O-2-Amino-6-(methoxyazylene)-2,3,4,6-tetradeoxy-alpha-D-glycero-hex-4-enopyranosyl(1->4)garamine

ID: ALA3245232

PubChem CID: 90672136

Max Phase: Preclinical

Molecular Formula: C20H37N5O8

Molecular Weight: 475.54

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H37N5O8/c1-20(28)8-30-19(14(27)17(20)24-2)33-16-12(23)6-11(22)15(13(16)26)32-18-10(21)5-4-9(31-18)7-25-29-3/h4,7,10-19,24,26-28H,5-6,8,21-23H2,1-3H3/b25-7-/t10-,11+,12-,13+,14-,15-,16+,17-,18-,19-,20+/m1/s1

Standard InChI Key:  YWVAZKXGVMPRHS-NNTVWAHRSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA3245232

   (2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[[(2S,3R)-3-amino-6-[(Z)-methoxyiminomethyl]-3,4-dihydro-2H-pyran-2-yl]oxy]-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol

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

Calculated Properties

Molecular Weight: 475.54

Molecular Weight (Monoisotopic): 475.2642

AlogP: -3.18

#Rotatable Bonds: 7

Polar Surface Area: 209.29

Molecular Species: BASE

HBA: 13

HBD: 7

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 10

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.55

CX Basic pKa: 9.68

CX LogP: -3.51

CX LogD: -9.20

Aromatic Rings: ┄

Heavy Atoms: 33

QED Weighted: 0.14

Np Likeness Score: 1.44

References

1. Davies DH, Mallams AK, Counelis M, Loebenberg D, Moss EL, Waitz JA..  (1978)  Semisynthetic aminoglycoside antibacterials. 6. Synthesis of sisomicin, Antibiotic G-52, and novel 6'-substituted analogues of sisomicin from aminoglycoside 66-40C.,  21  (2): [PMID:413921] [10.1021/jm00200a009]

Source

Source(1):

• Scientific Literature