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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2023-02-21 17:18:34 UTC

HMDB ID

HMDB0015677

Secondary Accession Numbers

HMDB15677

Metabolite Identification

Common Name

Dimercaprol

Description

Dimercaprol 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1,2-Dimercapto-3-propanol	ChEBI
1,2-Dithioglycerol	ChEBI
2,3-Dimercapto-1-propanol	ChEBI
2,3-Dimercaptol-1-propanol	ChEBI
2,3-Dimercaptopropanol	ChEBI
2,3-Dithiopropanol	ChEBI
2,3-Mercaptopropan-1-ol	ChEBI
2,3-Mercaptopropanol	ChEBI
3-Hydroxy-1,2-propanedithiol	ChEBI
alpha,beta-Dithioglycerol	ChEBI
BAL	ChEBI
British anti-lewisite	ChEBI
British antilewisite	ChEBI
Dimercaprolum	ChEBI
Dimercaptopropanol	ChEBI
Dithioglycerine	ChEBI
Dithioglycerol	ChEBI
Sulfactin	ChEBI
a,b-Dithioglycerol	Generator
Α,β-dithioglycerol	Generator
Sulphactin	Generator
2,3-Dimercapro	HMDB
2,3 Dithiopropan 1 O1	HMDB
2,3-Dimercaptopropanol, cadmium	HMDB
Cadmium 2,3-dimercaptopropanol	HMDB
Taylor brand OF dimercaprol	HMDB
2,3 Dimercaptopropanol	HMDB
Anti-lewisite agent, british	HMDB
British anti lewisite agent	HMDB
British anti-lewisite agent	HMDB
Knoll brand OF dimercaprol	HMDB
BAL in oil	HMDB
British anti lewisite	HMDB
Cadmium 2,3 dimercaptopropanol	HMDB
Dicaptol	HMDB
2,3-Dithiopropan-1-O1	HMDB
Anti-lewisite, british	HMDB
B.A.L.	HMDB
In oil, bal	HMDB
Oil, bal in	HMDB

Chemical Formula

C₃H₈OS₂

Average Molecular Weight

124.225

Monoisotopic Molecular Weight

124.001656258

IUPAC Name

2,3-disulfanylpropan-1-ol

Traditional Name

dimercaprol

CAS Registry Number

59-52-9

SMILES

OCC(S)CS

InChI Identifier

InChI=1S/C3H8OS2/c4-1-3(6)2-5/h3-6H,1-2H2

InChI Key

WQABCVAJNWAXTE-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.

Kingdom

Organic compounds

Super Class

Organosulfur compounds

Class

Thiols

Sub Class

Alkylthiols

Direct Parent

Alkylthiols

Alternative Parents

Substituents

Alkylthiol
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

primary alcohol (CHEBI:64198 )
dithiol (CHEBI:64198 )
a small molecule (23-DIMERCAPTOPROPAN-1-OL )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.76 g/L	ALOGPS
logP	0.58	ALOGPS
logP	0.21	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	9.58	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	32.91 m³·mol⁻¹	ChemAxon
Polarizability	12.88 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	124.281	31661259
DarkChem	[M-H]-	117.748	31661259
DeepCCS	[M+H]+	129.157	30932474
DeepCCS	[M-H]-	127.134	30932474
DeepCCS	[M-2H]-	162.66	30932474
DeepCCS	[M+Na]+	137.199	30932474
AllCCS	[M+H]+	128.8	32859911
AllCCS	[M+H-H2O]+	124.7	32859911
AllCCS	[M+NH4]+	132.6	32859911
AllCCS	[M+Na]+	133.7	32859911
AllCCS	[M-H]-	139.7	32859911
AllCCS	[M+Na-2H]-	144.4	32859911
AllCCS	[M+HCOO]-	149.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dimercaprol	OCC(S)CS	2013.7	Standard polar	33892256
Dimercaprol	OCC(S)CS	1094.5	Standard non polar	33892256
Dimercaprol	OCC(S)CS	1167.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dimercaprol,1TMS,isomer #1	C[Si](C)(C)OCC(S)CS	1307.3	Semi standard non polar	33892256
Dimercaprol,1TMS,isomer #2	C[Si](C)(C)SC(CO)CS	1314.2	Semi standard non polar	33892256
Dimercaprol,1TMS,isomer #3	C[Si](C)(C)SCC(S)CO	1374.8	Semi standard non polar	33892256
Dimercaprol,2TMS,isomer #1	C[Si](C)(C)OCC(CS)S[Si](C)(C)C	1460.8	Semi standard non polar	33892256
Dimercaprol,2TMS,isomer #1	C[Si](C)(C)OCC(CS)S[Si](C)(C)C	1380.4	Standard non polar	33892256
Dimercaprol,2TMS,isomer #1	C[Si](C)(C)OCC(CS)S[Si](C)(C)C	1531.0	Standard polar	33892256
Dimercaprol,2TMS,isomer #2	C[Si](C)(C)OCC(S)CS[Si](C)(C)C	1477.6	Semi standard non polar	33892256
Dimercaprol,2TMS,isomer #2	C[Si](C)(C)OCC(S)CS[Si](C)(C)C	1404.3	Standard non polar	33892256
Dimercaprol,2TMS,isomer #2	C[Si](C)(C)OCC(S)CS[Si](C)(C)C	1538.5	Standard polar	33892256
Dimercaprol,2TMS,isomer #3	C[Si](C)(C)SCC(CO)S[Si](C)(C)C	1478.2	Semi standard non polar	33892256
Dimercaprol,2TMS,isomer #3	C[Si](C)(C)SCC(CO)S[Si](C)(C)C	1450.8	Standard non polar	33892256
Dimercaprol,2TMS,isomer #3	C[Si](C)(C)SCC(CO)S[Si](C)(C)C	1679.9	Standard polar	33892256
Dimercaprol,3TMS,isomer #1	C[Si](C)(C)OCC(CS[Si](C)(C)C)S[Si](C)(C)C	1562.8	Semi standard non polar	33892256
Dimercaprol,3TMS,isomer #1	C[Si](C)(C)OCC(CS[Si](C)(C)C)S[Si](C)(C)C	1600.5	Standard non polar	33892256
Dimercaprol,3TMS,isomer #1	C[Si](C)(C)OCC(CS[Si](C)(C)C)S[Si](C)(C)C	1518.5	Standard polar	33892256
Dimercaprol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(S)CS	1512.5	Semi standard non polar	33892256
Dimercaprol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)SC(CO)CS	1538.7	Semi standard non polar	33892256
Dimercaprol,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)SCC(S)CO	1585.2	Semi standard non polar	33892256
Dimercaprol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(CS)S[Si](C)(C)C(C)(C)C	1926.2	Semi standard non polar	33892256
Dimercaprol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(CS)S[Si](C)(C)C(C)(C)C	1816.1	Standard non polar	33892256
Dimercaprol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(CS)S[Si](C)(C)C(C)(C)C	1816.3	Standard polar	33892256
Dimercaprol,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC(S)CS[Si](C)(C)C(C)(C)C	1932.3	Semi standard non polar	33892256
Dimercaprol,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC(S)CS[Si](C)(C)C(C)(C)C	1850.8	Standard non polar	33892256
Dimercaprol,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC(S)CS[Si](C)(C)C(C)(C)C	1823.2	Standard polar	33892256
Dimercaprol,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)SCC(CO)S[Si](C)(C)C(C)(C)C	1980.2	Semi standard non polar	33892256
Dimercaprol,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)SCC(CO)S[Si](C)(C)C(C)(C)C	1906.2	Standard non polar	33892256
Dimercaprol,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)SCC(CO)S[Si](C)(C)C(C)(C)C	1891.7	Standard polar	33892256
Dimercaprol,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(CS[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C	2280.2	Semi standard non polar	33892256
Dimercaprol,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(CS[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C	2243.9	Standard non polar	33892256
Dimercaprol,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(CS[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C	1944.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dimercaprol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-02d345f6932e4df7ae4c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dimercaprol GC-MS (1 TMS) - 70eV, Positive	splash10-00ds-9600000000-5c06a4ce37d095db5a1c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dimercaprol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimercaprol 10V, Positive-QTOF	splash10-056r-2900000000-5e1d01085e00977775ac	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimercaprol 20V, Positive-QTOF	splash10-0a6u-7900000000-2010199887988b9b1f5e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimercaprol 40V, Positive-QTOF	splash10-05fr-9100000000-e15a808f41fdd35de8fe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimercaprol 10V, Negative-QTOF	splash10-008i-9300000000-b6482fcdaeab876341d3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimercaprol 20V, Negative-QTOF	splash10-0acc-9200000000-f38fb9fba80629c643ff	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimercaprol 40V, Negative-QTOF	splash10-0a5c-9000000000-975b939359caaed4e935	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimercaprol 10V, Positive-QTOF	splash10-0adl-7900000000-9b2eced4f80479d4220b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimercaprol 20V, Positive-QTOF	splash10-0596-9000000000-dfbf45f840944602d259	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimercaprol 40V, Positive-QTOF	splash10-05fr-9000000000-f9a12c59d4f73bb8e6e3	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimercaprol 10V, Negative-QTOF	splash10-00di-0900000000-b6d4cfef7736df5ca9d2	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimercaprol 20V, Negative-QTOF	splash10-001l-9000000000-12de67a14d053353befb	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dimercaprol 40V, Negative-QTOF	splash10-000x-9000000000-72344935882f89d86e04	2021-10-11	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB06782	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB06782	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB06782

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2971

KEGG Compound ID

C02924

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dimercaprol

METLIN ID

Not Available

PubChem Compound

3080

PDB ID

Not Available

ChEBI ID

64198

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
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 ]
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 ]
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 ]

Showing metabocard for Dimercaprol (HMDB0015677)

MOL for HMDB0015677 (Dimercaprol)

3D MOL for HMDB0015677 (Dimercaprol)

3D SDF for HMDB0015677 (Dimercaprol)

3D-SDF for HMDB0015677 (Dimercaprol)

PDB for HMDB0015677 (Dimercaprol)

3D PDB for HMDB0015677 (Dimercaprol)

SMILES for HMDB0015677 (Dimercaprol)

INCHI for HMDB0015677 (Dimercaprol)

Structure for HMDB0015677 (Dimercaprol)

3D Structure for HMDB0015677 (Dimercaprol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra