ID: ALA1673205

Max Phase: Preclinical

Molecular Formula: C40H44N2O18

Molecular Weight: 840.79

Molecule Type: Small molecule

Representations

Synonyms (2): Pradimicin A | Pradimicin-A
Synonyms from Alternative Forms(2):

Canonical SMILES:  CN[C@@H]1[C@H](O[C@@H]2OC[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](O[C@H]2c3cc(C)c(C(=O)N[C@H](C)C(=O)O)c(O)c3-c3c(cc4c(c3O)C(=O)c3cc(OC)cc(O)c3C4=O)[C@@H]2O)O[C@@H]1C

Standard InChI:  InChI=1S/C40H44N2O18/c1-11-6-18-24(31(49)21(11)37(53)42-12(2)38(54)55)23-16(9-17-25(32(23)50)28(46)15-7-14(56-5)8-19(43)22(15)27(17)45)29(47)35(18)59-40-34(52)36(26(41-4)13(3)58-40)60-39-33(51)30(48)20(44)10-57-39/h6-9,12-13,20,26,29-30,33-36,39-41,43-44,47-52H,10H2,1-5H3,(H,42,53)(H,54,55)/t12-,13-,20-,26+,29+,30+,33-,34-,35+,36+,39+,40+/m1/s1

Standard InChI Key:  WPICPWIIIBCXCV-NJGWPHBESA-N

Molecule Features

Natural Product: Yes

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: 840.79

Molecular Weight (Monoisotopic): 840.2589

AlogP: -0.61

#Rotatable Bonds: 9

Polar Surface Area: 320.56

Molecular Species: ZWITTERION

HBA: 18

HBD: 11

#RO5 Violations: 3

HBA (Lipinski): 20

HBD (Lipinski): 11

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.04

CX Basic pKa: 8.97

CX LogP: -0.52

CX LogD: -1.10

Aromatic Rings: 3

Heavy Atoms: 60

QED Weighted: 0.10

Np Likeness Score: 1.53

References

1. Balzarini J, François KO, Van Laethem K, Hoorelbeke B, Renders M, Auwerx J, Liekens S, Oki T, Igarashi Y, Schols D..  (2010)  Pradimicin S, a highly soluble nonpeptidic small-size carbohydrate-binding antibiotic, is an anti-HIV drug lead for both microbicidal and systemic use.,  54  (4): [PMID:20047920] [10.1128/aac.01347-09]

2. Lozano V, Aguado L, Hoorelbeke B, Renders M, Camarasa MJ, Schols D, Balzarini J, San-Félix A, Pérez-Pérez MJ..  (2011)  Targeting HIV entry through interaction with envelope glycoprotein 120 (gp120): synthesis and antiviral evaluation of 1,3,5-triazines with aromatic amino acids.,  54  (15): [PMID:21749165] [10.1021/jm200560r]

3. Nakagawa Y, Doi T, Takegoshi K, Igarashi Y, Ito Y..  (2012)  Solid-state NMR analysis of calcium and d-mannose binding of BMY-28864, a water-soluble analogue of pradimicin A.,  22  (2): [PMID:22196119] [10.1016/j.bmcl.2011.11.106]

4. Rivero-Buceta E, Carrero P, Doyagüez EG, Madrona A, Quesada E, Camarasa MJ, Peréz-Pérez MJ, Leyssen P, Paeshuyse J, Balzarini J, Neyts J, San-Félix A..  (2015)  Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors.,  92  [PMID:25617695] [10.1016/j.ejmech.2015.01.033]

5. Nakagawa Y, Watanabe Y, Igarashi Y, Ito Y, Ojika M..  (2015)  Pradimicin A, a D-mannose-binding antibiotic, binds pyranosides of L-fucose and L-galactose in a calcium-sensitive manner.,  25  (15): [PMID:26045034] [10.1016/j.bmcl.2015.05.021]

6. Rivero-Buceta E, Doyagüez EG, Colomer I, Quesada E, Mathys L, Noppen S, Liekens S, Camarasa MJ, Pérez-Pérez MJ, Balzarini J, San-Félix A..  (2015)  Tryptophan dendrimers that inhibit HIV replication, prevent virus entry and bind to the HIV envelope glycoproteins gp120 and gp41.,  106  [PMID:26513643] [10.1016/j.ejmech.2015.10.031]

7. Rivero-Buceta E, Carrero P, Casanova E, Doyagüez EG, Madrona A, Quesada E, Peréz-Pérez MJ, Mateos R, Bravo L, Mathys L, Noppen S, Kiselev E, Marchand C, Pommier Y, Liekens S, Balzarini J, Camarasa MJ, San-Félix A..  (2015)  Anti-HIV-1 activity of a tripodal receptor that recognizes mannose oligomers.,  106  [PMID:26540494] [10.1016/j.ejmech.2015.10.027]

8. Martínez-Gualda B, Sun L, Martí-Marí O, Noppen S, Abdelnabi R, Bator CM, Quesada E, Delang L, Mirabelli C, Lee H, Schols D, Neyts J, Hafenstein S, Camarasa MJ, Gago F, San-Félix A..  (2020)  Scaffold Simplification Strategy Leads to a Novel Generation of Dual Human Immunodeficiency Virus and Enterovirus-A71 Entry Inhibitors.,  63  (1): [PMID:31809045] [10.1021/acs.jmedchem.9b01737]

9. Liu W,Yuan L,Wang S.  (2020)  Recent Progress in the Discovery of Antifungal Agents Targeting the Cell Wall.,  63  (21.0): [PMID:32692166] [10.1021/acs.jmedchem.0c00748]

10. Martí-Marí O, Martínez-Gualda B, de la Puente-Secades S, Mills A, Quesada E, Abdelnabi R, Sun L, Boonen A, Noppen S, Neyts J, Schols D, Camarasa MJ, Gago F, San-Félix A..  (2021)  Double Arylation of the Indole Side Chain of Tri- and Tetrapodal Tryptophan Derivatives Renders Highly Potent HIV-1 and EV-A71 Entry Inhibitors†.,  64  (14.0): [PMID:34229438] [10.1021/acs.jmedchem.1c00315]

11. Martí-Marí O, Martínez-Gualda B, Fernández-Barahona I, Mills A, Abdelnabi R, Noppen S, Neyts J, Schols D, Camarasa MJ, Herranz F, Gago F, San-Félix A..  (2022)  Organotropic dendrons with high potency as HIV-1, HIV-2 and EV-A71 cell entry inhibitors.,  237  [PMID:35512567] [10.1016/j.ejmech.2022.114414]

12. Miyanishi W, Ojika M, Akase D, Aida M, Igarashi Y, Ito Y, Nakagawa Y..  (2021)  d-Mannose binding, aggregation property, and antifungal activity of amide derivatives of pradimicin A.,  55  [PMID:34973516] [10.1016/j.bmc.2021.116590]

Source

Source(1):

• Scientific Literature