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Record Information
Version4.0
StatusPredicted
Creation Date2017-09-13 13:16:12 UTC
Update Date2019-11-12 17:21:03 UTC
HMDB IDHMDB0127528
Secondary Accession NumbersNone
Metabolite Identification
Common Name(1S,16R)-5,7,11-trihydroxy-3-{1-[2-(hydroxymethyl)-1,3-thiazol-4-yl]prop-1-en-2-yl}-8,8,10,12,16-pentamethyl-17-oxa-4-azabicyclo[14.1.0]heptadec-4-en-9-one
Description(1s,16r)-5,7,11-trihydroxy-3-{1-[2-(hydroxymethyl)-1,3-thiazol-4-yl]prop-1-en-2-yl}-8,8,10,12,16-pentamethyl-17-oxa-4-azabicyclo[14.1.0]heptadec-4-en-9-one is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of (1s,16r)-5,7,11-trihydroxy-8,8,10,12,16-pentamethyl-3-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-17-oxa-4-azabicyclo[14.1.0]heptadec-4-en-9-one. It is generated by cyp3a4 enzyme via an aliphatic-hydroxylation-of-methyl-carbon-adjacent-to-aromatic-ring reaction. This aliphatic-hydroxylation-of-methyl-carbon-adjacent-to-aromatic-ring occurs in humans.
Structure
Data?1563875262
SynonymsNot Available
Chemical FormulaC27H42N2O6S
Average Molecular Weight522.7
Monoisotopic Molecular Weight522.276358254
IUPAC Name(1S,16R)-5,7,11-trihydroxy-3-{1-[2-(hydroxymethyl)-1,3-thiazol-4-yl]prop-1-en-2-yl}-8,8,10,12,16-pentamethyl-17-oxa-4-azabicyclo[14.1.0]heptadec-4-en-9-one
Traditional Name(1S,16R)-5,7,11-trihydroxy-3-{1-[2-(hydroxymethyl)-1,3-thiazol-4-yl]prop-1-en-2-yl}-8,8,10,12,16-pentamethyl-17-oxa-4-azabicyclo[14.1.0]heptadec-4-en-9-one
CAS Registry NumberNot Available
SMILES
[H][C@]12CC([H])(N=C(O)CC([H])(O)C(C)(C)C(=O)C([H])(C)C([H])(O)C([H])(C)CCC[C@@]1(C)O2)C(C)=CC1=CSC(CO)=N1
InChI Identifier
InChI=1S/C27H42N2O6S/c1-15-8-7-9-27(6)21(35-27)11-19(16(2)10-18-14-36-23(13-30)28-18)29-22(32)12-20(31)26(4,5)25(34)17(3)24(15)33/h10,14-15,17,19-21,24,30-31,33H,7-9,11-13H2,1-6H3,(H,29,32)/t15?,17?,19?,20?,21-,24?,27+/m0/s1
InChI KeyPUDXWNAJFBDLKH-RVMNBAMRSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 2,4-disubstituted thiazoles. These are compounds containing a thiazole ring substituted at the positions 2 and 3.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassThiazoles
Direct Parent2,4-disubstituted thiazoles
Alternative Parents
Substituents
  • 2,4-disubstituted 1,3-thiazole
  • Cyclic carboximidic acid
  • Heteroaromatic compound
  • Ketone
  • Secondary alcohol
  • Cyclic ketone
  • Dialkyl ether
  • Oxirane
  • Ether
  • Polyol
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Azacycle
  • Oxacycle
  • Primary alcohol
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Aromatic alcohol
  • Organic oxide
  • Organic nitrogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxygen 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
logP2.76ALOGPS
logP3.4ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)5.38ChemAxon
pKa (Strongest Basic)3.22ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area135.77 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity138.93 m³·mol⁻¹ChemAxon
Polarizability57.46 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0udl-7200229000-272e6156aa6366a734b4JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-1206190000-3bf58040907b11449480JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0000390000-91b3c1c85b5a1b6b081aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-0000890000-01baf7e64da4e4cde3b9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0w29-2004900000-67f44f8e3c3eead61bdeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00dl-5000890000-47bd8de0a0da6024fdcaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fk9-0000960000-6acbadf836eed0aaa1b4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-9000000000-7a71368e3289062ff11aJSpectraViewer
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
FoodDB 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 CompoundNot Available
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
(1S,16R)-5,7,11-trihydroxy-3-{1-[2-(hydroxymethyl)-1,3-thiazol-4-yl]prop-1-en-2-yl}-8,8,10,12,16-pentamethyl-17-oxa-4-azabicyclo[14.1.0]heptadec-4-en-9-one → [(4-{2-[(16R)-5,7,11-trihydroxy-8,8,10,12,16-pentamethyl-9-oxo-17-oxa-4-azabicyclo[14.1.0]heptadec-4-en-3-yl]prop-1-en-1-yl}-1,3-thiazol-2-yl)methoxy]sulfonic aciddetails
(1S,16R)-5,7,11-trihydroxy-3-{1-[2-(hydroxymethyl)-1,3-thiazol-4-yl]prop-1-en-2-yl}-8,8,10,12,16-pentamethyl-17-oxa-4-azabicyclo[14.1.0]heptadec-4-en-9-one → [(16R)-5,7-dihydroxy-3-{1-[2-(hydroxymethyl)-1,3-thiazol-4-yl]prop-1-en-2-yl}-8,8,10,12,16-pentamethyl-9-oxo-17-oxa-4-azabicyclo[14.1.0]heptadec-4-en-11-yl]oxidanesulfonic aciddetails
(1S,16R)-5,7,11-trihydroxy-3-{1-[2-(hydroxymethyl)-1,3-thiazol-4-yl]prop-1-en-2-yl}-8,8,10,12,16-pentamethyl-17-oxa-4-azabicyclo[14.1.0]heptadec-4-en-9-one → [(16R)-5,11-dihydroxy-3-{1-[2-(hydroxymethyl)-1,3-thiazol-4-yl]prop-1-en-2-yl}-8,8,10,12,16-pentamethyl-9-oxo-17-oxa-4-azabicyclo[14.1.0]heptadec-4-en-7-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
(1S,16R)-5,7,11-trihydroxy-3-{1-[2-(hydroxymethyl)-1,3-thiazol-4-yl]prop-1-en-2-yl}-8,8,10,12,16-pentamethyl-17-oxa-4-azabicyclo[14.1.0]heptadec-4-en-9-one → 3,4,5-trihydroxy-6-[(4-{2-[(16R)-5,7,11-trihydroxy-8,8,10,12,16-pentamethyl-9-oxo-17-oxa-4-azabicyclo[14.1.0]heptadec-4-en-3-yl]prop-1-en-1-yl}-1,3-thiazol-2-yl)methoxy]oxane-2-carboxylic aciddetails
(1S,16R)-5,7,11-trihydroxy-3-{1-[2-(hydroxymethyl)-1,3-thiazol-4-yl]prop-1-en-2-yl}-8,8,10,12,16-pentamethyl-17-oxa-4-azabicyclo[14.1.0]heptadec-4-en-9-one → 6-{[(16S)-5,7-dihydroxy-3-{1-[2-(hydroxymethyl)-1,3-thiazol-4-yl]prop-1-en-2-yl}-8,8,10,12,16-pentamethyl-9-oxo-17-oxa-4-azabicyclo[14.1.0]heptadec-4-en-11-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
(1S,16R)-5,7,11-trihydroxy-3-{1-[2-(hydroxymethyl)-1,3-thiazol-4-yl]prop-1-en-2-yl}-8,8,10,12,16-pentamethyl-17-oxa-4-azabicyclo[14.1.0]heptadec-4-en-9-one → 6-{[(16R)-5,11-dihydroxy-3-{1-[2-(hydroxymethyl)-1,3-thiazol-4-yl]prop-1-en-2-yl}-8,8,10,12,16-pentamethyl-9-oxo-17-oxa-4-azabicyclo[14.1.0]heptadec-4-en-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails