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Showing NP-Card for (1s)-2-isopropyl-3-methyl-5-methylidene-4-oxocyclopent-2-ene-1-carboxylic acid (NP0272813)

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Record Information
Version2.0
Created at2022-09-08 19:36:26 UTC
Updated at2022-09-08 19:36:27 UTC
NP-MRD IDNP0272813
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1s)-2-isopropyl-3-methyl-5-methylidene-4-oxocyclopent-2-ene-1-carboxylic acid
Description(1S)-3-methyl-5-methylidene-4-oxo-2-(propan-2-yl)cyclopent-2-ene-1-carboxylic acid belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety. Based on a literature review very few articles have been published on (1S)-3-methyl-5-methylidene-4-oxo-2-(propan-2-yl)cyclopent-2-ene-1-carboxylic acid.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0272813 ((1s)-2-isopropyl-3-methyl-5-methylidene-4-oxocyclopent-2-ene-1-carboxylic acid)


  Mrv1652309082221362D          

 14 14  0  0  1  0            999 V2000
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0059   -1.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1501   -0.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0558    1.6913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4974    0.3323    0.0000 O   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
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  7 11  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
M  END
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3D MOL for NP0272813 ((1s)-2-isopropyl-3-methyl-5-methylidene-4-oxocyclopent-2-ene-1-carboxylic acid)

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3D SDF for NP0272813 ((1s)-2-isopropyl-3-methyl-5-methylidene-4-oxocyclopent-2-ene-1-carboxylic acid)

  Mrv1652309082221362D          

 14 14  0  0  1  0            999 V2000
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0059   -1.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1501   -0.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0558    1.6913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4974    0.3323    0.0000 O   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
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  7 11  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0272813

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1=C(C)C(=O)C(=C)[C@H]1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H14O3/c1-5(2)8-6(3)10(12)7(4)9(8)11(13)14/h5,9H,4H2,1-3H3,(H,13,14)/t9-/m1/s1

> <INCHI_KEY>
TZYRKABFSHPLIU-SECBINFHSA-N

> <FORMULA>
C11H14O3

> <MOLECULAR_WEIGHT>
194.23

> <EXACT_MASS>
194.094294311

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
20.52608405159814

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S)-3-methyl-5-methylidene-4-oxo-2-(propan-2-yl)cyclopent-2-ene-1-carboxylic acid

> <JCHEM_LOGP>
2.0860007743333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.417241400373017

> <JCHEM_PKA_STRONGEST_BASIC>
-6.564041167599687

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
53.1462

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S)-2-isopropyl-3-methyl-5-methylidene-4-oxocyclopent-2-ene-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0272813 ((1s)-2-isopropyl-3-methyl-5-methylidene-4-oxocyclopent-2-ene-1-carboxylic acid)
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PDB for NP0272813 ((1s)-2-isopropyl-3-methyl-5-methylidene-4-oxocyclopent-2-ene-1-carboxylic acid)
HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.770   1.651   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.735  -1.536   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.615  -1.536   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.011  -2.943   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.147  -1.375   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.651   1.651   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.971   3.157   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -2.795   0.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   11                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    7    2   12                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

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3D PDB for NP0272813 ((1s)-2-isopropyl-3-methyl-5-methylidene-4-oxocyclopent-2-ene-1-carboxylic acid)
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SMILES for NP0272813 ((1s)-2-isopropyl-3-methyl-5-methylidene-4-oxocyclopent-2-ene-1-carboxylic acid)
CC(C)C1=C(C)C(=O)C(=C)[C@H]1C(O)=O
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INCHI for NP0272813 ((1s)-2-isopropyl-3-methyl-5-methylidene-4-oxocyclopent-2-ene-1-carboxylic acid)
InChI=1S/C11H14O3/c1-5(2)8-6(3)10(12)7(4)9(8)11(13)14/h5,9H,4H2,1-3H3,(H,13,14)/t9-/m1/s1
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Synonyms
ValueSource
(1S)-3-Methyl-5-methylidene-4-oxo-2-(propan-2-yl)cyclopent-2-ene-1-carboxylateGenerator
Chemical FormulaC11H14O3
Average Mass194.2300 Da
Monoisotopic Mass194.09429 Da
IUPAC Name(1S)-3-methyl-5-methylidene-4-oxo-2-(propan-2-yl)cyclopent-2-ene-1-carboxylic acid
Traditional Name(1S)-2-isopropyl-3-methyl-5-methylidene-4-oxocyclopent-2-ene-1-carboxylic acid
CAS Registry NumberNot Available
SMILES
CC(C)C1=C(C)C(=O)C(=C)[C@H]1C(O)=O
InChI Identifier
InChI=1S/C11H14O3/c1-5(2)8-6(3)10(12)7(4)9(8)11(13)14/h5,9H,4H2,1-3H3,(H,13,14)/t9-/m1/s1
InChI KeyTZYRKABFSHPLIU-SECBINFHSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbonyl compounds  
Direct ParentCyclic ketones  
Alternative Parents
Substituents
  • Cyclic ketone
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • 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
logP2.09ChemAxon
pKa (Strongest Acidic)4.42ChemAxon
pKa (Strongest Basic)-6.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity53.15 m³·mol⁻¹ChemAxon
Polarizability20.53 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 Compound163113844  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]