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Record Information
Version3.6
Creation Date2013-07-04 18:55:53 UTC
Update Date2016-02-11 08:11:56 UTC
HMDB IDHMDB60732
Secondary Accession NumbersNone
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=1/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-/s2
InChI KeyInChIKey=KUJZTIJOBQNKDR-JSERWLTMNA-N
Chemical Taxonomy
ClassificationNot classified
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 Solubility0.048 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity217.19 m3·mol-1ChemAxon
Polarizability81.61 Å3ChemAxon
Number of Rings5ChemAxon
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 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
NuGOwiki LinkHMDB60732
Metagene LinkHMDB60732
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