(S)-N-(1-hydroxy-3-methylbutan-2-yl)-6-methoxy-9-oxo-9H-xanthene-2-carboxamide

ID: ALA2164780

Chembl Id: CHEMBL2164780

PubChem CID: 71455102

Max Phase: Preclinical

Molecular Formula: C20H21NO5

Molecular Weight: 355.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2c(=O)c3cc(C(=O)N[C@H](CO)C(C)C)ccc3oc2c1

Standard InChI:  InChI=1S/C20H21NO5/c1-11(2)16(10-22)21-20(24)12-4-7-17-15(8-12)19(23)14-6-5-13(25-3)9-18(14)26-17/h4-9,11,16,22H,10H2,1-3H3,(H,21,24)/t16-/m1/s1

Standard InChI Key:  HEVQDFFDQMAEAG-MRXNPFEDSA-N

Alternative Forms

1. Parent:

   

   ALA2164780

   N-[(2S)-1-hydroxy-3-methylbutan-2-yl]-6-methoxy-9-oxoxanthene-2-carboxamide

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: 355.39

Molecular Weight (Monoisotopic): 355.1420

AlogP: 2.70

#Rotatable Bonds: 5

Polar Surface Area: 88.77

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.49

CX LogD: 2.49

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.69

Np Likeness Score: -0.01

References

1. Fernandes C, Oliveira L, Tiritan ME, Leitao L, Pozzi A, Noronha-Matos JB, Correia-de-Sá P, Pinto MM..  (2012)  Synthesis of new chiral xanthone derivatives acting as nerve conduction blockers in the rat sciatic nerve.,  55  [PMID:22819594] [10.1016/j.ejmech.2012.06.049]

2. Fernandes C, Masawang K, Tiritan ME, Sousa E, de Lima V, Afonso C, Bousbaa H, Sudprasert W, Pedro M, Pinto MM..  (2014)  New chiral derivatives of xanthones: synthesis and investigation of enantioselectivity as inhibitors of growth of human tumor cell lines.,  22  (3): [PMID:24411197] [10.1016/j.bmc.2013.12.042]

Source

Source(1):

• Scientific Literature