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Showing NP-Card for (1r)-cyclohex-3-en-1-yl(oxo)acetic acid (NP0321449)

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Record Information
Version1.0
Created at2022-09-11 23:39:41 UTC
Updated at2022-09-11 23:39:41 UTC
NP-MRD IDNP0321449
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1r)-cyclohex-3-en-1-yl(oxo)acetic acid
Description23364-22-9, Also known as ketomycin, belongs to the class of organic compounds known as alpha-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon. Based on a literature review very few articles have been published on 23364-22-9.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0321449 ((1r)-cyclohex-3-en-1-yl(oxo)acetic acid)


  Mrv1652309122201392D          

 11 11  0  0  1  0            999 V2000
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  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
    0.0000    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  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  6  4  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 11  1  0  0  0  0
M  END
Download

3D MOL for NP0321449 ((1r)-cyclohex-3-en-1-yl(oxo)acetic acid)

     RDKit          3D

 21 21  0  0  0  0  0  0  0  0999 V2000
    2.1222    1.7577   -1.1315 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4348    1.2355   -0.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7073    1.4624    0.4494 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5126    0.4187    0.7044 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8592   -0.0801    1.7980 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1734    0.1673    0.1900 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1985   -0.5904   -1.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2358   -0.6748   -1.5862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2523   -0.5714   -0.7509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1226   -0.3642    0.7056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6766   -0.6822    1.1137 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9419    2.3459    0.9248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3388    1.1270    0.0442 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6073   -1.5996   -0.9039 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8100   -0.0148   -1.8271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3800   -0.8271   -2.6517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2536   -0.6433   -1.1604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8255   -0.9675    1.3029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2461    0.7221    0.8979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5245   -1.7536    0.8842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5114   -0.4675    2.1673 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  7  6  1  0
  3 12  1  0
  6 13  1  6
 11 20  1  0
 11 21  1  0
 10 18  1  0
 10 19  1  0
  9 17  1  0
  8 16  1  0
  7 14  1  0
  7 15  1  0
M  END
Download

3D SDF for NP0321449 ((1r)-cyclohex-3-en-1-yl(oxo)acetic acid)


  Mrv1652309122201392D          

 11 11  0  0  1  0            999 V2000
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  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
    0.0000    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  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  6  4  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0321449

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H10O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-2,6H,3-5H2,(H,10,11)/t6-/m0/s1

> <INCHI_KEY>
XJVDGWZMESEVTD-LURJTMIESA-N

> <FORMULA>
C8H10O3

> <MOLECULAR_WEIGHT>
154.165

> <EXACT_MASS>
154.062994182

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
15.1742005654042

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(1R)-cyclohex-3-en-1-yl]-2-oxoacetic acid

> <JCHEM_LOGP>
1.8174545143333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4315334693196706

> <JCHEM_PKA_STRONGEST_BASIC>
-9.736948154127603

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
40.3085

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R)-cyclohex-3-en-1-yl(oxo)acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0321449 ((1r)-cyclohex-3-en-1-yl(oxo)acetic acid)

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PDB for NP0321449 ((1r)-cyclohex-3-en-1-yl(oxo)acetic acid)
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  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    6                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for NP0321449 ((1r)-cyclohex-3-en-1-yl(oxo)acetic acid)
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SMILES for NP0321449 ((1r)-cyclohex-3-en-1-yl(oxo)acetic acid)
OC(=O)C(=O)[C@@H]1CCC=CC1
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INCHI for NP0321449 ((1r)-cyclohex-3-en-1-yl(oxo)acetic acid)
InChI=1S/C8H10O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-2,6H,3-5H2,(H,10,11)/t6-/m0/s1
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View in JSmol
Synonyms
ValueSource
KetomycinMeSH
Chemical FormulaC8H10O3
Average Mass154.1650 Da
Monoisotopic Mass154.06299 Da
IUPAC Name2-[(1R)-cyclohex-3-en-1-yl]-2-oxoacetic acid
Traditional Name(1R)-cyclohex-3-en-1-yl(oxo)acetic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C(=O)[C@@H]1CCC=CC1
InChI Identifier
InChI=1S/C8H10O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-2,6H,3-5H2,(H,10,11)/t6-/m0/s1
InChI KeyXJVDGWZMESEVTD-LURJTMIESA-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 OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassKeto acids and derivatives  
Sub ClassAlpha-keto acids and derivatives  
Direct ParentAlpha-keto acids and derivatives  
Alternative Parents
Substituents
  • Alpha-keto acid
    • 

  • Alpha-hydroxy ketone
    • 

  • Ketone
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • 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
logP1.82ChemAxon
pKa (Strongest Acidic)3.43ChemAxon
pKa (Strongest Basic)-9.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity40.31 m³·mol⁻¹ChemAxon
Polarizability15.17 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID18365  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound19489  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]