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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2)transporters (1) Show 3 proteins XML

enzymes (2)transporters (1) Show 3 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2023-02-21 17:18:13 UTC

HMDB ID

HMDB0014581

Secondary Accession Numbers

HMDB14581

Metabolite Identification

Common Name

Allopurinol

Description

Allopurinol is only found in individuals that have used or taken this drug. It is a xanthine oxidase inhibitor that decreases uric acid production. It also acts as an antimetabolite on some simpler organisms. [PubChem]Allopurinol and its active metabolite, oxypurinol, inhibits the enzyme xanthine oxidase, blocking the conversion of the oxypurines hypoxanthine and xanthine to uric acid. Elevated concentrations of oxypurine and oxypurine inhibition of xanthine oxidase through negative feedback results in a decrease in the concentrations of uric acid in the serum and urine. Allopurinol also facilitates the incorporation of hypoxanthine and xanthine into DNA and RNA, leading to a feedback inhibition of de novo purin synthesis and a decrease in serum uric acid concentrations as a result of an increase in nucleotide concentration.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1,5-Dihydro-4H-pyrazolo(3,4-D)pyrimidin-4-one	ChEBI
1,5-Dihydro-4H-pyrazolo(3,4-D)pyrimidine-4-one	ChEBI
1H-Pyrazolo(3,4-D)pyrimidin-4-ol	ChEBI
4'-Hydroxypyrazolol(3,4-D)pyrimidine	ChEBI
4-HPP	ChEBI
4-Hydroxy-1H-pyrazolo(3,4-D)pyrimidine	ChEBI
4-Hydroxy-3,4-pyrazolopyrimidine	ChEBI
4-Hydroxypyrazolo(3,4-D)pyrimidine	ChEBI
4-Hydroxypyrazolopyrimidine	ChEBI
4-Hydroxypyrazolyl(3,4-D)pyrimidine	ChEBI
4H-Pyrazolo(3,4-D)pyrimidin-4-one	ChEBI
AL-100	ChEBI
Allopurinolum	ChEBI
Alopurinol	ChEBI
Zyloprim	ChEBI
Allopurinol alphapharm brand	HMDB
Allopurinol basf brand	HMDB
Allopurinol merz brand	HMDB
Allopurinol pharmafarm brand	HMDB
Allopurinol roche brand	HMDB
Allopurinol tad brand	HMDB
Allopurinol thiemann brand	HMDB
Allopurinol wellcome brand	HMDB
Ashbourne brand OF allopurinol	HMDB
Boots brand OF allopurinol	HMDB
Fawns and mcallan brand OF allopurinol	HMDB
Foligan	HMDB
Hamarin	HMDB
Hennig brand OF allopurinol	HMDB
Horner brand OF allopurinol	HMDB
Jenapharm brand OF allopurinol	HMDB
Milurit	HMDB
Milurite	HMDB
Quimica, pan	HMDB
Remid	HMDB
Rima brand OF allopurinol	HMDB
Rimapurinol	HMDB
Rougier brand OF allopurinol	HMDB
Thiemann brand OF allopurinol	HMDB
Urtias	HMDB
Xanturic	HMDB
Allohexan	HMDB
Allopurinol horner brand	HMDB
Allopurinol merckle brand	HMDB
Allopurinol multipharma brand	HMDB
Allopurinol nicholas brand	HMDB
Allopurinol novopharm brand	HMDB
Allopurinol r.a.n. brand	HMDB
Allopurinol rima brand	HMDB
Allural	HMDB
Amrad brand OF allopurinol	HMDB
Atisuril	HMDB
Clonmel brand OF allopurinol	HMDB
Embarin	HMDB
Glaxo wellcome brand OF allopurinol	HMDB
ICN brand OF allopurinol	HMDB
Merz brand OF allopurinol	HMDB
Multipharma brand OF allopurinol	HMDB
Nicholas brand OF allopurinol	HMDB
Purinol	HMDB
Rhône-poulenc rorer brand OF allopurinol	HMDB
Rosen brand OF allopurinol	HMDB
Suspendol	HMDB
TAD brand OF allopurinol	HMDB
Tipuric	HMDB
Uripurinol	HMDB
Wellcome brand OF allopurinol	HMDB
Xanthomax	HMDB
APS brand OF allopurinol	HMDB
Alloprin	HMDB
Allopurinol ashbourne brand	HMDB
Allopurinol clonmel brand	HMDB
Allopurinol douglas brand	HMDB
Allopurinol hennig brand	HMDB
Allopurinol hexal brand	HMDB
Allopurinol rosen brand	HMDB
Allopurinol gepepharm brand	HMDB
Allpargin	HMDB
Alphapharm brand OF allopurinol	HMDB
Apulonga	HMDB
Apurin	HMDB
BASF brand OF allopurinol	HMDB
Bleminol	HMDB
Boehringer mannheim brand OF allopurinol	HMDB
Byk gulden brand OF allopurinol	HMDB
Capurate	HMDB
Dorsch brand OF allopurinol	HMDB
Douglas brand OF allopurinol	HMDB
Hexal brand OF allopurinol	HMDB
Jenapurinol	HMDB
Merckle brand OF allopurinol	HMDB
Novopurol	HMDB
Pan quimica	HMDB
Pureduct	HMDB
Rhône poulenc rorer brand OF allopurinol	HMDB
Roche brand OF allopurinol	HMDB
Roucol	HMDB
Urosin	HMDB
Gepepharm brand OF allopurinol	HMDB
Allohexal	HMDB
Allopurin	HMDB
Allopurinol aps brand	HMDB
Allopurinol amrad brand	HMDB
Allopurinol azupharma brand	HMDB
Allopurinol bicther brand	HMDB
Allopurinol boots brand	HMDB
Allopurinol dorsch brand	HMDB
Allopurinol icn brand	HMDB
Allopurinol jenapharm brand	HMDB
Allopurinol pinewood brand	HMDB
Allopurinol protea brand	HMDB
Allopurinol rougier brand	HMDB
Allorin	HMDB
Azupharma brand OF allopurinol	HMDB
Bicther brand OF allopurinol	HMDB
Caplenal	HMDB
Cellidrin	HMDB
Henning berlin brand OF allopurinol	HMDB
Lopurin	HMDB
Lysuron	HMDB
Novopharm brand OF allopurinol	HMDB
Pharmafarm brand OF allopurinol	HMDB
Pinewood brand OF allopurinol	HMDB
Progout	HMDB
Protea brand OF allopurinol	HMDB
R.A.N. brand OF allopurinol	HMDB
Reig jofre brand OF allopurinol	HMDB
Uribenz	HMDB
Uridocid	HMDB
Zygout	HMDB
Zyloric	HMDB

Chemical Formula

C₅H₄N₄O

Average Molecular Weight

136.1115

Monoisotopic Molecular Weight

136.03851077

IUPAC Name

1H,2H,4H-pyrazolo[3,4-d]pyrimidin-4-one

Traditional Name

ALLO

CAS Registry Number

315-30-0

SMILES

O=C1N=CN=C2NNC=C12

InChI Identifier

InChI=1S/C5H4N4O/c10-5-3-1-8-9-4(3)6-2-7-5/h1-2H,(H2,6,7,8,9,10)

InChI Key

OFCNXPDARWKPPY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrazolo[3,4-d]pyrimidines. These are aromatic heterocyclic compounds containing a pyrazolo[3,4-d]pyrimidine ring system, which consists of a pyrazole ring fused to but and not sharing a nitrogen atom with a pyrimidine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrazolopyrimidines

Sub Class

Pyrazolo[3,4-d]pyrimidines

Direct Parent

Pyrazolo[3,4-d]pyrimidines

Alternative Parents

Substituents

Pyrazolo[3,4-d]pyrimidine
Pyrimidone
Pyrimidine
Azole
Pyrazole
Vinylogous amide
Heteroaromatic compound
Azacycle
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heterobicyclic compound (CHEBI:40279 )
nucleobase analogue (CHEBI:40279 )
a small molecule (CPD-9024 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 10102915)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0014581)

Process

Not Available

Role

Biological role

Free radical scavenger (HMDB: HMDB0014581)
Antimetabolite (HMDB: HMDB0014581)

Modulator

Inhibitor

EC 1.17.3.2 (xanthine oxidase) inhibitor (HMDB: HMDB0014581)

Industrial application

Gout suppressant (HMDB: HMDB0014581)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	350 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	5.88 g/L	Not Available
LogP	-1	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	5.88 g/L	ALOGPS
logP	-1.7	ALOGPS
logP	-1.8	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	7.83	ChemAxon
pKa (Strongest Basic)	2.57	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	65.85 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	54.24 m³·mol⁻¹	ChemAxon
Polarizability	11.67 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]+	126.125	31661259
DarkChem	[M-H]-	122.372	31661259
DeepCCS	[M-2H]-	159.139	30932474
DeepCCS	[M+Na]+	134.041	30932474
AllCCS	[M+H]+	128.2	32859911
AllCCS	[M+H-H2O]+	123.3	32859911
AllCCS	[M+NH4]+	132.7	32859911
AllCCS	[M+Na]+	134.0	32859911
AllCCS	[M-H]-	121.5	32859911
AllCCS	[M+Na-2H]-	122.7	32859911
AllCCS	[M+HCOO]-	124.1	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.	1.98 minutes	32390414
Predicted by Siyang on May 30, 2022	8.7019 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.35 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	75.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	670.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	333.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	77.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	234.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	66.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	266.9 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	268.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	424.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	592.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	62.2 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	724.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	225.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	225.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	608.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	250.4 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	183.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Allopurinol	O=C1N=CN=C2NNC=C12	2169.2	Standard polar	33892256
Allopurinol	O=C1N=CN=C2NNC=C12	959.6	Standard non polar	33892256
Allopurinol	O=C1N=CN=C2NNC=C12	1941.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Allopurinol,1TMS,isomer #1	C[Si](C)(C)N1[NH]C=C2C1=NC=NC2=O	1546.3	Semi standard non polar	33892256
Allopurinol,1TMS,isomer #1	C[Si](C)(C)N1[NH]C=C2C1=NC=NC2=O	1797.2	Standard non polar	33892256
Allopurinol,1TMS,isomer #1	C[Si](C)(C)N1[NH]C=C2C1=NC=NC2=O	2508.0	Standard polar	33892256
Allopurinol,1TMS,isomer #2	C[Si](C)(C)N1C=C2C(=NC=NC2=O)[NH]1	1690.3	Semi standard non polar	33892256
Allopurinol,1TMS,isomer #2	C[Si](C)(C)N1C=C2C(=NC=NC2=O)[NH]1	1877.1	Standard non polar	33892256
Allopurinol,1TMS,isomer #2	C[Si](C)(C)N1C=C2C(=NC=NC2=O)[NH]1	2483.7	Standard polar	33892256
Allopurinol,2TMS,isomer #1	C[Si](C)(C)N1C=C2C(=NC=NC2=O)N1[Si](C)(C)C	1770.6	Semi standard non polar	33892256
Allopurinol,2TMS,isomer #1	C[Si](C)(C)N1C=C2C(=NC=NC2=O)N1[Si](C)(C)C	1990.4	Standard non polar	33892256
Allopurinol,2TMS,isomer #1	C[Si](C)(C)N1C=C2C(=NC=NC2=O)N1[Si](C)(C)C	2344.1	Standard polar	33892256
Allopurinol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1[NH]C=C2C1=NC=NC2=O	1851.8	Semi standard non polar	33892256
Allopurinol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1[NH]C=C2C1=NC=NC2=O	2008.7	Standard non polar	33892256
Allopurinol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1[NH]C=C2C1=NC=NC2=O	2538.8	Standard polar	33892256
Allopurinol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=C2C(=NC=NC2=O)[NH]1	1964.8	Semi standard non polar	33892256
Allopurinol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=C2C(=NC=NC2=O)[NH]1	2075.1	Standard non polar	33892256
Allopurinol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=C2C(=NC=NC2=O)[NH]1	2557.1	Standard polar	33892256
Allopurinol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=C2C(=NC=NC2=O)N1[Si](C)(C)C(C)(C)C	2171.0	Semi standard non polar	33892256
Allopurinol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=C2C(=NC=NC2=O)N1[Si](C)(C)C(C)(C)C	2397.8	Standard non polar	33892256
Allopurinol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=C2C(=NC=NC2=O)N1[Si](C)(C)C(C)(C)C	2393.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Allopurinol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0550-8900000000-225d53e43d6b82e006bf	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Allopurinol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-000i-7900000000-f5a7601a354a9d25428f	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Allopurinol LC-ESI-QFT , negative-QTOF	splash10-000i-4900000000-5d6d365d7525c7325e01	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Allopurinol LC-ESI-QFT , negative-QTOF	splash10-000i-4900000000-ea448e075f973faea5ec	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Allopurinol LC-ESI-QFT , negative-QTOF	splash10-000l-8900000000-98d308813f954ccc66e0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Allopurinol LC-ESI-QFT , negative-QTOF	splash10-0006-9300000000-a0c962d1b7e8e76fd526	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Allopurinol LC-ESI-QFT , negative-QTOF	splash10-0006-9100000000-d692c85314f5809e4758	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Allopurinol LC-ESI-QFT , negative-QTOF	splash10-01ox-9000000000-2662f35a8efe21c51958	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Allopurinol LC-ESI-QFT , positive-QTOF	splash10-000i-0900000000-4f38b316b66733e5ca8b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Allopurinol LC-ESI-QFT , positive-QTOF	splash10-000i-0900000000-547b3dac7e9b0d01ef66	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Allopurinol LC-ESI-QFT , positive-QTOF	splash10-000i-0900000000-43ea9e7d5a0f94da482f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Allopurinol LC-ESI-QFT , positive-QTOF	splash10-000i-1900000000-fee6f9103fdd4cb1b6ed	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Allopurinol LC-ESI-QFT , positive-QTOF	splash10-01p9-1900000000-eb9ece2b9b724a6af483	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Allopurinol LC-ESI-QFT , positive-QTOF	splash10-03dr-2900000000-85aef327ef1281780d05	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Allopurinol 90V, Negative-QTOF	splash10-01ox-9000000000-06c0452042d1533a15b9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Allopurinol 75V, Negative-QTOF	splash10-0006-9100000000-11cfb21dda6f6d415de0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Allopurinol 45V, Negative-QTOF	splash10-000l-8900000000-fe81b51b6b51c24c773c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Allopurinol 60V, Negative-QTOF	splash10-0006-9300000000-fa9960ae057885ac4068	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Allopurinol 75V, Positive-QTOF	splash10-01p9-1900000000-5d1b0178a6ae7719b325	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Allopurinol 60V, Positive-QTOF	splash10-000i-0900000000-9a825177a0acbf892733	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Allopurinol 90V, Positive-QTOF	splash10-03dr-2900000000-906c0f13426783f2ef86	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allopurinol 10V, Positive-QTOF	splash10-000i-0900000000-1eb7584dbb0630e49004	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allopurinol 20V, Positive-QTOF	splash10-000i-1900000000-4e5cd23deb565d2f87e0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allopurinol 40V, Positive-QTOF	splash10-07wc-9200000000-214c548ad4d15f5bfbf4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allopurinol 10V, Negative-QTOF	splash10-000i-0900000000-b7681f9e17751c711d37	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allopurinol 20V, Negative-QTOF	splash10-000i-2900000000-a7c487c6207a07bf2903	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allopurinol 40V, Negative-QTOF	splash10-0006-9100000000-af7211d0cc75dda0b005	2016-08-03	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

Cytoplasm
Membrane

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 DB00437	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00437	21059682	details
Urine	Detected and Quantified	18-23 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	31506554	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	630 umol/mmol creatinine	Adult (>18 years old)	Both	Molybdenum cofactor deficiency	10102915	details

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

Molybdenum cofactor deficiency
Wevers RA, Engelke UF, Moolenaar SH, Brautigam C, de Jong JG, Duran R, de Abreu RA, van Gennip AH: 1H-NMR spectroscopy of body fluids: inborn errors of purine and pyrimidine metabolism. Clin Chem. 1999 Apr;45(4):539-48. [PubMed:10102915 ]

Associated OMIM IDs

None

External Links

DrugBank ID

DB00437

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2010

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Allopurinol

METLIN ID

Not Available

PubChem Compound

2094

PDB ID

Not Available

ChEBI ID

40279

Food Biomarker Ontology

Not Available

VMH ID

ALLOP

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Suzuki I, Yamauchi T, Onuma M, Nozaki S: Allopurinol, an inhibitor of uric acid synthesis--can it be used for the treatment of metabolic syndrome and related disorders? Drugs Today (Barc). 2009 May;45(5):363-78. doi: 10.1358/dot.2009.45.5.1370460. [PubMed:19584965 ]
George J, Struthers AD: Role of urate, xanthine oxidase and the effects of allopurinol in vascular oxidative stress. Vasc Health Risk Manag. 2009;5(1):265-72. Epub 2009 Apr 8. [PubMed:19436671 ]
Terkeltaub R: Update on gout: new therapeutic strategies and options. Nat Rev Rheumatol. 2010 Jan;6(1):30-8. doi: 10.1038/nrrheum.2009.236. [PubMed:20046204 ]
Pacher P, Nivorozhkin A, Szabo C: Therapeutic effects of xanthine oxidase inhibitors: renaissance half a century after the discovery of allopurinol. Pharmacol Rev. 2006 Mar;58(1):87-114. [PubMed:16507884 ]
Schlesinger N: Diagnosing and treating gout: a review to aid primary care physicians. Postgrad Med. 2010 Mar;122(2):157-61. doi: 10.3810/pgm.2010.03.2133. [PubMed:20203467 ]

Enzymes

Enzyme Details

1. Aldehyde oxidase

General function:: Involved in oxidoreductase activity
Specific function:: Not Available
Gene Name:: AOX1
Uniprot ID:: Q06278
Molecular weight:: 147916.735

References

Moriwaki Y, Yamamoto T, Nasako Y, Takahashi S, Suda M, Hiroishi K, Hada T, Higashino K: In vitro oxidation of pyrazinamide and allopurinol by rat liver aldehyde oxidase. Biochem Pharmacol. 1993 Sep 14;46(6):975-81. [PubMed:8216357 ]

Enzyme Details

2. 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

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Suzuki I, Yamauchi T, Onuma M, Nozaki S: Allopurinol, an inhibitor of uric acid synthesis--can it be used for the treatment of metabolic syndrome and related disorders? Drugs Today (Barc). 2009 May;45(5):363-78. doi: 10.1358/dot.2009.45.5.1370460. [PubMed:19584965 ]
Carro MD, Falkenstein E, Radke WJ, Klandorf H: Effects of allopurinol on uric acid concentrations, xanthine oxidoreductase activity and oxidative stress in broiler chickens. Comp Biochem Physiol C Toxicol Pharmacol. 2010 Jan;151(1):12-7. doi: 10.1016/j.cbpc.2009.07.010. Epub 2009 Aug 3. [PubMed:19654053 ]
George J, Struthers AD: Role of urate, xanthine oxidase and the effects of allopurinol in vascular oxidative stress. Vasc Health Risk Manag. 2009;5(1):265-72. Epub 2009 Apr 8. [PubMed:19436671 ]
Higgins P, Dawson J, Walters M: The potential for xanthine oxidase inhibition in the prevention and treatment of cardiovascular and cerebrovascular disease. Cardiovasc Psychiatry Neurol. 2009;2009:282059. doi: 10.1155/2009/282059. Epub 2009 Nov 4. [PubMed:20029618 ]
Dincer HE, Dincer AP, Levinson DJ: Asymptomatic hyperuricemia: to treat or not to treat. Cleve Clin J Med. 2002 Aug;69(8):594, 597, 600-2 passim. [PubMed:12184468 ]
Kelley WN, Wyngaarden JB: Effects of allopurinol and oxipurinol on purine synthesis in cultured human cells. J Clin Invest. 1970 Mar;49(3):602-9. [PubMed:5415686 ]
Okamoto K: [Inhibitors of xanthine oxidoreductase]. Nihon Rinsho. 2008 Apr;66(4):748-53. [PubMed:18409526 ]
Taha MO, Simoes MJ, Noguerol EC, Mendonca FP, Pascoalick HM, Alves RA, Vivian ME, Morales FP, Campos AC, Magalhaes KG, Venerando PS, Tersariol IL, Monteiro HP, Oliveira-Junior IS, Jurkiewicz A, Caricati-Neto A: Effects of allopurinol on ischemia and reperfusion in rabbit livers. Transplant Proc. 2009 Apr;41(3):820-3. doi: 10.1016/j.transproceed.2009.02.051. [PubMed:19376361 ]
Terkeltaub R: Update on gout: new therapeutic strategies and options. Nat Rev Rheumatol. 2010 Jan;6(1):30-8. doi: 10.1038/nrrheum.2009.236. [PubMed:20046204 ]
Pacher P, Nivorozhkin A, Szabo C: Therapeutic effects of xanthine oxidase inhibitors: renaissance half a century after the discovery of allopurinol. Pharmacol Rev. 2006 Mar;58(1):87-114. [PubMed:16507884 ]
Moriwaki Y, Yamamoto T, Nasako Y, Takahashi S, Suda M, Hiroishi K, Hada T, Higashino K: In vitro oxidation of pyrazinamide and allopurinol by rat liver aldehyde oxidase. Biochem Pharmacol. 1993 Sep 14;46(6):975-81. [PubMed:8216357 ]

Transporters

Enzyme Details

1. Solute carrier family 22 member 7

General function:: Involved in transmembrane transport
Specific function:: Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulfate, allopurinol, 5-fluorouracil, paclitaxel, L-ascorbic acid, salicylate, ethotrexate, and alpha- ketoglutarate
Gene Name:: SLC22A7
Uniprot ID:: Q9Y694
Molecular weight:: 60025.0

References

Kobayashi Y, Ohshiro N, Shibusawa A, Sasaki T, Tokuyama S, Sekine T, Endou H, Yamamoto T: Isolation, characterization and differential gene expression of multispecific organic anion transporter 2 in mice. Mol Pharmacol. 2002 Jul;62(1):7-14. [PubMed:12065749 ]

Showing metabocard for Allopurinol (HMDB0014581)

MOL for HMDB0014581 (Allopurinol)

3D MOL for HMDB0014581 (Allopurinol)

3D SDF for HMDB0014581 (Allopurinol)

3D-SDF for HMDB0014581 (Allopurinol)

PDB for HMDB0014581 (Allopurinol)

3D PDB for HMDB0014581 (Allopurinol)

SMILES for HMDB0014581 (Allopurinol)

INCHI for HMDB0014581 (Allopurinol)

Structure for HMDB0014581 (Allopurinol)

3D Structure for HMDB0014581 (Allopurinol)

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

References

References

Transporters

References