ID: ALA241106

Max Phase: Preclinical

Molecular Formula: C42H62N2O7S

Molecular Weight: 739.03

Molecule Type: Small molecule

Representations

Canonical SMILES:  CNC(=O)O[C@@H](CC(C)C)c1nc([C@H]2OC(=O)/C(C)=C/C/C(C)=C/[C@@H](O)[C@@H](C)/C=C(C)\C=C(C)/C=C/[C@@H](O)[C@H](C)[C@H](OC)/C(C)=C/C=C/[C@@H]2C)cs1

Standard InChI:  InChI=1S/C42H62N2O7S/c1-25(2)20-37(50-42(48)43-11)40-44-34(24-52-40)39-30(7)15-13-14-29(6)38(49-12)33(10)35(45)19-17-26(3)21-28(5)22-32(9)36(46)23-27(4)16-18-31(8)41(47)51-39/h13-15,17-19,21-25,30,32-33,35-39,45-46H,16,20H2,1-12H3,(H,43,48)/b15-13+,19-17+,26-21-,27-23+,28-22-,29-14+,31-18+/t30-,32-,33-,35+,36+,37-,38+,39-/m0/s1

Standard InChI Key:  CUYVVUGLFUIZAZ-YYRKZZGWSA-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: 739.03

Molecular Weight (Monoisotopic): 738.4278

AlogP: 9.06

#Rotatable Bonds: 6

Polar Surface Area: 127.21

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa:

CX Basic pKa: 0.78

CX LogP: 8.25

CX LogD: 8.25

Aromatic Rings: 1

Heavy Atoms: 52

QED Weighted: 0.19

Np Likeness Score: 1.56

References

1. Menche D, Hassfeld J, Sasse F, Huss M, Wieczorek H..  (2007)  Design, synthesis, and biological evaluation of novel analogues of archazolid: a highly potent simplified V-ATPase inhibitor.,  17  (6): [PMID:17239591] [10.1016/j.bmcl.2006.12.073]

2. Horstmann N, Essig S, Bockelmann S, Wieczorek H, Huss M, Sasse F, Menche D..  (2011)  Archazolid A-15-O-β-D-glucopyranoside and iso-archazolid B: potent V-ATPase inhibitory polyketides from the myxobacteria Cystobacter violaceus and Archangium gephyra.,  74  (5): [PMID:21513292] [10.1021/np200036v]

3. Persch E, Basile T, Bockelmann S, Huss M, Wieczorek H, Carlomagno T, Menche D..  (2012)  Synthesis and biological evaluation of a water-soluble derivative of the potent V-ATPase inhibitor archazolid.,  22  (24): [PMID:23122818] [10.1016/j.bmcl.2012.09.081]

4. Kapoor S, Waldmann H, Ziegler S..  (2016)  Novel approaches to map small molecule-target interactions.,  24  (15): [PMID:27240466] [10.1016/j.bmc.2016.05.020]

5. Scheeff S, Rivière S, Ruiz J, Abdelrahman A, Schulz-Fincke AC, Köse M, Tiburcy F, Wieczorek H, Gütschow M, Müller CE, Menche D..  (2020)  Synthesis of Novel Potent Archazolids: Pharmacology of an Emerging Class of Anticancer Drugs.,  63  (4): [PMID:31990540] [10.1021/acs.jmedchem.9b01887]

Source

Source(1):

• Scientific Literature