Compound: Orotic acid
SMILES: O=c1[nH]c(C(=O)O)cc([nH]1)=O
InChIKey: PXQPEWDEAKTCGB-UHFFFAOYSA-N
Synonyms: Orotic acid, 65-86-1, 6-Carboxyuracil, Oropur, Orodin, Orotonin, Orotyl, Vitamin B13, Whey factor, Orotonsan, Animal galactose factor, Uracil-6-carboxylic acid, 6-Uracilcarboxylic acid, Molkensaeure, Orotsaeure, Uracil-6-carbosaeure, Acide orotique, Acido orotico, 4-Pyrimidinecarboxylic acid, 1,2,3,6-tetrahydro-2,6-dioxo-, 2,6-Dihydroxy-4-pyrimidinecarboxylic acid, 1,2,3,6-tetrahydro-2,6-dioxo-4-Pyrimidinecarboxylic acid, Acidum oroticum, 2,4-dioxo-1H-pyrimidine-6-carboxylic acid, Acidum oroticum [Latin], AI3-25478, Orotsaure, 1,2,3,6-Tetrahydro-2,6-dioxopyrimidin-4-carbonsaeure, 1,2,3,6-Tetrahydro-2,6-dioxo-4-pyrimidecarboxylic acid, NSC-9791, DTXSID0025814, 61H4T033E5, DTXCID005814, CHEBI:16742, Acidum oroticum (Latin), Orotate, Sodium, Orotate, Zinc, Acid, Orotic, Orotate, Potassium, RefChem:168574, 200-619-8, 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid, 2,6-Dihydroxypyrimidine-4-carboxylic acid, Orotsaeure [German], Acide orotique [French], Acido orotico [Spanish], NSC 9791, Acide orotique [INN-French], Acido orotico [INN-Spanish], Acidum oroticum [INN-Latin], CCRIS 3929, Orotic acid (6-Carboxyuracil), HSDB 6377, 6-Carboxy-2,4-dihydroxypyrimidine, MFCD00006027, Orotic acid anhydrous, NSC9791, Orotic Acid-15N2, 2,6-dihydroxy-pyrimidine-4-carboxylic acid, 2,6-Dioxo-1,2,3,6-tetrahydro-4-pyrimidinecarboxylic acid, Orotic acid, anhydrous, Orotic acid (JAN), NCGC00091357-01, 1,2,3,4-Tetrahydro-2,6-dioxopyrimidine-4-carboxylic acid, Oroticacid, OROTIC ACID [JAN], 15184-25-5, Orotic acid [INN:JAN], CAS-65-86-1, Orotic acid (VAN), NSC627082, 2,6-dioxo-1,3-dihydropyrimidine-4-carboxylic acid, EINECS 200-619-8, orotic-acid, Orotic acid [INN:BAN:JAN], UNII-61H4T033E5, OG6, uracil-6-carboxylate, Orotic acid (8CI), 2,6-Dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carboxylic acid, OROTIC-ACID-, Orotic acid (Standard), OROTIC ACID [MI], bmse000283, OROTIC ACID [INN], OROTIC ACID [HSDB], SCHEMBL20865, OROTIC ACID [MART.], MLS006011823, Orotic acid (VAN) (8CI), OROTIC ACID [WHO-DD], SCHEMBL185887, GTPL4690, orb1310330, CHEMBL1235017, SCHEMBL11013946, HY-N0157R, MSK1530, HMS3264K19, HMS3651I20, HMS5080J12, Pharmakon1600-01504525, HY-N0157, Tox21_111121, Tox21_201104, BBL013050, EBC-03221, NSC758903, s2336, SBB004017, STK301771, STK629991, AKOS000119689, AKOS004115502, Tox21_111121_1, CCG-213952, DB02262, FO33319, NSC-758903, SB55525, NCGC00091357-02, NCGC00188943-01, NCGC00188943-03, NCGC00188943-04, NCGC00258656-01, SMR001550463, ST094210, SY006030, TS-00078, 2,6-dihydroxy-pyrimidin-4-carboxylic acid, 2,6-dihydroxypyrimidine-4-carboxyli cacid, SBI-0207042.P001, DB-073669, 4-Pyrimidinecarboxylic acid, 2,6-dihydroxy-, NS00003862, O0065, Orotic acid, >=98% (titration), anhydrous, SW219707-1, EN300-16897, C00295, D00055, D70614, AB00373897_03, AB-323/25048164, F787585, Q425536, SR-01000872754, SR-01000872754-1, BRD-K32572029-001-04-4, BRD-K32572029-001-05-1, F2191-0093, 37C71C07-0D69-452C-8C54-7D01BE02C146, 4-Pyrimidinecarboxylic acid, 1,2,3,6-tetrahydro-2,6-dioxo- (9CI), InChI=1/C5H4N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h1H,(H,9,10)(H2,6,7,8,11
Theoretical properties:
molecular_formula: C5H4N2O4
molecular_weight: 156.10 g/mol
exact_mass: 156.01710661 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 3
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 1
heavy_atom_count: 11
topological_polar_surface_area: 95.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Crystals
color: Crystals
melting_point: 653 to 655 °F (NTP, 1992)
solubility: less than 1 mg/mL at 68 °F (NTP, 1992)
Descriptions:
pubchem: Orotic acid is a pyrimidinemonocarboxylic acid that is uracil bearing a carboxy substituent at position C-6. It has a role as a metabolite, a mouse metabolite and an Escherichia coli metabolite. It is functionally related to a uracil. It is a conjugate acid of an orotate.
chebi: A pyrimidinemonocarboxylic acid that is uracil bearing a carboxy substituent at position C-6.
chembl: OROTIC ACID is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.
wikipedia: Orotic acid () is a pyrimidinedione and a carboxylic acid.  Historically, it was believed to be part of the vitamin B complex and was called vitamin B13, but it is now known that it is not a vitamin.
The compound is synthesized in the body via a mitochondrial enzyme, dihydroorotate dehydrogenase or a cytoplasmic enzyme of pyrimidine synthesis pathway. It is sometimes used as a mineral carrier in some dietary supplements (to increase their bioavailability), most commonly for lithium orotate.