Dihydroorotic acid

Details

• Internal ID: 9a3eba4d-54b4-4e93-952c-07f9f330cc21
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Alpha amino acids and derivatives
• IUPAC Name: 2,6-dioxo-1,3-diazinane-4-carboxylic acid
• SMILES (Canonical): C1C(NC(=O)NC1=O)C(=O)O
• SMILES (Isomeric): C1C(NC(=O)NC1=O)C(=O)O
• InChI: InChI=1S/C5H6N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h2H,1H2,(H,9,10)(H2,6,7,8,11)
• InChI Key: UFIVEPVSAGBUSI-UHFFFAOYSA-N
• Popularity: 484 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅H₆N₂O₄
• Molecular Weight: 158.11 g/mol
• Exact Mass: 158.03275668 g/mol
• Topological Polar Surface Area (TPSA): 95.50 Ų
• XlogP: -1.50
• Atomic LogP (AlogP): -1.33
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

• hydroorotic acid
• 155-54-4
• DL-Dihydroorotic acid
• dihydroorotate
• 2,6-dioxohexahydropyrimidine-4-carboxylic acid
• 4,5-dihydroorotic acid
• 5,6-dihydroorotate
• 6202-10-4
• 2,6-dioxo-1,3-diazinane-4-carboxylic acid
• 4-pyrimidinecarboxylic acid, hexahydro-2,6-dioxo-
• 39LRK7UX5B
• CHEBI:30865
• 4,5-dihydroorotate
• Orotic acid, 4,5-dihydro-
• UNII-39LRK7UX5B
• L-hydroorotate
• MFCD00085339
• R,S-Hydroorotate
• DL-hydroorotic acid
• DL-dihydroortotic acid
• D-HYDROOROTICACID
• (S)-2,6-Dioxohexahydro-4-pyrimidinecarboxylic acid
• 5,6-dihydro-orotic acid
• 2,6-dioxo-hexahydro-pyrimidine-4-carboxylic acid
• CHEMBL75782
• HYDROOROTIC ACID [MI]
• HYDROOROTIC ACID, DL-
• SCHEMBL121953
• 5,6-DIHYDROOROTIC ACID
• DTXSID40861839
• (+/-)-DIHYDROOROTIC ACID
• DL-4,5-DIHYDROOROTIC ACID
• 6-HYDROURACILCARBOXYLIC ACID
• BCP33011
• HYDROOROTIC ACID, (+/-)-
• AKOS006228089
• HYDROOROTIC ACID DL-FORM [MI]
• SB45071
• SB56808
• AS-18439
• SY042036
• 5,6-DIHYDROURACIL-6-CARBOXYLIC ACID
• AM20100519
• CS-0046700
• FT-0602259
• FT-0627848
• FT-0747363
• 2,6-dioxo-hexahydro-pyrimidine-4-carboxylate
• 2,6-Dioxohexahydropyrimidine-4-carboxylicacid
• D72863
• EN300-297330
• 2,6-dioxo-hexahydro-pyrimidine-4-carboxylicacid
• (+)-2,6-dioxo-hexahydro-pyrimidine-4-carboxylate
• (R)-2,6-dioxo-hexahydro-pyrimidine-4-carboxylate
• (S)-2,6-dioxo-hexahydro-pyrimidine-4-carboxylate
• EBA89F91-9BA4-4F53-A555-AACB4A7DF0FA
• Q2823223
• (+)-2,6-dioxo-hexahydro-pyrimidine-4-carboxylic acid
• (R)-2,6-dioxo-hexahydro-pyrimidine-4-carboxylic acid
• (S)-2,6-dioxo-hexahydro-pyrimidine-4-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5713	57.13%
Caco-2	-	0.9686	96.86%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6961	69.61%
OATP2B1 inhibitior	-	0.8518	85.18%
OATP1B1 inhibitior	+	0.9585	95.85%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9813	98.13%
P-glycoprotein inhibitior	-	0.9879	98.79%
P-glycoprotein substrate	-	0.9359	93.59%
CYP3A4 substrate	-	0.6698	66.98%
CYP2C9 substrate	+	0.6233	62.33%
CYP2D6 substrate	-	0.8551	85.51%
CYP3A4 inhibition	-	0.9799	97.99%
CYP2C9 inhibition	-	0.9748	97.48%
CYP2C19 inhibition	-	0.9678	96.78%
CYP2D6 inhibition	-	0.9461	94.61%
CYP1A2 inhibition	-	0.9100	91.00%
CYP2C8 inhibition	-	0.9856	98.56%
CYP inhibitory promiscuity	-	1.0000	100.00%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8500	85.00%
Carcinogenicity (trinary)	Non-required	0.7459	74.59%
Eye corrosion	-	0.9879	98.79%
Eye irritation	+	0.6243	62.43%
Skin irritation	-	0.8049	80.49%
Skin corrosion	-	0.9565	95.65%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8670	86.70%
Micronuclear	+	0.8500	85.00%
Hepatotoxicity	+	0.7408	74.08%
skin sensitisation	-	0.8981	89.81%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.5135	51.35%
Acute Oral Toxicity (c)	III	0.6799	67.99%
Estrogen receptor binding	-	0.9037	90.37%
Androgen receptor binding	-	0.7928	79.28%
Thyroid receptor binding	-	0.8671	86.71%
Glucocorticoid receptor binding	-	0.8457	84.57%
Aromatase binding	-	0.7996	79.96%
PPAR gamma	-	0.7289	72.89%
Honey bee toxicity	-	0.9420	94.20%
Biodegradation	+	0.6500	65.00%
Crustacea aquatic toxicity	-	0.7900	79.00%
Fish aquatic toxicity	-	0.9632	96.32%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	98.59%	83.82%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.49%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.04%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.54%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.52%	97.09%
CHEMBL299	P17252	Protein kinase C alpha	85.33%	98.03%
CHEMBL2581	P07339	Cathepsin D	84.26%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.99%	95.56%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	80.39%	96.39%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.26%	85.14%

Plants that contains it

• Arabidopsis thaliana

Cross-Links

• PubChem: 648
• LOTUS: LTS0136421
• wikiData: Q2823223