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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:14:34 UTC
Update Date2017-12-07 18:44:05 UTC
HMDB IDHMDB0061043
Secondary Accession Numbers
  • HMDB61043
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=1S/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+/m1/s1
InChI KeyBZRNSFHHZZYSST-VBSJQSPRSA-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
  • Azaspirodecane
  • Naphthalene
  • Benzofuran
  • Coumaran
  • Aryl alkyl ketone
  • Aryl ketone
  • Ketal
  • Piperidine
  • Benzenoid
  • 3-imidazoline
  • Vinylogous amide
  • Vinylogous acid
  • Cyclic carboximidic acid
  • Ketimine
  • Ketone
  • Secondary alcohol
  • Amino acid or derivatives
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid ester
  • Acetal
  • Carboxylic acid derivative
  • Secondary aliphatic amine
  • Enamine
  • Oxacycle
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Secondary amine
  • Polyol
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Imine
  • Organic oxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Origin
  • Drug metabolite
  • Endogenous
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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity228.42 m³·mol⁻¹ChemAxon
Polarizability88.74 ųChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-2000000890-cb96b67c2be212009132View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4j-5000000920-d3384f9de939f82c9236View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000003600-1d6bb2691a99e3a043ecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01q9-0000000590-afd53580515c3a59cca1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0759-3000000970-59e04bd3836323fb98f3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05al-3000001900-795eb8b6fbecd5b6bcc7View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      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
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available