ID: ALA3138729

Max Phase: Preclinical

Molecular Formula: C20H37N3O13

Molecular Weight: 527.52

Molecule Type: Small molecule

Representations

Canonical SMILES:  CN[C@H]1C[C@@H](N)[C@H](O)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H]3O[C@@]4(O[C@H]23)O[C@H]([C@H](N)CO)[C@H](O)[C@H](O)[C@H]4O)[C@@H]1O

Standard InChI:  InChI=1S/C20H37N3O13/c1-23-7-2-5(21)9(26)15(10(7)27)33-19-17-16(11(28)8(4-25)32-19)35-20(36-17)18(31)13(30)12(29)14(34-20)6(22)3-24/h5-19,23-31H,2-4,21-22H2,1H3/t5-,6-,7+,8-,9+,10-,11+,12-,13+,14-,15-,16-,17+,18-,19+,20+/m1/s1

Standard InChI Key:  GRRNUXAQVGOGFE-OPDYUDDYSA-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: 527.52

Molecular Weight (Monoisotopic): 527.2326

AlogP: -7.27

#Rotatable Bonds: 6

Polar Surface Area: 272.06

Molecular Species: BASE

HBA: 16

HBD: 11

#RO5 Violations: 3

HBA (Lipinski): 16

HBD (Lipinski): 13

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.40

CX Basic pKa: 9.52

CX LogP: -6.37

CX LogD: -10.09

Aromatic Rings: 0

Heavy Atoms: 36

QED Weighted: 0.15

Np Likeness Score: 1.88

References

1. Allen NE, Alborn WE, Kirst HA, Toth JE..  (1987)  Comparison of aminoglycoside antibiotics with respect to uptake and lethal activity in Escherichia coli.,  30  (2): [PMID:3543366] [10.1021/jm00385a015]

2. McGaha SM, Champney WS..  (2007)  Hygromycin B inhibition of protein synthesis and ribosome biogenesis in Escherichia coli.,  51  (2): [PMID:17043113] [10.1128/aac.01116-06]

3. Wachino J, Shibayama K, Kurokawa H, Kimura K, Yamane K, Suzuki S, Shibata N, Ike Y, Arakawa Y..  (2007)  Novel plasmid-mediated 16S rRNA m1A1408 methyltransferase, NpmA, found in a clinically isolated Escherichia coli strain resistant to structurally diverse aminoglycosides.,  51  (12): [PMID:17875999] [10.1128/aac.00926-07]

4. Kogure T, Shimada R, Ishikawa J, Yazawa K, Brown JM, Mikami Y, Gonoi T..  (2010)  Homozygous triplicate mutations in three 16S rRNA genes responsible for high-level aminoglycoside resistance in Nocardia farcinica clinical isolates from a Canada-wide bovine mastitis epizootic.,  54  (6): [PMID:20308368] [10.1128/aac.00021-10]

5. Puri N, Prakash O, Manoharlal R, Sharma M, Ghosh I, Prasad R..  (2010)  Analysis of physico-chemical properties of substrates of ABC and MFS multidrug transporters of pathogenic Candida albicans.,  45  (11): [PMID:20739103] [10.1016/j.ejmech.2010.07.050]

6. 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]

7. Oya A, Tanaka N, Kusama T, Kim SY, Hayashi S, Kojoma M, Hishida A, Kawahara N, Sakai K, Gonoi T, Kobayashi J..  (2015)  Prenylated benzophenones from Triadenum japonicum.,  78  (2): [PMID:25602977] [10.1021/np500827h]

Source

Source(1):

• Scientific Literature