ID: ALA606552

Max Phase: Preclinical

Molecular Formula: C12H25N3O7

Molecular Weight: 323.35

Molecule Type: Small molecule

Representations

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

Canonical SMILES:  N[C@H]1[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](N)C[C@@H]2N)O[C@H](CO)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C12H25N3O7/c13-3-1-4(14)11(10(20)7(3)17)22-12-6(15)9(19)8(18)5(2-16)21-12/h3-12,16-20H,1-2,13-15H2/t3-,4+,5-,6-,7+,8-,9-,10-,11-,12-/m1/s1

Standard InChI Key:  JGSMDVGTXBPWIM-HKEUSBCWSA-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: 323.35

Molecular Weight (Monoisotopic): 323.1693

AlogP: -5.08

#Rotatable Bonds: 3

Polar Surface Area: 197.67

Molecular Species: BASE

HBA: 10

HBD: 8

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 11

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.64

CX Basic pKa: 9.15

CX LogP: -5.18

CX LogD: -8.18

Aromatic Rings: 0

Heavy Atoms: 22

QED Weighted: 0.25

Np Likeness Score: 2.02

References

1. Cashman DJ, Rife JP, Kellogg GE..  (2001)  Which aminoglycoside ring is most important for binding? A hydropathic analysis of gentamicin, paromomycin, and analogues.,  11  (2): [PMID:11206440] [10.1016/s0960-894x(00)00615-6]

2. Nudelman I, Glikin D, Smolkin B, Hainrichson M, Belakhov V, Baasov T..  (2010)  Repairing faulty genes by aminoglycosides: development of new derivatives of geneticin (G418) with enhanced suppression of diseases-causing nonsense mutations.,  18  (11): [PMID:20409719] [10.1016/j.bmc.2010.03.060]

3. Zimmermann L, Bussière A, Ouberai M, Baussanne I, Jolivalt C, Mingeot-Leclercq MP, Décout JL..  (2013)  Tuning the antibacterial activity of amphiphilic neamine derivatives and comparison to paromamine homologues.,  56  (19): [PMID:24083676] [10.1021/jm401148j]

4. Sabbavarapu NM, Shavit M, Degani Y, Smolkin B, Belakhov V, Baasov T..  (2016)  Design of Novel Aminoglycoside Derivatives with Enhanced Suppression of Diseases-Causing Nonsense Mutations.,  7  (4): [PMID:27096052] [10.1021/acsmedchemlett.6b00006]

Source

Source(1):

• Scientific Literature