Survey with prize
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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:09:14 UTC
Update Date2019-07-23 06:13:23 UTC
HMDB IDHMDB0033422
Secondary Accession Numbers
  • HMDB33422
Metabolite Identification
Common Name(2S,2''S,3S,3''R,4S)-3,4',5,7-Tetrahydroxyflavan(2->7,4->8)-3,4',5,7-tetrahydroxyflavan
Description(2S,2''S,3S,3''R,4S)-3,4',5,7-Tetrahydroxyflavan(2->7,4->8)-3,4',5,7-tetrahydroxyflavan belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8'' (2S,2''S,3S,3''R,4S)-3,4',5,7-Tetrahydroxyflavan(2->7,4->8)-3,4',5,7-tetrahydroxyflavan is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (2S,2''s,3S,3''r,4S)-3,4',5,7-tetrahydroxyflavan(2->7,4->8)-3,4',5,7-tetrahydroxyflavan has been detected, but not quantified in, fruits and peachs. This could make (2S,2''s,3S,3''r,4S)-3,4',5,7-tetrahydroxyflavan(2->7,4->8)-3,4',5,7-tetrahydroxyflavan a potential biomarker for the consumption of these foods.
Structure
Data?1563862403
SynonymsNot Available
Chemical FormulaC30H24O10
Average Molecular Weight544.5056
Monoisotopic Molecular Weight544.136946988
IUPAC Name5,13-bis(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15(20),16,18-hexaene-6,9,17,19,21-pentol
Traditional Name5,13-bis(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15(20),16,18-hexaene-6,9,17,19,21-pentol
CAS Registry NumberNot Available
SMILES
OC1CC2=C(OC1C1=CC=C(O)C=C1)C1=C(OC3(OC4=C(C1C3O)C(O)=CC(O)=C4)C1=CC=C(O)C=C1)C=C2O
InChI Identifier
InChI=1S/C30H24O10/c31-15-5-1-13(2-6-15)27-21(36)11-18-19(34)12-23-25(28(18)38-27)26-24-20(35)9-17(33)10-22(24)39-30(40-23,29(26)37)14-3-7-16(32)8-4-14/h1-10,12,21,26-27,29,31-37H,11H2
InChI KeyLQRHGTVFFPMWCG-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassBiflavonoids and polyflavonoids
Direct ParentBiflavonoids and polyflavonoids
Alternative Parents
Substituents
  • A-type proanthocyanidin
  • Bi- and polyflavonoid skeleton
  • Proanthocyanidin
  • Pyranoflavonoid
  • Flavan-3-ol
  • 3-hydroxyflavonoid
  • Hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavan
  • Pyranochromene
  • Benzopyran
  • 1-benzopyran
  • Chromane
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Ketal
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary alcohol
  • Polyol
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alcohol
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

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 Solubility0.069 g/LALOGPS
logP2.88ALOGPS
logP4.2ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)8.82ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area169.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity140.23 m³·mol⁻¹ChemAxon
Polarizability54.72 ųChemAxon
Number of Rings7ChemAxon
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, Positivesplash10-05r0-0310590000-709eab5ce01c9e82c523Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-1020019000-8f8e9433e4e1b29ab252Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0112390000-a51e8d5e25a217cf8e15Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1314940000-c8f967fd1d7ae47084ceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9703010000-8a523bb6310bc3621f9aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0010190000-bce17c09f58231404774Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-054x-1912460000-6200fb61ada592f84ddfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-1910000000-28f8fe9f8285de9570c6Spectrum
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
FooDB IDFDB016815
KNApSAcK IDNot Available
Chemspider ID3240798
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound4023574
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 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
(2S,2''S,3S,3''R,4S)-3,4',5,7-Tetrahydroxyflavan(2->7,4->8)-3,4',5,7-tetrahydroxyflavan → [6,9,17,19-tetrahydroxy-5,13-bis(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15,17,19-hexaen-21-yl]oxidanesulfonic aciddetails
(2S,2''S,3S,3''R,4S)-3,4',5,7-Tetrahydroxyflavan(2->7,4->8)-3,4',5,7-tetrahydroxyflavan → [9,17,19,21-tetrahydroxy-5,13-bis(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15,17,19-hexaen-6-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
(2S,2''S,3S,3''R,4S)-3,4',5,7-Tetrahydroxyflavan(2->7,4->8)-3,4',5,7-tetrahydroxyflavan → 3,4,5-trihydroxy-6-{[6,17,19,21-tetrahydroxy-5,13-bis(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15,17,19-hexaen-9-yl]oxy}oxane-2-carboxylic aciddetails
(2S,2''S,3S,3''R,4S)-3,4',5,7-Tetrahydroxyflavan(2->7,4->8)-3,4',5,7-tetrahydroxyflavan → 3,4,5-trihydroxy-6-{4-[6,9,17,19,21-pentahydroxy-5-(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15,17,19-hexaen-13-yl]phenoxy}oxane-2-carboxylic aciddetails
(2S,2''S,3S,3''R,4S)-3,4',5,7-Tetrahydroxyflavan(2->7,4->8)-3,4',5,7-tetrahydroxyflavan → 3,4,5-trihydroxy-6-{[6,9,19,21-tetrahydroxy-5,13-bis(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15,17,19-hexaen-17-yl]oxy}oxane-2-carboxylic aciddetails
(2S,2''S,3S,3''R,4S)-3,4',5,7-Tetrahydroxyflavan(2->7,4->8)-3,4',5,7-tetrahydroxyflavan → 3,4,5-trihydroxy-6-{[6,9,17,21-tetrahydroxy-5,13-bis(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15,17,19-hexaen-19-yl]oxy}oxane-2-carboxylic aciddetails
(2S,2''S,3S,3''R,4S)-3,4',5,7-Tetrahydroxyflavan(2->7,4->8)-3,4',5,7-tetrahydroxyflavan → 3,4,5-trihydroxy-6-{4-[6,9,17,19,21-pentahydroxy-13-(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15,17,19-hexaen-5-yl]phenoxy}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
(2S,2''S,3S,3''R,4S)-3,4',5,7-Tetrahydroxyflavan(2->7,4->8)-3,4',5,7-tetrahydroxyflavan → {4-[6,9,17,19,21-pentahydroxy-5-(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15,17,19-hexaen-13-yl]phenyl}oxidanesulfonic aciddetails
(2S,2''S,3S,3''R,4S)-3,4',5,7-Tetrahydroxyflavan(2->7,4->8)-3,4',5,7-tetrahydroxyflavan → {4-[6,9,17,19,21-pentahydroxy-13-(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15,17,19-hexaen-5-yl]phenyl}oxidanesulfonic aciddetails