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Record Information
Version4.0
StatusPredicted
Creation Date2017-09-18 17:33:07 UTC
Update Date2019-11-12 17:23:30 UTC
HMDB IDHMDB0136070
Secondary Accession NumbersNone
Metabolite Identification
Common Name3,4,5,12,13,21,22,23-octahydroxy-8,18-dioxo-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(23),2,4,6,19,21-hexaen-11-yl 3,4,5-trihydroxybenzoate
Description3,4,5,12,13,21,22,23-octahydroxy-8,18-dioxo-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(23),2,4,6,19,21-hexaen-11-yl 3,4,5-trihydroxybenzoate is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 3,4,5,12,21,22,23-heptahydroxy-8,18-dioxo-11-(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(23),2,4,6,19,21-hexaen-13-yl 2-({20-[2-({7,8,9,12,13,14,20,29,30,33,34,35-dodecahydroxy-4,17,25,38-tetraoxo-3,18,21,24,39-pentaoxaheptacyclo[20.17.0.0²,¹⁹.0⁵,¹⁰.0¹¹,¹⁶.0²⁶,³¹.0³²,³⁷]nonatriaconta-5,7,9,11,13,15,26,28,30,32,34,36-dodecaen-28-yl}oxy)-3,4,5-trihydroxybenzoyloxy]-7,8,9,12,13,14,29,30,33,34,35-undecahydroxy-4,17,25,38-tetraoxo-3,18,21,24,39-pentaoxaheptacyclo[20.17.0.0²,¹⁹.0⁵,¹⁰.0¹¹,¹⁶.0²⁶,³¹.0³²,³⁷]nonatriaconta-5,7,9,11,13,15,26,28,30,32,34,36-dodecaen-28-yl}oxy)-3,4,5-trihydroxybenzoate. It is generated by Liver carboxylesterase 1 (P23141) enzyme via a hydrolysis-of-carboxylic-acid-ester-pattern2 reaction. This hydrolysis-of-carboxylic-acid-ester-pattern2 occurs in humans and human gut microbiota.
Structure
Data?1563876462
Synonyms
ValueSource
3,4,5,12,13,21,22,23-Octahydroxy-8,18-dioxo-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(23),2,4,6,19,21-hexaen-11-yl 3,4,5-trihydroxybenzoic acidGenerator
Chemical FormulaC27H22O18
Average Molecular Weight634.4528
Monoisotopic Molecular Weight634.0806139
IUPAC Name3,4,5,12,13,21,22,23-octahydroxy-8,18-dioxo-9,14,17-trioxatetracyclo[17.4.0.0^{2,7}.0^{10,15}]tricosa-1(23),2,4,6,19,21-hexaen-11-yl 3,4,5-trihydroxybenzoate
Traditional Name3,4,5,12,13,21,22,23-octahydroxy-8,18-dioxo-9,14,17-trioxatetracyclo[17.4.0.0^{2,7}.0^{10,15}]tricosa-1(23),2,4,6,19,21-hexaen-11-yl 3,4,5-trihydroxybenzoate
CAS Registry NumberNot Available
SMILES
OC1OC2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C2=CC(O)=C(O)C(O)=C2)C1O
InChI Identifier
InChI=1S/C27H22O18/c28-9-1-6(2-10(29)16(9)32)24(38)45-23-21(37)27(41)43-13-5-42-25(39)7-3-11(30)17(33)19(35)14(7)15-8(26(40)44-22(13)23)4-12(31)18(34)20(15)36/h1-4,13,21-23,27-37,41H,5H2
InChI KeyRQOWLXQAJIAZMF-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassTannins
Sub ClassHydrolyzable tannins
Direct ParentHydrolyzable tannins
Alternative Parents
Substituents
  • Hydrolyzable tannin
  • Galloyl ester
  • Gallic acid or derivatives
  • P-hydroxybenzoic acid alkyl ester
  • M-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid ester
  • Benzoate ester
  • Pyrogallol derivative
  • Benzenetriol
  • Benzoic acid or derivatives
  • Tricarboxylic acid or derivatives
  • Benzoyl
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Monosaccharide
  • Monocyclic benzene moiety
  • Oxane
  • Benzenoid
  • Carboxylic acid ester
  • Secondary alcohol
  • Hemiacetal
  • Lactone
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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
logP1.69ALOGPS
logP1.1ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)7.41ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area310.66 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity142.3 m³·mol⁻¹ChemAxon
Polarizability56.41 ųChemAxon
Number of Rings5ChemAxon
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, Positivesplash10-004i-1509432000-f614aba3b49dc5fc7495Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gbi-0428319000-8472131511585bfc1bb8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0v00-0956327000-a48da809984797bf08fbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0973000000-89275e9a23063fd8f21bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0301169000-2d7f2eea5ad0fc93363cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-2922233000-cb3688b58469c5b6fb83Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0922000000-c2b7dc701c1e94278638Spectrum
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 IDFDB000668
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13932611
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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:
Lipid transport and metabolism
Specific function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
Gene Name:
CES1
Uniprot ID:
P23141
Molecular weight:
62520.62
Reactions
3,4,5,12,13,21,22,23-octahydroxy-8,18-dioxo-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(23),2,4,6,19,21-hexaen-11-yl 3,4,5-trihydroxybenzoate → 3,4,5,11,12,13,21,22,23-nonahydroxy-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(23),2,4,6,19,21-hexaene-8,18-dionedetails