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

ID: ALA100750

Chembl Id: CHEMBL100750

PubChem CID: 44332084

Max Phase: Preclinical

Molecular Formula: C20H25NO7

Molecular Weight: 391.42

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)cc1

Standard InChI:  InChI=1S/C20H25NO7/c1-3-8-26-13-6-4-12(5-7-13)9-11(2)20(25)21-14-15(22)17(24)19-18(16(14)23)27-10-28-19/h3-7,9,14-19,22-24H,1,8,10H2,2H3,(H,21,25)/b11-9+/t14-,15+,16-,17-,18+,19-/m1/s1

Standard InChI Key:  XUBGGMQPGQRZMO-FLUYPTESSA-N

Alternative Forms

1. Parent:

   

   ALA100750

   (E)-N-[(3aS,4R,5R,6S,7R,7aR)-4,6,7-trihydroxy-3a,4,5,6,7,7a-hexahydro-1,3-benzodioxol-5-yl]-2-methyl-3-(4-prop-2-enoxyphenyl)prop-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: 391.42

Molecular Weight (Monoisotopic): 391.1631

AlogP: -0.02

#Rotatable Bonds: 6

Polar Surface Area: 117.48

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.72

CX Basic pKa: ┄

CX LogP: 0.48

CX LogD: 0.48

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.40

Np Likeness Score: 0.67

References

1. 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]

Source

Source(1):

• Scientific Literature