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Showing NP-Card for 3,4,4-Trimethyl-1,2-cyclopentanedione (NP0049658)

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Record Information
Version2.0
Created at2022-03-17 21:16:01 UTC
Updated at2022-03-17 21:16:01 UTC
NP-MRD IDNP0049658
Secondary Accession NumbersNone
Natural Product Identification
Common Name3,4,4-Trimethyl-1,2-cyclopentanedione
Description3,4,4-Trimethyl-1,2-cyclopentanedione 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. 3,4,4-Trimethyl-1,2-cyclopentanedione is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 3,4,4-Trimethyl-1,2-cyclopentanedione has been detected, but not quantified in, coffee and coffee products. This could make 3,4,4-trimethyl-1,2-cyclopentanedione a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0049658 (3,4,4-Trimethyl-1,2-cyclopentanedione)


  Mrv0541 05061311552D          

 10 10  0  0  0  0            999 V2000
    1.3069    0.4087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6972    1.2518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4068    1.2518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8126    0.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5222    0.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5577   -0.6309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2673   -0.6309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1452    0.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0426   -1.2983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7522   -1.2983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  7  6  1  0  0  0  0
  8  2  1  0  0  0  0
  8  3  1  0  0  0  0
  8  4  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
 10  7  1  0  0  0  0
M  END
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3D MOL for NP0049658 (3,4,4-Trimethyl-1,2-cyclopentanedione)

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3D SDF for NP0049658 (3,4,4-Trimethyl-1,2-cyclopentanedione)

  Mrv0541 05061311552D          

 10 10  0  0  0  0            999 V2000
    1.3069    0.4087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6972    1.2518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4068    1.2518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8126    0.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5222    0.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5577   -0.6309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2673   -0.6309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1452    0.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0426   -1.2983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7522   -1.2983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  7  6  1  0  0  0  0
  8  2  1  0  0  0  0
  8  3  1  0  0  0  0
  8  4  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
 10  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049658

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(O)C(=O)CC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C8H12O2/c1-5-7(10)6(9)4-8(5,2)3/h10H,4H2,1-3H3

> <INCHI_KEY>
LTRJTLUJZFBIEN-UHFFFAOYSA-N

> <FORMULA>
C8H12O2

> <MOLECULAR_WEIGHT>
140.1797

> <EXACT_MASS>
140.083729628

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
15.16776453917032

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxy-3,4,4-trimethylcyclopent-2-en-1-one

> <ALOGPS_LOGP>
0.77

> <JCHEM_LOGP>
1.3532188960000004

> <ALOGPS_LOGS>
-0.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.405704891233366

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6142046805666004

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
40.0128

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.22e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-3,4,4-trimethylcyclopent-2-en-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0049658 (3,4,4-Trimethyl-1,2-cyclopentanedione)
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PDB for NP0049658 (3,4,4-Trimethyl-1,2-cyclopentanedione)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       2.440   0.763   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.301   2.337   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.759   2.337   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.517   0.287   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.975   0.287   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.041  -1.178   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.499  -1.178   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.271   1.192   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.946  -2.423   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.404  -2.423   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2    8                                                            
CONECT    3    8                                                            
CONECT    4    6    8                                                       
CONECT    5    1    7    8                                                  
CONECT    6    4    7    9                                                  
CONECT    7    5    6   10                                                  
CONECT    8    2    3    4    5                                             
CONECT    9    6                                                            
CONECT   10    7                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END

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3D PDB for NP0049658 (3,4,4-Trimethyl-1,2-cyclopentanedione)
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SMILES for NP0049658 (3,4,4-Trimethyl-1,2-cyclopentanedione)
CC1=C(O)C(=O)CC1(C)C
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INCHI for NP0049658 (3,4,4-Trimethyl-1,2-cyclopentanedione)
InChI=1S/C8H12O2/c1-5-7(10)6(9)4-8(5,2)3/h10H,4H2,1-3H3
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Synonyms
ValueSource
2-Hydroxy-3,4,4-trimethyl-2-cyclopenten-1-oneHMDB
Chemical FormulaC8H12O2
Average Mass140.1797 Da
Monoisotopic Mass140.08373 Da
IUPAC Name2-hydroxy-3,4,4-trimethylcyclopent-2-en-1-one
Traditional Name2-hydroxy-3,4,4-trimethylcyclopent-2-en-1-one
CAS Registry Number86702-81-0
SMILES
CC1=C(O)C(=O)CC1(C)C
InChI Identifier
InChI=1S/C8H12O2/c1-5-7(10)6(9)4-8(5,2)3/h10H,4H2,1-3H3
InChI KeyLTRJTLUJZFBIEN-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Coffea arabica L.FooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Coffea canephoraFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
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
    • 

  • Enol
    • 

  • 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
logP0.77ALOGPS
logP1.35ChemAxon
logS-0.8ALOGPS
pKa (Strongest Acidic)9.41ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity40.01 m³·mol⁻¹ChemAxon
Polarizability15.17 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0040526  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB020293  
KNApSAcK IDNot Available
Chemspider ID4934163  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6428785  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available