Cytidine 3'-monophosphate

Details

• Internal ID: 30b1dc88-5271-406c-85d4-4768152570d4
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Monosaccharides > Pentoses > Pentose phosphates
• IUPAC Name: [(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] dihydrogen phosphate
• SMILES (Canonical): C1=CN(C(=O)N=C1N)C2C(C(C(O2)CO)OP(=O)(O)O)O
• SMILES (Isomeric): C1=CN(C(=O)N=C1N)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)OP(=O)(O)O)O
• InChI: InChI=1S/C9H14N3O8P/c10-5-1-2-12(9(15)11-5)8-6(14)7(4(3-13)19-8)20-21(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: UOOOPKANIPLQPU-XVFCMESISA-N
• Popularity: 851 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: -3.80
• Atomic LogP (AlogP): -2.45
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

• 84-52-6
• 3'-Cytidylic acid
• Cytidine-3'-Monophosphate
• 3'-CMP
• 3-Cytidylic acid
• Cytidine 3'-phosphate
• Cytidine 3-monophosphate
• UNII-6DZL5I6D4D
• Cytidine-3/'-Monophosphate
• 6DZL5I6D4D
• CHEMBL258728
• CHEBI:53013
• EINECS 201-537-5
• [(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] dihydrogen phosphate
• (2R,3S,4R,5R)-5-(4-Amino-2-oxopyrimidin-1(2H)-yl)-4-hydroxy-2-(hydroxymethyl)tetrahydrofuran-3-yl dihydrogen phosphate
• C3P
• CYTIDINE3'-MONOPHOSPHATE
• Cytidylic acid B
• 3/'-Cytidylic acid
• cytidine-3'-phosphate
• CytidylsA currencyure b
• ST057096
• cytidine-3''-monophosphate
• SCHEMBL79966
• CYTIDINE, 3'-PHOSPHATE
• UOOOPKANIPLQPU-XVFCMESISA-
• 3'-CYTIDYLIC ACID [MI]
• UOOOPKANIPLQPU-XVFCMESISA-N
• 3'-CYTIDINEPHOSPHORIC ACID
• DTXSID301004260
• BDBM50233301
• MFCD00006543
• RIBOCYTIDINE 3'-MONOPHOSPHATE
• AKOS015856718
• AKOS015895646
• DB01961
• s10910
• NCGC00142494-01
• (3S,2R,4R,5R)-5-(4-amino-2-oxohydropyrimidinyl)-4-hydroxy-2-(hydroxymethyl)oxo lan-3-yl dihydrogen phosphate
• C05822
• A840831
• Q27104806
• 4-Imino-1-(3-O-phosphonopentofuranosyl)-1,4-dihydropyrimidin-2-ol
• [(2S,3S,4R,5R)-5-(4-amino-2-oxo-pyrimidin-1-yl)-4-hydroxy-2-(hydroxymethyl)oxola
• (2R,3S,4R,5R)-5-(4-Amino-2-oxopyrimidin-1(2H)-yl)-4-hydroxy-2-(hydroxymethyl)tetrahydrofuran-3-yldihydrogenphosphate
• [(2R,3S,4R,5R)-5-(4-amino-2-keto-pyrimidin-1-yl)-4-hydroxy-2-methylol-tetrahydrofuran-3-yl] dihydrogen phosphate
• [(2R,3S,4R,5R)-5-(4-azanyl-2-oxidanylidene-pyrimidin-1-yl)-2-(hydroxymethyl)-4-oxidanyl-oxolan-3-yl] dihydrogen phosphate
• InChI=1/C9H14N3O8P/c10-5-1-2-12(9(15)11-5)8-6(14)7(4(3-13)19-8)20-21(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

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5498	54.98%
Caco-2	-	0.9362	93.62%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.5602	56.02%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9453	94.53%
OATP1B3 inhibitior	+	0.9434	94.34%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9802	98.02%
P-glycoprotein inhibitior	-	0.8703	87.03%
P-glycoprotein substrate	-	0.9118	91.18%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.8740	87.40%
CYP3A4 inhibition	-	0.9338	93.38%
CYP2C9 inhibition	-	0.9111	91.11%
CYP2C19 inhibition	-	0.9013	90.13%
CYP2D6 inhibition	-	0.9241	92.41%
CYP1A2 inhibition	-	0.9302	93.02%
CYP2C8 inhibition	-	0.9455	94.55%
CYP inhibitory promiscuity	-	0.9616	96.16%
UGT catelyzed	-	1.0000	100.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.5083	50.83%
Eye corrosion	-	0.9841	98.41%
Eye irritation	-	0.9852	98.52%
Skin irritation	-	0.7749	77.49%
Skin corrosion	-	0.9300	93.00%
Ames mutagenesis	-	0.9600	96.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7852	78.52%
Micronuclear	+	0.9900	99.00%
Hepatotoxicity	+	0.6849	68.49%
skin sensitisation	-	0.8471	84.71%
Respiratory toxicity	+	0.9333	93.33%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	+	0.5903	59.03%
Acute Oral Toxicity (c)	III	0.5992	59.92%
Estrogen receptor binding	+	0.6266	62.66%
Androgen receptor binding	+	0.7614	76.14%
Thyroid receptor binding	-	0.5077	50.77%
Glucocorticoid receptor binding	-	0.6314	63.14%
Aromatase binding	+	0.5197	51.97%
PPAR gamma	+	0.6907	69.07%
Honey bee toxicity	-	0.8068	80.68%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	-	0.7269	72.69%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL340	P08684	Cytochrome P450 3A4	7943.3 nM; 7943.3 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.80%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	94.53%	95.93%
CHEMBL3230	O95977	Sphingosine 1-phosphate receptor Edg-6	91.53%	94.01%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.24%	94.00%
CHEMBL3137261	O14744	PRMT5/MEP50 complex	87.61%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.49%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.65%	97.09%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	83.97%	80.33%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	83.58%	98.46%

Plants that contains it

• Arabidopsis thaliana
• Heliotropium indicum

Cross-Links

• PubChem: 66535
• NPASS: NPC6166
• ChEMBL: CHEMBL258728
• LOTUS: LTS0173508
• wikiData: Q27104806