Compound: uracil
SMILES: O=c1[nH]c(=O)cc[nH]1
InChIKey: ISAKRJDGNUQOIC-UHFFFAOYSA-N
Synonyms: uracil, 66-22-8, pyrimidine-2,4(1H,3H)-dione, 2,4(1H,3H)-Pyrimidinedione, Pyrod, Hybar X, 2,4-Dioxopyrimidine, Pirod, 2,4-Pyrimidinedione, 1H-Pyrimidine-2,4-dione, 1,2,3,4-tetrahydropyrimidine-2,4-dione, NSC-3970, DTXSID4021424, SQ-6201, SQ-7726, SQ-8493, CHEBI:17568, BMS-205603-01, 56HH86ZVCT, NSC3970, DTXCID101424, 2, 4-Dioxopyrimidine, RefChem:6338, 2-hydroxy-4-(1H)-pyrimidione, 2-hydroxy-4-(3H)-pyrimidione, 4-hydroxy-2-(1H)-pyrimidione, 200-621-9, 2,4-Dihydroxypyrimidine, pyrimidine-2,4-diol, 2,4-Pyrimidinediol, 51953-14-1, Uracil [USAN], RU 12709, MFCD00006016, 2-Hydroxy-4(3H)-pyrimidinone, NSC 3970, Ura, 2,4-Pyrimidinediol (9CI), CCRIS 3077, 2-Hydroxy-4(1H)-pyrimidinone, SQ 6201, SQ 7726, SQ 8493, BMS 205603-01, AI3-25470, Lamivudine impurity e, 4-Hydroxy-2(1H)-pyrimidinone, 66255-05-8, Lamivudine impurity e rs, 144104-68-7, Fluorouracil specified compound c, NCGC00181030-01, 4-Hydroxyuracil, CAS-66-22-8, Pyrimidine-2,4(1H,3H)-dione (Uracil), Uracil (8CI), Uracil [USAN:JAN], 2(1H)-Pyrimidinone, 4-hydroxy-, 2(1H)-Pyrimidinone, 6-hydroxy-, 4(3H)-Pyrimidinone, 2-hydroxy-, EINECS 200-621-9, UNII-56HH86ZVCT, Uracyl, Urazil, 66224-60-0, 2,4(1H,3H)-PYRIMIDINEDIONE-2-13C-1,3-15N2(9CI), 8h-uracil, hydroxypyrimidinone, Uracil (Standard), 2,6-Dioxypyrimidin, 2,4-Dioxypyrimidine, 2,4(1H,3H)-Pyrimidinedione (9CI), pyrimidine-2,4-dione, Uracil, 99%, 1ui0, Uracil (JAN/USAN), 2,3H)-Pyrimidinedione, 2,6-Dihydroxypyrimidine, URACIL [JAN], URACIL [USP-RS], URACIL [WHO-DD], Lamivudine EP Impurity F, URACIL [MI], URACIL [MART.], bmse000187, bmse000940, CHEMBL566, Epitope ID:120356, NCIMech_000782, SCHEMBL8235, Fluorouracil impurity C CRS, Uracil, >=99.0%, pyrimidine, 2,4-dihydroxy-, SCHEMBL29730, SCHEMBL80962, SCHEMBL94310, 51953-19-6, MLS001304993, SCHEMBL144010, SCHEMBL151239, SCHEMBL537174, SCHEMBL877869, SCHEMBL925137, GTPL4560, orb1310972, SCHEMBL1050479, SCHEMBL5089507, SCHEMBL6286831, SCHEMBL6434097, SCHEMBL6434098, SCHEMBL7267501, SCHEMBL7335265, SCHEMBL9734266, SCHEMBL9779787, 2,4-(1h,3h)-pyrimidinedione, SCHEMBL10580164, SCHEMBL11607890, SCHEMBL13276278, SCHEMBL29525634, SCHEMBL31434533, HY-I0960R, Uracil, >=99.0% (T), 1,3-dihydropyrimidine-2,4-dione, HMS2234E19, HMS3264C13, HMS3373E18, HMS3652N05, HMS5082D06, Pharmakon1600-01502345, 4(1H)-Pyrimidinone, 2-hydroxy-, HY-I0960, NSC29742, ZAA89752, Tox21_112680, Tox21_201023, BDBM50549809, CCG-35866, EBC-13197, MSK000882, NSC-29742, NSC759649, s4177, SBB058492, STK301734, STL124066, AKOS000119989, AKOS002303991, Tox21_112680_1, 4(3H)-Pyrimidinone,2-hydroxy-(9ci), CCG-213042, CS-W020104, DB03419, FU01843, NSC-759649, PS-5279, SB55489, SB55884, NCGC00181030-02, NCGC00247663-01, NCGC00258576-01, Uracil, Vetec(TM) reagent grade, 98%, NCI60_003718, SMR000752912, SY008943, DB-030518, DB-103964, DB-268940, DB-268966, DB-272084, DB-272202, LAMIVUDINE IMPURITY F [EP IMPURITY], FLUOROURACIL IMPURITY C [EP IMPURITY], LAMIVUDINE IMPURITY E [USP IMPURITY], NS00002070, ST45061548, SW220239-1, U0013, EN300-17138, Uracil, suitable for cell culture, BioReagent, C00106, D00027, SBI-0053640.0002, AB00171810_03, AB00171810_04, AB00918623-05, AC-907/30002021, F036407, Q182990, BRD-K80129304-001-08-1, BRD-K80129304-001-09-9, Z56889474, F1796-0008, FLUOROURACIL SPECIFIED COMPOUND C [USP IMPURITY], E2FC11E5-1887-46DF-B415-82313CE9B2BD, Uracil, United States Pharmacopeia (USP) Reference Standard, Uracil; Lamivudine EP Impurity F; Fluorouracil EP Impurity C, 2,4(1H,3H)-Pyrimidinedione; 2,4-Dihydroxypyrimidine; 2,4-Pyrimidinediol, Fluorouracil impurity C, European Pharmacopoeia (EP) Reference Standard, InChI=1/C4H4N2O2/c7-3-1-2-5-4(8)6-3/h1-2H,(H2,5,6,7,8, Uracil, Pharmaceutical Secondary Standard; Certified Reference Material
Theoretical properties:
molecular_formula: C4H4N2O2
molecular_weight: 112.09 g/mol
exact_mass: 112.027277375 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 0
heavy_atom_count: 8
topological_polar_surface_area: 58.2 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Uracil is a common and naturally occurring pyrimidine nucleobase in which the pyrimidine ring is substituted with two oxo groups at positions 2 and 4. Found in RNA, it base pairs with adenine and replaces thymine during DNA transcription. It has a role as a prodrug, an allergen, a mouse metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite, a human metabolite and a Daphnia magna metabolite. It is a pyrimidine nucleobase and a pyrimidone. It is a tautomer of a (4S)-4-hydroxy-3,4-dihydropyrimidin-2(1H)-one.
chebi: A common and naturally occurring pyrimidine nucleobase in which the pyrimidine ring is substituted with two oxo groups at positions 2 and 4. Found in RNA, it base pairs with adenine and replaces thymine during DNA transcription.
chembl: URACIL is a small molecule listed in the ChEMBL database and has reached clinical trial phase 3.0.
wikipedia: Uracil () (symbol U or Ura) is one of the four nucleotide bases in the nucleic acid RNA. The others are adenine (A), cytosine (C), and guanine (G). In RNA, uracil binds to adenine via two hydrogen bonds. In DNA, the uracil nucleobase is replaced by thymine (T). Uracil is a demethylated form of thymine.
Uracil is a common and naturally occurring pyrimidine derivative. The name "uracil" was coined in 1885 by the German chemist Robert Behrend, who was attempting to synthesize derivatives of uric acid. Originally discovered in 1900 by Alberto Ascoli, it was isolated by hydrolysis of yeast nuclein; it was also found in bovine thymus and spleen, herring sperm, and wheat germ. It is a planar, unsaturated compound that has the ability to absorb light.
Uracil that was formed extraterrestrially has been detected in the Murchison meteorite, in near-Earth asteroid Ryugu, and possibly on the surface of the moon Titan. It has been synthesized under cold laboratory conditions similar to outer space, from pyrimidine embedded in water ice and exposed to ultraviolet light.