Orotidine 5'-monophosphate

Details

• Internal ID: 964bd4a1-f9fa-4ea2-918b-b0760bf7a43d
• Taxonomy: Nucleosides, nucleotides, and analogues > Pyrimidine nucleotides > Pyrimidine ribonucleotides > Pyrimidine ribonucleoside monophosphates
• IUPAC Name: 3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(phosphonooxymethyl)oxolan-2-yl]-2,6-dioxopyrimidine-4-carboxylic acid
• InChI: InChI=1S/C10H13N2O11P/c13-5-1-3(9(16)17)12(10(18)11-5)8-7(15)6(14)4(23-8)2-22-24(19,20)21/h1,4,6-8,14-15H,2H2,(H,16,17)(H,11,13,18)(H2,19,20,21)/t4-,6-,7-,8-/m1/s1
• InChI Key: KYOBSHFOBAOFBF-XVFCMESISA-N
• Popularity: 429 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₃N₂O₁₁P
• Molecular Weight: 368.19 g/mol
• Exact Mass: 368.02569623 g/mol
• Topological Polar Surface Area (TPSA): 203.00 Ų
• XlogP: -4.20
• Atomic LogP (AlogP): -3.04
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

• Orotidine 5'-monophosphate
• Orotidine 5'-phosphate
• 2149-82-8
• Orotidine monophosphate
• orotidine-5'-phosphate
• Ometoprim
• 5-(Dihydrogen phosphate)orotidine
• OROTIDINE-5'-MONOPHOSPHATE
• 6-carboxy-5'-uridylic acid
• OMP (nucleotide)
• orotidine 5'-(dihydrogen phosphate)
• H0ARN8U4Y9
• 5'-OMP
• CHEBI:15842
• Orotidine 5 inverted exclamation marka-monophosphate
• OMP
• 2,6-dioxo-3-(5-O-phosphono-beta-D-ribofuranosyl)-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid
• 3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid
• 4-Pyrimidinecarboxylic acid, 1,2,3,6-tetrahydro-2,6-dioxo-3-(5-O-phosphono-beta-D-ribofuranosyl)-
• Orotidylate
• 5'-phosphate Orotidine
• 6-carboxy-5'-uridylate
• Orotidine 5-monophosphate
• UNII-H0ARN8U4Y9
• Orotidine 5??-monophosphate
• SCHEMBL21891
• CHEMBL1207358
• BDBM21336
• DTXSID40944090
• KYOBSHFOBAOFBF-XVFCMESISA-N
• HY-N8060
• 5'-(dihydrogen phosphate) Orotidine
• AKOS030551158
• Orotidine, 5'-phosphate (6CI,7CI)
• DB02957
• 3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(phosphonooxymethyl)oxolan-2-yl]-2,6-dioxopyrimidine-4-carboxylic acid
• 5'-(dihydrogen phosphate) 6-carboxy-uridine
• CS-0139119
• Orotidine, 5'-(dihydrogen phosphate) (8CI)
• C01103
• uridine, 6-carboxy-, 5'-(dihydrogen phosphate)
• Q27098253
• 1,2,3,6-tetrahydro-2,6-dioxo-3-(5-O-phosphono-b-D-ribofuranosyl)-4-Pyrimidinecarboxylate
• 1,2,3,6-TETRAHYDRO-2,6-DIOXO-3-(5-O-PHOSPHONO-.BETA.-D-RIBOFURANOSYL)-4-PYRIMIDINECARBOXYLIC ACID
• 1,2,3,6-tetrahydro-2,6-dioxo-3-(5-O-phosphono-b-D-ribofuranosyl)-4-Pyrimidinecarboxylic acid
• 1,2,3,6-tetrahydro-2,6-dioxo-3-(5-O-phosphono-beta-delta-ribofuranosyl)-4-Pyrimidinecarboxylate
• 1,2,3,6-tetrahydro-2,6-dioxo-3-(5-O-phosphono-beta-delta-ribofuranosyl)-4-Pyrimidinecarboxylic acid
• 1-[3,4-dihydroxy-5-(phosphonooxymethyl)tetrahydrofuran-2-yl]-2, 4-dioxo-1H-pyrimidine-6-carboxylic acid
• 2,6-dioxo-3-(5-O-phosphono-beta-delta-ribofuranosyl)-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid
• 3-((2R,3R,4S,5R)-3,4-Dihydroxy-5-((phosphonooxy)methyl)tetrahydrofuran-2-yl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid
• 3-((2R,3R,4S,5R)-3,4-Dihydroxy-5-((phosphonooxy)methyl)tetrahydrofuran-2-yl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylicacid
• 4-PYRIMIDINECARBOXYLIC ACID, 1,2,3,6-TETRAHYDRO-2,6-DIOXO-3-(5-O-PHOSPHONO-.BETA.-D-RIBOFURANOSYL)-
• 4-Pyrimidinecarboxylic acid, 1,2,3,6-tetrahydro-2,6-dioxo-3-(5-O-phosphono-beta-D-ribofuranosyl)- (9CI)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9292	92.92%
Caco-2	-	0.9105	91.05%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.6290	62.90%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9101	91.01%
OATP1B3 inhibitior	+	0.9418	94.18%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9826	98.26%
P-glycoprotein inhibitior	-	0.8824	88.24%
P-glycoprotein substrate	-	0.9247	92.47%
CYP3A4 substrate	+	0.5091	50.91%
CYP2C9 substrate	-	0.7943	79.43%
CYP2D6 substrate	-	0.8766	87.66%
CYP3A4 inhibition	-	0.8657	86.57%
CYP2C9 inhibition	-	0.9033	90.33%
CYP2C19 inhibition	-	0.8726	87.26%
CYP2D6 inhibition	-	0.8962	89.62%
CYP1A2 inhibition	-	0.8960	89.60%
CYP2C8 inhibition	-	0.8823	88.23%
CYP inhibitory promiscuity	-	0.9457	94.57%
UGT catelyzed	-	0.9000	90.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.5267	52.67%
Eye corrosion	-	0.9845	98.45%
Eye irritation	-	0.9081	90.81%
Skin irritation	-	0.7787	77.87%
Skin corrosion	-	0.9321	93.21%
Ames mutagenesis	-	0.6118	61.18%
Human Ether-a-go-go-Related Gene inhibition	-	0.7532	75.32%
Micronuclear	+	0.9700	97.00%
Hepatotoxicity	+	0.6130	61.30%
skin sensitisation	-	0.8482	84.82%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.7998	79.98%
Acute Oral Toxicity (c)	III	0.5739	57.39%
Estrogen receptor binding	-	0.5373	53.73%
Androgen receptor binding	+	0.5564	55.64%
Thyroid receptor binding	-	0.5836	58.36%
Glucocorticoid receptor binding	-	0.4777	47.77%
Aromatase binding	+	0.5779	57.79%
PPAR gamma	+	0.5567	55.67%
Honey bee toxicity	-	0.7958	79.58%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	0.6437	64.37%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.96%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	94.69%	83.82%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	93.41%	86.92%
CHEMBL2581	P07339	Cathepsin D	91.49%	98.95%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	90.88%	91.71%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	89.16%	80.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.68%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.39%	91.11%
CHEMBL5957	P21589	5'-nucleotidase	86.62%	97.78%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	86.58%	87.67%
CHEMBL3230	O95977	Sphingosine 1-phosphate receptor Edg-6	86.34%	94.01%
CHEMBL5255	O00206	Toll-like receptor 4	85.22%	92.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.14%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	82.81%	94.73%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.51%	93.00%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	81.58%	81.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.32%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.79%	99.23%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 160617
• LOTUS: LTS0219344
• wikiData: Q27098253