Showing Compound Allopurinol riboside (FDB022067)

Record Information

Version

1.0

Creation date

2011-09-21 00:07:54 UTC

Update date

2015-07-21 06:56:57 UTC

Primary ID

FDB022067

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Allopurinol riboside

Description

Allopurinol is an analog of the natural purines in the body, and is quickly metabolized to oxypurines which is also a xanthine oxidase inhibitor. Allopurinol is a white, powdery drug used to treat gout. Its use in the United States was started in 1964. It is an isomer of hypoxanthine and inhibits the production of uric acid, the metabolite responsible for gout, by inhibiting the enzyme xanthine oxidase. The side effects of high levels of precursors are usually minor. A small percentage of people develop a rash and must discontinue this drug. The most serious adverse event is a hypersensitivity syndrome consisting of fever, skin rash, eosinophilia, hepatitis, and worsening renal function. In some cases, allopurinol hypersensitivity syndrome. [HMDB]

CAS Number

16220-07-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Showing 1 to 5 of 5 entries

Predicted Properties

Property	Value	Source
Water Solubility	14.8 g/L	ALOGPS
logP	-1.7	ALOGPS
logP	-2	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	7.36	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	129.2 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	72.32 m³·mol⁻¹	ChemAxon
Polarizability	24.35 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C10H12N4O5

IUPAC name

1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H,4H,7H-pyrazolo[3,4-d]pyrimidin-4-one

InChI Identifier

InChI=1S/C10H12N4O5/c15-2-5-6(16)7(17)10(19-5)14-8-4(1-13-14)9(18)12-3-11-8/h1,3,5-7,10,15-17H,2H2,(H,11,12,18)/t5-,6-,7-,10-/m1/s1

InChI Key

KFQUAMTWOJHPEJ-DAGMQNCNSA-N

Isomeric SMILES

OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1N=CC2=C1NC=NC2=O

Average Molecular Weight

268.2261

Monoisotopic Molecular Weight

268.080769514

Classification

Description

Belongs to the class of organic compounds known as pyrazolo[3,4-d]pyrimidine glycosides. These are nucleosides or derivatives thereof that consist of a pyazolo[3,2-d]pyrimidine ring system that is N-glycosidically linked to a ribose or deoxyribose. They bear the sugar moiety on the pyrimidine part of the molecule.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrazolo[3,4-d]pyrimidine glycosides

Sub Class

Not Available

Direct Parent

Pyrazolo[3,4-d]pyrimidine glycosides

Alternative Parents

Substituents

Pyrazolo[3,4-d]pyrimidine glycoside
Glycosyl compound
N-glycosyl compound
Pentose monosaccharide
Pyrazolo[3,4-d]pyrimidine
Pyrazolopyrimidine
Pyrimidone
Monosaccharide
Pyrimidine
Azole
Heteroaromatic compound
Pyrazole
Vinylogous amide
Tetrahydrofuran
Secondary alcohol
Organoheterocyclic compound
Azacycle
Oxacycle
Primary alcohol
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

nucleoside analogue (CHEBI:74074 )

Ontology

Disposition

Source:

Endogenous

Biological location:

Subcellular:

Cytoplasm

Biofluid and excreta:

Blood

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Allopurinol riboside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0adl-9230000000-f2b42573dba0039df9fc	Spectrum
Predicted GC-MS	Allopurinol riboside, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0gir-5955300000-84fcb654b6b0639a529b	Spectrum
Predicted GC-MS	Allopurinol riboside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Allopurinol riboside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Allopurinol riboside, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Allopurinol riboside, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Allopurinol riboside, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Allopurinol riboside, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Allopurinol riboside, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Allopurinol riboside, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Allopurinol riboside, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Allopurinol riboside, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Allopurinol riboside, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Allopurinol riboside, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Allopurinol riboside, TMS_3_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Allopurinol riboside, TMS_3_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Allopurinol riboside, TMS_3_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Allopurinol riboside, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Allopurinol riboside, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Allopurinol riboside, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Allopurinol riboside, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Allopurinol riboside, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Allopurinol riboside, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Allopurinol riboside, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Allopurinol riboside, TBDMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0920000000-a9fa0dd7e6fa50ea6984	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-21c7b658689fb9512f0b	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052r-1900000000-a0d5d35743edd0e2288b	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-ab1c150a018c7c95cfcf	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-c23b7002c1cf46d80397	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4r-4900000000-94845c316294342528a8	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014j-0290000000-1fe2c9a9f3ca1ec73a39	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-dc2d53701ff620e1a6e4	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-4900000000-32ca35fb23ae98d9baef	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0910000000-8f996cedd72f2106a9ba	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-2fcf648123cc944c1522	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-2900000000-36c56b92eacd3d7ca10d	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

18512601

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

283570

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00481

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

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Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound Allopurinol riboside (FDB022067)

Structure for FDB022067 (Allopurinol riboside)