(5S,8R)-3,8-dimethoxy-2-methyl-5-(5-phenylpentyl)-5,6,7,8-tetrahydroquinolin-4(1H)-one

ID: ALA3799106

Chembl Id: CHEMBL3799106

PubChem CID: 127047094

Max Phase: Preclinical

Molecular Formula: C23H31NO3

Molecular Weight: 369.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1c(C)[nH]c2c(c1=O)[C@@H](CCCCCc1ccccc1)CC[C@H]2OC

Standard InChI:  InChI=1S/C23H31NO3/c1-16-23(27-3)22(25)20-18(14-15-19(26-2)21(20)24-16)13-9-5-8-12-17-10-6-4-7-11-17/h4,6-7,10-11,18-19H,5,8-9,12-15H2,1-3H3,(H,24,25)/t18-,19+/m0/s1

Standard InChI Key:  HDTZPKLRJBGXSO-RBUKOAKNSA-N

Alternative Forms

1. Parent:

   

   ALA3799106

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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: 369.51

Molecular Weight (Monoisotopic): 369.2304

AlogP: 5.06

#Rotatable Bonds: 8

Polar Surface Area: 51.32

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.42

CX Basic pKa:

CX LogP: 4.65

CX LogD: 4.65

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.66

Np Likeness Score: 0.96

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]

3. Liu F, O'Donnell TJ, Park EJ, Kovacs S, Nakamura K, Dave A, Luo Y, Sun R, Wall M, Wongwiwatthananukit S, Silva DK, Williams PG, Pezzuto JM, Chang LC..  (2023)  Anti-inflammatory Quinoline Alkaloids from the Roots of Waltheria indica.,  86  (2.0): [PMID:36746775] [10.1021/acs.jnatprod.2c00861]

Source

Source(1):

• Scientific Literature