ring, which is a cycloheptatrienone ring bearing a ketone group (R)-11,12,13-Trinor-1(5),6,9-guaiatrien-8-one is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (R)-11,12,13-Trinor-1(5),6,9-guaiatrien-8-one has been detected, but not quantified in, herbs and spices and root vegetables. 1,4-dimethyl-2,3-dihydro-1h-azulen-6-one is found in Acorus calamus. This could make (R)-11,12,13-trinor-1(5),6,9-guaiatrien-8-one a potential biomarker for the consumption of these foods.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0142330 (1,4-dimethyl-2,3-dihydro-1h-azulen-6-one)


  Mrv0541 05061310532D          

 13 14  0  0  0  0            999 V2000
    1.6680    1.2466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1690   -1.9367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4380   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569    0.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230   -0.8729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526    0.7214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569   -0.9488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230    0.4619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526   -1.1324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5149   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076    0.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076   -0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399   -0.2055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  8  1  1  0  0  0  0
  8  3  1  0  0  0  0
  9  2  1  0  0  0  0
  9  7  2  0  0  0  0
 10  4  1  0  0  0  0
 10  7  1  0  0  0  0
 11  6  1  0  0  0  0
 11  8  1  0  0  0  0
 12  5  1  0  0  0  0
 12  9  1  0  0  0  0
 12 11  2  0  0  0  0
 13 10  2  0  0  0  0
M  END
Download

3D MOL for NP0142330 (1,4-dimethyl-2,3-dihydro-1h-azulen-6-one)

     RDKit          3D

 27 28  0  0  0  0  0  0  0  0999 V2000
   -2.2365    1.9947    0.0952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6691    0.6142   -0.0560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5967   -0.3734   -0.1896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4025   -1.7221   -0.0651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4226   -2.4000    0.2137 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2004   -2.3843   -0.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0835   -1.8753   -0.3479 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5232   -0.5754   -0.2626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2929    0.5233   -0.0404 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5308    1.7281    0.2477 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8521    1.0753    0.6582 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8867   -0.0581   -0.3786 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9491   -1.0605   -0.0296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2367    2.0451   -0.3550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2773    2.3052    1.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5558    2.6594   -0.5103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6094   -0.0445   -0.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3088   -3.4549   -0.2356 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8649   -2.5955   -0.5456 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7646    2.2848   -0.6948 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1158    2.3656    1.0290 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7453    0.6099    1.6651 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6971    1.7491    0.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0990    0.3976   -1.3546 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9220   -1.8634   -0.7715 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8390   -1.4056    1.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9356   -0.5393   -0.1723 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  7  6  2  0
  6  4  1  0
  4  5  2  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  8 12  1  0
  2  9  1  0
 13 25  1  0
 13 26  1  0
 13 27  1  0
 12 24  1  6
 11 22  1  0
 11 23  1  0
 10 20  1  0
 10 21  1  0
  7 19  1  0
  6 18  1  0
  3 17  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
M  END
Download

3D SDF for NP0142330 (1,4-dimethyl-2,3-dihydro-1h-azulen-6-one)


  Mrv0541 05061310532D          

 13 14  0  0  0  0            999 V2000
    1.6680    1.2466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1690   -1.9367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4380   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569    0.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230   -0.8729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526    0.7214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569   -0.9488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230    0.4619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526   -1.1324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5149   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076    0.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076   -0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399   -0.2055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  8  1  1  0  0  0  0
  8  3  1  0  0  0  0
  9  2  1  0  0  0  0
  9  7  2  0  0  0  0
 10  4  1  0  0  0  0
 10  7  1  0  0  0  0
 11  6  1  0  0  0  0
 11  8  1  0  0  0  0
 12  5  1  0  0  0  0
 12  9  1  0  0  0  0
 12 11  2  0  0  0  0
 13 10  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0142330

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCC2=C1C=CC(=O)C=C2C

> <INCHI_IDENTIFIER>
InChI=1S/C12H14O/c1-8-3-5-12-9(2)7-10(13)4-6-11(8)12/h4,6-8H,3,5H2,1-2H3

> <INCHI_KEY>
MDFATIDEXXOYPV-UHFFFAOYSA-N

> <FORMULA>
C12H14O

> <MOLECULAR_WEIGHT>
174.239

> <EXACT_MASS>
174.10446507

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
20.202987734107005

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,4-dimethyl-1,2,3,6-tetrahydroazulen-6-one

> <ALOGPS_LOGP>
2.86

> <JCHEM_LOGP>
2.3322672593333333

> <ALOGPS_LOGS>
-2.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.159634760812342

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
56.345000000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.95e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,4-dimethyl-2,3-dihydro-1H-azulen-6-one

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0142330 (1,4-dimethyl-2,3-dihydro-1h-azulen-6-one)

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PDB for NP0142330 (1,4-dimethyl-2,3-dihydro-1h-azulen-6-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       3.114   2.327   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.915  -3.615   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.684  -0.384   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.760   1.004   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.590  -1.629   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.258   1.347   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.760  -1.771   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.590   0.862   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.258  -2.114   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.428  -0.384   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.054   0.386   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.054  -1.154   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.968  -0.384   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3    5    8                                                       
CONECT    4    6   10                                                       
CONECT    5    3   12                                                       
CONECT    6    4   11                                                       
CONECT    7    9   10                                                       
CONECT    8    1    3   11                                                  
CONECT    9    2    7   12                                                  
CONECT   10    4    7   13                                                  
CONECT   11    6    8   12                                                  
CONECT   12    5    9   11                                                  
CONECT   13   10                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

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3D PDB for NP0142330 (1,4-dimethyl-2,3-dihydro-1h-azulen-6-one)
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SMILES for NP0142330 (1,4-dimethyl-2,3-dihydro-1h-azulen-6-one)
CC1CCC2=C1C=CC(=O)C=C2C
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INCHI for NP0142330 (1,4-dimethyl-2,3-dihydro-1h-azulen-6-one)
InChI=1S/C12H14O/c1-8-3-5-12-9(2)7-10(13)4-6-11(8)12/h4,6-8H,3,5H2,1-2H3
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View in JSmol
SynonymsNot Available
Chemical FormulaC12H14O
Average Mass174.2390 Da
Monoisotopic Mass174.10447 Da
IUPAC Name1,4-dimethyl-1,2,3,6-tetrahydroazulen-6-one
Traditional Name1,4-dimethyl-2,3-dihydro-1H-azulen-6-one
CAS Registry NumberNot Available
SMILES
CC1CCC2=C1C=CC(=O)C=C2C
InChI Identifier
InChI=1S/C12H14O/c1-8-3-5-12-9(2)7-10(13)4-6-11(8)12/h4,6-8H,3,5H2,1-2H3
InChI KeyMDFATIDEXXOYPV-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
Acorus calamusLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tropones. Tropones are compounds containing a tropone ring, which is a cycloheptatrienone ring bearing a ketone group.
KingdomOrganic compounds  
Super ClassHydrocarbon derivatives  
ClassTropones  
Sub ClassNot Available
Direct ParentTropones  
Alternative Parents
Substituents
  • Tropone
    • 

  • Cyclic ketone
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Organooxygen compound
    • 

  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic 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
logP2.86ALOGPS
logP2.33ChemAxon
logS-2.6ALOGPS
pKa (Strongest Basic)-7.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity56.34 m³·mol⁻¹ChemAxon
Polarizability20.2 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0039153  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB018673  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound85977048  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]