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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2019-01-11 19:33:40 UTC
HMDB IDHMDB0014474
Secondary Accession Numbers
  • HMDB14474
Metabolite Identification
Common NameEthambutol
DescriptionAn antitubercular agent that inhibits the transfer of mycolic acids into the cell wall of the tubercle bacillus. It may also inhibit the synthesis of spermidine in mycobacteria. The action is usually bactericidal, and the drug can penetrate human cell membranes to exert its lethal effect. (From Smith and Reynard, Textbook of Pharmacology, 1992, p863)
Structure
Data?1547235220
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
AethambutolumHMDB
D-EthambutolHMDB
EtambutoloHMDB
Ethambutol, racemic mixtureHMDB
Fatol brand OF ethambutol hydrochlorideMeSH
Sanavita brand OF ethambutol hydrochlorideMeSH
Wyeth brand OF ethambutol hydrochlorideMeSH
AHP brand OF ethambutol hydrochlorideMeSH
Hydrochloride, ethambutolMeSH
ICN brand OF ethambutol hydrochlorideMeSH
Lederle brand OF ethambutol hydrochlorideMeSH
MiambutolMeSH
EMB hefaMeSH
EMB-fatolMeSH
EMB-hefaMeSH
Etambutol llorenteMeSH
EtibiMeSH
Genopharm brand OF ethambutol hydrochlorideMeSH
Llorente brand OF ethambutol hydrochlorideMeSH
MyambutolMeSH
Riemser brand OF ethambutol hydrochlorideMeSH
DexambutolMeSH
EMB fatolMeSH
Elan brand OF ethambutol hydrochlorideMeSH
Ethambutol hydrochlorideMeSH
Llorente, etambutolMeSH
SERB brand OF ethambutol hydrochlorideMeSH
Wernigerode brand OF ethambutol hydrochlorideMeSH
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
DescriptionThis compound 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ul0-5900000000-89e4dd363b62972788ddView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-9835000000-a128bc7a900264abaa54View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0900000000-1c5922845499f5b38b9cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0090000000-d6867efe25d3bd98a3d6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0900000000-c5e5bdae927a908239cbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0900000000-c5e5bdae927a908239cbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0900000000-3fd99ca7b30bbde49d3aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0090000000-f3bae435be629eb01dfbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0aor-0890000000-ccfd6d7643c035e85154View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0900000000-1c5922845499f5b38b9cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0900000000-c5e5bdae927a908239cbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0900000000-f11341611c9cfa579095View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-1970000000-ce1c06e6eb8996487768View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-6910000000-def39cb7a4a0a270d07cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0603-9300000000-19c8f4c824cb5cc892dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1390000000-8dcf9353517b3cd58746View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uki-3940000000-3f54617420cf5327e70aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05ar-9800000000-dd533e6e939cf8386b06View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00330 details
UrineExpected but not Quantified Not 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
FoodDB 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
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available