MiMeDB: Showing metabocard for (2R,3S)-2,3-dihydroxy-2,3-dihydro-p-cumic acid (MMDBc0054809)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:35:21 UTC

Update Date

2022-08-12 20:09:05 UTC

Metabolite ID

MMDBc0054809

Metabolite Identification

Common Name

(2R,3S)-2,3-dihydroxy-2,3-dihydro-p-cumic acid

Description

cis-5,6-Dihydroxy-4-isopropylcyclohexa-1,3-dienecarboxylate, also known as (2R,3S)-2,3-dihydroxy-2,3-dihydro-p-cumate, belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Based on a literature review very few articles have been published on cis-5,6-Dihydroxy-4-isopropylcyclohexa-1,3-dienecarboxylate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221352D          

 16 16  0  0  1  0            999 V2000
   -1.4289    0.0000    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
    0.7145   -0.4125    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
   -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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  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
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  5  1  1  0  0  0  0
  5  2  1  0  0  0  0
  6  3  2  0  0  0  0
  6  5  1  0  0  0  0
  7  4  2  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  7  1  0  0  0  0
  8 11  1  6  0  0  0
  9 12  1  6  0  0  0
 13 10  1  0  0  0  0
 14 10  2  0  0  0  0
  8 15  1  1  0  0  0
  9 16  1  1  0  0  0
M  CHG  1  13  -1
M  END
> <DATABASE_ID>
MMDBc0054809

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H14O4/c1-5(2)6-3-4-7(10(13)14)9(12)8(6)11/h3-5,8-9,11-12H,1-2H3,(H,13,14)/p-1/t8-,9+/m0/s1

> <INCHI_KEY>
BUZNWVREDOAOGD-DTWKUNHWSA-M

> <FORMULA>
C10H13O4

> <MOLECULAR_WEIGHT>
197.211

> <EXACT_MASS>
197.081932479

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
19.748159644496738

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S,6R)-5,6-dihydroxy-4-(propan-2-yl)cyclohexa-1,3-diene-1-carboxylate

> <JCHEM_LOGP>
0.20376436633333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.267819024188846

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.434239457281602

> <JCHEM_PKA_STRONGEST_BASIC>
-3.45036203847145

> <JCHEM_POLAR_SURFACE_AREA>
80.59

> <JCHEM_REFRACTIVITY>
62.8301

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(5S,6R)-5,6-dihydroxy-4-isopropylcyclohexa-1,3-diene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.000   0.000   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       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O-1
HETATM   14  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   15  H   UNK     0       0.000   3.080   0.000  0.00  0.00           H+0
HETATM   16  H   UNK     0       2.667   3.080   0.000  0.00  0.00           H+0
CONECT    1    5                                                            
CONECT    2    5                                                            
CONECT    3    4    6                                                       
CONECT    4    3    7                                                       
CONECT    5    1    2    6                                                  
CONECT    6    3    5    8                                                  
CONECT    7    4    9   10                                                  
CONECT    8    6    9   11   15                                             
CONECT    9    7    8   12   16                                             
CONECT   10    7   13   14                                                  
CONECT   11    8                                                            
CONECT   12    9                                                            
CONECT   13   10                                                            
CONECT   14   10                                                            
CONECT   15    8                                                            
CONECT   16    9                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

Synonyms

Value	Source
(2R,3S)-2,3-Dihydroxy-2,3-dihydro-p-cumate	ChEBI
(2R,3S)-2,3-Dihydroxy-2,3-dihydro-p-cumic acid	Generator
cis-5,6-Dihydroxy-4-isopropylcyclohexa-1,3-dienecarboxylic acid	Generator

Molecular Formula

C₁₀H₁₃O₄

Average Mass

197.211

Monoisotopic Mass

197.081932479

IUPAC Name

(5S,6R)-5,6-dihydroxy-4-(propan-2-yl)cyclohexa-1,3-diene-1-carboxylate

Traditional Name

(5S,6R)-5,6-dihydroxy-4-isopropylcyclohexa-1,3-diene-1-carboxylate

CAS Registry Number

Not Available

SMILES

[H][C@]1(O)C(=CC=C(C([O-])=O)[C@@]1([H])O)C(C)C

InChI Identifier

InChI=1S/C10H14O4/c1-5(2)6-3-4-7(10(13)14)9(12)8(6)11/h3-5,8-9,11-12H,1-2H3,(H,13,14)/p-1/t8-,9+/m0/s1

InChI Key

BUZNWVREDOAOGD-DTWKUNHWSA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Menthane monoterpenoids

Alternative Parents

Substituents

Monocyclic monoterpenoid
P-menthane monoterpenoid
Beta-hydroxy acid
Hydroxy acid
1,2-diol
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Carbonyl group
Organic oxide
Organooxygen compound
Organic anion
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

hydroxy monocarboxylic acid anion (CHEBI:58420 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	0.2	ChemAxon
pKa (Strongest Acidic)	4.43	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	80.59 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	62.83 m³·mol⁻¹	ChemAxon
Polarizability	19.75 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

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0014380	(2R,3S)-2,3-dihydroxy-2,3-dihydro-p-cumic acid	2,3-dihydroxy-p-cumic acid	2,3-dihydroxy-2,3-dihydro-p-cumate dehydrogenase	Dehydrogenation	RHEA	34755880
MMDBr0015843	Hydrogen Ion	(2R,3S)-2,3-dihydroxy-2,3-dihydro-p-cumic acid	p-cumate 2,3-dioxygenase system, large oxygenase component	Oxygenation	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	2	Human feces; Human

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

7822061

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9543088

PDB ID

Not Available

ChEBI ID

58420

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for (2R,3S)-2,3-dihydroxy-2,3-dihydro-p-cumic acid (MMDBc0054809)

MOL for #<Metabolite:0x0000564af37195f0>

3D MOL for #<Metabolite:0x0000564af37195f0>

3D SDF for #<Metabolite:0x0000564af37195f0>

3D-SDF for #<Metabolite:0x0000564af37195f0>

PDB for #<Metabolite:0x0000564af37195f0>

3D PDB for #<Metabolite:0x0000564af37195f0>

SMILES for #<Metabolite:0x0000564af37195f0>

INCHI for #<Metabolite:0x0000564af37195f0>

Structure for #<Metabolite:0x0000564af37195f0>

3D Structure for #<Metabolite:0x0000564af37195f0>