CMP-Neu5Ac

Details

• Internal ID: 5d4f7b6c-8fac-49d8-9208-ba5fb719eb93
• Taxonomy: Nucleosides, nucleotides, and analogues > Pyrimidine nucleotides > Pyrimidine nucleotide sugars
• IUPAC Name: (2R,4S,5R,6R)-5-acetamido-2-[[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• InChI: InChI=1S/C20H31N4O16P/c1-7(26)22-12-8(27)4-20(18(32)33,39-16(12)13(29)9(28)5-25)40-41(35,36)37-6-10-14(30)15(31)17(38-10)24-3-2-11(21)23-19(24)34/h2-3,8-10,12-17,25,27-31H,4-6H2,1H3,(H,22,26)(H,32,33)(H,35,36)(H2,21,23,34)/t8-,9+,10+,12+,13+,14+,15+,16+,17+,20+/m0/s1
• InChI Key: TXCIAUNLDRJGJZ-BILDWYJOSA-N
• Popularity: 421 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₁N₄O₁₆P
• Molecular Weight: 614.50 g/mol
• Exact Mass: 614.14726791 g/mol
• Topological Polar Surface Area (TPSA): 321.00 Ų
• XlogP: -6.70
• Atomic LogP (AlogP): -5.27
• H-Bond Acceptor: 17
• H-Bond Donor: 10
• Rotatable Bonds: 11

Synonyms

• cytidine monophosphate N-acetylneuraminic acid
• CMP-N-acetylneuraminate
• CMP-NeuNAc
• Cmp-D-N-acetylneuraminic acid
• 3063-71-6
• CYTIDINE 5'-MONOPHOSPHO-N-
• CYTIDINE-5'-MONOPHOSPHATE-5-N-ACETYLNEURAMINIC ACID
• CHEBI:16556
• CMP-Neu5Ac
• (2R,4S,5R,6R)-5-acetamido-2-[[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• Cytidine 5'-monophosphate-N-acetylneuraminic acid
• 22-12-8
• CMP-N-acetylneuraminic acid
• (2R,4S,5R,6R)-2-[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• NCC
• T8I6M8AXA0
• CMP-beta-Neu5Ac
• CMP-N-acylneuraminate
• SCHEMBL122854
• GTPL4663
• CHEMBL1234647
• TXCIAUNLDRJGJZ-BILDWYJOSA-N
• CMP-N-acetyl-beta-neuraminic acid
• DB02485
• cytidine monophosphate N-acetylneuraminate
• HY-112942
• CS-0069697
• Cytidine-5-monophospho-N-acetylneuraminic acid
• C00128
• CMP-Neu5Ac; CMP-Sialic Acid, Monosodium Salt
• cytidine-5'-monophospho-N-acetylneuraminic acid
• F76225
• cytidine-5'-monophosphono-N-acetylneuraminic acid
• Cytidine 5'-monophosphate N-acetylneuraminic acid
• Q27076132
• N-ACETYL-.BETA.-NEURAMINIC ACID 2-(HYDROGEN 5'-CYTIDYLATE)
• NEURAMINIC ACID, N-ACETYL-, 2-ESTER WITH 5'-CYTIDYLIC ACID
• .BETA.-NEURAMINIC ACID, N-ACETYL-, 2-(HYDROGEN 5'-CYTIDYLATE)
• (2R,4S,5R)-5-acetamido-2-((((2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(hydroxy)phosphoryloxy)-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylic acid
• (2R,4S,5R,6R)-5-(acetylamino)-2-{[(S)-{[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methoxy}(hydroxy)phosphoryl]oxy}-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]tetrahydro-2H-pyran-2-carboxylic acid (non-preferred name)
• (2R,4S,5R,6R)-5-Acetamido-2-(((((2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(hydroxy)phosphoryl)oxy)-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylic acid
• (2S,4S,5S,6S)-5-ACETAMIDO-2-(((2R,3S,4S,5R)-5-(4-AZANYL-2-OXIDANYLIDENE-PYRIMIDIN-1-YL)-3,4-BIS(OXIDANYL)OXOLAN-2-YL)METHOXY-OXIDANYL-PHOSPHORYL)OXY-4-OXIDANYL-6-((1S,2S)-1,2,3-TRIS(OXIDANYL)PROPYL)OXANE-2-CARBOXYLIC ACID
• cytidine 5'-(5-acetamido-3,5-dideoxy-D-glycero-beta-D-galacto-non-2-ulopyranosylonic acid monophosphate)
• Cytidine-5'-monophospho 5-acetamido-3,5-dideoxy-D-glycero-beta-D-galacto-2-nonulopyranosonic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7947	79.47%
Caco-2	-	0.8811	88.11%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.3598	35.98%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8677	86.77%
OATP1B3 inhibitior	+	0.9427	94.27%
MATE1 inhibitior	-	0.9419	94.19%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8041	80.41%
P-glycoprotein inhibitior	-	0.4558	45.58%
P-glycoprotein substrate	+	0.6154	61.54%
CYP3A4 substrate	+	0.6748	67.48%
CYP2C9 substrate	-	0.6000	60.00%
CYP2D6 substrate	-	0.8699	86.99%
CYP3A4 inhibition	-	0.6780	67.80%
CYP2C9 inhibition	-	0.8684	86.84%
CYP2C19 inhibition	-	0.8400	84.00%
CYP2D6 inhibition	-	0.8561	85.61%
CYP1A2 inhibition	-	0.8830	88.30%
CYP2C8 inhibition	-	0.5720	57.20%
CYP inhibitory promiscuity	-	0.8745	87.45%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.4836	48.36%
Eye corrosion	-	0.9837	98.37%
Eye irritation	-	0.9355	93.55%
Skin irritation	-	0.7817	78.17%
Skin corrosion	-	0.9297	92.97%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6742	67.42%
Micronuclear	+	0.9800	98.00%
Hepatotoxicity	-	0.5688	56.88%
skin sensitisation	-	0.8468	84.68%
Respiratory toxicity	+	0.9111	91.11%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	+	0.6473	64.73%
Acute Oral Toxicity (c)	III	0.5471	54.71%
Estrogen receptor binding	+	0.6963	69.63%
Androgen receptor binding	+	0.7453	74.53%
Thyroid receptor binding	-	0.4919	49.19%
Glucocorticoid receptor binding	+	0.6157	61.57%
Aromatase binding	+	0.6825	68.25%
PPAR gamma	+	0.6750	67.50%
Honey bee toxicity	-	0.7759	77.59%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	-	0.5405	54.05%

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	99.59%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	96.42%	95.93%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	95.57%	95.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.06%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.43%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	93.35%	83.82%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.08%	94.45%
CHEMBL3137261	O14744	PRMT5/MEP50 complex	91.98%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.73%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.59%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	90.24%	94.73%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	87.03%	80.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.90%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.86%	97.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.66%	96.00%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	85.04%	93.10%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.68%	96.90%
CHEMBL3384	Q16512	Protein kinase N1	82.40%	80.71%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	82.04%	96.39%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.94%	99.17%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	81.89%	100.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.87%	93.04%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.80%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.56%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.23%	86.33%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 448209
• LOTUS: LTS0198603
• wikiData: Q27076132