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Showing NP-Card for (4s)-4-hydroxy-3,5,5-trimethylcyclohex-2-en-1-one (NP0305136)

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Record Information
Version2.0
Created at2022-09-10 20:42:33 UTC
Updated at2022-09-10 20:42:33 UTC
NP-MRD IDNP0305136
Secondary Accession NumbersNone
Natural Product Identification
Common Name(4s)-4-hydroxy-3,5,5-trimethylcyclohex-2-en-1-one
Description(S)-hydroxyisophorone belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. (4s)-4-hydroxy-3,5,5-trimethylcyclohex-2-en-1-one is found in Crocus sativus. Based on a literature review very few articles have been published on (S)-hydroxyisophorone.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0305136 ((4s)-4-hydroxy-3,5,5-trimethylcyclohex-2-en-1-one)


  Mrv1652309102222422D          

 11 11  0  0  1  0            999 V2000
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    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
  4  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  1  6  0  0  0
M  END
Download

3D MOL for NP0305136 ((4s)-4-hydroxy-3,5,5-trimethylcyclohex-2-en-1-one)

     RDKit          3D

 25 25  0  0  0  0  0  0  0  0999 V2000
    2.8364    0.0164   -0.4719 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5237    0.0674    0.2098 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3422   -0.4432    1.4133 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0444   -0.3905    2.0823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0629   -0.8085    3.2627 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1569    0.1511    1.3892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9434    0.1565   -0.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1458   -1.2586   -0.6147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0020    1.0321   -0.7659 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3977    0.7096   -0.4878 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5180    0.6422   -1.8722 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8009   -0.8275   -1.2071 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0466    0.9704   -0.9805 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6370   -0.1706    0.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1741   -0.9135    1.9198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4012    1.1609    1.7806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9899   -0.5558    1.6291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0265   -1.6745   -0.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3608   -1.2532   -1.7173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2782   -1.9086   -0.3866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9910    0.9255   -0.2785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1237    0.7623   -1.8344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7131    2.1186   -0.6951 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3896    1.7942   -0.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4849   -0.3030   -2.2022 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
  7  9  1  0
  7 10  1  0
 10 11  1  0
 10  2  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  6 16  1  0
  6 17  1  0
  8 18  1  0
  8 19  1  0
  8 20  1  0
  9 21  1  0
  9 22  1  0
  9 23  1  0
 10 24  1  1
 11 25  1  0
M  END
Download

3D SDF for NP0305136 ((4s)-4-hydroxy-3,5,5-trimethylcyclohex-2-en-1-one)


  Mrv1652309102222422D          

 11 11  0  0  1  0            999 V2000
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    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
  4  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  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0305136

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H14O2/c1-6-4-7(10)5-9(2,3)8(6)11/h4,8,11H,5H2,1-3H3/t8-/m1/s1

> <INCHI_KEY>
RLDREDRZMOWDOA-MRVPVSSYSA-N

> <FORMULA>
C9H14O2

> <MOLECULAR_WEIGHT>
154.209

> <EXACT_MASS>
154.099379691

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
16.893497326641214

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4S)-4-hydroxy-3,5,5-trimethylcyclohex-2-en-1-one

> <JCHEM_LOGP>
1.241541635333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.753830466001126

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.107684651468166

> <JCHEM_PKA_STRONGEST_BASIC>
-3.189095259641806

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
44.0079

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4S)-4-hydroxy-3,5,5-trimethylcyclohex-2-en-1-one

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0305136 ((4s)-4-hydroxy-3,5,5-trimethylcyclohex-2-en-1-one)

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PDB for NP0305136 ((4s)-4-hydroxy-3,5,5-trimethylcyclohex-2-en-1-one)
HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.344   3.490   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.324   3.490   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    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

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3D PDB for NP0305136 ((4s)-4-hydroxy-3,5,5-trimethylcyclohex-2-en-1-one)
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SMILES for NP0305136 ((4s)-4-hydroxy-3,5,5-trimethylcyclohex-2-en-1-one)
CC1=CC(=O)CC(C)(C)[C@@H]1O
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INCHI for NP0305136 ((4s)-4-hydroxy-3,5,5-trimethylcyclohex-2-en-1-one)
InChI=1S/C9H14O2/c1-6-4-7(10)5-9(2,3)8(6)11/h4,8,11H,5H2,1-3H3/t8-/m1/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC9H14O2
Average Mass154.2090 Da
Monoisotopic Mass154.09938 Da
IUPAC Name(4S)-4-hydroxy-3,5,5-trimethylcyclohex-2-en-1-one
Traditional Name(4S)-4-hydroxy-3,5,5-trimethylcyclohex-2-en-1-one
CAS Registry NumberNot Available
SMILES
CC1=CC(=O)CC(C)(C)[C@@H]1O
InChI Identifier
InChI=1S/C9H14O2/c1-6-4-7(10)5-9(2,3)8(6)11/h4,8,11H,5H2,1-3H3/t8-/m1/s1
InChI KeyRLDREDRZMOWDOA-MRVPVSSYSA-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
Crocus sativusLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbonyl compounds  
Direct ParentCyclohexenones  
Alternative Parents
Substituents
  • Cyclohexenone
    • 

  • Secondary alcohol
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Alcohol
    • 

  • 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
logP1.24ChemAxon
pKa (Strongest Acidic)14.11ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity44.01 m³·mol⁻¹ChemAxon
Polarizability16.89 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 ID9542038  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11367121  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]