NP-MRD: Showing NP-Card for (1r,5r)-5-hydroxy-4-methoxy-5-methyl-2,6-dioxocyclohex-3-en-1-yl (2r)-2-methylbutanoate (NP0217346)

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Record Information

Version

2.0

Created at

2022-09-05 17:40:01 UTC

Updated at

2022-09-05 17:40:01 UTC

NP-MRD ID

NP0217346

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,5r)-5-hydroxy-4-methoxy-5-methyl-2,6-dioxocyclohex-3-en-1-yl (2r)-2-methylbutanoate

Description

(1R,5R)-5-hydroxy-4-methoxy-5-methyl-2,6-dioxocyclohex-3-en-1-yl (2R)-2-methylbutanoate belongs to the class of organic compounds known as m-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 3-position, respectively. Based on a literature review very few articles have been published on (1R,5R)-5-hydroxy-4-methoxy-5-methyl-2,6-dioxocyclohex-3-en-1-yl (2R)-2-methylbutanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 37  0  0  0  0  0  0  0  0999 V2000
   -4.6947    1.8628    0.4906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4320    1.2215   -0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2809   -0.1827    0.4987 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4675   -1.0171    0.0746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0504   -0.8409    0.0584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1010   -1.9069   -0.6067 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7689   -0.3590    0.3296 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4023   -1.0040   -0.1011 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1876   -1.3931    1.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6903   -2.2150    1.9108 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5307   -0.8313    1.3516 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2689   -0.3991    0.3382 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5319    0.1311    0.5563 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6927    1.4768    0.9821 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7014   -0.5029   -1.0140 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4462    0.2864   -2.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7663   -1.8507   -1.3906 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2664   -0.1456   -0.9406 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8622    0.8144   -1.5565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5732    1.9236    1.5983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8423    2.8438    0.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5247    1.1460    0.2732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5239    1.2075   -1.1493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5887    1.8616    0.2175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3494   -0.0917    1.6169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2725   -0.9685    0.8310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8483   -0.7121   -0.9286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1172   -2.0830    0.0612 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2045   -1.9300   -0.6753 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8983   -0.7789    2.3660 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1863    1.6501    1.9576 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7520    1.7441    1.1136 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2601    2.1709    0.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4834   -0.0985   -2.0847 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4842    1.3629   -1.8645 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9947    0.0504   -3.0343 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8250   -2.4429   -0.5751 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 15 17  1  6
 15 18  1  0
 18 19  2  0
 18  8  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  1
  4 26  1  0
  4 27  1  0
  4 28  1  0
  8 29  1  6
 11 30  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
M  END


  Mrv1652309052219402D          

 19 19  0  0  1  0            999 V2000
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8171   -4.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7565   -4.7570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   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
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  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
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  1  0  0  0
 15 18  1  0  0  0  0
  8 18  1  0  0  0  0
 18 19  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0217346

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H18O6/c1-5-7(2)12(16)19-10-8(14)6-9(18-4)13(3,17)11(10)15/h6-7,10,17H,5H2,1-4H3/t7-,10-,13-/m1/s1

> <INCHI_KEY>
JWUYCQNPNLREFR-XBURVNOZSA-N

> <FORMULA>
C13H18O6

> <MOLECULAR_WEIGHT>
270.281

> <EXACT_MASS>
270.1103383

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
26.799936236947435

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,5R)-5-hydroxy-4-methoxy-5-methyl-2,6-dioxocyclohex-3-en-1-yl (2R)-2-methylbutanoate

> <JCHEM_LOGP>
1.3923800486666664

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.547744278747615

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.845329646973576

> <JCHEM_PKA_STRONGEST_BASIC>
-4.143324564772176

> <JCHEM_POLAR_SURFACE_AREA>
89.9

> <JCHEM_REFRACTIVITY>
67.021

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,5R)-5-hydroxy-4-methoxy-5-methyl-2,6-dioxocyclohex-3-en-1-yl (2R)-2-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         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  -5.390   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       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      10.669  -7.700   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.992  -8.880   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.012  -8.880   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   18                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15    8   19                                                  
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol

Synonyms

Value	Source
(1R,5R)-5-Hydroxy-4-methoxy-5-methyl-2,6-dioxocyclohex-3-en-1-yl (2R)-2-methylbutanoic acid	Generator

Chemical Formula

C₁₃H₁₈O₆

Average Mass

270.2810 Da

Monoisotopic Mass

270.11034 Da

IUPAC Name

(1R,5R)-5-hydroxy-4-methoxy-5-methyl-2,6-dioxocyclohex-3-en-1-yl (2R)-2-methylbutanoate

Traditional Name

(1R,5R)-5-hydroxy-4-methoxy-5-methyl-2,6-dioxocyclohex-3-en-1-yl (2R)-2-methylbutanoate

CAS Registry Number

Not Available

SMILES

CC[C@@H](C)C(=O)O[C@@H]1C(=O)C=C(OC)[C@@](C)(O)C1=O

InChI Identifier

InChI=1S/C13H18O6/c1-5-7(2)12(16)19-10-8(14)6-9(18-4)13(3,17)11(10)15/h6-7,10,17H,5H2,1-4H3/t7-,10-,13-/m1/s1

InChI Key

JWUYCQNPNLREFR-XBURVNOZSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as m-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 3-position, respectively.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

M-benzoquinones

Alternative Parents

Substituents

M-benzoquinone
Cyclohexenone
1,3-diketone
Fatty acid ester
Alpha-acyloxy ketone
Acyloin
Cyclitol or derivatives
Fatty acyl
1,3-dicarbonyl compound
Vinylogous ester
Tertiary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxide
Hydrocarbon derivative
Alcohol
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	1.39	ChemAxon
pKa (Strongest Acidic)	9.85	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	89.9 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	67.02 m³·mol⁻¹	ChemAxon
Polarizability	26.8 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

162984693

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,5r)-5-hydroxy-4-methoxy-5-methyl-2,6-dioxocyclohex-3-en-1-yl (2r)-2-methylbutanoate (NP0217346)

MOL for NP0217346 ((1r,5r)-5-hydroxy-4-methoxy-5-methyl-2,6-dioxocyclohex-3-en-1-yl (2r)-2-methylbutanoate)

3D MOL for NP0217346 ((1r,5r)-5-hydroxy-4-methoxy-5-methyl-2,6-dioxocyclohex-3-en-1-yl (2r)-2-methylbutanoate)

3D SDF for NP0217346 ((1r,5r)-5-hydroxy-4-methoxy-5-methyl-2,6-dioxocyclohex-3-en-1-yl (2r)-2-methylbutanoate)

3D-SDF for NP0217346 ((1r,5r)-5-hydroxy-4-methoxy-5-methyl-2,6-dioxocyclohex-3-en-1-yl (2r)-2-methylbutanoate)

PDB for NP0217346 ((1r,5r)-5-hydroxy-4-methoxy-5-methyl-2,6-dioxocyclohex-3-en-1-yl (2r)-2-methylbutanoate)

3D PDB for NP0217346 ((1r,5r)-5-hydroxy-4-methoxy-5-methyl-2,6-dioxocyclohex-3-en-1-yl (2r)-2-methylbutanoate)

SMILES for NP0217346 ((1r,5r)-5-hydroxy-4-methoxy-5-methyl-2,6-dioxocyclohex-3-en-1-yl (2r)-2-methylbutanoate)

INCHI for NP0217346 ((1r,5r)-5-hydroxy-4-methoxy-5-methyl-2,6-dioxocyclohex-3-en-1-yl (2r)-2-methylbutanoate)

Structure for NP0217346 ((1r,5r)-5-hydroxy-4-methoxy-5-methyl-2,6-dioxocyclohex-3-en-1-yl (2r)-2-methylbutanoate)

3D Structure for NP0217346 ((1r,5r)-5-hydroxy-4-methoxy-5-methyl-2,6-dioxocyclohex-3-en-1-yl (2r)-2-methylbutanoate)