MiMeDB: Showing metabocard for S-Dihydrogenistein (MMDBc0057131)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-10-25 16:47:44 UTC

Update Date

2024-04-30 20:56:22 UTC

Metabolite ID

MMDBc0057131

Metabolite Identification

Common Name

S-Dihydrogenistein

Description

S-Dihydrogenistein is a metabolite of the soy isoflavone genistin (the glycoside conjugate of genistein) by intestinal bacteria. Isoflavones are one of the three major classes of phytoestrogens; phytoestrogens are a diverse group of plant-derived compounds that structurally and functionally mimic mammalian estrogen. The isoflavone genistin is one of the most prevalent in soy foods. They are biologically inactive; once ingested, they are cleaved by glucosidases to "aglycones", genistein. Epidemiological studies have associated high soy intake with a lowered risk for certain hormone-dependent disease. Many studies reveal that the incidence of prostate cancer and breast cancer is much lower in Asian people in comparison to people from the West and, and the prevailing contribution to this difference has been attributed to the diet. Soy foods and soy-derived products which contain abundant isoflavones are consumed in large quantities by Asian people. In vitro, isoflavone metabolites have dual functions: they can act as an estrogenic agonist or antagonist depending on the estrogen concentration. (PMID: 17499260 , 16965913 ). Dihydrogenistein is a biomarker for the consumption of soy beans and other soy products.

Structure

MOL SDF PDB SMILES InChI

14544209
  Mrv0541 02271202132D          

 20 22  0  0  1  0            999 V2000
    5.6654    1.1780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6654   -1.2970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1078   -1.3255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5777    1.1980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0929   -1.7095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9508   -0.0595    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9508    0.7655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6654   -0.4720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364   -0.4720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3798   -0.0595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3798    0.7655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1173   -0.5005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5219   -0.0595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364   -1.2970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1173    1.2066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8648   -0.0766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8648    0.7827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.4720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5219   -1.7095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -1.2970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  1 11  1  0  0  0  0
  2  8  2  0  0  0  0
  3 12  1  0  0  0  0
  4 17  1  0  0  0  0
  5 20  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  1  0  0  0
  8 10  1  0  0  0  0
  9 13  2  0  0  0  0
  9 14  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 11 15  2  0  0  0  0
 12 16  1  0  0  0  0
 13 18  1  0  0  0  0
 14 19  2  0  0  0  0
 15 17  1  0  0  0  0
 16 17  2  0  0  0  0
 18 20  2  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0057131

> <DATABASE_NAME>
MIME

> <SMILES>
OC1=CC=C(C=C1)[C@H]1COC2=CC(O)=CC(O)=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)11-7-20-13-6-10(17)5-12(18)14(13)15(11)19/h1-6,11,16-18H,7H2/t11-/m1/s1

> <INCHI_KEY>
UQGVUYNHDKMLSE-LLVKDONJSA-N

> <FORMULA>
C15H12O5

> <MOLECULAR_WEIGHT>
272.2528

> <EXACT_MASS>
272.068473494

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
27.033336048970064

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S)-5,7-dihydroxy-3-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
2.45

> <JCHEM_LOGP>
2.7276581139999996

> <ALOGPS_LOGS>
-3.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.47348114517299

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.8952448344775

> <JCHEM_PKA_STRONGEST_BASIC>
-3.864851377500867

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
71.67650000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.28e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-5,7-dihydroxy-3-(4-hydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 14544209                                          
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  O   UNK     0      10.575   2.199   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      10.575  -2.421   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      13.268  -2.474   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      16.012   2.236   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       3.907  -3.191   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       9.241  -0.111   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.241   1.429   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.575  -0.881   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.908  -0.881   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.909  -0.111   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.909   1.429   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.286  -0.934   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.574  -0.111   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.908  -2.421   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.286   2.252   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.681  -0.143   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.681   1.461   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.241  -0.881   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.574  -3.191   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.241  -2.421   0.000  0.00  0.00           C+0
CONECT    1    7   11                                                       
CONECT    2    8                                                            
CONECT    3   12                                                            
CONECT    4   17                                                            
CONECT    5   20                                                            
CONECT    6    7    8    9                                                  
CONECT    7    1    6                                                       
CONECT    8    2    6   10                                                  
CONECT    9    6   13   14                                                  
CONECT   10    8   11   12                                                  
CONECT   11    1   10   15                                                  
CONECT   12    3   10   16                                                  
CONECT   13    9   18                                                       
CONECT   14    9   19                                                       
CONECT   15   11   17                                                       
CONECT   16   12   17                                                       
CONECT   17    4   15   16                                                  
CONECT   18   13   20                                                       
CONECT   19   14   20                                                       
CONECT   20    5   18   19                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

Synonyms

Not Available

Molecular Formula

C₁₅H₁₂O₅

Average Mass

272.2528

Monoisotopic Mass

272.068473494

IUPAC Name

(3S)-5,7-dihydroxy-3-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

(3S)-5,7-dihydroxy-3-(4-hydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

480-41-1

SMILES

OC1=CC=C(C=C1)[C@H]1COC2=CC(O)=CC(O)=C2C1=O

InChI Identifier

InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)11-7-20-13-6-10(17)5-12(18)14(13)15(11)19/h1-6,11,16-18H,7H2/t11-/m1/s1

InChI Key

UQGVUYNHDKMLSE-LLVKDONJSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavanones. These are polycyclic compounds containing an isoflavan skeleton which bears a ketone at position C4.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflavans

Direct Parent

Isoflavanones

Alternative Parents

Substituents

Isoflavanone
Isoflavanol
Hydroxyisoflavonoid
Chromone
1-benzopyran
Benzopyran
Chromane
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.23 g/L	ALOGPS
logP	2.45	ALOGPS
logP	2.73	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	7.9	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	71.68 m³·mol⁻¹	ChemAxon
Polarizability	27.03 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

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0290000000-67314fd704a2ca62f247	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ab9-0960000000-ca5bc0f4bb9be2f46d21	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05r9-8900000000-58d3c30024248f281de2	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0090000000-2d02bd35fd14350b3ba9	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0290000000-fd1ddcaa465b5f5b826b	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0hfx-4940000000-219088b1d18e90e2c8d6	2019-02-23	View Spectrum

Biological Properties

Cellular Locations

Membrane

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

Exposure Sources

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

14544209

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Mayo B, Vazquez L, Florez AB: Equol: A Bacterial Metabolite from The Daidzein Isoflavone and Its Presumed Beneficial Health Effects. Nutrients. 2019 Sep 16;11(9). pii: nu11092231. doi: 10.3390/nu11092231. [PubMed:31527435 ]
Chen L, Zhao X, Fang L, Games DE: Quantitative determination of acetyl glucoside isoflavones and their metabolites in human urine using combined liquid chromatography-mass spectrometry. J Chromatogr A. 2007 Jun 22;1154(1-2):103-10. doi: 10.1016/j.chroma.2007.03.010. Epub 2007 Mar 15. [PubMed:17499260 ]
Hwang CS, Kwak HS, Lim HJ, Lee SH, Kang YS, Choe TB, Hur HG, Han KO: Isoflavone metabolites and their in vitro dual functions: they can act as an estrogenic agonist or antagonist depending on the estrogen concentration. J Steroid Biochem Mol Biol. 2006 Nov;101(4-5):246-53. doi: 10.1016/j.jsbmb.2006.06.020. Epub 2006 Sep 11. [PubMed:16965913 ]

Showing metabocard for S-Dihydrogenistein (MMDBc0057131)

MOL for #<Metabolite:0x00007fdb453e0080>

3D MOL for #<Metabolite:0x00007fdb453e0080>

3D SDF for #<Metabolite:0x00007fdb453e0080>

3D-SDF for #<Metabolite:0x00007fdb453e0080>

PDB for #<Metabolite:0x00007fdb453e0080>

3D PDB for #<Metabolite:0x00007fdb453e0080>

SMILES for #<Metabolite:0x00007fdb453e0080>

INCHI for #<Metabolite:0x00007fdb453e0080>

Structure for #<Metabolite:0x00007fdb453e0080>

3D Structure for #<Metabolite:0x00007fdb453e0080>