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Human Metabolome Database Version 3.5

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Showing metabocard for Formononetin (HMDB05808)

Record Information
Version 3.5
Creation Date 2007-01-23 06:20:48 -0700
Update Date 2013-05-29 13:42:08 -0600
HMDB ID HMDB05808
Secondary Accession Numbers None
Metabolite Identification
Common Name Formononetin
Description Formononetin are abundant in vegetables. It is a phyto-oestrogen that is a polyphenolic non-steroidal plant compound with oestrogen-like biological activity (PMID: 16108819 Link_out). It can be the source of considerable estrogenic activity (http://www.herbalchem.net/Intermediate.htm).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 7-Hydroxy-3-(4-methoxyphenyl)-4-benzopyrone
  2. 7-Hydroxy-3-(4-methoxyphenyl)-4H-benzopyran-4-one
  3. 7-Hydroxy-3-(4-methoxyphenyl)-4H-benzopyran-4-one(9CI)
  4. 7-Hydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one
  5. 7-Hydroxy-4'-methoxy-Isoflavone
  6. 7-Hydroxy-4'-methoxy-Isoflavone (8CI)
  7. 7-Hydroxy-4'-methoxyisoflavone
  8. Biochanin b
  9. Formononetin
  10. Formononetol
Chemical Formula C16H12O4
Average Molecular Weight 268.2641
Monoisotopic Molecular Weight 268.073558872
IUPAC Name 7-hydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one
Traditional IUPAC Name formononetin
CAS Registry Number 485-72-3
SMILES COC1=CC=C(C=C1)C1=COC2=C(C=CC(O)=C2)C1=O
InChI Identifier InChI=1S/C16H12O4/c1-19-12-5-2-10(3-6-12)14-9-20-15-8-11(17)4-7-13(15)16(14)18/h2-9,17H,1H3
InChI Key HKQYGTCOTHHOMP-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Flavonoids
Sub Class Isoflavones
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Isoflavones(KEGG)
  • Isoflavonoids(KEGG)
  • Isoflavonoids(Lipidmaps)
  • a 4'-methoxyisoflavone(Cyc)
  • hydroxyisoflavone(ChEBI)
  • methoxyisoflavone(ChEBI)
Substituents
  • Alkyl Aryl Ether
  • Anisole
  • Benzopyran
  • Chromone
  • Phenol
  • Phenol Derivative
  • Pyran
  • Pyranone
Direct Parent Isoflavones
Ontology
Status Detected and Quantified
Origin
  • Food
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 256 - 258 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.04 g/L ALOGPS
LogP 3.56 ALOGPS
LogP 2.88 ChemAxon
LogS -3.82 ALOGPS
pKa (strongest acidic) 6.48 ChemAxon
pKa (strongest basic) -4.7 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 55.76 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 74.18 ChemAxon
Polarizability 27.86 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Expected but not Quantified
Not Applicable Not Available Not Available Comment Normal
Urine Detected and Quantified
0.0007 (0.0002-0.0011) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
  • Bouatra, S. ...
Urine Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 395
Urine Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 395
Urine Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 395
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID 395 Link_out
Phenol Explorer Metabolite ID 395 Link_out
FoodDB ID FDB012219
KNApSAcK ID C00002525 Link_out
Chemspider ID 4444070 Link_out
KEGG Compound ID C00858 Link_out
BioCyc ID 2-HYDROXYFORMONONETIN Link_out
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB05808 Link_out
Metagene Link HMDB05808 Link_out
METLIN ID Not Available
PubChem Compound 5280378 Link_out
PDB ID Not Available
ChEBI ID 18088 Link_out
References
Synthesis Reference Whalley J L; Bond T J; Botting N P Synthesis of 13C labelled daidzein and formononetin. Bioorganic & medicinal chemistry letters (1998), 8(18), 2569-72.
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. Park J, Kim SH, Cho D, Kim TS: Formononetin, a phyto-oestrogen, and its metabolites up-regulate interleukin-4 production in activated T cells via increased AP-1 DNA binding activity. Immunology. 2005 Sep;116(1):71-81. Pubmed: 16108819 Link_out