1,2,3-Trimethoxy-6-methylene-9-methylsulfanyl-5,6-dihydro-cyclohepta[a]naphthalen-8-one

ID: ALA153629

Chembl Id: CHEMBL153629

PubChem CID: 372992

Max Phase: Preclinical

Molecular Formula: C20H20O4S

Molecular Weight: 356.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1Cc2cc(OC)c(OC)c(OC)c2-c2ccc(SC)c(=O)cc21

Standard InChI:  InChI=1S/C20H20O4S/c1-11-8-12-9-16(22-2)19(23-3)20(24-4)18(12)13-6-7-17(25-5)15(21)10-14(11)13/h6-7,9-10H,1,8H2,2-5H3

Standard InChI Key:  FUYPJTCITNJHCZ-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA153629

   Antineoplastic-648780

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: 356.44

Molecular Weight (Monoisotopic): 356.1082

AlogP: 4.03

#Rotatable Bonds: 4

Polar Surface Area: 44.76

Molecular Species: NEUTRAL

HBA: 5

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 2.84

CX LogP: 3.26

CX LogD: 3.26

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.77

Np Likeness Score: 0.84

References

1. Sun L, McPhail AT, Hamel E, Lin CM, Hastie SB, Chang JJ, Lee KH..  (1993)  Antitumor agents. 139. Synthesis and biological evaluation of thiocolchicine analogs 5,6-dihydro-6(S)-(acyloxy)- and 5,6-dihydro-6(S)-[(aroyloxy)methyl]-1,2,3-trimethoxy-9-(methylthio)-8H- cyclohepta[a]naphthalen-8-ones as novel cytotoxic and antimitotic agents.,  36  (5): [PMID:8496935] [10.1021/jm00057a004]

2. PubChem BioAssay data set, 

3. Gracheva IA,Shchegravina ES,Schmalz HG,Beletskaya IP,Fedorov AY.  (2020)  Colchicine Alkaloids and Synthetic Analogues: Current Progress and Perspectives.,  63  (19.0): [PMID:32432867] [10.1021/acs.jmedchem.0c00222]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays