MiMeDB: Showing metabocard for cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol (MMDBc0030048)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:51:59 UTC

Update Date

2022-08-31 17:39:13 UTC

Metabolite ID

MMDBc0030048

Metabolite Identification

Common Name

cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol

Description

Cis-3-(3-carboxyethenyl)-3,5-cyclohexadiene-1,2-diol belongs to the class of Unsaturated Fatty Acids. These are fatty acids whose chain contains at least one CC double bond. (inferred from compound structure)

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 08131209282D          

 17 17  0  0  0  0            999 V2000
    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
   -0.0000    0.0000    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
    2.8579    0.8250    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
    3.5724    1.2375    0.0000 C   0  0  0  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
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    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 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    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
  2  1  1  0  0  0  0
  3  1  2  0  0  0  0
  5  4  2  0  0  0  0
  6  2  2  0  0  0  0
  6  4  1  0  0  0  0
  7  3  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
  9  7  1  0  0  0  0
  7 10  1  6  0  0  0
 11  8  2  0  0  0  0
 12  8  1  0  0  0  0
  9 13  1  6  0  0  0
 14  4  1  0  0  0  0
 15  5  1  0  0  0  0
  7 16  1  1  0  0  0
  9 17  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0030048

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O4/c10-7-3-1-2-6(9(7)13)4-5-8(11)12/h1-5,7,9-10,13H,(H,11,12)/b5-4+/t7-,9+/m0/s1

> <INCHI_KEY>
AEUBLTTWYCDTGM-HXOXMVQHSA-N

> <FORMULA>
C9H10O4

> <MOLECULAR_WEIGHT>
182.1733

> <EXACT_MASS>
182.057908808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
17.712300873068983

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]prop-2-enoic acid

> <ALOGPS_LOGP>
0.22

> <JCHEM_LOGP>
-0.39615821100000026

> <ALOGPS_LOGS>
-1.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.308312508610566

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.447460916672011

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3466707470105623

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
48.804899999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.65e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-AUG-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-AUG-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   14  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   15  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   16  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   17  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    2    3                                                       
CONECT    2    1    6                                                       
CONECT    3    1    7                                                       
CONECT    4    5    6   14                                                  
CONECT    5    4    8   15                                                  
CONECT    6    2    4    9                                                  
CONECT    7    3    9   10   16                                             
CONECT    8    5   11   12                                                  
CONECT    9    6    7   13   17                                             
CONECT   10    7                                                            
CONECT   11    8                                                            
CONECT   12    8                                                            
CONECT   13    9                                                            
CONECT   14    4                                                            
CONECT   15    5                                                            
CONECT   16    7                                                            
CONECT   17    9                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

Synonyms

Value	Source
(2E)-3-(cis-5,6-Dihydroxycyclohexa-1,3-dien-1-yl)prop-2-enoate	Kegg
(2E)-3-(cis-5,6-Dihydroxycyclohexa-1,3-dien-1-yl)prop-2-enoic acid	Generator

Molecular Formula

C₉H₁₀O₄

Average Mass

182.1733

Monoisotopic Mass

182.057908808

IUPAC Name

(2E)-3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]prop-2-enoic acid

Traditional Name

(2E)-3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]prop-2-enoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C9H10O4/c10-7-3-1-2-6(9(7)13)4-5-8(11)12/h1-5,7,9-10,13H,(H,11,12)/b5-4+/t7-,9+/m0/s1

InChI Key

AEUBLTTWYCDTGM-HXOXMVQHSA-N

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
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dienyl]acrylic acid (CHEBI:61462 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	8.65 g/L	ALOGPS
logP	0.22	ALOGPS
logP	-0.4	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	4.45	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	48.8 m³·mol⁻¹	ChemAxon
Polarizability	17.71 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 GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-ccbff341ae73666fa73b	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01qi-1900000000-5ccb9b79c971454d53e3	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-06rf-7900000000-c29d91db275a61f25d16	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-26e5345d8825749c0023	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01bi-3900000000-0564d83ddf2238ad3e2b	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gbc-9200000000-62518c2e69f097044747	2015-09-14	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	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

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	20	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown

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
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

C12622

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5282145

PDB ID

Not Available

ChEBI ID

61462

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol (MMDBc0030048)

MOL for #<Metabolite:0x00007fecf499ec68>

3D MOL for #<Metabolite:0x00007fecf499ec68>

3D SDF for #<Metabolite:0x00007fecf499ec68>

3D-SDF for #<Metabolite:0x00007fecf499ec68>

PDB for #<Metabolite:0x00007fecf499ec68>

3D PDB for #<Metabolite:0x00007fecf499ec68>

SMILES for #<Metabolite:0x00007fecf499ec68>

INCHI for #<Metabolite:0x00007fecf499ec68>

Structure for #<Metabolite:0x00007fecf499ec68>

3D Structure for #<Metabolite:0x00007fecf499ec68>