(S)-N-(1-hydroxy-4-methylpentan-2-yl)-6-methoxy-9-oxo-9H-xanthene-2-carboxamide

ID: ALA2164781

Chembl Id: CHEMBL2164781

PubChem CID: 71451562

Max Phase: Preclinical

Molecular Formula: C21H23NO5

Molecular Weight: 369.42

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H23NO5/c1-12(2)8-14(11-23)22-21(25)13-4-7-18-17(9-13)20(24)16-6-5-15(26-3)10-19(16)27-18/h4-7,9-10,12,14,23H,8,11H2,1-3H3,(H,22,25)/t14-/m0/s1

Standard InChI Key:  OFPORPUGEMWONW-AWEZNQCLSA-N

Alternative Forms

1. Parent:

   

   ALA2164781

   N-[(2S)-1-hydroxy-4-methylpentan-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: 369.42

Molecular Weight (Monoisotopic): 369.1576

AlogP: 3.09

#Rotatable Bonds: 6

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: 2.86

CX LogD: 2.86

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.65

Np Likeness Score: -0.02

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