MiMeDB: Showing metabocard for Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol (MMDBc0031650)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:42:53 UTC

Update Date

2022-08-31 18:22:48 UTC

Metabolite ID

MMDBc0031650

Metabolite Identification

Common Name

Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol

Description

Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol is a member of the chemical class known as Cyclic Alcohols and Derivatives. These are organic compounds containing an aliphatic ring substituted with at least one hydroxyl group. Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol is invovled in Phenylpropionic acid degradation. r 15;80(8):2939-48.)

Structure

MOL SDF PDB SMILES InChI

9543127
  Mrv0541 07101212472D          

 24 24  0  0  1  0            999 V2000
    5.2224    1.1096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    0.2846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.1279    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    2.3645    1.1096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.2846    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5080   -0.1279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.1279    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7935    0.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.9529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.9529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.1279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655    0.5404    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799   -0.3836    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1223    0.6764    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4647    0.6764    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0650   -1.2087    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799   -1.2087    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7502   -0.5197    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4078   -0.5197    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.8769    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655    1.3654    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0944    0.0289    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  6  0  0  0
  1 23  1  0  0  0  0
  7  2  1  6  0  0  0
  2 24  1  0  0  0  0
  3 13  1  0  0  0  0
  4 13  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5 14  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  2  0  0  0  0
  7 10  1  0  0  0  0
  7 15  1  0  0  0  0
  8 11  1  0  0  0  0
  8 16  1  0  0  0  0
  8 17  1  0  0  0  0
  9 12  1  0  0  0  0
  9 18  1  0  0  0  0
 10 12  2  0  0  0  0
 10 19  1  0  0  0  0
 11 13  1  0  0  0  0
 11 20  1  0  0  0  0
 11 21  1  0  0  0  0
 12 22  1  0  0  0  0
M  CHG  1   3  -1
M  END
> <DATABASE_ID>
MMDBc0031650

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H12O4/c10-7-3-1-2-6(9(7)13)4-5-8(11)12/h1-3,7,9-10,13H,4-5H2,(H,11,12)/p-1/t7-,9+/m1/s1

> <INCHI_KEY>
RKDFGWAXBBGKMR-APPZFPTMSA-M

> <FORMULA>
C9H11O4

> <MOLECULAR_WEIGHT>
183.1812

> <EXACT_MASS>
183.06573384

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
17.768535290119818

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[(5R,6S)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]propanoate

> <ALOGPS_LOGP>
0.11

> <JCHEM_LOGP>
-0.3939817006666665

> <ALOGPS_LOGS>
-0.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.340947886242418

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.383294991115847

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3417817916463246

> <JCHEM_POLAR_SURFACE_AREA>
80.59

> <JCHEM_REFRACTIVITY>
58.54870000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.10e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(5R,6S)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-JUL-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 9543127                                           
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-JUL-12         0                                  
HETATM    1  O   UNK     0       9.749   2.071   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      12.416   0.531   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       3.080  -0.239   0.000  0.00  0.00           O-1
HETATM    4  O   UNK     0       4.414   2.071   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       9.749   0.531   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.415  -0.239   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.082  -0.239   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.081   0.531   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.415  -1.779   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.082  -1.779   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.747  -0.239   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.749  -2.549   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414   0.531   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0      10.576   1.009   0.000  0.00  0.00           H+0
HETATM   15  H   UNK     0      11.909  -0.716   0.000  0.00  0.00           H+0
HETATM   16  H   UNK     0       7.695   1.263   0.000  0.00  0.00           H+0
HETATM   17  H   UNK     0       6.468   1.263   0.000  0.00  0.00           H+0
HETATM   18  H   UNK     0       7.588  -2.256   0.000  0.00  0.00           H+0
HETATM   19  H   UNK     0      11.909  -2.256   0.000  0.00  0.00           H+0
HETATM   20  H   UNK     0       5.134  -0.970   0.000  0.00  0.00           H+0
HETATM   21  H   UNK     0       6.361  -0.970   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0       9.749  -3.504   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0      10.576   2.549   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      13.243   0.054   0.000  0.00  0.00           H+0
CONECT    1    5   23                                                       
CONECT    2    7   24                                                       
CONECT    3   13                                                            
CONECT    4   13                                                            
CONECT    5    1    6    7   14                                             
CONECT    6    5    8    9                                                  
CONECT    7    2    5   10   15                                             
CONECT    8    6   11   16   17                                             
CONECT    9    6   12   18                                                  
CONECT   10    7   12   19                                                  
CONECT   11    8   13   20   21                                             
CONECT   12    9   10   22                                                  
CONECT   13    3    4   11                                                  
CONECT   14    5                                                            
CONECT   15    7                                                            
CONECT   16    8                                                            
CONECT   17    8                                                            
CONECT   18    9                                                            
CONECT   19   10                                                            
CONECT   20   11                                                            
CONECT   21   11                                                            
CONECT   22   12                                                            
CONECT   23    1                                                            
CONECT   24    2                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   48    0
END

Synonyms

Value	Source
3-(cis-5,6-Dihydroxycyclohexa-1,3-dien-1-yl)propanoate	ChEBI
3-(cis-5,6-Dihydroxycyclohexa-1,3-dienyl)propionate	ChEBI
3-(cis-5,6-Dihydroxycyclohexa-1,3-dien-1-yl)propanoic acid	Generator
3-(cis-5,6-Dihydroxycyclohexa-1,3-dienyl)propionic acid	Generator

Molecular Formula

C₉H₁₁O₄

Average Mass

183.1812

Monoisotopic Mass

183.06573384

IUPAC Name

3-[(5R,6S)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]propanoate

Traditional Name

3-[(5R,6S)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]propanoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C9H12O4/c10-7-3-1-2-6(9(7)13)4-5-8(11)12/h1-3,7,9-10,13H,4-5H2,(H,11,12)/p-1/t7-,9+/m1/s1

InChI Key

RKDFGWAXBBGKMR-APPZFPTMSA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,2-diols. These are polyols containing an alcohol group at two adjacent positions.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

1,2-diols

Alternative Parents

Substituents

Secondary alcohol
1,2-diol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic anion
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

monocarboxylic acid anion (CHEBI:60087 )
cyclohexadienediol (CHEBI:60087 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	110 g/L	ALOGPS
logP	0.11	ALOGPS
logP	-0.39	ChemAxon
logS	-0.26	ALOGPS
pKa (Strongest Acidic)	4.38	ChemAxon
pKa (Strongest Basic)	-3.3	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	3	ChemAxon
Refractivity	58.55 m³·mol⁻¹	ChemAxon
Polarizability	17.77 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

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-cc2c9931c60d508f8019	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00e9-2900000000-cf8bb3986b08d1ccb57c	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9100000000-e271782d2112ea3e2d7b	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-c741fa27abb7d9fb835e	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-1900000000-a367f068c9ccca892187	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-6900000000-e50087b55d65486dac49	2015-09-15	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

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

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0008149	Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol	3-(2,3-Dihydroxyphenyl)propanoate	Not Available		VMH	30371894
MMDBr0008174	Phenylpropanoate	Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol	Not Available		VMH	30371894

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	50	Human feces; Human sputum; Human ; Human feces; pleural fluid plaque; bal; Human stool	Unknown; Metabolic reconstruction
Bacteria	Actinobacteria	3	Human feces; Human	Metabolic reconstruction

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

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

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

9543127

PDB ID

Not Available

ChEBI ID

60087

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]
Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]
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 Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol (MMDBc0031650)

MOL for #<Metabolite:0x00007fdb712115c0>

3D MOL for #<Metabolite:0x00007fdb712115c0>

3D SDF for #<Metabolite:0x00007fdb712115c0>

3D-SDF for #<Metabolite:0x00007fdb712115c0>

PDB for #<Metabolite:0x00007fdb712115c0>

3D PDB for #<Metabolite:0x00007fdb712115c0>

SMILES for #<Metabolite:0x00007fdb712115c0>

INCHI for #<Metabolite:0x00007fdb712115c0>

Structure for #<Metabolite:0x00007fdb712115c0>

3D Structure for #<Metabolite:0x00007fdb712115c0>