Orotic acid

Details

• Internal ID: 192af211-c815-43f6-b9dc-1f4e94a06e2e
• Taxonomy: Organoheterocyclic compounds > Diazines > Pyrimidines and pyrimidine derivatives > Pyrimidinecarboxylic acids and derivatives > Pyrimidinecarboxylic acids
• IUPAC Name: 2,4-dioxo-1H-pyrimidine-6-carboxylic acid
• SMILES (Canonical): C1=C(NC(=O)NC1=O)C(=O)O
• SMILES (Isomeric): C1=C(NC(=O)NC1=O)C(=O)O
• InChI: InChI=1S/C5H4N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h1H,(H,9,10)(H2,6,7,8,11)
• InChI Key: PXQPEWDEAKTCGB-UHFFFAOYSA-N
• Popularity: 5,559 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅H₄N₂O₄
• Molecular Weight: 156.10 g/mol
• Exact Mass: 156.01710661 g/mol
• Topological Polar Surface Area (TPSA): 95.50 Ų
• XlogP: -1.40
• Atomic LogP (AlogP): -1.24
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

• 65-86-1
• 6-Carboxyuracil
• Oropur
• Orodin
• Orotonin
• Orotyl
• Orotonsan
• Vitamin B13
• Whey factor
• Oroturic
• 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid
• Uracil-6-carboxylic acid
• Animal galactose factor
• 6-Uracilcarboxylic acid
• Molkensaeure
• Orotsaeure
• orotate
• 2,6-Dihydroxypyrimidine-4-carboxylic acid
• Uracil-6-carbosaeure
• 4-Pyrimidinecarboxylic acid, 1,2,3,6-tetrahydro-2,6-dioxo-
• 2,6-Dihydroxy-4-pyrimidinecarboxylic acid
• Orotsaeure [German]
• Acidum oroticum
• Acide orotique
• Acido orotico
• Acide orotique [French]
• Acido orotico [Spanish]
• Acidum oroticum [Latin]
• NSC 9791
• Acide orotique [INN-French]
• Acido orotico [INN-Spanish]
• Acidum oroticum [INN-Latin]
• CCRIS 3929
• Orotic acid (6-Carboxyuracil)
• HSDB 6377
• AI3-25478
• 2,4-dioxo-1H-pyrimidine-6-carboxylic acid
• 1,2,3,6-Tetrahydro-2,6-dioxopyrimidin-4-carbonsaeure
• 1,2,3,6-Tetrahydro-2,6-dioxo-4-pyrimidecarboxylic acid
• Orotic Acid-15N2
• 6-Carboxy-2,4-dihydroxypyrimidine
• NSC9791
• NSC-9791
• 2,6-Dioxo-1,2,3,6-tetrahydro-4-pyrimidinecarboxylic acid
• MFCD00006027
• 61791-00-2
• 2,6-dihydroxy-pyrimidine-4-carboxylic acid
• 1,2,3,6-tetrahydro-2,6-dioxo-4-Pyrimidinecarboxylic acid
• DTXSID0025814
• CHEBI:16742
• Orotic acid, anhydrous
• Orotic acid (JAN)
• 61H4T033E5
• NCGC00091357-01
• 1,2,3,4-Tetrahydro-2,6-dioxopyrimidine-4-carboxylic acid
• OROTIC ACID [JAN]
• 15184-25-5
• DTXCID005814
• Oroticacid
• Orotic acid [INN:JAN]
• CAS-65-86-1
• Orotic acid (VAN)
• NSC627082
• EINECS 200-619-8
• Orotsaure
• orotic-acid
• Orotic acid [INN:BAN:JAN]
• UNII-61H4T033E5
• uracil-6-carboxylate
• Orotic acid anhydrous
• Orotic acid (8CI)
• 2,6-Dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carboxylic acid
• OROTIC-ACID-
• OROTIC ACID [MI]
• bmse000283
• OROTIC ACID [INN]
• OROTIC ACID [HSDB]
• OROTIC ACID [INCI]
• SCHEMBL20865
• OROTIC ACID [MART.]
• MLS006011823
• Orotic acid(6-Carboxyuracil)
• Orotic acid (VAN) (8CI)
• OROTIC ACID [WHO-DD]
• GTPL4690
• CHEMBL1235017
• AMY4076
• HMS3264K19
• HMS3651I20
• Pharmakon1600-01504525
• BCP09063
• HY-N0157
• Tox21_111121
• Tox21_201104
• NSC758903
• s2336
• AKOS000119689
• AKOS004115502
• Tox21_111121_1
• CCG-213952
• DB02262
• NSC-758903
• SB55525
• NCGC00091357-02
• NCGC00188943-01
• NCGC00188943-03
• NCGC00188943-04
• NCGC00258656-01
• SMR001550463
• SY006030
• TS-00078
• 2,6-dihydroxy-pyrimidin-4-carboxylic acid
• SBI-0207042.P001
• 4-Pyrimidinecarboxylic acid, 2,6-dihydroxy-
• A8909
• BB 0242405
• FT-0603612
• FT-0648914
• O0065
• Orotic acid, >=98% (titration), anhydrous
• SW219707-1
• EN300-16897
• C00295
• D00055
• D70614
• AB00373897_03
• AB-323/25048164
• Q425536
• SR-01000872754
• SR-01000872754-1
• W-104782
• F2191-0093
• 2,6-Dioxo-1,2,3,6-tetrahydro-pyrimidine-4-ca rboxylic acid
• 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

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6793	67.93%
Caco-2	-	0.8856	88.56%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6822	68.22%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9672	96.72%
OATP1B3 inhibitior	+	0.9523	95.23%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9687	96.87%
P-glycoprotein inhibitior	-	0.9835	98.35%
P-glycoprotein substrate	-	0.9873	98.73%
CYP3A4 substrate	-	0.7738	77.38%
CYP2C9 substrate	-	0.7977	79.77%
CYP2D6 substrate	-	0.9006	90.06%
CYP3A4 inhibition	-	0.9457	94.57%
CYP2C9 inhibition	-	0.9709	97.09%
CYP2C19 inhibition	-	0.9604	96.04%
CYP2D6 inhibition	-	0.9400	94.00%
CYP1A2 inhibition	-	0.5857	58.57%
CYP2C8 inhibition	-	0.9839	98.39%
CYP inhibitory promiscuity	-	1.0000	100.00%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7950	79.50%
Carcinogenicity (trinary)	Non-required	0.7223	72.23%
Eye corrosion	-	0.9906	99.06%
Eye irritation	+	0.8455	84.55%
Skin irritation	-	0.8175	81.75%
Skin corrosion	-	0.9642	96.42%
Ames mutagenesis	-	0.8400	84.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8862	88.62%
Micronuclear	+	0.8300	83.00%
Hepatotoxicity	+	0.6323	63.23%
skin sensitisation	-	0.8920	89.20%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.6626	66.26%
Acute Oral Toxicity (c)	III	0.5222	52.22%
Estrogen receptor binding	-	0.9063	90.63%
Androgen receptor binding	-	0.7947	79.47%
Thyroid receptor binding	-	0.7957	79.57%
Glucocorticoid receptor binding	-	0.8520	85.20%
Aromatase binding	-	0.7559	75.59%
PPAR gamma	-	0.7991	79.91%
Honey bee toxicity	-	0.9669	96.69%
Biodegradation	+	0.6000	60.00%
Crustacea aquatic toxicity	-	0.8800	88.00%
Fish aquatic toxicity	-	0.8077	80.77%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.19%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.72%	94.45%
CHEMBL4040	P28482	MAP kinase ERK2	87.49%	83.82%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.80%	95.56%
CHEMBL2581	P07339	Cathepsin D	82.70%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.22%	96.09%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.94%	93.03%

Plants that contains it

• Arabidopsis thaliana
• Lotus corniculatus

Cross-Links

• PubChem: 967
• LOTUS: LTS0134695
• wikiData: Q425536