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
Version4.0
Creation Date2013-07-04 18:57:30 UTC
Update Date2017-09-27 08:43:53 UTC
HMDB IDHMDB0060754
Secondary Accession Numbers
  • HMDB60754
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)
Structure
Thumb
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[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,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[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
CO[C@H]1\C=C/O[C@@]2(C)OC3=C(C2=O)C2=C(C(O)=C3C)C(=O)C(N=C(O)\C(C)=C/C=C\[C@H](CO)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C)=C1NC3(CCN(CC(C)C)CC3)N=C21
InChI Identifier
InChI=1S/C46H62N4O12/c1-22(2)20-50-17-15-46(16-18-50)48-34-31-32-39(55)27(7)42-33(31)43(57)45(9,62-42)60-19-14-30(59-10)24(4)41(61-28(8)52)26(6)37(53)25(5)38(54)29(21-51)13-11-12-23(3)44(58)47-36(40(32)56)35(34)49-46/h11-14,19,22,24-26,29-30,37-38,41,49,51,53-55H,15-18,20-21H2,1-10H3,(H,47,58)/b13-11-,19-14-,23-12-/t24-,25+,26-,29-,30+,37-,38-,41-,45+/m1/s1
InChI KeyPANFHCPHSZTZMK-AWARHZTMSA-N
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
Substituents
  • 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
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

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
logP3.49ALOGPS
logP2.63ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)6.88ChemAxon
pKa (Strongest Basic)8.62ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area229.27 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity235 m³·mol⁻¹ChemAxon
Polarizability91.91 ųChemAxon
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
NameSMPDB/PathwhizKEGG
No entries found
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
      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
      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