(R)-3,6,7-trimethoxy-11,12,13,14,14a,15-hexahydro-9H-dibenzo[f,h]pyrido[1,2-b]isoquinoline

ID: ALA1958071

Chembl Id: CHEMBL1958071

PubChem CID: 46201585

Max Phase: Preclinical

Molecular Formula: C24H27NO3

Molecular Weight: 377.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2c3c(c4cc(OC)c(OC)cc4c2c1)CN1CCCC[C@@H]1C3

Standard InChI:  InChI=1S/C24H27NO3/c1-26-16-7-8-17-18-10-15-6-4-5-9-25(15)14-22(18)21-13-24(28-3)23(27-2)12-20(21)19(17)11-16/h7-8,11-13,15H,4-6,9-10,14H2,1-3H3/t15-/m1/s1

Standard InChI Key:  ANTGAFQZQJMDNP-OAHLLOKOSA-N

Alternative Forms

1. Parent:

   

   ALA1958071

   (14aR)-3,6,7-trimethoxy-11,12,13,14,14a,15-hexahydro-9H-phenanthro[9,10-b]quinolizine

2. Alternative Forms:

   

   ALA1958071

   (14aR)-3,6,7-trimethoxy-11,12,13,14,14a,15-hexahydro-9H-phenanthro[9,10-b]quinolizine;hydrochloride

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: 377.48

Molecular Weight (Monoisotopic): 377.1991

AlogP: 4.93

#Rotatable Bonds: 3

Polar Surface Area: 30.93

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.75

CX LogP: 4.37

CX LogD: 3.86

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.61

Np Likeness Score: 0.39

References

1. Wang Z, Wu M, Wang Y, Li Z, Wang L, Han G, Chen F, Liu Y, Wang K, Zhang A, Meng L, Wang Q..  (2012)  Synthesis and SAR studies of phenanthroindolizidine and phenanthroquinolizidine alkaloids as potent anti-tumor agents.,  51  [PMID:22417638] [10.1016/j.ejmech.2012.02.048]

2. Christodoulou MS, Calogero F, Baumann M, García-Argáez AN, Pieraccini S, Sironi M, Dapiaggi F, Bucci R, Broggini G, Gazzola S, Liekens S, Silvani A, Lahtela-Kakkonen M, Martinet N, Nonell-Canals A, Santamaría-Navarro E, Baxendale IR, Dalla Via L, Passarella D..  (2015)  Boehmeriasin A as new lead compound for the inhibition of topoisomerases and SIRT2.,  92  [PMID:25626146] [10.1016/j.ejmech.2015.01.038]

3. Kumar A, Chauhan S..  (2016)  How much successful are the medicinal chemists in modulation of SIRT1: A critical review.,  119  [PMID:27153347] [10.1016/j.ejmech.2016.04.063]

4. Güzelcan EA, Baxendale IR, Cetin-Atalay R, Baumann M..  (2019)  Synthesis of new derivatives of boehmeriasin A and their biological evaluation in liver cancer.,  166  [PMID:30716712] [10.1016/j.ejmech.2019.01.056]

Source

Source(1):

• Scientific Literature