Compound: xanthine
SMILES: Oc1nc(O)c2[nH]cnc2n1
InChIKey: LRFVTYWOQMYALW-UHFFFAOYSA-N
Synonyms: xanthine, 69-89-6, 2,6-Dihydroxypurine, 2,6-dioxopurine, Xanthin, Xanthic oxide, 1H-Purine-2,6-diol, 9H-Purine-2,6-diol, Isoxanthine, Pseudoxanthine, 3,7-Dihydro-1H-purine-2,6-dione, Purine-2,6-diol, 1H-Purine-2,6-dione, 3,7-dihydro-, 3,7-dihydropurine-2,6-dione, 2,6(1,3)-Purinedion, 3,9-dihydro-1H-purine-2,6-dione, 2,6-Dioxo-1,2,3,6-tetrahydropurine, 1H-Purine-2,6-dione, 3,9-dihydro-, 9H-Purine-2,6-(1H,3H)-dione, Purine-2,6(1H,3H)-dione, 9H-Purine-2,6(1H,3H)-dione, 1AVZ07U9S7, DTXSID4035120, NSC-14664, 2,3,6,7-tetrahydro-1H-purine-2,6-dione, RefChem:902259, DTXCID2015120, CHEBI:15318, 200-718-6, 1H-Purine-2,6(3H,7H)-dione, USAF CB-17, XAN, 9H-xanthine, Purine-2(3H),6(1H)-dione, Purine-2,6-(1H,3H)-dione, MFCD00078453, NSC 14664, EPA Pesticide Chemical Code 116900, AI3-52268, CHEMBL1424, 3,9-dihydropurine-2,6-dione, 2,3,6,9-tetrahydro-1H-purine-2,6-dione, CHEBI:17712, purine, 2,6-dihydroxy-, 1,3-dihydropurine-2,6-dione, Xanthine (VAN), CCRIS 994, 7H-purine-2,6-diol, EINECS 200-718-6, UNII-1AVZ07U9S7, Dioxopurine, Dioxypurin, 7H-xanthine, 2-Oxohypoxanthine, 2,6-dioxypurine, 2,6-Dihydroxypurin, Xanthine (Standard), Xanthine, 98%, Purine-2,3H)-dione, Xanthine, >=99%, 2uz9, XANTHINE [MI], bmse000127, MolMap_000070, XANTHINE [WHO-DD], Xanthine, p.a., 99%, 9H-Purine-2,3H)-dione, Cambridge id 5126190, SCHEMBL4965, SCHEMBL4966, Xanthine (VAN) (8CI), 2,2,3,6-tetrahydropurine, Oprea1_474175, 1H,3H,7H-XANTHINE, 1H,3H,9H-XANTHINE, SCHEMBL170835, SCHEMBL662729, SCHEMBL662730, SCHEMBL918381, Xanthine, BioUltra, >=99%, GTPL4557, orb1310405, orb3141453, SCHEMBL1246788, SCHEMBL2733971, SCHEMBL6501028, SCHEMBL7011289, SCHEMBL29180270, 3,7-dihydro-purine-2,6-dione, 3,9-Dihydro-purine-2,6-dione, BDBM82009, CHEBI:48517, LRFVTYWOQMYALW-UHFFFAOYSA-, MSK6930, 2,6-Dihydroxypurine; Isoxanthine, HMS1659G11, HMS3604G12, HMS5081J20, SMSSF-0052556, ALBB-038637, CAS_1188, HY-W017389R, NSC_1188, NSC14664, 1H-purine-2,6(3H, 7H)-dione, BBL028159, BDBM50227193, EBC-06199, SBB004054, STL064827, STL453051, AKOS000498219, AKOS005208756, AKOS015896921, AC-8422, CCG-266216, CS-W018105, DB02134, EBC-152276, FS-3231, FX01318, HY-W017389, SDCCGMLS-0065805.P001, 2,6-Dioxo-1,2,3, 6-tetrahydropurine, NCGC00164338-01, 3,9-dihydro-2H-purine-2,6(1H)-dione, SY030113, 2,6-Dihydroxypurine; 7H-purine-2,6-diol, DB-015929, NS00001219, S3693, ST45045352, X0004, EN300-18289, C00385, D71218, Q50980, AB00171825-02, AG-670/31548007, F079518, Z57825360, 92AB342E-6550-4B2B-AD76-E75AC1C2EB45, F3034-0083, Xanthine, >=99.5% (HPLC), purified by recrystallization, InChI=1/C5H4N4O2/c10-4-2-3(7-1-6-2)8-5(11)9-4/h1H,(H3,6,7,8,9,10,11)
Theoretical properties:
molecular_formula: C5H4N4O2
molecular_weight: 152.11 g/mol
exact_mass: 152.03342538 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 3
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 0
heavy_atom_count: 11
topological_polar_surface_area: 86.9 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: > 300 °C
Descriptions:
pubchem: 9H-xanthine is an oxopurine in which the purine ring is substituted by oxo groups at positions 2 and 6 and N-9 is protonated. It has a role as a Saccharomyces cerevisiae metabolite. It is a tautomer of a 7H-xanthine.
chebi: An oxopurine in which the purine ring is substituted by oxo groups at positions 2 and 6 and N-9 is protonated.
chembl: XANTHINE is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Xanthine ( or , from Ancient Greek ξανθός xanthós 'yellow' for its yellowish-white appearance; archaically xanthic acid; systematic name 3,7-dihydropurine-2,6-dione) is a purine base found in most human body tissues and fluids, as well as in other organisms. Several stimulants are derived from xanthine, including caffeine, theophylline, and theobromine.
Xanthine is a product on the pathway of purine degradation.

It is created from guanine by guanine deaminase.
It is created from hypoxanthine by xanthine oxidoreductase.
It is also created from xanthosine by purine nucleoside phosphorylase.
Xanthine is subsequently converted to uric acid by the action of the xanthine oxidase enzyme.