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Record Information
Version4.0
Creation Date2013-07-04 18:55:53 UTC
Update Date2017-09-27 08:43:53 UTC
HMDB IDHMDB0060732
Secondary Accession Numbers
  • HMDB60732
Metabolite Identification
Common Name25-O-Desacetyl rifabutin
Description25-O-Desacetyl 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 FormulaC41H56N4O11
Average Molecular Weight780.9035
Monoisotopic Molecular Weight780.394558654
IUPAC Name(7S,9Z,11S,12R,13S,14R,15R,16R,17S,18S,19Z,21Z)-2,13,15,17,23,27,29-heptahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-{[(4-methylpiperazin-1-yl)imino]methyl}-8,30-dioxa-24-azatetracyclo[23.3.1.1⁴,⁷.0⁵,²⁸]triaconta-1(28),2,4,9,19,21,23,25(29),26-nonaen-6-one
Traditional Name(7S,9Z,11S,12R,13S,14R,15R,16R,17S,18S,19Z,21Z)-2,13,15,17,23,27,29-heptahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-{[(4-methylpiperazin-1-yl)imino]methyl}-8,30-dioxa-24-azatetracyclo[23.3.1.1⁴,⁷.0⁵,²⁸]triaconta-1(28),2,4,9,19,21,23,25(29),26-nonaen-6-one
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](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](O)[C@H]1C)C(C=NN1CCN(C)CC1)=C2O
InChI Identifier
InChI=1S/C41H56N4O11/c1-20-11-10-12-21(2)40(53)43-31-26(19-42-45-16-14-44(8)15-17-45)36(50)28-29(37(31)51)35(49)25(6)38-30(28)39(52)41(7,56-38)55-18-13-27(54-9)22(3)33(47)24(5)34(48)23(4)32(20)46/h10-13,18-20,22-24,27,32-34,46-51H,14-17H2,1-9H3,(H,43,53)/b11-10-,18-13-,21-12-,42-19-/t20-,22-,23+,24-,27-,32-,33+,34+,41-/m0/s1
InChI KeyKUJZTIJOBQNKDR-WINKZEBYSA-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
  • 1-naphthol
  • Naphthalene
  • Benzofuran
  • Coumaran
  • Hydroquinone
  • Aryl alkyl ketone
  • Aryl ketone
  • Ketal
  • N-methylpiperazine
  • N-alkylpiperazine
  • 1,4-diazinane
  • Piperazine
  • Benzenoid
  • Cyclic carboximidic acid
  • Ketone
  • Secondary alcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Propargyl-type 1,3-dipolar organic compound
  • Dialkyl ether
  • Ether
  • Hydrazone
  • Organic 1,3-dipolar compound
  • Oxacycle
  • Azacycle
  • Polyol
  • Acetal
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • 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 Solubility0.048 g/LALOGPS
logP3.41ALOGPS
logP2.57ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)-0.037ChemAxon
pKa (Strongest Basic)15.13ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area217.57 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity217.19 m³·mol⁻¹ChemAxon
Polarizability81.61 ųChemAxon
Number of Rings5ChemAxon
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, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot AvailableView in JSpectraViewer
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 IDDBMET00696
      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