(Z)-3-[4-((2S,3S,4S,5S)-5-Acetyl-3,4-dihydroxy-tetrahydro-furan-2-yloxy)-3-hydroxy-phenyl]-N-((3aS,4R,5R,6S,7R,7aR)-6,7-dihydroxy-4-methoxy-hexahydro-benzo[1,3]dioxol-5-yl)-2-methyl-acrylamide

ID: ALA7764

Chembl Id: CHEMBL7764

PubChem CID: 44263878

Max Phase: Preclinical

Molecular Formula: C24H31NO12

Molecular Weight: 525.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO[C@@H]1[C@H](NC(=O)/C(C)=C\c2ccc(O[C@@H]3O[C@H](C(C)=O)[C@@H](O)[C@@H]3O)c(O)c2)[C@H](O)[C@@H](O)[C@H]2OCO[C@H]21

Standard InChI:  InChI=1S/C24H31NO12/c1-9(23(32)25-14-15(28)16(29)21-22(20(14)33-3)35-8-34-21)6-11-4-5-13(12(27)7-11)36-24-18(31)17(30)19(37-24)10(2)26/h4-7,14-22,24,27-31H,8H2,1-3H3,(H,25,32)/b9-6-/t14-,15+,16-,17+,18+,19-,20-,21-,22+,24-/m1/s1

Standard InChI Key:  PCYRQQOYBAIXSI-IVYMTVJHSA-N

Alternative Forms

1. Parent:

   

   ALA7764

   (Z)-N-[(3aS,4R,5R,6S,7R,7aR)-6,7-dihydroxy-4-methoxy-3a,4,5,6,7,7a-hexahydro-1,3-benzodioxol-5-yl]-3-[4-[(2S,3S,4S,5S)-5-acetyl-3,4-dihydroxyoxolan-2-yl]oxy-3-hydroxyphenyl]-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: 525.51

Molecular Weight (Monoisotopic): 525.1846

AlogP: -1.81

#Rotatable Bonds: 7

Polar Surface Area: 193.47

Molecular Species: NEUTRAL

HBA: 12

HBD: 6

#RO5 Violations: 3

HBA (Lipinski): 13

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 9.66

CX Basic pKa: ┄

CX LogP: -1.04

CX LogD: -1.04

Aromatic Rings: 1

Heavy Atoms: 37

QED Weighted: 0.22

Np Likeness Score: 1.50

References

1. Hecker SJ, Lilley SC, Minich ML, Werner KM.  (1992)  Semisynthetic modification of hygromycin A. 3. synthesis and antibacterial activity of aminocyclitol analogs.,  2  (9): [10.1016/S0960-894X(00)80609-5]

Source

Source(1):

• Scientific Literature