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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2021-09-14 15:44:55 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. Based on a literature review a significant number of articles have been published on Ethambutol.
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

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point88 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility7.58 g/LNot Available
LogP-0.3Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available147.001http://allccs.zhulab.cn/database/detail?ID=AllCCS00000701
Predicted Molecular Properties
PropertyValueSource
Water Solubility7.58 g/LALOGPS
logP10(-0.12) g/LALOGPS
logP10(-0.059) g/LChemAxon
logS10(-1.4) g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+148.29731661259
DarkChem[M-H]-147.56431661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
EthambutolCC[C@@H](CO)NCCN[C@@H](CC)CO3045.4Standard polar33892256
EthambutolCC[C@@H](CO)NCCN[C@@H](CC)CO1712.7Standard non polar33892256
EthambutolCC[C@@H](CO)NCCN[C@@H](CC)CO1691.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Ethambutol,1TMS,isomer #1CC[C@@H](CO)NCCN[C@@H](CC)CO[Si](C)(C)C1757.9Semi standard non polar33892256
Ethambutol,1TMS,isomer #2CC[C@@H](CO)NCCN([C@@H](CC)CO)[Si](C)(C)C1802.9Semi standard non polar33892256
Ethambutol,2TMS,isomer #1CC[C@@H](CO[Si](C)(C)C)NCCN[C@@H](CC)CO[Si](C)(C)C1760.1Semi standard non polar33892256
Ethambutol,2TMS,isomer #2CC[C@@H](CO[Si](C)(C)C)NCCN([C@@H](CC)CO)[Si](C)(C)C1797.0Semi standard non polar33892256
Ethambutol,2TMS,isomer #3CC[C@@H](CO)NCCN([C@@H](CC)CO[Si](C)(C)C)[Si](C)(C)C1845.2Semi standard non polar33892256
Ethambutol,2TMS,isomer #4CC[C@@H](CO)N(CCN([C@@H](CC)CO)[Si](C)(C)C)[Si](C)(C)C1869.1Semi standard non polar33892256
Ethambutol,3TMS,isomer #1CC[C@@H](CO[Si](C)(C)C)NCCN([C@@H](CC)CO[Si](C)(C)C)[Si](C)(C)C1828.9Semi standard non polar33892256
Ethambutol,3TMS,isomer #1CC[C@@H](CO[Si](C)(C)C)NCCN([C@@H](CC)CO[Si](C)(C)C)[Si](C)(C)C2033.2Standard non polar33892256
Ethambutol,3TMS,isomer #1CC[C@@H](CO[Si](C)(C)C)NCCN([C@@H](CC)CO[Si](C)(C)C)[Si](C)(C)C2022.4Standard polar33892256
Ethambutol,3TMS,isomer #2CC[C@@H](CO)N(CCN([C@@H](CC)CO[Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C1949.4Semi standard non polar33892256
Ethambutol,3TMS,isomer #2CC[C@@H](CO)N(CCN([C@@H](CC)CO[Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2069.9Standard non polar33892256
Ethambutol,3TMS,isomer #2CC[C@@H](CO)N(CCN([C@@H](CC)CO[Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2170.5Standard polar33892256
Ethambutol,4TMS,isomer #1CC[C@@H](CO[Si](C)(C)C)N(CCN([C@@H](CC)CO[Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2041.0Semi standard non polar33892256
Ethambutol,4TMS,isomer #1CC[C@@H](CO[Si](C)(C)C)N(CCN([C@@H](CC)CO[Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2098.5Standard non polar33892256
Ethambutol,4TMS,isomer #1CC[C@@H](CO[Si](C)(C)C)N(CCN([C@@H](CC)CO[Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C1952.1Standard polar33892256
Ethambutol,1TBDMS,isomer #1CC[C@@H](CO)NCCN[C@@H](CC)CO[Si](C)(C)C(C)(C)C1980.1Semi standard non polar33892256
Ethambutol,1TBDMS,isomer #2CC[C@@H](CO)NCCN([C@@H](CC)CO)[Si](C)(C)C(C)(C)C2039.5Semi standard non polar33892256
Ethambutol,2TBDMS,isomer #1CC[C@@H](CO[Si](C)(C)C(C)(C)C)NCCN[C@@H](CC)CO[Si](C)(C)C(C)(C)C2228.9Semi standard non polar33892256
Ethambutol,2TBDMS,isomer #2CC[C@@H](CO[Si](C)(C)C(C)(C)C)NCCN([C@@H](CC)CO)[Si](C)(C)C(C)(C)C2303.2Semi standard non polar33892256
Ethambutol,2TBDMS,isomer #3CC[C@@H](CO)NCCN([C@@H](CC)CO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2322.7Semi standard non polar33892256
Ethambutol,2TBDMS,isomer #4CC[C@@H](CO)N(CCN([C@@H](CC)CO)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2353.8Semi standard non polar33892256
Ethambutol,3TBDMS,isomer #1CC[C@@H](CO[Si](C)(C)C(C)(C)C)NCCN([C@@H](CC)CO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2576.5Semi standard non polar33892256
Ethambutol,3TBDMS,isomer #1CC[C@@H](CO[Si](C)(C)C(C)(C)C)NCCN([C@@H](CC)CO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2578.2Standard non polar33892256
Ethambutol,3TBDMS,isomer #1CC[C@@H](CO[Si](C)(C)C(C)(C)C)NCCN([C@@H](CC)CO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2387.8Standard polar33892256
Ethambutol,3TBDMS,isomer #2CC[C@@H](CO)N(CCN([C@@H](CC)CO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2657.6Semi standard non polar33892256
Ethambutol,3TBDMS,isomer #2CC[C@@H](CO)N(CCN([C@@H](CC)CO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2592.4Standard non polar33892256
Ethambutol,3TBDMS,isomer #2CC[C@@H](CO)N(CCN([C@@H](CC)CO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2480.1Standard polar33892256
Ethambutol,4TBDMS,isomer #1CC[C@@H](CO[Si](C)(C)C(C)(C)C)N(CCN([C@@H](CC)CO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2963.5Semi standard non polar33892256
Ethambutol,4TBDMS,isomer #1CC[C@@H](CO[Si](C)(C)C(C)(C)C)N(CCN([C@@H](CC)CO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2779.9Standard non polar33892256
Ethambutol,4TBDMS,isomer #1CC[C@@H](CO[Si](C)(C)C(C)(C)C)N(CCN([C@@H](CC)CO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2440.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Ethambutol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ul0-5900000000-89e4dd363b62972788dd2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ethambutol GC-MS (2 TMS) - 70eV, Positivesplash10-00di-9835000000-a128bc7a900264abaa542017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ethambutol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Ethambutol LC-ESI-ITFT , positive-QTOFsplash10-014i-0900000000-1c5922845499f5b38b9c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ethambutol LC-ESI-ITFT , positive-QTOFsplash10-0a4i-0090000000-d6867efe25d3bd98a3d62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ethambutol LC-ESI-ITFT , positive-QTOFsplash10-014i-0900000000-c5e5bdae927a908239cb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ethambutol LC-ESI-ITFT , positive-QTOFsplash10-014i-0900000000-c5e5bdae927a908239cb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ethambutol LC-ESI-ITFT , positive-QTOFsplash10-014i-0900000000-3fd99ca7b30bbde49d3a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ethambutol LC-ESI-ITFT , positive-QTOFsplash10-0a4i-0090000000-f3bae435be629eb01dfb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ethambutol LC-ESI-ITFT , positive-QTOFsplash10-0aor-0890000000-ccfd6d7643c035e851542017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ethambutol LC-ESI-ITFT , positive-QTOFsplash10-014i-0900000000-1c5922845499f5b38b9c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ethambutol LC-ESI-ITFT , positive-QTOFsplash10-014i-0900000000-c5e5bdae927a908239cb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ethambutol LC-ESI-ITFT , positive-QTOFsplash10-014i-0900000000-f11341611c9cfa5790952017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ethambutol 75V, Positive-QTOFsplash10-014i-4900000000-3b54453f7861fac2d8562021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ethambutol 10V, Positive-QTOFsplash10-014i-1920000000-9e3493ee255f54f383d72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ethambutol 40V, Positive-QTOFsplash10-0a4i-9000000000-0b03d6426c85fa730fc62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ethambutol 70V, Positive-QTOFsplash10-014i-3900000000-d4311c76cc80b7e3d3962021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ethambutol 15V, Positive-QTOFsplash10-014i-2900000000-377cd86c5dd9f4a8e1a22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ethambutol 20V, Positive-QTOFsplash10-014i-4900000000-81bbfa4fd47c6e268bb32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ethambutol 35V, Positive-QTOFsplash10-0a4i-9000000000-47e43dcfde5f0401e6e02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ethambutol 30V, Positive-QTOFsplash10-0a4i-9300000000-d220d9d540fda89a590f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ethambutol 80V, Positive-QTOFsplash10-014i-5900000000-4f50a6985e4bd0f003c92021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethambutol 10V, Positive-QTOFsplash10-0a4r-1970000000-ce1c06e6eb89964877682016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethambutol 20V, Positive-QTOFsplash10-014j-6910000000-def39cb7a4a0a270d07c2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethambutol 40V, Positive-QTOFsplash10-0603-9300000000-19c8f4c824cb5cc892db2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethambutol 10V, Negative-QTOFsplash10-0udi-1390000000-8dcf9353517b3cd587462016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethambutol 20V, Negative-QTOFsplash10-0uki-3940000000-3f54617420cf5327e70a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethambutol 40V, Negative-QTOFsplash10-05ar-9800000000-dd533e6e939cf8386b062016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
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 IDC00037452
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
MarkerDB IDNot Available
Good Scents IDrw1630491
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available