5'-Cytidylic acid

Details

• Internal ID: 597c9559-bd80-4945-b6c3-27900687eeb6
• Taxonomy: Nucleosides, nucleotides, and analogues > Pyrimidine nucleotides > Pyrimidine ribonucleotides > Pyrimidine ribonucleoside monophosphates
• IUPAC Name: [(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
• SMILES (Canonical): C1=CN(C(=O)N=C1N)C2C(C(C(O2)COP(=O)(O)O)O)O
• SMILES (Isomeric): C1=CN(C(=O)N=C1N)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)O)O)O
• InChI: InChI=1S/C9H14N3O8P/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1
• InChI Key: IERHLVCPSMICTF-XVFCMESISA-N
• Popularity: 1,738 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₁₄N₃O₈P
• Molecular Weight: 323.20 g/mol
• Exact Mass: 323.05185141 g/mol
• Topological Polar Surface Area (TPSA): 175.00 Ų
• XlogP: -3.40
• Atomic LogP (AlogP): -2.45
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

• Cytidine 5'-monophosphate
• 63-37-6
• cytidylic acid
• Cytidine monophosphate
• Cytidine-5'-monophosphate
• 5'-CMP
• cytidylate
• Cytidine 5'-phosphate
• CMP (nucleotide)
• Cytidine 5'-phosphoric acid
• Cytidine 5'-monophosphoric acid
• ((2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl dihydrogen phosphate
• Cytidine 5'-(dihydrogenphosphate)
• CMP
• cytidine-P
• cytidine-phosphate
• Cytidine 3'-(dihydrogen phosphate)
• 1beta-Ribofuranosylcytosine 5'-phosphate, d-
• C-5'-P
• CHEBI:17361
• MFCD00006544
• Cytidine 5'-monophosphate, free acid
• CHEMBL307679
• [(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
• DTXSID50889322
• 5'-Cytidylic acid (8CI,9CI)
• [(2R,3S,4R,5R)-5-(4-amino-2-oxo-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methyl dihydrogen phosphate
• {[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
• Cytidine, mono(dihydrogen phosphate) (ester)
• F469818O25
• 2(1H)-pyrimidinone, 4-amino-1-(5-O-phosphono-beta-D-ribofuranosyl)-
• Cytidine-5' Monophosphate
• cytidine-monophosphate
• 5'-Cytidylate monophosphate
• C5P
• 5'-CYTIDYLIC ACID (USP-RS)
• 5'-CYTIDYLIC ACID [USP-RS]
• C9H14N3O8P
• EINECS 200-556-6
• Cytidine 5 -monophosphate
• BRN 0046982
• 5-cytidylate
• 5-Cytidylic acid
• UNII-F469818O25
• cytidine mono phosphate
• CytidylsA currencyure a
• cytidine 5''-phosphate
• Cytidine 5'-phosphorate
• 5'-CYTIDYLICACID
• bmse000311
• Epitope ID:196257
• Cytidine 5'-monophosphorate
• 3H-Cytidin-5'-monophosphat
• SCHEMBL16189
• 4-25-00-03673 (Beilstein Handbook Reference)
• CYTIDYLIC ACID [WHO-DD]
• CYTOSINE 5'-MONOPHOSPHATE
• 5'-CYTIDYLIC ACID [FCC]
• DTXCID701028585
• Cytidine mono(dihydrogen phosphate)
• CYTIDINE-5''-MONOPHOSPHATE
• AMY30020
• BDBM50310540
• s5374
• AKOS015854843
• AKOS015888565
• CCG-267735
• CS-W009878
• DB03403
• HY-W009162
• AC-32139
• AS-56853
• BP-58604
• C25
• SY030157
• 5,(S)
• C1675
• C00055
• W18546
• EN300-7376706
• A820633
• Q412622
• Cytidine 5 inverted exclamation mark -Monophosphate
• Q-101433
• B755C4F3-3D29-45E0-9432-16F902ABCFE1
• 5'-Cytidylic acid; Cytidine monophosphate, Cytidine 5'-phosphate
• 5'-Cytidylic acid, United States Pharmacopeia (USP) Reference Standard
• Cytidine 5'-monophosphate, Sigma Grade, >=99% (HPLC), synthetic, powder
• ((2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl)methyl dihydrogen phosphate
• FN5
• Phosphoric acid mono-[5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl] ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6976	69.76%
Caco-2	-	0.8874	88.74%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6037	60.37%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9526	95.26%
OATP1B3 inhibitior	+	0.9445	94.45%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9743	97.43%
P-glycoprotein inhibitior	-	0.9126	91.26%
P-glycoprotein substrate	-	0.9486	94.86%
CYP3A4 substrate	-	0.5103	51.03%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.8722	87.22%
CYP3A4 inhibition	-	0.9429	94.29%
CYP2C9 inhibition	-	0.9229	92.29%
CYP2C19 inhibition	-	0.9049	90.49%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9282	92.82%
CYP2C8 inhibition	-	0.9423	94.23%
CYP inhibitory promiscuity	-	0.9761	97.61%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.5214	52.14%
Eye corrosion	-	0.9849	98.49%
Eye irritation	-	0.9717	97.17%
Skin irritation	-	0.7708	77.08%
Skin corrosion	-	0.9285	92.85%
Ames mutagenesis	-	0.9900	99.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6906	69.06%
Micronuclear	+	0.9900	99.00%
Hepatotoxicity	+	0.6635	66.35%
skin sensitisation	-	0.8398	83.98%
Respiratory toxicity	+	0.9222	92.22%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.6592	65.92%
Acute Oral Toxicity (c)	III	0.6049	60.49%
Estrogen receptor binding	-	0.5000	50.00%
Androgen receptor binding	+	0.8555	85.55%
Thyroid receptor binding	+	0.5359	53.59%
Glucocorticoid receptor binding	-	0.5105	51.05%
Aromatase binding	+	0.6080	60.80%
PPAR gamma	-	0.4860	48.60%
Honey bee toxicity	-	0.8129	81.29%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	-	0.5649	56.49%

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	96.81%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	96.39%	95.93%
CHEMBL3230	O95977	Sphingosine 1-phosphate receptor Edg-6	94.37%	94.01%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	92.40%	80.33%
CHEMBL3137261	O14744	PRMT5/MEP50 complex	90.42%	100.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.83%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	84.55%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.96%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.19%	99.23%
CHEMBL3891	P07384	Calpain 1	81.11%	93.04%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	80.54%	91.11%

Plants that contains it

• Arabidopsis thaliana

Cross-Links

• PubChem: 6131
• LOTUS: LTS0025690
• wikiData: Q412622