ID: ALA215226

Max Phase: Preclinical

Molecular Formula: C20H40N4O10

Molecular Weight: 496.56

Molecule Type: Small molecule

Representations

Synonyms (1): G418
Synonyms from Alternative Forms(1):

Canonical SMILES:  CN[C@@H]1[C@@H](O)[C@@H](O[C@@H]2[C@@H](O)[C@H](O[C@H]3O[C@H]([C@@H](C)O)[C@@H](O)[C@H](O)[C@H]3N)[C@@H](N)C[C@H]2N)OC[C@]1(C)O

Standard InChI:  InChI=1S/C20H40N4O10/c1-6(25)14-11(27)10(26)9(23)18(32-14)33-15-7(21)4-8(22)16(12(15)28)34-19-13(29)17(24-3)20(2,30)5-31-19/h6-19,24-30H,4-5,21-23H2,1-3H3/t6-,7+,8-,9-,10-,11+,12+,13-,14-,15-,16+,17-,18-,19-,20+/m1/s1

Standard InChI Key:  BRZYSWJRSDMWLG-DJWUNRQOSA-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: 496.56

Molecular Weight (Monoisotopic): 496.2744

AlogP: -5.61

#Rotatable Bonds: 6

Polar Surface Area: 248.39

Molecular Species: BASE

HBA: 14

HBD: 10

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 13

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.39

CX Basic pKa: 9.59

CX LogP: -5.30

CX LogD: -10.24

Aromatic Rings: 0

Heavy Atoms: 34

QED Weighted: 0.16

Np Likeness Score: 1.62

References

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9. De Bruyn T, van Westen GJ, Ijzerman AP, Stieger B, de Witte P, Augustijns PF, Annaert PP..  (2013)  Structure-based identification of OATP1B1/3 inhibitors.,  83  (6): [PMID:23571415] [10.1124/mol.112.084152]

10. Andrioli WJ, Conti R, Araújo MJ, Zanasi R, Cavalcanti BC, Manfrim V, Toledo JS, Tedesco D, de Moraes MO, Pessoa C, Cruz AK, Bertucci C, Sabino J, Nanayakkara DN, Pupo MT, Bastos JK..  (2014)  Mycoleptones A-C and polyketides from the endophyte Mycoleptodiscus indicus.,  77  (1): [PMID:24387625] [10.1021/np4006822]

11. Hamada K, Taguchi A, Kotake M, Aita S, Murakami S, Takayama K, Yakushiji F, Hayashi Y..  (2015)  Structure-Activity Relationship Studies of 3-epi-Deoxynegamycin Derivatives as Potent Readthrough Drug Candidates.,  6  (6): [PMID:26101575] [10.1021/acsmedchemlett.5b00121]

12. Pibiri I,Lentini L,Melfi R,Tutone M,Baldassano S,Ricco Galluzzo P,Di Leonardo A,Pace A.  (2018)  Rescuing the CFTR protein function: Introducing 1,3,4-oxadiazoles as translational readthrough inducing drugs.,  159  [PMID:30278331] [10.1016/j.ejmech.2018.09.057]

Source

Source(1):

• Scientific Literature