(5S,8R)-8-hydroxy-3-methoxy-2-methyl-5-octyl-5,6,7,8-tetrahydroquinolin-4(1H)-one

ID: ALA3799490

Chembl Id: CHEMBL3799490

PubChem CID: 6426681

Max Phase: Preclinical

Molecular Formula: C19H31NO3

Molecular Weight: 321.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCC[C@H]1CC[C@@H](O)c2[nH]c(C)c(OC)c(=O)c21

Standard InChI:  InChI=1S/C19H31NO3/c1-4-5-6-7-8-9-10-14-11-12-15(21)17-16(14)18(22)19(23-3)13(2)20-17/h14-15,21H,4-12H2,1-3H3,(H,20,22)/t14-,15+/m0/s1

Standard InChI Key:  CWYBYEMWRGFCLL-LSDHHAIUSA-N

Alternative Forms

1. Parent:

   

   ALA3799490

   (5S,8R)-8-hydroxy-3-methoxy-2-methyl-5-octyl-5,6,7,8-tetrahydro-1H-quinolin-4-one

Molecule Features

Natural Product: Yes

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: 321.46

Molecular Weight (Monoisotopic): 321.2304

AlogP: 4.35

#Rotatable Bonds: 8

Polar Surface Area: 62.32

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 11.43

CX Basic pKa:

CX LogP: 3.77

CX LogD: 3.77

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.70

Np Likeness Score: 1.18

References

1. Cretton S, Dorsaz S, Azzollini A, Favre-Godal Q, Marcourt L, Ebrahimi SN, Voinesco F, Michellod E, Sanglard D, Gindro K, Wolfender JL, Cuendet M, Christen P..  (2016)  Antifungal Quinoline Alkaloids from Waltheria indica.,  79  (2): [PMID:26848627] [10.1021/acs.jnatprod.5b00896]

2. Cretton S,Kaiser M,Karimou S,Ebrahimi SN,Mäser P,Cuendet M,Christen P.  (2020)  Pyridine-4(1H)-one Alkaloids from Waltheria indica as Antitrypanosomatid Agents.,  83  (11): [PMID:33095014] [10.1021/acs.jnatprod.0c00671]

Source

Source(1):

• Scientific Literature