(3R,4S)-1-((4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl)-4-((4-chlorophenylthio)methyl)pyrrolidin-3-ol

ID: ALA1230265

Chembl Id: CHEMBL1230265

PubChem CID: 9952319

Max Phase: Preclinical

Molecular Formula: C18H20ClN5OS

Molecular Weight: 389.91

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c(CN3C[C@H](CSc4ccc(Cl)cc4)[C@@H](O)C3)c[nH]c12

Standard InChI:  InChI=1S/C18H20ClN5OS/c19-13-1-3-14(4-2-13)26-9-12-7-24(8-15(12)25)6-11-5-21-17-16(11)22-10-23-18(17)20/h1-5,10,12,15,21,25H,6-9H2,(H2,20,22,23)/t12-,15+/m1/s1

Standard InChI Key:  MZZBHZOHYGEGEE-DOMZBBRYSA-N

Alternative Forms

1. Parent:

   

   ALA1230265

   (3r,4s)-1-[(4-Amino-5h-Pyrrolo[3,2-D]pyrimidin-7-Yl)methyl]-4-{[(4-Chlorophenyl)sulfanyl]methyl}pyrrolidin-3-Ol

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: 389.91

Molecular Weight (Monoisotopic): 389.1077

AlogP: 2.78

#Rotatable Bonds: 5

Polar Surface Area: 91.06

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.47

CX Basic pKa: 8.26

CX LogP: 2.42

CX LogD: 1.51

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.58

Np Likeness Score: -0.80

References

1. Gutierrez JA, Crowder T, Rinaldo-Matthis A, Ho MC, Almo SC, Schramm VL..  (2009)  Transition state analogs of 5'-methylthioadenosine nucleosidase disrupt quorum sensing.,  5  (4): [PMID:19270684] [10.1038/nchembio.153]

2. Harijan RK, Hoff O, Ducati RG, Firestone RS, Hirsch BM, Evans GB, Schramm VL, Tyler PC..  (2019)  Selective Inhibitors of Helicobacter pylori Methylthioadenosine Nucleosidase and Human Methylthioadenosine Phosphorylase.,  62  (7): [PMID:30860833] [10.1021/acs.jmedchem.8b01642]

Source

Source(1):

• Scientific Literature