NP-MRD: Showing NP-Card for (5-hydroxy-2,4-dimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl acetate (NP0161147)

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Record Information

Version

2.0

Created at

2022-09-02 19:15:20 UTC

Updated at

2022-09-02 19:15:20 UTC

NP-MRD ID

NP0161147

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5-hydroxy-2,4-dimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl acetate

Description

(5-Hydroxy-2,4-dimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl acetate belongs to the class of organic compounds known as p-benzoquinones. (5-hydroxy-2,4-dimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl acetate is found in Shanorella spirotricha. These are benzoquinones where the two C=O groups are attached at the 1- and 4-positions, respectively (5-hydroxy-2,4-dimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 28 28  0  0  0  0  0  0  0  0999 V2000
    4.4643    1.5211   -0.5328 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5819    0.7214    0.3901 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0593    0.1354    1.3981 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2246    0.5992    0.1700 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4324   -0.1746    1.0810 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0102   -0.1782    0.6666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6146   -1.3066    0.3783 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1172   -2.6201    0.4675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0208   -1.2700   -0.0278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5768   -2.3675   -0.2932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7434   -0.0061   -0.1191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1654   -0.0600   -0.5383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1249    1.1274    0.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8495    2.3046    0.0679 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7398    1.0673    0.5656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1523    2.1536    0.8391 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1330    2.1170    0.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8469    2.2645   -1.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0650    0.8729   -1.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8452   -1.2028    1.0221 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5638    0.2711    2.1061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6196   -3.4369    0.3239 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8673   -2.6445   -0.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5855   -2.7637    1.4494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2785   -0.5897   -1.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7987   -0.6283    0.1989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5853    0.9807   -0.6092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5269    3.1129   -0.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 15  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  5 20  1  0
  5 21  1  0
  8 22  1  0
  8 23  1  0
  8 24  1  0
 12 25  1  0
 12 26  1  0
 12 27  1  0
 14 28  1  0
M  END


  Mrv1533004241511082D          

 16 16  0  0  0  0            999 V2000
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    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
    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 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
   -0.7145   -0.4125    0.0000 O   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  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  2  0  0  0  0
 11 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0161147

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OCC1=C(C)C(=O)C(C)=C(O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H12O5/c1-5-8(4-16-7(3)12)11(15)10(14)6(2)9(5)13/h14H,4H2,1-3H3

> <INCHI_KEY>
INZBHHNCVMCFJN-UHFFFAOYSA-N

> <FORMULA>
C11H12O5

> <MOLECULAR_WEIGHT>
224.212

> <EXACT_MASS>
224.068473486

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
21.87236958132342

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5-hydroxy-2,4-dimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl acetate

> <ALOGPS_LOGP>
0.53

> <JCHEM_LOGP>
0.8524618516666672

> <ALOGPS_LOGS>
-1.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.71249972648602

> <JCHEM_PKA_STRONGEST_BASIC>
-5.229612619635049

> <JCHEM_POLAR_SURFACE_AREA>
80.67000000000002

> <JCHEM_REFRACTIVITY>
56.993700000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.85e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5-hydroxy-2,4-dimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

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      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334   3.850   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  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   2.310   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  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+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                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   14                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   16                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    6   15                                                  
CONECT   15   14                                                            
CONECT   16   11                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Value	Source
(5-Hydroxy-2,4-dimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl acetic acid	Generator

Chemical Formula

C₁₁H₁₂O₅

Average Mass

224.2120 Da

Monoisotopic Mass

224.06847 Da

IUPAC Name

(5-hydroxy-2,4-dimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl acetate

Traditional Name

(5-hydroxy-2,4-dimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OCC1=C(C)C(=O)C(C)=C(O)C1=O

InChI Identifier

InChI=1S/C11H12O5/c1-5-8(4-16-7(3)12)11(15)10(14)6(2)9(5)13/h14H,4H2,1-3H3

InChI Key

INZBHHNCVMCFJN-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Shanorella spirotricha	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
Vinylogous acid
Carboxylic acid ester
Monocarboxylic acid or derivatives
Enol
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	0.53	ALOGPS
logP	0.85	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	5.71	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.67 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	56.99 m³·mol⁻¹	ChemAxon
Polarizability	21.87 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (5-hydroxy-2,4-dimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl acetate (NP0161147)

MOL for NP0161147 ((5-hydroxy-2,4-dimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl acetate)

3D MOL for NP0161147 ((5-hydroxy-2,4-dimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl acetate)

3D SDF for NP0161147 ((5-hydroxy-2,4-dimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl acetate)

3D-SDF for NP0161147 ((5-hydroxy-2,4-dimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl acetate)

PDB for NP0161147 ((5-hydroxy-2,4-dimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl acetate)

3D PDB for NP0161147 ((5-hydroxy-2,4-dimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl acetate)

SMILES for NP0161147 ((5-hydroxy-2,4-dimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl acetate)

INCHI for NP0161147 ((5-hydroxy-2,4-dimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl acetate)

Structure for NP0161147 ((5-hydroxy-2,4-dimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl acetate)

3D Structure for NP0161147 ((5-hydroxy-2,4-dimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methyl acetate)