MiMeDB: Showing metabocard for (2S)-2-(4-hydoxybenzyl)-3-(4-hydroxyphenyl)-2-furonol carboxylic acid (MMDBc0054847)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:36:15 UTC

Update Date

2022-08-12 20:09:06 UTC

Metabolite ID

MMDBc0054847

Metabolite Identification

Common Name

(2S)-2-(4-hydoxybenzyl)-3-(4-hydroxyphenyl)-2-furonol carboxylic acid

Description

Butyrolactone IIa belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid. Based on a literature review very few articles have been published on Butyrolactone IIa.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221362D          

 25 27  0  0  1  0            999 V2000
   -0.4731    4.3010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8321    3.8594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7429    1.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3014    2.8672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7280    5.0856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0871    4.6440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5275    1.7631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0860    3.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7702    2.9033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0251    3.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1298    2.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5350    5.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6991    2.5701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6548    1.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9097    1.0206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7347    1.0206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8743    2.9033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222    2.2902    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7900    6.0418    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    2.4837    2.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4248    0.3532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2197    0.3532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1292    3.6879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6812    2.7317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9897    1.8053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  2  2  0  0  0  0
  7  3  1  0  0  0  0
  8  4  2  0  0  0  0
 10  1  2  0  0  0  0
 10  2  1  0  0  0  0
 10  9  1  0  0  0  0
 11  3  2  0  0  0  0
 11  4  1  0  0  0  0
 12  5  2  0  0  0  0
 12  6  1  0  0  0  0
 13  7  2  0  0  0  0
 13  8  1  0  0  0  0
 14 11  1  0  0  0  0
 15 14  2  0  0  0  0
 16 15  1  0  0  0  0
 18  9  1  1  0  0  0
 18 14  1  0  0  0  0
 18 17  1  6  0  0  0
 19 12  1  0  0  0  0
 20 13  1  0  0  0  0
 21 15  1  0  0  0  0
 22 16  2  0  0  0  0
 23 17  2  0  0  0  0
 24 17  1  0  0  0  0
 25 16  1  0  0  0  0
 25 18  1  0  0  0  0
M  CHG  1  19  -1
M  END


  Mrv1652306172221362D          

 25 27  0  0  1  0            999 V2000
   -0.4731    4.3010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8321    3.8594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7429    1.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3014    2.8672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7280    5.0856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0871    4.6440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5275    1.7631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0860    3.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7702    2.9033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0251    3.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1298    2.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5350    5.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6991    2.5701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6548    1.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9097    1.0206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7347    1.0206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8743    2.9033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222    2.2902    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7900    6.0418    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    2.4837    2.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4248    0.3532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2197    0.3532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1292    3.6879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6812    2.7317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9897    1.8053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  2  2  0  0  0  0
  7  3  1  0  0  0  0
  8  4  2  0  0  0  0
 10  1  2  0  0  0  0
 10  2  1  0  0  0  0
 10  9  1  0  0  0  0
 11  3  2  0  0  0  0
 11  4  1  0  0  0  0
 12  5  2  0  0  0  0
 12  6  1  0  0  0  0
 13  7  2  0  0  0  0
 13  8  1  0  0  0  0
 14 11  1  0  0  0  0
 15 14  2  0  0  0  0
 16 15  1  0  0  0  0
 18  9  1  1  0  0  0
 18 14  1  0  0  0  0
 18 17  1  6  0  0  0
 19 12  1  0  0  0  0
 20 13  1  0  0  0  0
 21 15  1  0  0  0  0
 22 16  2  0  0  0  0
 23 17  2  0  0  0  0
 24 17  1  0  0  0  0
 25 16  1  0  0  0  0
 25 18  1  0  0  0  0
M  CHG  1  19  -1
M  END
> <DATABASE_ID>
MMDBc0054847

> <DATABASE_NAME>
MIME

> <SMILES>
OC(=O)[C@@]1(CC2=CC=C([O-])C=C2)OC(=O)C(O)=C1C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H14O7/c19-12-5-1-10(2-6-12)9-18(17(23)24)14(15(21)16(22)25-18)11-3-7-13(20)8-4-11/h1-8,19-21H,9H2,(H,23,24)/p-1/t18-/m0/s1

> <INCHI_KEY>
DVKOSMUSPQXJAK-SFHVURJKSA-M

> <FORMULA>
C18H13O7

> <MOLECULAR_WEIGHT>
341.296

> <EXACT_MASS>
341.066676339

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
31.701200036361165

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-{[(2S)-2-carboxy-4-hydroxy-3-(4-hydroxyphenyl)-5-oxo-2,5-dihydrofuran-2-yl]methyl}benzen-1-olate

> <JCHEM_LOGP>
2.705757691333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.582474979807413

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1634758551263036

> <JCHEM_PKA_STRONGEST_BASIC>
-3.338022840847362

> <JCHEM_POLAR_SURFACE_AREA>
127.12

> <JCHEM_REFRACTIVITY>
97.2661

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4-{[(2S)-2-carboxy-4-hydroxy-3-(4-hydroxyphenyl)-5-oxofuran-2-yl]methyl}benzenolate

> <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      -0.883   8.029   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.420   7.204   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.387   2.815   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.563   5.352   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.359   9.493   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.896   8.669   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.851   3.291   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.027   5.828   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.438   5.419   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.914   6.884   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.242   3.846   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.865   9.813   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.172   4.797   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.222   3.370   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.698   1.905   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.238   1.905   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.499   5.419   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.468   4.275   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -3.341  11.278   0.000  0.00  0.00           O-1
HETATM   20  O   UNK     0       4.636   5.273   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -0.793   0.659   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -4.143   0.659   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -3.975   6.884   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -5.005   5.099   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -3.714   3.370   0.000  0.00  0.00           O+0
CONECT    1    5   10                                                       
CONECT    2    6   10                                                       
CONECT    3    7   11                                                       
CONECT    4    8   11                                                       
CONECT    5    1   12                                                       
CONECT    6    2   12                                                       
CONECT    7    3   13                                                       
CONECT    8    4   13                                                       
CONECT    9   10   18                                                       
CONECT   10    1    2    9                                                  
CONECT   11    3    4   14                                                  
CONECT   12    5    6   19                                                  
CONECT   13    7    8   20                                                  
CONECT   14   11   15   18                                                  
CONECT   15   14   16   21                                                  
CONECT   16   15   22   25                                                  
CONECT   17   18   23   24                                                  
CONECT   18    9   14   17   25                                             
CONECT   19   12                                                            
CONECT   20   13                                                            
CONECT   21   15                                                            
CONECT   22   16                                                            
CONECT   23   17                                                            
CONECT   24   17                                                            
CONECT   25   16   18                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

Synonyms

Not Available

Molecular Formula

C₁₈H₁₃O₇

Average Mass

341.296

Monoisotopic Mass

341.066676339

IUPAC Name

4-{[(2S)-2-carboxy-4-hydroxy-3-(4-hydroxyphenyl)-5-oxo-2,5-dihydrofuran-2-yl]methyl}benzen-1-olate

Traditional Name

4-{[(2S)-2-carboxy-4-hydroxy-3-(4-hydroxyphenyl)-5-oxofuran-2-yl]methyl}benzenolate

CAS Registry Number

Not Available

SMILES

OC(=O)[C@@]1(CC2=CC=C([O-])C=C2)OC(=O)C(O)=C1C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C18H14O7/c19-12-5-1-10(2-6-12)9-18(17(23)24)14(15(21)16(22)25-18)11-3-7-13(20)8-4-11/h1-8,19-21H,9H2,(H,23,24)/p-1/t18-/m0/s1

InChI Key

DVKOSMUSPQXJAK-SFHVURJKSA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Phenylpropanoic acids

Sub Class

Not Available

Direct Parent

Phenylpropanoic acids

Alternative Parents

Substituents

3-phenylpropanoic-acid
1-hydroxy-2-unsubstituted benzenoid
Phenoxide
Phenol
Benzenoid
Dicarboxylic acid or derivatives
2-furanone
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Dihydrofuran
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Enol
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Organic anion
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	2.71	ChemAxon
pKa (Strongest Acidic)	3.16	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	127.12 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	97.27 m³·mol⁻¹	ChemAxon
Polarizability	31.7 Å³	ChemAxon
Number of Rings	3	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
MMDBr0017375	3-(4-hydroxyphenyl)pyruvic acid	(2S)-2-(4-hydoxybenzyl)-3-(4-hydroxyphenyl)-2-furonol carboxylic acid	Nonribosomal peptide synthetase btyA	Synthesis	RHEA	34755880
MMDBr0017376	3-(4-hydroxyphenyl)pyruvic acid	(2S)-2-(4-hydoxybenzyl)-3-(4-hydroxyphenyl)-2-furonol carboxylic acid	Nonribosomal peptide synthetase btyA	Synthesis	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
Eukaryota/Fungi	Ascomycota	1

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

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

146170824

PDB ID

Not Available

ChEBI ID

Not Available

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 (2S)-2-(4-hydoxybenzyl)-3-(4-hydroxyphenyl)-2-furonol carboxylic acid (MMDBc0054847)

MOL for #<Metabolite:0x00007fa4ed6baac8>

3D MOL for #<Metabolite:0x00007fa4ed6baac8>

3D SDF for #<Metabolite:0x00007fa4ed6baac8>

3D-SDF for #<Metabolite:0x00007fa4ed6baac8>

PDB for #<Metabolite:0x00007fa4ed6baac8>

3D PDB for #<Metabolite:0x00007fa4ed6baac8>

SMILES for #<Metabolite:0x00007fa4ed6baac8>

INCHI for #<Metabolite:0x00007fa4ed6baac8>

Structure for #<Metabolite:0x00007fa4ed6baac8>

3D Structure for #<Metabolite:0x00007fa4ed6baac8>