4-ethyl-17-methyl-11,15-dioxacyclopenta[a]phenanthren-12-one

ID: ALA215797

Chembl Id: CHEMBL215797

PubChem CID: 16083023

Max Phase: Preclinical

Molecular Formula: C18H14O3

Molecular Weight: 278.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1cccc2c1ccc1c3occ(C)c3c(=O)oc21

Standard InChI:  InChI=1S/C18H14O3/c1-3-11-5-4-6-13-12(11)7-8-14-16(13)21-18(19)15-10(2)9-20-17(14)15/h4-9H,3H2,1-2H3

Standard InChI Key:  MEEWKYUFROITOK-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA215797

   6-Ethyl-14-methyl-12,17-dioxatetracyclo[8.7.0.02,7.011,15]heptadeca-1(10),2,4,6,8,11(15),13-heptaen-16-one

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: 278.31

Molecular Weight (Monoisotopic): 278.0943

AlogP: 4.56

#Rotatable Bonds: 1

Polar Surface Area: 43.35

Molecular Species: NEUTRAL

HBA: 3

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 3

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 4.45

CX LogD: 4.45

Aromatic Rings: 4

Heavy Atoms: 21

QED Weighted: 0.38

Np Likeness Score: 0.69

References

1. Wang X, Nakagawa-Goto K, Bastow KF, Don MJ, Lin YL, Wu TS, Lee KH..  (2006)  Antitumor agents. 254. Synthesis and biological evaluation of novel neo-tanshinlactone analogues as potent anti-breast cancer agents.,  49  (18): [PMID:16942038] [10.1021/jm060184d]

2. Dong Y, Shi Q, Liu YN, Wang X, Bastow KF, Lee KH..  (2009)  Antitumor agents. 266. Design, synthesis, and biological evaluation of novel 2-(furan-2-yl)naphthalen-1-ol derivatives as potent and selective antibreast cancer agents.,  52  (11): [PMID:19425534] [10.1021/jm9001567]

3. Dong Y, Shi Q, Pai HC, Peng CY, Pan SL, Teng CM, Nakagawa-Goto K, Yu D, Liu YN, Wu PC, Bastow KF, Morris-Natschke SL, Brossi A, Lang JY, Hsu JL, Hung MC, Lee EY, Lee KH..  (2010)  Antitumor agents. 272. Structure-activity relationships and in vivo selective anti-breast cancer activity of novel neo-tanshinlactone analogues.,  53  (5): [PMID:20148565] [10.1021/jm1000858]

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. Zhang M, Liu J, Wang Y, Wang P, Morris-Natschke S, Lee KH..  (2022)  Molecular hybridization used to design and synthesize neo-tanshinlactone derivatives as PD-1/PD-L1 inhibitors.,  54  [PMID:34954618] [10.1016/j.bmc.2021.116579]

Source

Source(1):

• Scientific Literature