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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-04 18:57:30 UTC
Update Date2019-07-23 07:15:01 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
Data?1563866101
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
Description Belongs to the class of organic compounds known as naphthofurans. Naphthofurans 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 ketone
  • Aryl alkyl ketone
  • Ketal
  • Piperidine
  • Benzenoid
  • Vinylogous acid
  • Cyclic carboximidic acid
  • Vinylogous amide
  • 3-imidazoline
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Ketimine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Ketone
  • Secondary alcohol
  • Azacycle
  • Oxacycle
  • Carboxylic acid derivative
  • Organic 1,3-dipolar compound
  • Dialkyl ether
  • Secondary aliphatic amine
  • Enamine
  • Ether
  • Propargyl-type 1,3-dipolar organic compound
  • Secondary amine
  • Monocarboxylic acid or derivatives
  • Acetal
  • Polyol
  • Carbonyl group
  • Amine
  • Imine
  • Alcohol
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Primary alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-313.88730932474
DeepCCS[M+Na]+287.77130932474
AllCCS[M+H]+285.432859911
AllCCS[M+H-H2O]+285.232859911
AllCCS[M+NH4]+285.632859911
AllCCS[M+Na]+285.632859911
AllCCS[M-H]-255.732859911
AllCCS[M+Na-2H]-261.732859911
AllCCS[M+HCOO]-268.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
31-Hydroxy rifabutinCO[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=C217660.5Standard polar33892256
31-Hydroxy rifabutinCO[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=C214700.5Standard non polar33892256
31-Hydroxy rifabutinCO[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=C215873.9Semi standard non polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 31-Hydroxy rifabutin 10V, Positive-QTOFsplash10-002b-1000000090-00e065229292d68276c42019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 31-Hydroxy rifabutin 20V, Positive-QTOFsplash10-0pdj-4000000290-0455f8758a572b9ed88b2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 31-Hydroxy rifabutin 40V, Positive-QTOFsplash10-0a4i-9000002520-72ad899a21d2049273c32019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 31-Hydroxy rifabutin 10V, Negative-QTOFsplash10-03dl-0000000090-27e26a46cb3eaecb79672019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 31-Hydroxy rifabutin 20V, Negative-QTOFsplash10-0j4l-1000000190-7bad62f2308e32ba01f42019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 31-Hydroxy rifabutin 40V, Negative-QTOFsplash10-114r-3000000960-d3eeca75808e6c2daf3d2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 31-Hydroxy rifabutin 10V, Positive-QTOFsplash10-03dj-0000000190-6a84b6f1e96b922a6ff02021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 31-Hydroxy rifabutin 20V, Positive-QTOFsplash10-0wbj-0000000590-7f980effad1349f34a0f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 31-Hydroxy rifabutin 40V, Positive-QTOFsplash10-0400-0000000290-2355408391146e56f3052021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 31-Hydroxy rifabutin 10V, Negative-QTOFsplash10-0iki-0000000390-ce96ddcf8465f30ca3262021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 31-Hydroxy rifabutin 20V, Negative-QTOFsplash10-0a4i-9000000010-d3a3a85ecd0a37d723852021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 31-Hydroxy rifabutin 40V, Negative-QTOFsplash10-03di-0000000190-b28c1d53a49370dc01562021-10-12Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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 Compound131769942
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available