ID: ALA2171791

Max Phase: Preclinical

Molecular Formula: C20H19N3O2

Molecular Weight: 333.39

Molecule Type: Small molecule

Representations

Synonyms (1): 4-Methoxyevodiamine
Synonyms from Alternative Forms(1):

Canonical SMILES:  COc1cccc2c1C(=O)N1CCc3c([nH]c4ccccc34)C1N2C

Standard InChI:  InChI=1S/C20H19N3O2/c1-22-15-8-5-9-16(25-2)17(15)20(24)23-11-10-13-12-6-3-4-7-14(12)21-18(13)19(22)23/h3-9,19,21H,10-11H2,1-2H3

Standard InChI Key:  AVLFPUHBJIXSIY-UHFFFAOYSA-N

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

Properties

Molecular Weight: 333.39

Molecular Weight (Monoisotopic): 333.1477

AlogP: 3.32

#Rotatable Bonds: 1

Polar Surface Area: 48.57

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 3.16

CX LogD: 3.16

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.74

Np Likeness Score: 0.28

References

1. Dong G, Wang S, Miao Z, Yao J, Zhang Y, Guo Z, Zhang W, Sheng C..  (2012)  New tricks for an old natural product: discovery of highly potent evodiamine derivatives as novel antitumor agents by systemic structure-activity relationship analysis and biological evaluations.,  55  (17): [PMID:22867019] [10.1021/jm300605m]

2. Zhang T,Lai Z,Yuan S,Huang YY,Dong G,Sheng C,Ke H,Luo HB.  (2020)  Discovery of Evodiamine Derivatives as Highly Selective PDE5 Inhibitors Targeting a Unique Allosteric Pocket.,  63  (17): [PMID:32794708] [10.1021/acs.jmedchem.0c00983]

Source

Source(1):

• Scientific Literature