ID: ALA399454

Max Phase: Preclinical

Molecular Formula: C24H27NO5

Molecular Weight: 409.48

Molecule Type: Small molecule

Representations

Synonyms (1): DCB-3503
Synonyms from Alternative Forms(1):

Canonical SMILES:  COc1cc2c3c(c4cc(OC)c(OC)cc4c2cc1OC)[C@H](O)[C@@H]1CCCN1C3

Standard InChI:  InChI=1S/C24H27NO5/c1-27-19-8-13-14-9-20(28-2)22(30-4)11-16(14)23-17(15(13)10-21(19)29-3)12-25-7-5-6-18(25)24(23)26/h8-11,18,24,26H,5-7,12H2,1-4H3/t18-,24+/m0/s1

Standard InChI Key:  JWHWLMNMGLICQZ-MHECFPHRSA-N

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

Properties

Molecular Weight: 409.48

Molecular Weight (Monoisotopic): 409.1889

AlogP: 4.04

#Rotatable Bonds: 4

Polar Surface Area: 60.39

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 13.86

CX Basic pKa: 8.18

CX LogP: 2.85

CX LogD: 2.01

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.66

Np Likeness Score: 0.90

References

1. Gao W, Bussom S, Grill SP, Gullen EA, Hu YC, Huang X, Zhong S, Kaczmarek C, Gutierrez J, Francis S, Baker DC, Yu S, Cheng YC..  (2007)  Structure-activity studies of phenanthroindolizidine alkaloids as potential antitumor agents.,  17  (15): [PMID:17531481] [10.1016/j.bmcl.2007.05.021]

2. 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]

3. PubChem BioAssay data set, 

4. Wang Z, Wei P, Wang L, Wang Q..  (2012)  Design, synthesis, and anti-tobacco mosaic virus (TMV) activity of phenanthroindolizidines and their analogues.,  60  (41): [PMID:23035814] [10.1021/jf303550a]

5. Wen T, Wang Z, Meng X, Wu M, Li Y, Wu X, Zhao L, Wang P, Yin Z, Li-Ling J, Wang Q..  (2014)  Synthesis of novel tylophorine derivatives and evaluation of their anti-inflammatory activity.,  5  (9): [PMID:25221661] [10.1021/ml500255j]

6. Liu Y, Qing L, Meng C, Shi J, Yang Y, Wang Z, Han G, Wang Y, Ding J, Meng LH, Wang Q..  (2017)  6-OH-Phenanthroquinolizidine Alkaloid and Its Derivatives Exert Potent Anticancer Activity by Delaying S Phase Progression.,  60  (7): [PMID:28333459] [10.1021/acs.jmedchem.6b01502]

7. Wang Y, Chen SR, Yang X, Lee KH, Cheng YC..  (2018)  Structure-activity relationships of cryptopleurine analogs with E-ring modifications as anti-hepatitis C virus agents.,  26  (3): [PMID:29317151] [10.1016/j.bmc.2017.12.027]

8. Han G,Qing L,Wu M,Wang Y,Liu Y,Liu X,Wang Z,Ding J,Meng LH,Wang Q.  (2019)  Design, synthesis, and biological activity evaluation of (-)-6-O-desmethylantofine analogues as potent anti-cancer agents.,  27  (14.0): [PMID:31171403] [10.1016/j.bmc.2019.05.030]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays