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Record Information
Version3.6
Creation Date2013-07-09 16:14:34 UTC
Update Date2016-02-11 08:17:32 UTC
HMDB IDHMDB61043
Secondary Accession NumbersNone
Metabolite Identification
Common Name27-O-demethylrifabutin
Description27-O-demethylrifabutin 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)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC45H60N4O11
Average Molecular Weight832.9781
Monoisotopic Molecular Weight832.425858782
IUPAC Name(7S,9Z,11R,12R,13S,14R,15S,16S,17S,18R,19Z,21Z)-2,11,15,17,23-pentahydroxy-3,7,12,14,16,18,22-heptamethyl-1'-(2-methylpropyl)-6,32-dioxo-8,33-dioxa-24,27,29-triazaspiro[pentacyclo[23.6.1.1⁴,⁷.0⁵,³¹.0²⁶,³⁰]tritriacontane-28,4'-piperidine]-1(31),2,4,9,19,21,23,25,29-nonaen-13-yl acetate
Traditional Name(7S,9Z,11R,12R,13S,14R,15S,16S,17S,18R,19Z,21Z)-2,11,15,17,23-pentahydroxy-3,7,12,14,16,18,22-heptamethyl-1'-(2-methylpropyl)-6,32-dioxo-8,33-dioxa-24,27,29-triazaspiro[pentacyclo[23.6.1.1⁴,⁷.0⁵,³¹.0²⁶,³⁰]tritriacontane-28,4'-piperidine]-1(31),2,4,9,19,21,23,25,29-nonaen-13-yl acetate
CAS Registry NumberNot Available
SMILES
CC(C)CN1CCC2(CC1)NC1=C3N=C(O)\C(C)=C/C=C\[C@@H](C)[C@H](O)[C@H](C)[C@H](O)[C@@H](C)[C@@H](OC(C)=O)[C@H](C)[C@H](O)\C=C/O[C@@]4(C)OC5=C(C4=O)C(C1=N2)=C(C(O)=C5C)C3=O
InChI Identifier
InChI=1/C45H60N4O11/c1-21(2)20-49-17-15-45(16-18-49)47-33-30-31-38(54)27(8)41-32(30)42(56)44(10,60-41)58-19-14-29(51)24(5)40(59-28(9)50)26(7)37(53)25(6)36(52)22(3)12-11-13-23(4)43(57)46-35(39(31)55)34(33)48-45/h11-14,19,21-22,24-26,29,36-37,40,48,51-54H,15-18,20H2,1-10H3,(H,46,57)/b12-11-,19-14-,23-13-/t22-,24-,25+,26-,29-,36+,37+,40+,44+/s2
InChI KeyInChIKey=BZRNSFHHZZYSST-QRURVEEMNA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassNaphthofurans
Sub ClassNot Available
Direct ParentNaphthofurans
Alternative Parents
Substituents
  • Naphthofuran
  • Naphthalene
  • Azaspirodecane
  • Benzofuran
  • Aryl alkyl ketone
  • Aryl ketone
  • Benzenoid
  • Piperidine
  • Acetate salt
  • Vinylogous amide
  • Vinylogous acid
  • Cyclic carboximidic acid
  • 3-imidazoline
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Polyol
  • Ketone
  • Ketimine
  • Carboxylic acid ester
  • Oxacycle
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboxylic acid derivative
  • Acetal
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Membrane (predicted from logP)
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
Water Solubility0.016 mg/mLALOGPS
logP3.65ALOGPS
logP3.4ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)6.9ChemAxon
pKa (Strongest Basic)8.62ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area220.04 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity228.42 m3·mol-1ChemAxon
Polarizability88.74 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00384
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 LinkHMDB61043
Metagene LinkHMDB61043
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available