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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:43:04 UTC
Update Date2019-07-23 06:08:45 UTC
HMDB IDHMDB0031428
Secondary Accession Numbers
  • HMDB31428
Metabolite Identification
Common NameFarnisin
DescriptionFarnisin belongs to the class of organic compounds known as 4'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C4' atom of the flavonoid backbone. Thus, farnisin is considered to be a flavonoid lipid molecule. Farnisin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563862125
Synonyms
ValueSource
3',7-Dihydroxy-4'-methoxyflavoneHMDB
7-Hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-oneHMDB
Chemical FormulaC16H12O5
Average Molecular Weight284.2635
Monoisotopic Molecular Weight284.068473494
IUPAC Name7-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one
Traditional Namefarnisin
CAS Registry Number54867-60-6
SMILES
COC1=C(O)C=C(C=C1)C1=CC(=O)C2=C(O1)C=C(O)C=C2
InChI Identifier
InChI=1S/C16H12O5/c1-20-14-5-2-9(6-13(14)19)15-8-12(18)11-4-3-10(17)7-16(11)21-15/h2-8,17,19H,1H3
InChI KeyQAGGICSUEVNSGH-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 4'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C4' atom of the flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassO-methylated flavonoids
Direct Parent4'-O-methylated flavonoids
Alternative Parents
Substituents
  • 4p-methoxyflavonoid-skeleton
  • 3'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • Methoxyphenol
  • 1-benzopyran
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Pyranone
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point264 - 265 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.058 g/LALOGPS
logP3.37ALOGPS
logP2.2ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)6.51ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity77.4 m³·mol⁻¹ChemAxon
Polarizability28.89 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-067i-0490000000-3210eaca1a8a52cb736aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-08ml-3429700000-3e2f6d9decfbf79b8976Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-aee55d6250fe8366dde4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0190000000-cec4d7c1ec89eafffd5fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01w0-5950000000-ac3d6ec1132c10d7e14bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-f847deeaa5ab44da9ea6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0090000000-fde9c7cc9fa1a38da07cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kr-1590000000-3ad23096bc522b7ceb93Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003506
KNApSAcK IDC00013297
Chemspider ID4527102
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5378220
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Farnisin → 3,4,5-trihydroxy-6-{[2-(3-hydroxy-4-methoxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxane-2-carboxylic aciddetails
Farnisin → 3,4,5-trihydroxy-6-[5-(7-hydroxy-4-oxo-4H-chromen-2-yl)-2-methoxyphenoxy]oxane-2-carboxylic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
Farnisin → [5-(7-hydroxy-4-oxo-4H-chromen-2-yl)-2-methoxyphenyl]oxidanesulfonic aciddetails