MiMeDB: Showing metabocard for 3-hydroxy-4-(4-hydroxyphenyl)-5-methoxycarbonyl-5-(4-hydroxy-3-formylbenzyl)-2,5-dihydro-2-furanone (MMDBc0014437)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 05:27:37 UTC

Update Date

2022-08-31 06:37:40 UTC

Metabolite ID

MMDBc0014437

Metabolite Identification

Common Name

3-hydroxy-4-(4-hydroxyphenyl)-5-methoxycarbonyl-5-(4-hydroxy-3-formylbenzyl)-2,5-dihydro-2-furanone

Description

CHEMBL4643065 belongs to the class of organic compounds known as hydroxybenzaldehydes. These are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group. Based on a literature review very few articles have been published on CHEMBL4643065.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152107272D          

 28 30  0  0  1  0            999 V2000
   -3.2333    3.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4731    4.3010    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
    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
   -0.7280    5.0856    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
   -0.7702    2.9033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8940    4.8156    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
   -2.0871    4.6440    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
   -1.5350    5.2571    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  1  0  0  0  0  0  0  0  0  0
   -3.1490    5.6002    0.0000 O   0  0  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
   -1.7900    6.0418    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  3  1  0  0  0  0
  6  4  2  0  0  0  0
  7  2  2  0  0  0  0
 11  2  1  0  0  0  0
 11  8  2  0  0  0  0
 11  9  1  0  0  0  0
 12  3  2  0  0  0  0
 12  4  1  0  0  0  0
 13  8  1  0  0  0  0
 13 10  1  0  0  0  0
 14  5  2  0  0  0  0
 14  6  1  0  0  0  0
 15  7  1  0  0  0  0
 15 13  2  0  0  0  0
 16 12  1  0  0  0  0
 17 16  2  0  0  0  0
 18 17  1  0  0  0  0
 20  9  1  6  0  0  0
 20 16  1  0  0  0  0
 20 19  1  1  0  0  0
 21 10  2  0  0  0  0
 22 14  1  0  0  0  0
 23 15  1  0  0  0  0
 24 17  1  0  0  0  0
 25 18  2  0  0  0  0
 26 19  2  0  0  0  0
 27  1  1  0  0  0  0
 27 19  1  0  0  0  0
 28 18  1  0  0  0  0
 28 20  1  0  0  0  0
M  END


  Mrv1652305152107272D          

 28 30  0  0  1  0            999 V2000
   -3.2333    3.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4731    4.3010    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
    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
   -0.7280    5.0856    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
   -0.7702    2.9033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8940    4.8156    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
   -2.0871    4.6440    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
   -1.5350    5.2571    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  1  0  0  0  0  0  0  0  0  0
   -3.1490    5.6002    0.0000 O   0  0  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
   -1.7900    6.0418    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  3  1  0  0  0  0
  6  4  2  0  0  0  0
  7  2  2  0  0  0  0
 11  2  1  0  0  0  0
 11  8  2  0  0  0  0
 11  9  1  0  0  0  0
 12  3  2  0  0  0  0
 12  4  1  0  0  0  0
 13  8  1  0  0  0  0
 13 10  1  0  0  0  0
 14  5  2  0  0  0  0
 14  6  1  0  0  0  0
 15  7  1  0  0  0  0
 15 13  2  0  0  0  0
 16 12  1  0  0  0  0
 17 16  2  0  0  0  0
 18 17  1  0  0  0  0
 20  9  1  6  0  0  0
 20 16  1  0  0  0  0
 20 19  1  1  0  0  0
 21 10  2  0  0  0  0
 22 14  1  0  0  0  0
 23 15  1  0  0  0  0
 24 17  1  0  0  0  0
 25 18  2  0  0  0  0
 26 19  2  0  0  0  0
 27  1  1  0  0  0  0
 27 19  1  0  0  0  0
 28 18  1  0  0  0  0
 28 20  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0014437

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H16O8/c1-27-19(26)20(9-11-2-7-15(23)13(8-11)10-21)16(17(24)18(25)28-20)12-3-5-14(22)6-4-12/h2-8,10,22-24H,9H2,1H3/t20-/m1/s1

> <INCHI_KEY>
XRPSJKOYIJOFHY-HXUWFJFHSA-N

> <FORMULA>
C20H16O8

> <MOLECULAR_WEIGHT>
384.34

> <EXACT_MASS>
384.084517475

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
36.10572671063625

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2R)-2-[(3-formyl-4-hydroxyphenyl)methyl]-4-hydroxy-3-(4-hydroxyphenyl)-5-oxo-2,5-dihydrofuran-2-carboxylate

> <ALOGPS_LOGP>
2.34

> <JCHEM_LOGP>
3.2141540919999994

> <ALOGPS_LOGS>
-4.18

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.67082277458391

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.08714554092574

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3806641471104673

> <JCHEM_POLAR_SURFACE_AREA>
130.36

> <JCHEM_REFRACTIVITY>
98.06889999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.57e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2R)-2-[(3-formyl-4-hydroxyphenyl)methyl]-4-hydroxy-3-(4-hydroxyphenyl)-5-oxofuran-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0      -6.035   6.244   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.883   8.029   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       2.851   3.291   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.027   5.828   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.359   9.493   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.420   7.204   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      -5.402   8.989   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.914   6.884   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.242   3.846   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.896   8.669   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.172   4.797   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.865   9.813   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.222   3.370   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.698   1.905   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.238   1.905   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.499   5.419   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.468   4.275   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -5.878  10.454   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.636   5.273   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -3.341  11.278   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -0.793   0.659   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -4.143   0.659   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -3.975   6.884   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -5.005   5.099   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -3.714   3.370   0.000  0.00  0.00           O+0
CONECT    1   27                                                            
CONECT    2    7   11                                                       
CONECT    3    5   12                                                       
CONECT    4    6   12                                                       
CONECT    5    3   14                                                       
CONECT    6    4   14                                                       
CONECT    7    2   15                                                       
CONECT    8   11   13                                                       
CONECT    9   11   20                                                       
CONECT   10   13   21                                                       
CONECT   11    2    8    9                                                  
CONECT   12    3    4   16                                                  
CONECT   13    8   10   15                                                  
CONECT   14    5    6   22                                                  
CONECT   15    7   13   23                                                  
CONECT   16   12   17   20                                                  
CONECT   17   16   18   24                                                  
CONECT   18   17   25   28                                                  
CONECT   19   20   26   27                                                  
CONECT   20    9   16   19   28                                             
CONECT   21   10                                                            
CONECT   22   14                                                            
CONECT   23   15                                                            
CONECT   24   17                                                            
CONECT   25   18                                                            
CONECT   26   19                                                            
CONECT   27    1   19                                                       
CONECT   28   18   20                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

Synonyms

Value	Source
3-Hydroxy-4-(4-hydroxyphenyl)-5-methoxycarbonyl-5-(4-hydroxy-3-formylbenzyl)-2,5-dihydro-2-furanone	MeSH

Molecular Formula

C₂₀H₁₆O₈

Average Mass

384.34

Monoisotopic Mass

384.084517475

IUPAC Name

methyl (2R)-2-[(3-formyl-4-hydroxyphenyl)methyl]-4-hydroxy-3-(4-hydroxyphenyl)-5-oxo-2,5-dihydrofuran-2-carboxylate

Traditional Name

methyl (2R)-2-[(3-formyl-4-hydroxyphenyl)methyl]-4-hydroxy-3-(4-hydroxyphenyl)-5-oxofuran-2-carboxylate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H16O8/c1-27-19(26)20(9-11-2-7-15(23)13(8-11)10-21)16(17(24)18(25)28-20)12-3-5-14(22)6-4-12/h2-8,10,22-24H,9H2,1H3/t20-/m1/s1

InChI Key

XRPSJKOYIJOFHY-HXUWFJFHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxybenzaldehydes. These are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Hydroxybenzaldehydes

Alternative Parents

Substituents

Hydroxybenzaldehyde
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acid ester
Fatty acyl
Benzenoid
Dicarboxylic acid or derivatives
2-furanone
Monocyclic benzene moiety
Vinylogous acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Dihydrofuran
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Enol
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
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
Water Solubility	0.026 g/L	ALOGPS
logP	2.34	ALOGPS
logP	3.21	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	8.09	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	130.36 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	98.07 m³·mol⁻¹	ChemAxon
Polarizability	36.11 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	Yes	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

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
Eukaryota/Fungi	Ascomycota	2	Human feces; Human sputum; Human	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	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

29784818

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139587026

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for 3-hydroxy-4-(4-hydroxyphenyl)-5-methoxycarbonyl-5-(4-hydroxy-3-formylbenzyl)-2,5-dihydro-2-furanone (MMDBc0014437)

MOL for #<Metabolite:0x00007f92008ff130>

3D MOL for #<Metabolite:0x00007f92008ff130>

3D SDF for #<Metabolite:0x00007f92008ff130>

3D-SDF for #<Metabolite:0x00007f92008ff130>

PDB for #<Metabolite:0x00007f92008ff130>

3D PDB for #<Metabolite:0x00007f92008ff130>

SMILES for #<Metabolite:0x00007f92008ff130>

INCHI for #<Metabolite:0x00007f92008ff130>

Structure for #<Metabolite:0x00007f92008ff130>

3D Structure for #<Metabolite:0x00007f92008ff130>