ID: ALA1173445

Max Phase: Preclinical

Molecular Formula: C29H42N4O5S3

Molecular Weight: 622.88

Molecule Type: Small molecule

Representations

Synonyms (1): Largazole
Synonyms from Alternative Forms(1):

Canonical SMILES:  CCCCCCCC(=O)SCC/C=C/[C@@H]1CC(=O)NCc2nc(cs2)C2=N[C@@](C)(CS2)C(=O)N[C@@H](C(C)C)C(=O)O1

Standard InChI:  InChI=1S/C29H42N4O5S3/c1-5-6-7-8-9-13-24(35)39-14-11-10-12-20-15-22(34)30-16-23-31-21(17-40-23)26-33-29(4,18-41-26)28(37)32-25(19(2)3)27(36)38-20/h10,12,17,19-20,25H,5-9,11,13-16,18H2,1-4H3,(H,30,34)(H,32,37)/b12-10+/t20-,25+,29+/m1/s1

Standard InChI Key:  AXESYCSCGBQJBL-SZPBEECKSA-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: 622.88

Molecular Weight (Monoisotopic): 622.2317

AlogP: 5.03

#Rotatable Bonds: 11

Polar Surface Area: 126.82

Molecular Species: NEUTRAL

HBA: 10

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.36

CX Basic pKa: 1.06

CX LogP: 5.16

CX LogD: 5.16

Aromatic Rings: 1

Heavy Atoms: 41

QED Weighted: 0.20

Np Likeness Score: 1.33

References

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21. Zhang B, Liu J, Gao D, Yu X, Wang J, Lei X..  (2019)  A fluorine scan on the Zn²⁺-binding thiolate side chain of HDAC inhibitor largazole: Synthesis, biological evaluation, and molecular modeling.,  182  [PMID:31505452] [10.1016/j.ejmech.2019.111672]

22. Borgini M, Zamperini C, Poggialini F, Ferrante L, Summa V, Botta M, Fabio RD..  (2020)  Synthesis and Antiproliferative Activity of Nitric Oxide-Donor Largazole Prodrugs.,  11  (5): [PMID:32435394] [10.1021/acsmedchemlett.9b00643]

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Source

Source(1):

• Scientific Literature