(E)-3-(4-Allyloxy-3-hydroxy-phenyl)-2-methyl-N-((3aS,4R,5R,6S,7R,7aR)-4,6,7-trihydroxy-hexahydro-benzo[1,3]dioxol-5-yl)-acrylamide

ID: ALA9301

Chembl Id: CHEMBL9301

PubChem CID: 10024357

Max Phase: Preclinical

Molecular Formula: C20H25NO8

Molecular Weight: 407.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CCOc1ccc(/C=C(\C)C(=O)N[C@@H]2[C@H](O)[C@@H](O)[C@H]3OCO[C@H]3[C@@H]2O)cc1O

Standard InChI:  InChI=1S/C20H25NO8/c1-3-6-27-13-5-4-11(8-12(13)22)7-10(2)20(26)21-14-15(23)17(25)19-18(16(14)24)28-9-29-19/h3-5,7-8,14-19,22-25H,1,6,9H2,2H3,(H,21,26)/b10-7+/t14-,15+,16-,17-,18+,19-/m1/s1

Standard InChI Key:  NGSRLTSVOTUMKD-ZKVKIDQDSA-N

Alternative Forms

1. Parent:

   

   ALA9301

   (E)-N-[(3aS,4R,5R,6S,7R,7aR)-4,6,7-trihydroxy-3a,4,5,6,7,7a-hexahydro-1,3-benzodioxol-5-yl]-3-(3-hydroxy-4-prop-2-enoxyphenyl)-2-methylprop-2-enamide

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: 407.42

Molecular Weight (Monoisotopic): 407.1580

AlogP: -0.32

#Rotatable Bonds: 6

Polar Surface Area: 137.71

Molecular Species: NEUTRAL

HBA: 8

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.79

CX Basic pKa: ┄

CX LogP: 0.18

CX LogD: 0.18

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.32

Np Likeness Score: 0.97

References

1. Hecker SJ, Lilley SC, Werner KM.  (1992)  Hygromycin A: preparation of aminocyclitol analogs defining the minimum functionality required for biological activity,  2  (9): [10.1016/S0960-894X(00)80615-0]

2. Jaynes BH, Cooper CB, Hecker SJ, Blair KT, Elliott NC, Lilley SC, Minich ML, Schicho DL, Werner KM.  (1993)  Synthesis and vitro antibacterial activity of hygromycin a analogs modified at the C4 aryl position,  3  (8): [10.1016/S0960-894X(00)80012-8]

3. Hecker SJ, Lilley SC, Minich ML, Werner KM.  (1993)  Application of hygromycin a structure activity relationships to the antibiotic A201A.,  3  (2): [10.1016/S0960-894X(01)80896-9]

4. Visser MS, Freeman-Cook KD, Brickner SJ, Brighty KE, Le PT, Wade SK, Monahan R, Martinelli GJ, Blair KT, Moore DE..  (2010)  Synthesis and biological evaluation of novel hygromycin A antibacterial agents.,  20  (22): [PMID:20864341] [10.1016/j.bmcl.2010.08.139]

Source

Source(1):

• Scientific Literature