You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Creation Date2013-07-04 18:57:30 UTC
Update Date2017-03-02 22:05:23 UTC
Secondary Accession NumbersNone
Metabolite Identification
Common Name31-Hydroxy rifabutin
Description31-Hydroxy rifabutin is a metabolite of rifabutin. Rifabutin (Rfb) is a bactericidal antibiotic drug primarily used in the treatment of tuberculosis. The drug is a semi-synthetic derivative of rifamycin S. Its effect is based on blocking the DNA-dependent RNA-polymerase of the bacteria. It is effective against Gram-positive and some Gram-negative bacteria, but also against the highly resistant Mycobacteria, e.g. Mycobacterium tuberculosis, M. leprae and M. avium intracellulare. (Wikipedia)
SynonymsNot Available
Chemical FormulaC46H62N4O12
Average Molecular Weight863.0041
Monoisotopic Molecular Weight862.436423468
IUPAC Name(7S,9Z,11S,12R,13S,14R,15R,16R,17S,18R,19Z,21Z)-2,15,17,23-tetrahydroxy-18-(hydroxymethyl)-11-methoxy-3,7,12,14,16,22-hexamethyl-1'-(2-methylpropyl)-6,32-dioxo-8,33-dioxa-24,27,29-triazaspiro[pentacyclo[⁴,⁷.0⁵,³¹.0²⁶,³⁰]tritriacontane-28,4'-piperidine]-1(31),2,4,9,19,21,23,25,29-nonaen-13-yl acetate
Traditional Name(7S,9Z,11S,12R,13S,14R,15R,16R,17S,18R,19Z,21Z)-2,15,17,23-tetrahydroxy-18-(hydroxymethyl)-11-methoxy-3,7,12,14,16,22-hexamethyl-1'-(2-methylpropyl)-6,32-dioxo-8,33-dioxa-24,27,29-triazaspiro[pentacyclo[⁴,⁷.0⁵,³¹.0²⁶,³⁰]tritriacontane-28,4'-piperidine]-1(31),2,4,9,19,21,23,25,29-nonaen-13-yl acetate
CAS Registry NumberNot Available
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as naphthofurans. These are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassNaphthofurans
Direct ParentNaphthofurans
Alternative Parents
  • Naphthofuran
  • Azaspirodecane
  • Naphthalene
  • Benzofuran
  • Coumaran
  • Aryl ketone
  • Aryl alkyl ketone
  • Ketal
  • Piperidine
  • Benzenoid
  • 3-imidazoline
  • Vinylogous amide
  • Cyclic carboximidic acid
  • Vinylogous acid
  • Ketimine
  • Ketone
  • Carboxylic acid ester
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Amino acid or derivatives
  • Polyol
  • Azacycle
  • Carboxylic acid derivative
  • Oxacycle
  • Dialkyl ether
  • Enamine
  • Monocarboxylic acid or derivatives
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Ether
  • Acetal
  • Primary alcohol
  • Imine
  • Organopnictogen compound
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Alcohol
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
StatusExpected but not Quantified
  • Drug metabolite
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Membrane (predicted from logP)
Physical Properties
StateNot Available
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.016 mg/mLALOGPS
pKa (Strongest Acidic)6.88ChemAxon
pKa (Strongest Basic)8.62ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area229.27 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity235 m3·mol-1ChemAxon
Polarizability91.91 Å3ChemAxon
Number of Rings6ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00722
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB60754
Metagene LinkHMDB60754
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available