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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:55:35 UTC
Update Date2019-07-23 06:19:46 UTC
HMDB IDHMDB0035883
Secondary Accession Numbers
  • HMDB35883
Metabolite Identification
Common Name2'-Hydroxyisoorientin
Description2'-Hydroxyisoorientin belongs to the class of organic compounds known as flavonoid c-glycosides. Flavonoid C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. 2'-Hydroxyisoorientin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 2'-hydroxyisoorientin has been detected, but not quantified in, barley and cereals and cereal products. This could make 2'-hydroxyisoorientin a potential biomarker for the consumption of these foods.
Structure
Data?1563862786
SynonymsNot Available
Chemical FormulaC21H20O12
Average Molecular Weight464.3763
Monoisotopic Molecular Weight464.095476104
IUPAC Name5,7-dihydroxy-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-(2,4,5-trihydroxyphenyl)-4H-chromen-4-one
Traditional Name5,7-dihydroxy-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-(2,4,5-trihydroxyphenyl)chromen-4-one
CAS Registry NumberNot Available
SMILES
OCC1OC(C(O)C(O)C1O)C1=C(O)C2=C(OC(=CC2=O)C2=CC(O)=C(O)C=C2O)C=C1O
InChI Identifier
InChI=1S/C21H20O12/c22-5-14-17(28)19(30)20(31)21(33-14)16-11(27)4-13-15(18(16)29)10(26)3-12(32-13)6-1-8(24)9(25)2-7(6)23/h1-4,14,17,19-25,27-31H,5H2
InChI KeyVGWBNVOKYXNHPW-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as flavonoid c-glycosides. Flavonoid C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid C-glycosides
Alternative Parents
Substituents
  • Flavonoid c-glycoside
  • Hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Phenolic glycoside
  • Hexose monosaccharide
  • Glycosyl compound
  • C-glycosyl compound
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Hydroxyquinol derivative
  • Pyranone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Oxane
  • Monosaccharide
  • Vinylogous acid
  • Heteroaromatic compound
  • Secondary alcohol
  • Ether
  • Dialkyl ether
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Primary alcohol
  • Alcohol
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.34 g/LALOGPS
logP0.27ALOGPS
logP-0.66ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)6.2ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area217.6 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity109.99 m³·mol⁻¹ChemAxon
Polarizability44.36 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0hu1-4209700000-35bcc90c0ff7b44657d1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-014i-2400439000-06a2ad9c3c6fd5650ec9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0001900000-bc80206008b514670b04Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ot-2304900000-147665005945d200c5ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-3169200000-fde84de8d0d417fa66edSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0002900000-c9ad25a33937390bec8eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0h94-6308900000-9eb10f46ec2fd7af8ac8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kbf-9517100000-4ae9b70083955ed0457dSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB014665
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound74977759
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 magnesium ion binding
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular weight:
30036.77
Reactions
2'-Hydroxyisoorientin → 2-(2,5-dihydroxy-4-methoxyphenyl)-5,7-dihydroxy-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-onedetails
General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular weight:
39598.595
Reactions
2'-Hydroxyisoorientin → ({6-[5,7-dihydroxy-4-oxo-2-(2,4,5-trihydroxyphenyl)-4H-chromen-6-yl]-3,4,5-trihydroxyoxan-2-yl}methoxy)sulfonic aciddetails
2'-Hydroxyisoorientin → {2-[5,7-dihydroxy-4-oxo-2-(2,4,5-trihydroxyphenyl)-4H-chromen-6-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl}oxidanesulfonic aciddetails
2'-Hydroxyisoorientin → {2-[5,7-dihydroxy-4-oxo-2-(2,4,5-trihydroxyphenyl)-4H-chromen-6-yl]-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl}oxidanesulfonic aciddetails
2'-Hydroxyisoorientin → {6-[5,7-dihydroxy-4-oxo-2-(2,4,5-trihydroxyphenyl)-4H-chromen-6-yl]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl}oxidanesulfonic aciddetails
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
2'-Hydroxyisoorientin → 6-(2-{5,7-dihydroxy-4-oxo-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-2-yl}-4,5-dihydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
2'-Hydroxyisoorientin → 3,4,5-trihydroxy-6-({7-hydroxy-4-oxo-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-(2,4,5-trihydroxyphenyl)-4H-chromen-5-yl}oxy)oxane-2-carboxylic aciddetails
2'-Hydroxyisoorientin → 6-(4-{5,7-dihydroxy-4-oxo-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-2-yl}-2,5-dihydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
2'-Hydroxyisoorientin → 6-(5-{5,7-dihydroxy-4-oxo-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-2-yl}-2,4-dihydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
2'-Hydroxyisoorientin → 3,4,5-trihydroxy-6-({5-hydroxy-4-oxo-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-(2,4,5-trihydroxyphenyl)-4H-chromen-7-yl}oxy)oxane-2-carboxylic aciddetails