Buprenorphine, 6-glucuronide (CHEM045944)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-06-03 13:50:20 UTC
Update Date2016-11-09 01:23:26 UTC
Accession NumberCHEM045944
Identification
Common NameBuprenorphine, 6-glucuronide
ClassSmall Molecule
Description
Contaminant Sources
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Buprenorphine-3-O-glucuronideMeSH
b-3-gMeSH
(2S,3S,4S,5R,6S)-6-{[(1S,2R,6S,14R,15R,16R)-3-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylbutan-2-yl]-15-methoxy-13-oxa-3-azahexacyclo[13.2.2.1²,⁸.0¹,⁶.0⁶,¹⁴.0⁷,¹²]icosa-7,9,11-trien-11-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylateGenerator
Chemical FormulaC35H49NO10
Average Molecular Mass643.774 g/mol
Monoisotopic Mass643.336 g/mol
CAS Registry Number101224-22-0
IUPAC Name(2S,3S,4S,5R,6S)-6-{[(1S,2R,6S,14R,15R,16R)-3-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylbutan-2-yl]-15-methoxy-13-oxa-3-azahexacyclo[13.2.2.1^{2,8}.0^{1,6}.0^{6,14}.0^{7,12}]icosa-7,9,11-trien-11-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6S)-6-{[(1S,2R,6S,14R,15R,16R)-3-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylbutan-2-yl]-15-methoxy-13-oxa-3-azahexacyclo[13.2.2.1^{2,8}.0^{1,6}.0^{6,14}.0^{7,12}]icosa-7,9,11-trien-11-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
SMILES[H][C@@]12OC3=C(O[C@]4([H])O[C@]([H])(C(O)=O)[C@@]([H])(O)[C@]([H])(O)[C@@]4([H])O)C=CC4=C3[C@@]11CCN(CC3CC3)[C@]([H])(C4)[C@]11CC[C@@]2(OC)[C@]([H])(C1)[C@](C)(O)C(C)(C)C
InChI IdentifierInChI=1S/C35H49NO10/c1-31(2,3)32(4,42)20-15-33-10-11-35(20,43-5)30-34(33)12-13-36(16-17-6-7-17)21(33)14-18-8-9-19(26(46-30)22(18)34)44-29-25(39)23(37)24(38)27(45-29)28(40)41/h8-9,17,20-21,23-25,27,29-30,37-39,42H,6-7,10-16H2,1-5H3,(H,40,41)/t20-,21-,23+,24+,25-,27+,29-,30-,32+,33-,34+,35-/m1/s1
InChI KeyCZULHKGIAJASAA-WWIHBJMFSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPhenolic glycosides
Alternative Parents
Substituents
  • Phenolic glycoside
  • Fatty acyl glycoside
  • Fatty acyl glycoside of mono- or disaccharide
  • 1-o-glucuronide
  • O-glucuronide
  • Phenanthrene
  • Glucuronic acid or derivatives
  • Alkyl glycoside
  • Hexose monosaccharide
  • O-glycosyl compound
  • Azaspirodecane
  • Tetralin
  • Coumaran
  • Aralkylamine
  • Alkyl aryl ether
  • Beta-hydroxy acid
  • Benzenoid
  • Fatty acyl
  • Monosaccharide
  • Oxane
  • Hydroxy acid
  • Piperidine
  • Pyran
  • Tertiary alcohol
  • Tertiary aliphatic amine
  • Amino acid
  • Tertiary amine
  • Amino acid or derivatives
  • Secondary alcohol
  • Acetal
  • Oxacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Dialkyl ether
  • Ether
  • Azacycle
  • Organoheterocyclic compound
  • Polyol
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organopnictogen compound
  • Amine
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP2.94ALOGPS
logP-0.65ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)2.67ChemAxon
pKa (Strongest Basic)9.84ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area158.38 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity163.77 m³·mol⁻¹ChemAxon
Polarizability68.85 ųChemAxon
Number of Rings8ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0kxr-3100809000-31127829533f85921935Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pvi-4100901000-2617dbef663385d1d573Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9100200000-8cce590a2c49a58615b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kg-2400659000-f96b4f477e75cf8b5879Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-2200932000-069d931635666632294dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02t9-4202900000-981ad3c6d8e785b4b853Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID92131860
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available