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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2020-02-26 21:39:43 UTC
HMDB IDHMDB0014474
Secondary Accession Numbers
  • HMDB14474
Metabolite Identification
Common NameEthambutol
DescriptionEthambutol, also known as EMB or (S,S)-ethambutol, belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom. It is used (as the dihydrochloride salt) in combination with other antituberculous drugs in the treatment of pulmonary and extrapulmonary tuberculosis; resistant strains of M. tuberculosis are readily produced if ethambutol is used alone. Ethambutol is a drug. Ethambutol is a very strong basic compound (based on its pKa). It is a bacteriostatic antimycobacterial drug, effective against Mycobacterium tuberculosis and some other mycobacteria. An ethylenediamine derivative that is ethane-1,2-diamine in which one hydrogen attached to each of the nitrogens is sutstituted by a 1-hydroxybutan-2-yl group (S,S-configuration).
Structure
Data?1582753183
Synonyms
ValueSource
(+)-2,2'-(Ethylenediimino)di-1-butanolChEBI
(+)-EthambutolChEBI
(+)-N,N'-bis(1-(hydroxymethyl)propyl)ethylenediamineChEBI
(+)-S,S-EthambutolChEBI
(2S,7S)-2,7-Diethyl-3,6-diazaoctane-1,8-diolChEBI
(S,S)-EthambutolChEBI
EMBChEBI
EtambutolChEBI
EthambutolumChEBI
S,S-EthambutolChEBI
ServambutolKegg
AethambutolumHMDB
D-EthambutolHMDB
EtambutoloHMDB
Ethambutol, racemic mixtureHMDB
Fatol brand OF ethambutol hydrochlorideHMDB
Sanavita brand OF ethambutol hydrochlorideHMDB
Wyeth brand OF ethambutol hydrochlorideHMDB
AHP brand OF ethambutol hydrochlorideHMDB
Hydrochloride, ethambutolHMDB
ICN brand OF ethambutol hydrochlorideHMDB
Lederle brand OF ethambutol hydrochlorideHMDB
MiambutolHMDB
EMB hefaHMDB
EMB-fatolHMDB
EMB-hefaHMDB
Etambutol llorenteHMDB
EtibiHMDB
Genopharm brand OF ethambutol hydrochlorideHMDB
Llorente brand OF ethambutol hydrochlorideHMDB
MyambutolHMDB
Riemser brand OF ethambutol hydrochlorideHMDB
DexambutolHMDB
EMB fatolHMDB
Elan brand OF ethambutol hydrochlorideHMDB
Ethambutol hydrochlorideHMDB
Llorente, etambutolHMDB
SERB brand OF ethambutol hydrochlorideHMDB
Wernigerode brand OF ethambutol hydrochlorideHMDB
Chemical FormulaC10H24N2O2
Average Molecular Weight204.3098
Monoisotopic Molecular Weight204.183778022
IUPAC Name(2S)-2-[(2-{[(2S)-1-hydroxybutan-2-yl]amino}ethyl)amino]butan-1-ol
Traditional Nameethambutol
CAS Registry Number74-55-5
SMILES
CC[C@@H](CO)NCCN[C@@H](CC)CO
InChI Identifier
InChI=1S/C10H24N2O2/c1-3-9(7-13)11-5-6-12-10(4-2)8-14/h9-14H,3-8H2,1-2H3/t9-,10-/m0/s1
InChI KeyAEUTYOVWOVBAKS-UWVGGRQHSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct Parent1,2-aminoalcohols
Alternative Parents
Substituents
  • 1,2-aminoalcohol
  • Secondary amine
  • Secondary aliphatic amine
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point88 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility7.58 g/LNot Available
LogP-0.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility7.58 g/LALOGPS
logP-0.12ALOGPS
logP-0.059ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)14.82ChemAxon
pKa (Strongest Basic)9.55ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area64.52 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity57.89 m³·mol⁻¹ChemAxon
Polarizability24.47 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ul0-5900000000-89e4dd363b62972788ddSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-9835000000-a128bc7a900264abaa54Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0900000000-1c5922845499f5b38b9cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0090000000-d6867efe25d3bd98a3d6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0900000000-c5e5bdae927a908239cbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0900000000-c5e5bdae927a908239cbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0900000000-3fd99ca7b30bbde49d3aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0090000000-f3bae435be629eb01dfbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0aor-0890000000-ccfd6d7643c035e85154Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0900000000-1c5922845499f5b38b9cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0900000000-c5e5bdae927a908239cbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0900000000-f11341611c9cfa579095Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-1970000000-ce1c06e6eb8996487768Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-6910000000-def39cb7a4a0a270d07cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0603-9300000000-19c8f4c824cb5cc892dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1390000000-8dcf9353517b3cd58746Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uki-3940000000-3f54617420cf5327e70aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05ar-9800000000-dd533e6e939cf8386b06Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00330 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00330 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00330
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID13433
KEGG Compound IDC06984
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEthambutol
METLIN IDNot Available
PubChem Compound14052
PDB IDNot Available
ChEBI ID4877
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available