(S)-1-[(2R,3S,4R,5S)-5-(6-Amino-purin-9-ylmethyl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethoxycarbonyl]-3-methylsulfanyl-propyl-ammonium

ID: ALA1161585

Chembl Id: CHEMBL1161585

PubChem CID: 10476772

Max Phase: Preclinical

Molecular Formula: C16H24N6O5S

Molecular Weight: 412.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CSCC[C@H](N)C(=O)OC[C@H]1O[C@@H](Cn2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C16H24N6O5S/c1-28-3-2-8(17)16(25)26-5-10-13(24)12(23)9(27-10)4-22-7-21-11-14(18)19-6-20-15(11)22/h6-10,12-13,23-24H,2-5,17H2,1H3,(H2,18,19,20)/t8-,9-,10+,12-,13+/m0/s1

Standard InChI Key:  HQXDQVBDUIILNZ-VKISENBKSA-N

Alternative Forms

1. Parent:

   

   ALA1161585

   [(2R,3S,4R,5S)-5-[(6-aminopurin-9-yl)methyl]-3,4-dihydroxyoxolan-2-yl]methyl (2S)-2-amino-4-methylsulfanylbutanoate

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: 412.47

Molecular Weight (Monoisotopic): 412.1529

AlogP: -1.48

#Rotatable Bonds: 8

Polar Surface Area: 171.63

Molecular Species: NEUTRAL

HBA: 12

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.78

CX Basic pKa: 7.37

CX LogP: -1.62

CX LogD: -1.91

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.37

Np Likeness Score: 0.39

References

1. Lee J, Kang SU, Kim SY, Kim SE, Kang MK, Jo YJ, Kim S..  (2001)  Ester and hydroxamate analogues of methionyl and isoleucyl adenylates as inhibitors of methionyl-tRNA and isoleucyl-tRNA synthetases.,  11  (8): [PMID:11327600] [10.1016/s0960-894x(01)00095-6]

2. Wróblewski AE, Głowacka IE, Piotrowska DG..  (2016)  1'-Homonucleosides and their structural analogues: A review.,  118  [PMID:27128178] [10.1016/j.ejmech.2016.04.034]

3. Serpi M, Ferrari V, Pertusati F..  (2016)  Nucleoside Derived Antibiotics to Fight Microbial Drug Resistance: New Utilities for an Established Class of Drugs?,  59  (23): [PMID:27607900] [10.1021/acs.jmedchem.6b00325]

Source

Source(1):

• Scientific Literature