{[5-(6-Amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethoxy]-hydroxy-phosphorylmethyl}-phosphonic acid mono-[5-(4-carbamoyl-thiazol-2-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl] ester

ID: ALA3144029

Chembl Id: CHEMBL3144029

PubChem CID: 90663694

Max Phase: Preclinical

Molecular Formula: C20H27N7O13P2S

Molecular Weight: 667.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)c1csc([C@@H]2O[C@H](COP(=O)(O)CP(=O)(O)OC[C@@H]3O[C@H](n4cnc5c(N)ncnc54)[C@@H](O)[C@H]3O)[C@@H](O)[C@H]2O)n1

Standard InChI:  InChI=1S/C20H27N7O13P2S/c21-16-10-18(24-4-23-16)27(5-25-10)20-14(31)12(29)9(40-20)2-38-42(35,36)6-41(33,34)37-1-8-11(28)13(30)15(39-8)19-26-7(3-43-19)17(22)32/h3-5,8-9,11-15,20,28-31H,1-2,6H2,(H2,22,32)(H,33,34)(H,35,36)(H2,21,23,24)/t8-,9+,11-,12+,13-,14+,15-,20+/m1/s1

Standard InChI Key:  CRWWKLKZKYLFQV-VSKCBFOOSA-N

Alternative Forms

1. Parent:

   

   ALA3144029

   [(2S,3R,4S,5S)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-[[[(2R,3S,4R,5R)-5-(4-carbamoyl-1,3-thiazol-2-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]methyl]phosphinic acid

Molecule Features

Natural Product: No

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: 667.49

Molecular Weight (Monoisotopic): 667.0863

AlogP: -2.19

#Rotatable Bonds: 11

Polar Surface Area: 318.04

Molecular Species: ACID

HBA: 18

HBD: 8

#RO5 Violations: 3

HBA (Lipinski): 20

HBD (Lipinski): 10

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 0.81

CX Basic pKa: 4.92

CX LogP: -7.39

CX LogD: -9.23

Aromatic Rings: 3

Heavy Atoms: 43

QED Weighted: 0.10

Np Likeness Score: 0.57

References

1. Zatorski A, Goldstein BM, Colby TD, Jones JP, Pankiewicz KW..  (1995)  Potent inhibitors of human inosine monophosphate dehydrogenase type II. Fluorine-substituted analogues of thiazole-4-carboxamide adenine dinucleotide.,  38  (7): [PMID:7707313] [10.1021/jm00007a007]

2. Pankiewicz KW, Lesiak K, Zatorski A, Goldstein BM, Carr SF, Sochacki M, Majumdar A, Seidman M, Watanabe KA..  (1997)  The practical synthesis of a methylenebisphosphonate analogue of benzamide adenine dinucleotide: inhibition of human inosine monophosphate dehydrogenase (type I and II).,  40  (8): [PMID:9111303] [10.1021/jm960641y]

3. Marquez VE, Tseng CK, Gebeyehu G, Cooney DA, Ahluwalia GS, Kelley JA, Dalal M, Fuller RW, Wilson YA, Johns DG..  (1986)  Thiazole-4-carboxamide adenine dinucleotide (TAD). Analogues stable to phosphodiesterase hydrolysis.,  29  (9): [PMID:2875185] [10.1021/jm00159a027]

4. Lesiak K, Watanabe KA, Majumdar A, Seidman M, Vanderveen K, Goldstein BM, Pankiewicz KW..  (1997)  Synthesis of nonhydrolyzable analogues of thiazole-4-carboxamide and benzamide adenine dinucleotide containing fluorine atom at the C2' of adenine nucleoside: induction of K562 differentiation and inosine monophosphate dehydrogenase inhibitory activity.,  40  (16): [PMID:9258359] [10.1021/jm970247f]

5. Pankiewicz KW, Lesiak-Watanabe KB, Watanabe KA, Patterson SE, Jayaram HN, Yalowitz JA, Miller MD, Seidman M, Majumdar A, Prehna G, Goldstein BM..  (2002)  Novel mycophenolic adenine bis(phosphonate) analogues as potential differentiation agents against human leukemia.,  45  (3): [PMID:11806722] [10.1021/jm0104116]

Source

Source(1):

• Scientific Literature