MiMeDB: Showing metabocard for 5-Carboxymethyl-2-hydroxymuconate semialdehyde (MMDBc0048260)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-04-29 21:54:57 UTC

Update Date

2022-09-01 02:14:29 UTC

MiMeDB ID

MMDBc0048260

Metabolite Identification

Common Name

5-Carboxymethyl-2-hydroxymuconate semialdehyde

Description

5-formyl-2-hydroxyhepta-2,4-dienedioic acid, also known as 2-hydroxy-5-carboxymethylmuconate semialdehyde or 5-carboxymethyl-2-hydroxymuconic semialdehyde, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Based on a literature review a significant number of articles have been published on 5-formyl-2-hydroxyhepta-2,4-dienedioic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304292223542D          

 15 14  0  0  0  0            999 V2000
    3.3000    0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    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
   -0.4125    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 O   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  1  0  0  0  0
  6  8  2  0  0  0  0
  4  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0048260

> <DATABASE_NAME>
MIME

> <SMILES>
[H]C(=O)C(\CC(O)=O)=C/C=C(\O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H8O6/c9-4-5(3-7(11)12)1-2-6(10)8(13)14/h1-2,4,10H,3H2,(H,11,12)(H,13,14)/b5-1-,6-2-

> <INCHI_KEY>
NLXIEJRQAIHYPN-IOBHVTPZSA-N

> <FORMULA>
C8H8O6

> <MOLECULAR_WEIGHT>
200.146

> <EXACT_MASS>
200.032087978

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
17.36387263898922

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z,4Z)-5-formyl-2-hydroxyhepta-2,4-dienedioic acid

> <ALOGPS_LOGP>
0.02

> <JCHEM_LOGP>
-0.6710952023333334

> <ALOGPS_LOGS>
-2.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.027284694795907

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1952610648560267

> <JCHEM_PKA_STRONGEST_BASIC>
-5.764754952448356

> <JCHEM_POLAR_SURFACE_AREA>
111.9

> <JCHEM_REFRACTIVITY>
46.591100000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.11e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z,4Z)-5-formyl-2-hydroxyhepta-2,4-dienedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  H   UNK     0       6.160   0.000   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       4.620   0.000   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.850  -1.334   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.160   2.667   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.930   4.001   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       6.930   1.334   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.770   1.334   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.000  -2.667   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -2.310  -1.334   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    4   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

Synonyms

Value	Source
2-Hydroxy-5-carboxymethylmuconate semialdehyde	ChEBI
5-Carboxymethyl-2-hydroxymuconate semialdehyde	ChEBI
5-Carboxymethyl-2-hydroxymuconic semialdehyde	ChEBI
2-Hydroxy-5-carboxymethylmuconic acid semialdehyde	Generator
5-Carboxymethyl-2-hydroxymuconic acid semialdehyde	Generator
5-Formyl-2-hydroxyhepta-2,4-dienedioate	Generator

Chemical Formula

C₈H₈O₆

Average Molecular Weight

200.146

Monoisotopic Molecular Weight

200.032087978

IUPAC Name

(2Z,4Z)-5-formyl-2-hydroxyhepta-2,4-dienedioic acid

Traditional Name

(2Z,4Z)-5-formyl-2-hydroxyhepta-2,4-dienedioic acid

CAS Registry Number

Not Available

SMILES

[H]C(=O)C(\CC(O)=O)=C/C=C(\O)C(O)=O

InChI Identifier

InChI=1S/C8H8O6/c9-4-5(3-7(11)12)1-2-6(10)8(13)14/h1-2,4,10H,3H2,(H,11,12)(H,13,14)/b5-1-,6-2-

InChI Key

NLXIEJRQAIHYPN-IOBHVTPZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-chain fatty acids

Alternative Parents

Substituents

Medium-chain fatty acid
Branched fatty acid
Hydroxy fatty acid
Dicarboxylic acid or derivatives
Unsaturated fatty acid
Alpha,beta-unsaturated aldehyde
Enal
Enol
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Aldehyde
Hydrocarbon derivative
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

muconic semialdehyde (CHEBI:17142 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	1.11 g/L	ALOGPS
logP	0.02	ALOGPS
logP	-0.67	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	3.2	ChemAxon
pKa (Strongest Basic)	-5.8	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	111.9 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	46.59 m³·mol⁻¹	ChemAxon
Polarizability	17.36 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-09	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

Proteins

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Related Health Condition	Evidence Type	Measured in Matrix	Data Source	Reference

Microbial Sources

Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
	Proteobacteria	43	Human Feces; Human	Metabolic reconstruction
	Firmicutes	14	Human Feces; Human	Metabolic reconstruction
	Actinobacteria	16	Human Feces; Human	Metabolic reconstruction
Fungi	Ascomycota	1		Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference	Details

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		details

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

20118005

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

17142

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 ]

Showing metabocard for 5-Carboxymethyl-2-hydroxymuconate semialdehyde (MMDBc0048260)

MOL for #<Metabolite:0x0000564abf7abc40>

3D MOL for #<Metabolite:0x0000564abf7abc40>

3D SDF for #<Metabolite:0x0000564abf7abc40>

3D-SDF for #<Metabolite:0x0000564abf7abc40>

PDB for #<Metabolite:0x0000564abf7abc40>

3D PDB for #<Metabolite:0x0000564abf7abc40>

SMILES for #<Metabolite:0x0000564abf7abc40>

INCHI for #<Metabolite:0x0000564abf7abc40>

Structure for #<Metabolite:0x0000564abf7abc40>

3D Structure for #<Metabolite:0x0000564abf7abc40>