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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3)transporters (2) Show 5 proteins XML

enzymes (3)transporters (2) Show 5 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2023-02-21 17:18:25 UTC

HMDB ID

HMDB0015167

Secondary Accession Numbers

HMDB15167

Metabolite Identification

Common Name

Mercaptopurine

Description

Mercaptopurine is only found in individuals that have used or taken this drug. It is an antimetabolite antineoplastic agent with immunosuppressant properties. It interferes with nucleic acid synthesis by inhibiting purine metabolism and is used, usually in combination with other drugs, in the treatment of or in remission maintenance programs for leukemia. [PubChem]Mercaptopurine competes with hypoxanthine and guanine for the enzyme hypoxanthine-guanine phosphoribosyltransferase (HGPRTase) and is itself converted to thioinosinic acid (TIMP). This intracellular nucleotide inhibits several reactions involving inosinic acid (IMP), including the conversion of IMP to xanthylic acid (XMP) and the conversion of IMP to adenylic acid (AMP) via adenylosuccinate (SAMP). In addition, 6-methylthioinosinate (MTIMP) is formed by the methylation of TIMP. Both TIMP and MTIMP have been reported to inhibit glutamine-5-phosphoribosylpyrophosphate amidotransferase, the first enzyme unique to the de novo pathway for purine ribonucleotide synthesis. Experiments indicate that radiolabeled mercaptopurine may be recovered from the DNA in the form of deoxythioguanosine. Some mercaptopurine is converted to nucleotide derivatives of 6-thioguanine (6-TG) by the sequential actions of inosinate (IMP) dehydrogenase and xanthylate (XMP) aminase, converting TIMP to thioguanylic acid (TGMP).

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1,7-Dihydro-6H-purine-6-thione	ChEBI
3H-Purine-6-thiol	ChEBI
6-MP	ChEBI
6-Thiohypoxanthine	ChEBI
Mercaptopurine anhydrous	Kegg
Purinethol	Kegg
6 MP	HMDB
6-Mercaptopurine	HMDB
Mercaptopurine monohydrate	HMDB
Mercapurin	HMDB
MP	HMDB
6 Mercaptopurine monohydrate	HMDB
6-Mercaptopurine monohydrate	HMDB
Puri-nethol	HMDB
6 Mercaptopurine	HMDB
GlaxoSmithKline brand OF 6 mercaptopurine	HMDB
Leupurin	HMDB
Wellcome brand OF 6-mercaptopurine	HMDB
6 Thiohypoxanthine	HMDB
6 Thiopurine	HMDB
Glaxo wellcome brand OF 6 mercaptopurine	HMDB
GlaxoSmithKline brand OF 6-mercaptopurine	HMDB
Puri nethol	HMDB
Wellcome brand OF 6 mercaptopurine	HMDB
6-Thiopurine	HMDB
Glaxo wellcome brand OF 6-mercaptopurine	HMDB
Mercaptopurina wellcome	HMDB
Purimethol	HMDB

Chemical Formula

C₅H₄N₄S

Average Molecular Weight

152.177

Monoisotopic Molecular Weight

152.015666838

IUPAC Name

6,7-dihydro-3H-purine-6-thione

Traditional Name

mercaptopurine

CAS Registry Number

50-44-2

SMILES

S=C1N=CNC2=C1NC=N2

InChI Identifier

InChI=1S/C5H4N4S/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10)

InChI Key

GLVAUDGFNGKCSF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purinethiones. These are purines in which the purine moiety bears a thioketone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyrimidines

Sub Class

Purines and purine derivatives

Direct Parent

Purinethiones

Alternative Parents

Substituents

Purinethione
Pyrimidinethione
Pyrimidine
Heteroaromatic compound
Imidazole
Azole
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organosulfur compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aryl thiol (CHEBI:2208 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Organ

Liver (HMDB: HMDB0015167)
Kidney (HMDB: HMDB0015167)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015167)
Membrane (HMDB: HMDB0015167)

Source

Exogenous

Exogenous (HMDB: HMDB0015167)

Endogenous

Endogenous (HMDB: HMDB0015167)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Azathioprine Action Pathway (PathBank: SMP0000427)
Mercaptopurine Action Pathway (PathBank: SMP0000428)
Thioguanine Action Pathway (PathBank: SMP0000430)

Metabolic pathway

Mercaptopurine Metabolism Pathway (PathBank: SMP0000609)
Azathioprine Metabolism Pathway (PathBank: SMP0000645)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	313 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.74 g/L	Not Available
LogP	-0.4	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.74 g/L	ALOGPS
logP	-0.13	ALOGPS
logP	-0.12	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	9.5	ChemAxon
pKa (Strongest Basic)	2.99	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	53.07 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	43.6 m³·mol⁻¹	ChemAxon
Polarizability	14.04 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	128.45	31661259
DarkChem	[M-H]-	126.652	31661259
DeepCCS	[M+H]+	125.016	30932474
DeepCCS	[M-H]-	122.877	30932474
DeepCCS	[M-2H]-	158.939	30932474
DeepCCS	[M+Na]+	133.709	30932474
AllCCS	[M+H]+	131.0	32859911
AllCCS	[M+H-H2O]+	126.3	32859911
AllCCS	[M+NH4]+	135.4	32859911
AllCCS	[M+Na]+	136.7	32859911
AllCCS	[M-H]-	124.5	32859911
AllCCS	[M+Na-2H]-	125.8	32859911
AllCCS	[M+HCOO]-	127.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.67 minutes	32390414
Predicted by Siyang on May 30, 2022	9.3812 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.79 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	177.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	685.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	367.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	61.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	259.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	110.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	294.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	248.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	770.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	613.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	38.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	668.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	227.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	391.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	712.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	362.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	314.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Mercaptopurine	S=C1N=CNC2=C1NC=N2	2464.4	Standard polar	33892256
Mercaptopurine	S=C1N=CNC2=C1NC=N2	1612.5	Standard non polar	33892256
Mercaptopurine	S=C1N=CNC2=C1NC=N2	2359.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Mercaptopurine,1TMS,isomer #1	C[Si](C)(C)N1C=NC(=S)C2=C1N=C[NH]2	1933.6	Semi standard non polar	33892256
Mercaptopurine,1TMS,isomer #1	C[Si](C)(C)N1C=NC(=S)C2=C1N=C[NH]2	2087.1	Standard non polar	33892256
Mercaptopurine,1TMS,isomer #1	C[Si](C)(C)N1C=NC(=S)C2=C1N=C[NH]2	2722.5	Standard polar	33892256
Mercaptopurine,1TMS,isomer #2	C[Si](C)(C)N1C=NC2=C1C(=S)N=C[NH]2	1871.2	Semi standard non polar	33892256
Mercaptopurine,1TMS,isomer #2	C[Si](C)(C)N1C=NC2=C1C(=S)N=C[NH]2	1945.7	Standard non polar	33892256
Mercaptopurine,1TMS,isomer #2	C[Si](C)(C)N1C=NC2=C1C(=S)N=C[NH]2	2583.3	Standard polar	33892256
Mercaptopurine,2TMS,isomer #1	C[Si](C)(C)N1C=NC(=S)C2=C1N=CN2[Si](C)(C)C	2074.9	Semi standard non polar	33892256
Mercaptopurine,2TMS,isomer #1	C[Si](C)(C)N1C=NC(=S)C2=C1N=CN2[Si](C)(C)C	2152.7	Standard non polar	33892256
Mercaptopurine,2TMS,isomer #1	C[Si](C)(C)N1C=NC(=S)C2=C1N=CN2[Si](C)(C)C	2394.8	Standard polar	33892256
Mercaptopurine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=NC(=S)C2=C1N=C[NH]2	2160.6	Semi standard non polar	33892256
Mercaptopurine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=NC(=S)C2=C1N=C[NH]2	2325.9	Standard non polar	33892256
Mercaptopurine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=NC(=S)C2=C1N=C[NH]2	2791.6	Standard polar	33892256
Mercaptopurine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=NC2=C1C(=S)N=C[NH]2	2111.4	Semi standard non polar	33892256
Mercaptopurine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=NC2=C1C(=S)N=C[NH]2	2172.4	Standard non polar	33892256
Mercaptopurine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=NC2=C1C(=S)N=C[NH]2	2686.6	Standard polar	33892256
Mercaptopurine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=NC(=S)C2=C1N=CN2[Si](C)(C)C(C)(C)C	2432.8	Semi standard non polar	33892256
Mercaptopurine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=NC(=S)C2=C1N=CN2[Si](C)(C)C(C)(C)C	2554.5	Standard non polar	33892256
Mercaptopurine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=NC(=S)C2=C1N=CN2[Si](C)(C)C(C)(C)C	2529.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Mercaptopurine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-6900000000-6a7f989ad4995b3bfb3b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mercaptopurine 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mercaptopurine LC-ESI-QQ , negative-QTOF	splash10-0udi-1900000000-80fade3542b1b7a4f542	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mercaptopurine LC-ESI-QQ , negative-QTOF	splash10-0udi-4900000000-ae3cab845511e09fd7d8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mercaptopurine LC-ESI-QQ , negative-QTOF	splash10-052f-9400000000-eb3a9e5b93f0954dda1f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mercaptopurine LC-ESI-QQ , negative-QTOF	splash10-066u-9300000000-e920208db376745577ae	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mercaptopurine LC-ESI-QQ , negative-QTOF	splash10-014r-9100000000-9452425dda09b342a804	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mercaptopurine LC-ESI-QQ , positive-QTOF	splash10-000i-0900000000-fb1e1ed0d15536d940b5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mercaptopurine LC-ESI-QQ , positive-QTOF	splash10-00di-9300000000-ae82c485895af50f18e0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mercaptopurine LC-ESI-QQ , positive-QTOF	splash10-01ba-9700000000-70542617d846459d1edb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mercaptopurine LC-ESI-QQ , positive-QTOF	splash10-00kb-9400000000-34922db319d482f338c7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mercaptopurine LC-ESI-QQ , positive-QTOF	splash10-0006-9000000000-7de65dacfd12ff92f5e4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mercaptopurine 40V, Positive-QTOF	splash10-014i-0900000000-f85c1903d3c0e56417e1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mercaptopurine 20V, Positive-QTOF	splash10-0udi-0900000000-ea506d4c3735e8341ab4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mercaptopurine 10V, Positive-QTOF	splash10-0udi-0900000000-f8b71bfd941d3b3f3373	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mercaptopurine 10V, Positive-QTOF	splash10-0udi-0900000000-7a22823f32dc64d60c70	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mercaptopurine 20V, Positive-QTOF	splash10-0udi-0900000000-3dac1862e412a02b04c7	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mercaptopurine 40V, Positive-QTOF	splash10-0ufr-7900000000-86f3475856644175beb5	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mercaptopurine 10V, Negative-QTOF	splash10-0udi-0900000000-65499423bcb28e8ec450	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mercaptopurine 20V, Negative-QTOF	splash10-0uk9-0900000000-e72e8a55b92000661bf6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mercaptopurine 40V, Negative-QTOF	splash10-01b9-9600000000-b86d5a7c7cd083d92e19	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mercaptopurine 10V, Positive-QTOF	splash10-0udi-0900000000-67dad22e2593a56a8777	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mercaptopurine 20V, Positive-QTOF	splash10-0udi-0900000000-804445f5cb6f103d3d1d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mercaptopurine 40V, Positive-QTOF	splash10-067i-9200000000-91b7dfe5d6dabda4e777	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mercaptopurine 10V, Negative-QTOF	splash10-0udi-0900000000-cbc84ccd8657a0abcedc	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mercaptopurine 20V, Negative-QTOF	splash10-0udi-4900000000-63ec34a1f43cd509d6ef	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mercaptopurine 40V, Negative-QTOF	splash10-0aor-9000000000-d4dd4afbcb5bdd8e05b5	2021-10-11	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	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

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Azathioprine Action Pathway		Not Available
Mercaptopurine Action Pathway		Not Available
Thioguanine Action Pathway		Not Available
Mercaptopurine Metabolism Pathway		Not Available
Azathioprine Metabolism Pathway		Not Available

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 DB01033	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01033	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01033

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

580869

KEGG Compound ID

C02380

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Mercaptopurine

METLIN ID

Not Available

PubChem Compound

667490

PDB ID

PM6

ChEBI ID

2208

Food Biomarker Ontology

Not Available

VMH ID

M02989

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Xanthine dehydrogenase/oxidase

General function:: Involved in oxidoreductase activity
Specific function:: Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Has also low oxidase activity towards aldehydes (in vitro).
Gene Name:: XDH
Uniprot ID:: P47989
Molecular weight:: 146422.99

Reactions

Mercaptopurine + Water + Oxygen → 6-Thiourate + Hydrogen peroxide	details

References

Dubinsky MC: Azathioprine, 6-mercaptopurine in inflammatory bowel disease: pharmacology, efficacy, and safety. Clin Gastroenterol Hepatol. 2004 Sep;2(9):731-43. [PubMed:15354273 ]

Enzyme Details

2. Thiopurine S-methyltransferase

General function:: Involved in thiopurine S-methyltransferase activity
Specific function:: Catalyzes the S-methylation of thiopurine drugs such as 6-mercaptopurine.
Gene Name:: TPMT
Uniprot ID:: P51580
Molecular weight:: 28180.09

Reactions

Mercaptopurine + S-Adenosylmethionine → 6-Methylmercaptopurine + S-Adenosylhomocysteine	details

References

Dubinsky MC: Azathioprine, 6-mercaptopurine in inflammatory bowel disease: pharmacology, efficacy, and safety. Clin Gastroenterol Hepatol. 2004 Sep;2(9):731-43. [PubMed:15354273 ]

Enzyme Details

3. Hypoxanthine-guanine phosphoribosyltransferase

General function:: Involved in hypoxanthine phosphoribosyltransferase activity
Specific function:: Converts guanine to guanosine monophosphate, and hypoxanthine to inosine monophosphate. Transfers the 5-phosphoribosyl group from 5-phosphoribosylpyrophosphate onto the purine. Plays a central role in the generation of purine nucleotides through the purine salvage pathway.
Gene Name:: HPRT1
Uniprot ID:: P00492
Molecular weight:: 24579.155

Reactions

Mercaptopurine + Phosphoribosyl pyrophosphate → 6-Thioinosine-5'-monophosphate + Pyrophosphate	details

References

Dubinsky MC: Azathioprine, 6-mercaptopurine in inflammatory bowel disease: pharmacology, efficacy, and safety. Clin Gastroenterol Hepatol. 2004 Sep;2(9):731-43. [PubMed:15354273 ]

Transporters

Enzyme Details

1. Multidrug resistance-associated protein 4

General function:: Involved in ATP binding
Specific function:: May be an organic anion pump relevant to cellular detoxification
Gene Name:: ABCC4
Uniprot ID:: O15439
Molecular weight:: 149525.3

References

Chen ZS, Lee K, Kruh GD: Transport of cyclic nucleotides and estradiol 17-beta-D-glucuronide by multidrug resistance protein 4. Resistance to 6-mercaptopurine and 6-thioguanine. J Biol Chem. 2001 Sep 7;276(36):33747-54. Epub 2001 Jul 10. [PubMed:11447229 ]

Enzyme Details

2. Multidrug resistance-associated protein 5

General function:: Involved in ATP binding
Specific function:: Acts as a multispecific organic anion pump which can transport nucleotide analogs
Gene Name:: ABCC5
Uniprot ID:: O15440
Molecular weight:: 160658.8

References

Wijnholds J, Mol CA, van Deemter L, de Haas M, Scheffer GL, Baas F, Beijnen JH, Scheper RJ, Hatse S, De Clercq E, Balzarini J, Borst P: Multidrug-resistance protein 5 is a multispecific organic anion transporter able to transport nucleotide analogs. Proc Natl Acad Sci U S A. 2000 Jun 20;97(13):7476-81. [PubMed:10840050 ]

Showing metabocard for Mercaptopurine (HMDB0015167)

MOL for HMDB0015167 (Mercaptopurine)

3D MOL for HMDB0015167 (Mercaptopurine)

3D SDF for HMDB0015167 (Mercaptopurine)

3D-SDF for HMDB0015167 (Mercaptopurine)

PDB for HMDB0015167 (Mercaptopurine)

3D PDB for HMDB0015167 (Mercaptopurine)

SMILES for HMDB0015167 (Mercaptopurine)

INCHI for HMDB0015167 (Mercaptopurine)

Structure for HMDB0015167 (Mercaptopurine)

3D Structure for HMDB0015167 (Mercaptopurine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

References

Reactions

References

Reactions

References

Transporters

References

References