ID: ALA579882

Max Phase: Preclinical

Molecular Formula: C21H22N4O4S

Molecular Weight: 426.50

Molecule Type: Small molecule

Representations

Synonyms (2): TCMDC-124310 | TCMDC-124310
Synonyms from Alternative Forms(2):

Canonical SMILES:  O=C(Nc1ccc(S(=O)(=O)N2CCCCC2)cc1)c1cc(-c2ccccc2O)n[nH]1

Standard InChI:  InChI=1S/C21H22N4O4S/c26-20-7-3-2-6-17(20)18-14-19(24-23-18)21(27)22-15-8-10-16(11-9-15)30(28,29)25-12-4-1-5-13-25/h2-3,6-11,14,26H,1,4-5,12-13H2,(H,22,27)(H,23,24)

Standard InChI Key:  VHYUALWDIXAVIZ-UHFFFAOYSA-N

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

Properties

Molecular Weight: 426.50

Molecular Weight (Monoisotopic): 426.1362

AlogP: 3.21

#Rotatable Bonds: 5

Polar Surface Area: 115.39

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 8.66

CX Basic pKa: 1.13

CX LogP: 2.92

CX LogD: 2.90

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.58

Np Likeness Score: -1.86

References

1. Gamo FJ, Sanz LM, Vidal J, de Cozar C, Alvarez E, Lavandera JL, Vanderwall DE, Green DV, Kumar V, Hasan S, Brown JR, Peishoff CE, Cardon LR, Garcia-Bustos JF..  (2010)  Thousands of chemical starting points for antimalarial lead identification.,  465  (7296): [PMID:20485427] [10.1038/nature09107]

2. Ferri N, Bernini SK, Corsini A, Clerici F, Erba E, Stragliotto S, Contini A.  (2013)  3-Aryl-N-aminoylsulfonylphenyl-1H-pyrazole-5-carboxamides: a new class of selective Rac inhibitors,  4  (3): [10.1039/C2MD20328F]

3. St. Jude Leishmania screening dataset.,  [10.6019/CHEMBL3433997]

4. Ravez S, Spillier Q, Marteau R, Feron O, Frédérick R..  (2017)  Challenges and Opportunities in the Development of Serine Synthetic Pathway Inhibitors for Cancer Therapy.,  60  (4): [PMID:27959531] [10.1021/acs.jmedchem.6b01167]

5. Zhao JY, Feng KR, Wang F, Zhang JW, Cheng JF, Lin GQ, Gao D, Tian P..  (2021)  A retrospective overview of PHGDH and its inhibitors for regulating cancer metabolism.,  217  [PMID:33756126] [10.1016/j.ejmech.2021.113379]

Source

Source(3):

• Scientific Literature
• GSK Malaria Screening
• St Jude Leishmania Screening