5-Acetylamino-2-{[5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethoxy]-hydroxy-phosphoryloxy}-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid

ID: ALA1234647

Chembl Id: CHEMBL1234647

Cas Number: 22-12-8

PubChem CID: 448209

Max Phase: Preclinical

Molecular Formula: C20H31N4O16P

Molecular Weight: 614.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)O[C@](OP(=O)(O)OC[C@H]2O[C@@H](n3ccc(N)nc3=O)[C@H](O)[C@@H]2O)(C(=O)O)C[C@@H]1O

Standard 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

Standard InChI Key:  TXCIAUNLDRJGJZ-BILDWYJOSA-N

Alternative Forms

1. Parent:

   

   ALA1234647

   cytidine monophosphate N-acetylneuraminic acid

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 614.45

Molecular Weight (Monoisotopic): 614.1473

AlogP: -5.27

#Rotatable Bonds: 11

Polar Surface Area: 322.91

Molecular Species: ACID

HBA: 17

HBD: 10

#RO5 Violations: 3

HBA (Lipinski): 20

HBD (Lipinski): 11

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 1.47

CX Basic pKa: ┄

CX LogP: -5.59

CX LogD: -11.45

Aromatic Rings: 1

Heavy Atoms: 41

QED Weighted: 0.10

Np Likeness Score: 1.38

References

1. Traynor AJ, Hall ET, Walker G, Miller WH, Melançon P, Kuchta RD..  (1996)  Inhibition of UDP-N-acetylglucosamine import into Golgi membranes by nucleoside monophosphates.,  39  (15): [PMID:8709123] [10.1021/jm960175c]

2. Montgomery AP,Dobie C,Szabo R,Hallam L,Ranson M,Yu H,Skropeta D.  (2020)  Design, synthesis and evaluation of carbamate-linked uridyl-based inhibitors of human ST6Gal I.,  28  (14): [PMID:32616185] [10.1016/j.bmc.2020.115561]

3. Dobie C, Montgomery AP, Szabo R, Yu H, Skropeta D..  (2021)  Synthesis and biological evaluation of selective phosphonate-bearing 1,2,3-triazole-linked sialyltransferase inhibitors.,  12  (10.0): [PMID:34778769] [10.1039/D1MD00079A]

Source

Source(1):

• Scientific Literature