ID: ALA231594

Max Phase: Preclinical

Molecular Formula: C23H25NO4

Molecular Weight: 379.46

Molecule Type: Small molecule

Representations

Canonical SMILES:  COc1ccc2c(CN3CCC(CO)CC3)cc3cc4c(cc3c2c1)OCO4

Standard InChI:  InChI=1S/C23H25NO4/c1-26-18-2-3-19-17(12-24-6-4-15(13-25)5-7-24)8-16-9-22-23(28-14-27-22)11-20(16)21(19)10-18/h2-3,8-11,15,25H,4-7,12-14H2,1H3

Standard InChI Key:  GFBRRLPJNPKOEJ-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: 379.46

Molecular Weight (Monoisotopic): 379.1784

AlogP: 3.93

#Rotatable Bonds: 4

Polar Surface Area: 51.16

Molecular Species: BASE

HBA: 5

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 9.20

CX LogP: 3.14

CX LogD: 1.34

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.70

Np Likeness Score: -0.11

References

1. Wei L, Shi Q, Bastow KF, Brossi A, Morris-Natschke SL, Nakagawa-Goto K, Wu TS, Pan SL, Teng CM, Lee KH..  (2007)  Antitumor agents 253. Design, synthesis, and antitumor evaluation of novel 9-substituted phenanthrene-based tylophorine derivatives as potential anticancer agents.,  50  (15): [PMID:17585747] [10.1021/jm061366a]

2. Lin JC, Yang SC, Hong TM, Yu SL, Shi Q, Wei L, Chen HY, Yang PC, Lee KH..  (2009)  Phenanthrene-based tylophorine-1 (PBT-1) inhibits lung cancer cell growth through the Akt and NF-kappaB pathways.,  52  (7): [PMID:19284764] [10.1021/jm801344j]

3. Yang X, Shi Q, Liu YN, Zhao G, Bastow KF, Lin JC, Yang SC, Yang PC, Lee KH..  (2009)  Antitumor agents 268. Design, synthesis, and mechanistic studies of new 9-substituted phenanthrene-based tylophorine analogues as potent cytotoxic agents.,  52  (16): [PMID:19645447] [10.1021/jm9009263]

4. Lee KH..  (2010)  Discovery and development of natural product-derived chemotherapeutic agents based on a medicinal chemistry approach.,  73  (3): [PMID:20187635] [10.1021/np900821e]

5. Chen CY, Yang SC, Lee KH, Yang X, Wei LY, Chow LP, Wang TC, Hong TM, Lin JC, Kuan C, Yang PC..  (2014)  The antitumor agent PBT-1 directly targets HSP90 and hnRNP A2/B1 and inhibits lung adenocarcinoma growth and metastasis.,  57  (3): [PMID:24428777] [10.1021/jm401686b]

6. Xie L, Goto M, Chen X, Morris-Natschke SL, Lee KH..  (2021)  Lead Optimization: Synthesis and Biological Evaluation of PBT-1 Derivatives as Novel Antitumor Agents.,  12  (12.0): [PMID:34917259] [10.1021/acsmedchemlett.1c00505]

Source

Source(1):

• Scientific Literature