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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:04 UTC
HMDB IDHMDB0015677
Secondary Accession Numbers
  • HMDB15677
Metabolite Identification
Common NameDimercaprol
DescriptionDimercaprol is a traditional chelating agent developed by British biochemists at Oxford University during World War II. It was developed as an experimental antidote against the arsenic-based poison gas Lewisite. It has been used clinically since 1949 in arsenic, cadmium and mercury poisoning. In addition, it has in the past been used for the treatment of Wilson's disease, a genetic disorder in which the body tends to retain copper. Dimercaprol is a potentially toxic drug, and its use may be accompanied by multiple side effects.
Structure
Data?1582753322
Synonyms
ValueSource
1,2-Dimercapto-3-propanolChEBI
1,2-DithioglycerolChEBI
2,3-Dimercapto-1-propanolChEBI
2,3-Dimercaptol-1-propanolChEBI
2,3-DimercaptopropanolChEBI
2,3-DithiopropanolChEBI
2,3-Mercaptopropan-1-olChEBI
2,3-MercaptopropanolChEBI
3-Hydroxy-1,2-propanedithiolChEBI
alpha,beta-DithioglycerolChEBI
BALChEBI
British anti-lewisiteChEBI
British antilewisiteChEBI
DimercaprolumChEBI
DimercaptopropanolChEBI
DithioglycerineChEBI
DithioglycerolChEBI
SulfactinChEBI
a,b-DithioglycerolGenerator
Α,β-dithioglycerolGenerator
SulphactinGenerator
2,3-DimercaproHMDB
2,3 Dithiopropan 1 O1HMDB
2,3-Dimercaptopropanol, cadmiumHMDB
Cadmium 2,3-dimercaptopropanolHMDB
Taylor brand OF dimercaprolHMDB
2,3 DimercaptopropanolHMDB
Anti-lewisite agent, britishHMDB
British anti lewisite agentHMDB
British anti-lewisite agentHMDB
Knoll brand OF dimercaprolHMDB
BAL in oilHMDB
British anti lewisiteHMDB
Cadmium 2,3 dimercaptopropanolHMDB
DicaptolHMDB
2,3-Dithiopropan-1-O1HMDB
Anti-lewisite, britishHMDB
B.A.L.HMDB
In oil, balHMDB
Oil, bal inHMDB
Chemical FormulaC3H8OS2
Average Molecular Weight124.225
Monoisotopic Molecular Weight124.001656258
IUPAC Name2,3-disulfanylpropan-1-ol
Traditional Namedimercaprol
CAS Registry Number59-52-9
SMILES
OCC(S)CS
InChI Identifier
InChI=1S/C3H8OS2/c4-1-3(6)2-5/h3-6H,1-2H2
InChI KeyWQABCVAJNWAXTE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alkylthiols. These are organic compounds containing the thiol functional group linked to an alkyl chain.
KingdomOrganic compounds
Super ClassOrganosulfur compounds
ClassThiols
Sub ClassAlkylthiols
Direct ParentAlkylthiols
Alternative Parents
Substituents
  • Alkylthiol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
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 Solubility2.76 g/LALOGPS
logP0.58ALOGPS
logP0.21ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)9.58ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity32.91 m³·mol⁻¹ChemAxon
Polarizability12.88 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+124.28131661259
DarkChem[M-H]-117.74831661259
DeepCCS[M+H]+129.15730932474
DeepCCS[M-H]-127.13430932474
DeepCCS[M-2H]-162.6630932474
DeepCCS[M+Na]+137.19930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DimercaprolOCC(S)CS2013.7Standard polar33892256
DimercaprolOCC(S)CS1094.5Standard non polar33892256
DimercaprolOCC(S)CS1167.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dimercaprol,1TMS,isomer #1C[Si](C)(C)OCC(S)CS1307.3Semi standard non polar33892256
Dimercaprol,1TMS,isomer #2C[Si](C)(C)SC(CO)CS1314.2Semi standard non polar33892256
Dimercaprol,1TMS,isomer #3C[Si](C)(C)SCC(S)CO1374.8Semi standard non polar33892256
Dimercaprol,2TMS,isomer #1C[Si](C)(C)OCC(CS)S[Si](C)(C)C1460.8Semi standard non polar33892256
Dimercaprol,2TMS,isomer #1C[Si](C)(C)OCC(CS)S[Si](C)(C)C1380.4Standard non polar33892256
Dimercaprol,2TMS,isomer #1C[Si](C)(C)OCC(CS)S[Si](C)(C)C1531.0Standard polar33892256
Dimercaprol,2TMS,isomer #2C[Si](C)(C)OCC(S)CS[Si](C)(C)C1477.6Semi standard non polar33892256
Dimercaprol,2TMS,isomer #2C[Si](C)(C)OCC(S)CS[Si](C)(C)C1404.3Standard non polar33892256
Dimercaprol,2TMS,isomer #2C[Si](C)(C)OCC(S)CS[Si](C)(C)C1538.5Standard polar33892256
Dimercaprol,2TMS,isomer #3C[Si](C)(C)SCC(CO)S[Si](C)(C)C1478.2Semi standard non polar33892256
Dimercaprol,2TMS,isomer #3C[Si](C)(C)SCC(CO)S[Si](C)(C)C1450.8Standard non polar33892256
Dimercaprol,2TMS,isomer #3C[Si](C)(C)SCC(CO)S[Si](C)(C)C1679.9Standard polar33892256
Dimercaprol,3TMS,isomer #1C[Si](C)(C)OCC(CS[Si](C)(C)C)S[Si](C)(C)C1562.8Semi standard non polar33892256
Dimercaprol,3TMS,isomer #1C[Si](C)(C)OCC(CS[Si](C)(C)C)S[Si](C)(C)C1600.5Standard non polar33892256
Dimercaprol,3TMS,isomer #1C[Si](C)(C)OCC(CS[Si](C)(C)C)S[Si](C)(C)C1518.5Standard polar33892256
Dimercaprol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(S)CS1512.5Semi standard non polar33892256
Dimercaprol,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)SC(CO)CS1538.7Semi standard non polar33892256
Dimercaprol,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)SCC(S)CO1585.2Semi standard non polar33892256
Dimercaprol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(CS)S[Si](C)(C)C(C)(C)C1926.2Semi standard non polar33892256
Dimercaprol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(CS)S[Si](C)(C)C(C)(C)C1816.1Standard non polar33892256
Dimercaprol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(CS)S[Si](C)(C)C(C)(C)C1816.3Standard polar33892256
Dimercaprol,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCC(S)CS[Si](C)(C)C(C)(C)C1932.3Semi standard non polar33892256
Dimercaprol,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCC(S)CS[Si](C)(C)C(C)(C)C1850.8Standard non polar33892256
Dimercaprol,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCC(S)CS[Si](C)(C)C(C)(C)C1823.2Standard polar33892256
Dimercaprol,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)SCC(CO)S[Si](C)(C)C(C)(C)C1980.2Semi standard non polar33892256
Dimercaprol,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)SCC(CO)S[Si](C)(C)C(C)(C)C1906.2Standard non polar33892256
Dimercaprol,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)SCC(CO)S[Si](C)(C)C(C)(C)C1891.7Standard polar33892256
Dimercaprol,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(CS[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C2280.2Semi standard non polar33892256
Dimercaprol,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(CS[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C2243.9Standard non polar33892256
Dimercaprol,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(CS[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C1944.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dimercaprol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-02d345f6932e4df7ae4c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dimercaprol GC-MS (1 TMS) - 70eV, Positivesplash10-00ds-9600000000-5c06a4ce37d095db5a1c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dimercaprol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimercaprol 10V, Positive-QTOFsplash10-056r-2900000000-5e1d01085e00977775ac2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimercaprol 20V, Positive-QTOFsplash10-0a6u-7900000000-2010199887988b9b1f5e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimercaprol 40V, Positive-QTOFsplash10-05fr-9100000000-e15a808f41fdd35de8fe2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimercaprol 10V, Negative-QTOFsplash10-008i-9300000000-b6482fcdaeab876341d32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimercaprol 20V, Negative-QTOFsplash10-0acc-9200000000-f38fb9fba80629c643ff2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimercaprol 40V, Negative-QTOFsplash10-0a5c-9000000000-975b939359caaed4e9352016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimercaprol 10V, Positive-QTOFsplash10-0adl-7900000000-9b2eced4f80479d4220b2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimercaprol 20V, Positive-QTOFsplash10-0596-9000000000-dfbf45f840944602d2592021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimercaprol 40V, Positive-QTOFsplash10-05fr-9000000000-f9a12c59d4f73bb8e6e32021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimercaprol 10V, Negative-QTOFsplash10-00di-0900000000-b6d4cfef7736df5ca9d22021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimercaprol 20V, Negative-QTOFsplash10-001l-9000000000-12de67a14d053353befb2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimercaprol 40V, Negative-QTOFsplash10-000x-9000000000-72344935882f89d86e042021-10-11Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06782 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06782 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB06782
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2971
KEGG Compound IDC02924
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDimercaprol
METLIN IDNot Available
PubChem Compound3080
PDB IDNot Available
ChEBI ID64198
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 References
  1. Andersen O: Chemical and biological considerations in the treatment of metal intoxications by chelating agents. Mini Rev Med Chem. 2004 Jan;4(1):11-21. [PubMed:14754439 ]
  2. Walshe JM: The conquest of Wilson's disease. Brain. 2009 Aug;132(Pt 8):2289-95. doi: 10.1093/brain/awp149. Epub 2009 Jul 13. [PubMed:19596747 ]
  3. Boscolo M, Antonucci S, Volpe AR, Carmignani M, Di Gioacchino M: Acute mercury intoxication and use of chelating agents. J Biol Regul Homeost Agents. 2009 Oct-Dec;23(4):217-23. [PubMed:20003760 ]
  4. Flora SJ, Pachauri V: Chelation in metal intoxication. Int J Environ Res Public Health. 2010 Jul;7(7):2745-88. doi: 10.3390/ijerph7072745. Epub 2010 Jun 28. [PubMed:20717537 ]