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Showing NP-Card for 6-acetyl-2-hydroxycyclohepta-2,4,6-trien-1-one (NP0184829)

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Record Information
Version1.0
Created at2022-09-04 00:03:32 UTC
Updated at2022-09-04 00:03:32 UTC
NP-MRD IDNP0184829
Secondary Accession NumbersNone
Natural Product Identification
Common Name6-acetyl-2-hydroxycyclohepta-2,4,6-trien-1-one
Description6-Acetyl-2-hydroxycyclohepta-2,4,6-trien-1-one, also known as 4-acetyltropolone, belongs to the class of organic compounds known as tropolones. Tropolones are compounds containing tropone ring with a hydroxyl group at ring position 2. 6-acetyl-2-hydroxycyclohepta-2,4,6-trien-1-one is found in Thujopsis dolabrata. 6-Acetyl-2-hydroxycyclohepta-2,4,6-trien-1-one is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0184829 (6-acetyl-2-hydroxycyclohepta-2,4,6-trien-1-one)


  Mrv1533004231515062D          

 12 12  0  0  0  0            999 V2000
    1.5710    2.6007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8566    2.1882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1421    2.6007    0.0000 O   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
    1.5999    1.0053    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
    0.0861   -1.1874    0.0000 O   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
   -0.8746    0.0174    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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
  4 11  1  0  0  0  0
 10 12  1  0  0  0  0
M  END
Download

3D MOL for NP0184829 (6-acetyl-2-hydroxycyclohepta-2,4,6-trien-1-one)

     RDKit          3D

 20 20  0  0  0  0  0  0  0  0999 V2000
    3.1050   -0.2645   -0.1372 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9607    0.6307   -0.2303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1652    1.8424   -0.5321 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5691    0.2170    0.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3552   -1.1052    0.3335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8280   -1.8254    0.2953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1214   -1.3595    0.1907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5680   -0.0443    0.0660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8147    0.1248    0.0689 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7928    1.0866   -0.0597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5029    2.2770   -0.1326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4029    1.1847   -0.1221 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8337   -1.2752   -0.5402 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9403    0.1215   -0.7927 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5598   -0.3308    0.8777 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2229   -1.6353    0.6592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7480   -2.8918    0.3537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9349   -2.0634    0.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9783    3.1477   -0.2266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0200    2.1630   -0.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
 12  4  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  5 16  1  0
  6 17  1  0
  7 18  1  0
 11 19  1  0
 12 20  1  0
M  END
Download

3D SDF for NP0184829 (6-acetyl-2-hydroxycyclohepta-2,4,6-trien-1-one)


  Mrv1533004231515062D          

 12 12  0  0  0  0            999 V2000
    1.5710    2.6007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8566    2.1882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1421    2.6007    0.0000 O   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
    1.5999    1.0053    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
    0.0861   -1.1874    0.0000 O   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
   -0.8746    0.0174    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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
  4 11  1  0  0  0  0
 10 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0184829

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H8O3/c1-6(10)7-3-2-4-8(11)9(12)5-7/h2-5H,1H3,(H,11,12)

> <INCHI_KEY>
YXAHHYHNIJIRDA-UHFFFAOYSA-N

> <FORMULA>
C9H8O3

> <MOLECULAR_WEIGHT>
164.16

> <EXACT_MASS>
164.047344118

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
16.156929249441724

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-acetyl-2-hydroxycyclohepta-2,4,6-trien-1-one

> <ALOGPS_LOGP>
0.72

> <JCHEM_LOGP>
0.8521766309999996

> <ALOGPS_LOGS>
-1.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.399276818284099

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1796163193607496

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
47.6693

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.23e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-acetyl-2-hydroxycyclohepta-2,4,6-trien-1-one

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0184829 (6-acetyl-2-hydroxycyclohepta-2,4,6-trien-1-one)

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PDB for NP0184829 (6-acetyl-2-hydroxycyclohepta-2,4,6-trien-1-one)
HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       2.933   4.855   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.599   4.085   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.265   4.855   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.599   2.545   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.986   1.876   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.329   0.375   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.369  -0.829   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.829  -0.829   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.161  -2.216   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.131   0.375   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.211   1.876   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.633   0.032   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10    4                                                       
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

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3D PDB for NP0184829 (6-acetyl-2-hydroxycyclohepta-2,4,6-trien-1-one)
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SMILES for NP0184829 (6-acetyl-2-hydroxycyclohepta-2,4,6-trien-1-one)
CC(=O)C1=CC=CC(=O)C(O)=C1
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INCHI for NP0184829 (6-acetyl-2-hydroxycyclohepta-2,4,6-trien-1-one)
InChI=1S/C9H8O3/c1-6(10)7-3-2-4-8(11)9(12)5-7/h2-5H,1H3,(H,11,12)
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View in JSmol
Synonyms
ValueSource
4-AcetyltropoloneMeSH
Chemical FormulaC9H8O3
Average Mass164.1600 Da
Monoisotopic Mass164.04734 Da
IUPAC Name4-acetyl-2-hydroxycyclohepta-2,4,6-trien-1-one
Traditional Name4-acetyl-2-hydroxycyclohepta-2,4,6-trien-1-one
CAS Registry NumberNot Available
SMILES
CC(=O)C1=CC=CC(=O)C(O)=C1
InChI Identifier
InChI=1S/C9H8O3/c1-6(10)7-3-2-4-8(11)9(12)5-7/h2-5H,1H3,(H,11,12)
InChI KeyYXAHHYHNIJIRDA-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
Thujopsis dolabrataLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tropolones. Tropolones are compounds containing tropone ring with a hydroxyl group at ring position 2.
KingdomOrganic compounds  
Super ClassHydrocarbon derivatives  
ClassTropones  
Sub ClassTropolones  
Direct ParentTropolones  
Alternative Parents
Substituents
  • Tropolone
    • 

  • Aryl alkyl ketone
    • 

  • Aryl ketone
    • 

  • Cyclic ketone
    • 

  • Ketone
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Organooxygen compound
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic 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
logP0.72ALOGPS
logP0.85ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)10.4ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.67 m³·mol⁻¹ChemAxon
Polarizability16.16 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
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 IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound596299  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]