NP-MRD: Showing NP-Card for 2-isopropyl-5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl acetate (NP0191797)

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Record Information

Version

2.0

Created at

2022-09-04 08:51:58 UTC

Updated at

2022-09-04 08:51:58 UTC

NP-MRD ID

NP0191797

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-isopropyl-5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl acetate

Description

5-Methyl-3,6-dioxo-2-(propan-2-yl)cyclohexa-1,4-dien-1-yl acetate belongs to the class of organic compounds known as p-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 4-positions, respectively. 2-isopropyl-5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl acetate is found in Antiphiona pinnatisecta and Laggera decurrens. 5-Methyl-3,6-dioxo-2-(propan-2-yl)cyclohexa-1,4-dien-1-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004161504452D          

 16 16  0  0  0  0            999 V2000
    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    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
    1.4289    0.8250    0.0000 C   0  0  0  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
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    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
    2.1434   -0.4125    0.0000 O   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
   -0.7145    1.2375    0.0000 O   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
  1  2  1  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
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  4 14  1  0  0  0  0
 14 15  2  0  0  0  0
 12 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0191797

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1=C(OC(C)=O)C(=O)C(C)=CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H14O4/c1-6(2)10-9(14)5-7(3)11(15)12(10)16-8(4)13/h5-6H,1-4H3

> <INCHI_KEY>
VGIKIXGNPGVZPT-UHFFFAOYSA-N

> <FORMULA>
C12H14O4

> <MOLECULAR_WEIGHT>
222.24

> <EXACT_MASS>
222.089208931

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
22.873710739375348

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-methyl-3,6-dioxo-2-(propan-2-yl)cyclohexa-1,4-dien-1-yl acetate

> <ALOGPS_LOGP>
1.67

> <JCHEM_LOGP>
1.9389711659999995

> <ALOGPS_LOGS>
-2.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.155079434536832

> <JCHEM_POLAR_SURFACE_AREA>
60.440000000000005

> <JCHEM_REFRACTIVITY>
60.01150000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.31e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-isopropyl-5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   14                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    5   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13    4   15                                                  
CONECT   15   14                                                            
CONECT   16   12                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Value	Source
5-Methyl-3,6-dioxo-2-(propan-2-yl)cyclohexa-1,4-dien-1-yl acetic acid	Generator

Chemical Formula

C₁₂H₁₄O₄

Average Mass

222.2400 Da

Monoisotopic Mass

222.08921 Da

IUPAC Name

5-methyl-3,6-dioxo-2-(propan-2-yl)cyclohexa-1,4-dien-1-yl acetate

Traditional Name

2-isopropyl-5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl acetate

CAS Registry Number

Not Available

SMILES

CC(C)C1=C(OC(C)=O)C(=O)C(C)=CC1=O

InChI Identifier

InChI=1S/C12H14O4/c1-6(2)10-9(14)5-7(3)11(15)12(10)16-8(4)13/h5-6H,1-4H3

InChI Key

VGIKIXGNPGVZPT-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Antiphiona pinnatisecta	LOTUS Database	35616633
Laggera decurrens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as p-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 4-positions, respectively.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

P-benzoquinones

Alternative Parents

Substituents

P-benzoquinone
Enol ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.67	ALOGPS
logP	1.94	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Basic)	-7.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	60.44 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	60.01 m³·mol⁻¹	ChemAxon
Polarizability	22.87 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14287135

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-isopropyl-5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl acetate (NP0191797)

MOL for NP0191797 (2-isopropyl-5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl acetate)

3D MOL for NP0191797 (2-isopropyl-5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl acetate)

3D SDF for NP0191797 (2-isopropyl-5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl acetate)

3D-SDF for NP0191797 (2-isopropyl-5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl acetate)

PDB for NP0191797 (2-isopropyl-5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl acetate)

3D PDB for NP0191797 (2-isopropyl-5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl acetate)

SMILES for NP0191797 (2-isopropyl-5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl acetate)

INCHI for NP0191797 (2-isopropyl-5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl acetate)

Structure for NP0191797 (2-isopropyl-5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl acetate)

3D Structure for NP0191797 (2-isopropyl-5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl acetate)