ID: ALA19954

Max Phase: Preclinical

Molecular Formula: C18H16N2O

Molecular Weight: 276.34

Molecule Type: Small molecule

Representations

Synonyms (1): NSC-69187
Synonyms from Alternative Forms(1):

Canonical SMILES:  COc1ccc2[nH]c3c(C)c4ccncc4c(C)c3c2c1

Standard InChI:  InChI=1S/C18H16N2O/c1-10-15-9-19-7-6-13(15)11(2)18-17(10)14-8-12(21-3)4-5-16(14)20-18/h4-9,20H,1-3H3

Standard InChI Key:  BKRMCDAOAQWNTG-UHFFFAOYSA-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: 276.34

Molecular Weight (Monoisotopic): 276.1263

AlogP: 4.49

#Rotatable Bonds: 1

Polar Surface Area: 37.91

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 5.88

CX LogP: 3.73

CX LogD: 3.72

Aromatic Rings: 4

Heavy Atoms: 21

QED Weighted: 0.56

Np Likeness Score: 0.27

References

1. Ducrocq C, Wendling F, Tourbez-Perrin M, Rivalle C, Tambourin P, Pochon F, Bisagni E, Chermann JC..  (1980)  Structure-activity relationships in a series of newly synthesized 1-amino-substituted ellipticine derivatives.,  23  (11): [PMID:7452670] [10.1021/jm00185a012]

2. Acton EM, Narayanan VL, Risbood PA, Shoemaker RH, Vistica DT, Boyd MR..  (1994)  Anticancer specificity of some ellipticinium salts against human brain tumors in vitro.,  37  (14): [PMID:8035425] [10.1021/jm00040a010]

3. Auclair C, Paoletti C..  (1981)  Bioactivation of the antitumor drugs 9-hydroxyellipticine and derivatives by a peroxidase-hydrogen peroxide system.,  24  (3): [PMID:7265115] [10.1021/jm00135a010]

4. Delbarre A, Oberlin R, Roques BP, Borgna JL, Rochefort H, Le Pecq JB, Jacquemin-Sablon A..  (1985)  Ellipticine derivatives with an affinity to the estrogen receptor, an approach to develop intercalating drugs with a specific effect on the hormone-dependent breast cancer.,  28  (6): [PMID:4009597] [10.1021/jm00383a011]

5. Vendôme J, Letard S, Martin F, Svinarchuk F, Dubreuil P, Auclair C, Le Bret M..  (2005)  Molecular modeling of wild-type and D816V c-Kit inhibition based on ATP-competitive binding of ellipticine derivatives to tyrosine kinases.,  48  (20): [PMID:16190746] [10.1021/jm050231m]

6. Perdue RE..  (1982)  KB cell culture I. Role in discovery of antitumor agents from higher plants.,  45  (4): [PMID:7130986] [10.1021/np50022a010]

7. Carroll AR, Addepalli R, Fechner G, Smith J, Guymer GP, Forster PI, Quinn RJ..  (2008)  Alkaloids from the Australian rainforest tree Ochrosia moorei.,  71  (6): [PMID:18412397] [10.1021/np070655e]

8. Tan GT, Pezzuto JM, Kinghorn AD, Hughes SH..  (1991)  Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.,  54  (1): [PMID:1710653] [10.1021/np50073a012]

9. PubChem BioAssay data set, 

10. Vehar B, Hrast M, Kovač A, Konc J, Mariner K, Chopra I, O'Neill A, Janežič D, Gobec S..  (2011)  Ellipticines and 9-acridinylamines as inhibitors of D-alanine:D-alanine ligase.,  19  (17): [PMID:21831641] [10.1016/j.bmc.2011.07.020]

11. PubChem BioAssay data set, 

12. Montoia A, Rocha E Silva LF, Torres ZE, Costa DS, Henrique MC, Lima ES, Vasconcellos MC, Souza RC, Costa MR, Grafov A, Grafova I, Eberlin MN, Tadei WP, Amorim RC, Pohlit AM..  (2014)  Antiplasmodial activity of synthetic ellipticine derivatives and an isolated analog.,  24  (12): [PMID:24813729] [10.1016/j.bmcl.2014.04.070]

13. Brown DG, Shorter J, Wobst HJ..  (2020)  Emerging small-molecule therapeutic approaches for amyotrophic lateral sclerosis and frontotemporal dementia.,  30  (4): [PMID:31926785] [10.1016/j.bmcl.2019.126942]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays