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Showing NP-Card for 4-Hydroxy-4-(methoxycarbonylmethyl)cyclohexanone (NP0138766)

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Record Information
Version1.0
Created at2022-06-29 18:35:15 UTC
Updated at2022-06-29 18:35:15 UTC
NP-MRD IDNP0138766
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-Hydroxy-4-(methoxycarbonylmethyl)cyclohexanone
DescriptionMethyl 2-(1-hydroxy-4-oxocyclohexyl)acetate belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ). 4-Hydroxy-4-(methoxycarbonylmethyl)cyclohexanone is found in Jacobaea argunensis and Pseudogynoxys chenopodioides. Methyl 2-(1-hydroxy-4-oxocyclohexyl)acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0138766 (4-Hydroxy-4-(methoxycarbonylmethyl)cyclohexanone)


  Mrv1533004241506332D          

 13 13  0  0  0  0            999 V2000
    3.4000    2.2150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5875    2.3582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0572    1.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3394    0.9510    0.0000 O   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
    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 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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
    0.7145   -1.2375    0.0000 O   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
    0.0000    0.8250    0.0000 C   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
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  6 13  1  0  0  0  0
M  END
Download

3D MOL for NP0138766 (4-Hydroxy-4-(methoxycarbonylmethyl)cyclohexanone)

     RDKit          3D

 27 27  0  0  0  0  0  0  0  0999 V2000
    4.4100    0.5621   -0.2027 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2213    0.4613    0.5596 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0142    0.0546    0.0624 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9315   -0.2560   -1.1526 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8170   -0.0208    0.9393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4024   -0.4998    0.1461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0223   -1.7798   -0.3310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6559    0.3592   -1.0086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0428    0.7876   -1.2867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9724    0.6941   -0.1335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7296    1.5710    0.2093 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8819   -0.6300    0.5889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4981   -0.7155    1.1269 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2127    1.3231   -0.9920 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1805    0.9944    0.4691 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7452   -0.4060   -0.5999 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5546    0.9920    1.3088 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9590   -0.6811    1.8002 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6438   -2.1975    0.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0380    1.3016   -0.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2510   -0.0905   -1.9658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0921    1.8232   -1.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4961    0.1344   -2.0907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6012   -0.5815    1.4119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1688   -1.4613   -0.0848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3961   -1.7344    1.6052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4412   -0.0045    1.9858 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13  6  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  5 17  1  0
  5 18  1  0
  7 19  1  0
  8 20  1  0
  8 21  1  0
  9 22  1  0
  9 23  1  0
 12 24  1  0
 12 25  1  0
 13 26  1  0
 13 27  1  0
M  END
Download

3D SDF for NP0138766 (4-Hydroxy-4-(methoxycarbonylmethyl)cyclohexanone)


  Mrv1533004241506332D          

 13 13  0  0  0  0            999 V2000
    3.4000    2.2150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5875    2.3582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0572    1.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3394    0.9510    0.0000 O   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
    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 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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
    0.7145   -1.2375    0.0000 O   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
    0.0000    0.8250    0.0000 C   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
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  6 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0138766

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CC1(O)CCC(=O)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C9H14O4/c1-13-8(11)6-9(12)4-2-7(10)3-5-9/h12H,2-6H2,1H3

> <INCHI_KEY>
UYLWRBIQRPNVNZ-UHFFFAOYSA-N

> <FORMULA>
C9H14O4

> <MOLECULAR_WEIGHT>
186.207

> <EXACT_MASS>
186.089208931

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
18.733132979432266

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 2-(1-hydroxy-4-oxocyclohexyl)acetate

> <ALOGPS_LOGP>
-0.44

> <JCHEM_LOGP>
-0.11386544800000001

> <ALOGPS_LOGS>
-0.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.277943537441942

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.476302541119871

> <JCHEM_PKA_STRONGEST_BASIC>
-3.027710690999159

> <JCHEM_POLAR_SURFACE_AREA>
63.6

> <JCHEM_REFRACTIVITY>
45.3596

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.34e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2-(1-hydroxy-4-oxocyclohexyl)acetate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0138766 (4-Hydroxy-4-(methoxycarbonylmethyl)cyclohexanone)

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PDB for NP0138766 (4-Hydroxy-4-(methoxycarbonylmethyl)cyclohexanone)
HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       6.347   4.135   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.830   4.402   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.840   3.222   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.367   1.775   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.324   3.490   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.344   3.490   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    8   13                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12    6                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

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3D PDB for NP0138766 (4-Hydroxy-4-(methoxycarbonylmethyl)cyclohexanone)
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SMILES for NP0138766 (4-Hydroxy-4-(methoxycarbonylmethyl)cyclohexanone)
COC(=O)CC1(O)CCC(=O)CC1
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INCHI for NP0138766 (4-Hydroxy-4-(methoxycarbonylmethyl)cyclohexanone)
InChI=1S/C9H14O4/c1-13-8(11)6-9(12)4-2-7(10)3-5-9/h12H,2-6H2,1H3
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View in JSmol
Synonyms
ValueSource
Methyl 2-(1-hydroxy-4-oxocyclohexyl)acetic acidGenerator
Chemical FormulaC9H14O4
Average Mass186.2070 Da
Monoisotopic Mass186.08921 Da
IUPAC Namemethyl 2-(1-hydroxy-4-oxocyclohexyl)acetate
Traditional Namemethyl 2-(1-hydroxy-4-oxocyclohexyl)acetate
CAS Registry Number81053-14-7
SMILES
COC(=O)CC1(O)CCC(=O)CC1
InChI Identifier
InChI=1S/C9H14O4/c1-13-8(11)6-9(12)4-2-7(10)3-5-9/h12H,2-6H2,1H3
InChI KeyUYLWRBIQRPNVNZ-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
Jacobaea argunensisLOTUS Database
Pseudogynoxys chenopodioidesLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassAlcohols and polyols  
Direct ParentTertiary alcohols  
Alternative Parents
Substituents
  • Methyl ester
    • 

  • Tertiary alcohol
    • 

  • Cyclic alcohol
    • 

  • Cyclic ketone
    • 

  • Ketone
    • 

  • Carboxylic acid ester
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Carbonyl group
    • 

  • 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
logP-0.44ALOGPS
logP-0.11ChemAxon
logS-0.9ALOGPS
pKa (Strongest Acidic)14.48ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.36 m³·mol⁻¹ChemAxon
Polarizability18.73 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 CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available