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Record Information
Version4.0
StatusPredicted
Creation Date2017-09-16 00:12:39 UTC
Update Date2019-11-12 17:21:31 UTC
HMDB IDHMDB0128224
Secondary Accession NumbersNone
Metabolite Identification
Common Name5,6-dihydroxy-4-[hydroxy(3,4,5-trihydroxyoxan-2-yl)methyl]-2-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohex-4-ene-1,3-dione
Description5,6-dihydroxy-4-[hydroxy(3,4,5-trihydroxyoxan-2-yl)methyl]-2-[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohex-4-ene-1,3-dione is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 3,4,5-trihydroxy-2-[hydroxy(3,4,5-trihydroxyoxan-2-yl)methyl]-6-[3-(4-hydroxyphenyl)prop-2-enoyl]-4-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohexa-2,5-dien-1-one. It is generated by EC.5.3.2. enzyme via a keto-enol-tautomerization-pattern1 reaction. This keto-enol-tautomerization-pattern1 occurs in humans.
Structure
Data?1563875359
SynonymsNot Available
Chemical FormulaC27H32O16
Average Molecular Weight612.537
Monoisotopic Molecular Weight612.16903495
IUPAC Name5,6-dihydroxy-4-[hydroxy(3,4,5-trihydroxyoxan-2-yl)methyl]-2-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohex-4-ene-1,3-dione
Traditional Name5,6-dihydroxy-4-[hydroxy(3,4,5-trihydroxyoxan-2-yl)methyl]-2-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohex-4-ene-1,3-dione
CAS Registry NumberNot Available
SMILES
[H]\C(=C(\[H])C1=CC=C(O)C=C1)C(=O)C1C(=O)C(C(O)C2OCC(O)C(O)C2O)=C(O)C(O)(C2OC(CO)C(O)C(O)C2O)C1=O
InChI Identifier
InChI=1S/C27H32O16/c28-7-13-17(33)20(36)22(38)26(43-13)27(41)24(39)14(11(30)6-3-9-1-4-10(29)5-2-9)18(34)15(25(27)40)19(35)23-21(37)16(32)12(31)8-42-23/h1-6,12-14,16-17,19-23,26,28-29,31-33,35-38,40-41H,7-8H2/b6-3+
InChI KeyNOHOMRZHYMKJQA-ZZXKWVIFSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. Hydroxycinnamic acids and derivatives are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentHydroxycinnamic acids and derivatives
Alternative Parents
Substituents
  • Hydroxycinnamic acid or derivatives
  • C-glycosyl compound
  • Glycosyl compound
  • M-benzoquinone
  • Styrene
  • Quinone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Cyclohexenone
  • 1,3-diketone
  • Phenol
  • Acyloin
  • Monocyclic benzene moiety
  • Monosaccharide
  • Benzenoid
  • Oxane
  • 1,3-dicarbonyl compound
  • Acryloyl-group
  • Enone
  • Vinylogous acid
  • Alpha,beta-unsaturated ketone
  • Tertiary alcohol
  • Secondary alcohol
  • Cyclic ketone
  • Ketone
  • Polyol
  • Dialkyl ether
  • Enol
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Primary alcohol
  • Carbonyl group
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

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
logP-1ALOGPS
logP-3.9ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.39ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area292.2 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity140.5 m³·mol⁻¹ChemAxon
Polarizability57.63 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0kmi-7600059000-f0c12ab2101ec7b9198bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zn9-4500190000-a14901b1e7181330925bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-0300693000-2d19f963d29da2934ab8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dj-1900350000-fe4e198bf8e9745023f7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03yj-4839880000-1a662e761f08d20a148fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1112922000-cbdd2db48b83b9bbc955Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01x4-3903440000-ff79f5fd0400df6f95e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9400010000-1313b726778ae8c52efaSpectrum
Biological Properties
Cellular LocationsNot Available
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 IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131834565
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. Djoumbou Feunang, Yannick (2017). Cheminformatics Tools for Enabling Metabolomics, 2017 (PhD thesis). University of Alberta.

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
5,6-dihydroxy-4-[hydroxy(3,4,5-trihydroxyoxan-2-yl)methyl]-2-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohex-4-ene-1,3-dione → [(6-{1,2-dihydroxy-3-[hydroxy(3,4,5-trihydroxyoxan-2-yl)methyl]-5-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-4,6-dioxocyclohex-2-en-1-yl}-3,4,5-trihydroxyoxan-2-yl)methoxy]sulfonic aciddetails
5,6-dihydroxy-4-[hydroxy(3,4,5-trihydroxyoxan-2-yl)methyl]-2-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohex-4-ene-1,3-dione → [2-({2,3-dihydroxy-5-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-4,6-dioxo-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohex-1-en-1-yl}(hydroxy)methyl)-4,5-dihydroxyoxan-3-yl]oxidanesulfonic aciddetails
5,6-dihydroxy-4-[hydroxy(3,4,5-trihydroxyoxan-2-yl)methyl]-2-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohex-4-ene-1,3-dione → [2-({2,3-dihydroxy-5-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-4,6-dioxo-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohex-1-en-1-yl}(hydroxy)methyl)-3,5-dihydroxyoxan-4-yl]oxidanesulfonic aciddetails
5,6-dihydroxy-4-[hydroxy(3,4,5-trihydroxyoxan-2-yl)methyl]-2-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohex-4-ene-1,3-dione → [6-({2,3-dihydroxy-5-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-4,6-dioxo-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohex-1-en-1-yl}(hydroxy)methyl)-4,5-dihydroxyoxan-3-yl]oxidanesulfonic aciddetails
5,6-dihydroxy-4-[hydroxy(3,4,5-trihydroxyoxan-2-yl)methyl]-2-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohex-4-ene-1,3-dione → ({2,3-dihydroxy-5-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-4,6-dioxo-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohex-1-en-1-yl}(3,4,5-trihydroxyoxan-2-yl)methoxy)sulfonic aciddetails
5,6-dihydroxy-4-[hydroxy(3,4,5-trihydroxyoxan-2-yl)methyl]-2-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohex-4-ene-1,3-dione → (6-{1,2-dihydroxy-3-[hydroxy(3,4,5-trihydroxyoxan-2-yl)methyl]-5-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-4,6-dioxocyclohex-2-en-1-yl}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl)oxidanesulfonic aciddetails
5,6-dihydroxy-4-[hydroxy(3,4,5-trihydroxyoxan-2-yl)methyl]-2-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohex-4-ene-1,3-dione → (2-{1,2-dihydroxy-3-[hydroxy(3,4,5-trihydroxyoxan-2-yl)methyl]-5-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-4,6-dioxocyclohex-2-en-1-yl}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl)oxidanesulfonic aciddetails
5,6-dihydroxy-4-[hydroxy(3,4,5-trihydroxyoxan-2-yl)methyl]-2-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohex-4-ene-1,3-dione → (2-{1,2-dihydroxy-3-[hydroxy(3,4,5-trihydroxyoxan-2-yl)methyl]-5-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-4,6-dioxocyclohex-2-en-1-yl}-4,5-dihydroxy-6-(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
5,6-dihydroxy-4-[hydroxy(3,4,5-trihydroxyoxan-2-yl)methyl]-2-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohex-4-ene-1,3-dione → 6-{4-[(1E)-3-{4,5-dihydroxy-3-[hydroxy(3,4,5-trihydroxyoxan-2-yl)methyl]-2,6-dioxo-5-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohex-3-en-1-yl}-3-oxoprop-1-en-1-yl]phenoxy}-3,4,5-trihydroxyoxane-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
5,6-dihydroxy-4-[hydroxy(3,4,5-trihydroxyoxan-2-yl)methyl]-2-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohex-4-ene-1,3-dione → {4-[(1E)-3-{4,5-dihydroxy-3-[hydroxy(3,4,5-trihydroxyoxan-2-yl)methyl]-2,6-dioxo-5-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohex-3-en-1-yl}-3-oxoprop-1-en-1-yl]phenyl}oxidanesulfonic aciddetails