ID: ALA235934

Max Phase: Preclinical

Molecular Formula: C14H11NO3

Molecular Weight: 241.25

Molecule Type: Small molecule

Representations

Synonyms (1): Clausine E
Synonyms from Alternative Forms(1):

Canonical SMILES:  COC(=O)c1cc(O)c2[nH]c3ccccc3c2c1

Standard InChI:  InChI=1S/C14H11NO3/c1-18-14(17)8-6-10-9-4-2-3-5-11(9)15-13(10)12(16)7-8/h2-7,15-16H,1H3

Standard InChI Key:  ZWPODTIRGFOENJ-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: 241.25

Molecular Weight (Monoisotopic): 241.0739

AlogP: 2.81

#Rotatable Bonds: 1

Polar Surface Area: 62.32

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 8.88

CX Basic pKa:

CX LogP: 2.79

CX LogD: 2.78

Aromatic Rings: 3

Heavy Atoms: 18

QED Weighted: 0.64

Np Likeness Score: 0.58

References

1. Liger F, Popowycz F, Besson T, Picot L, Galmarini CM, Joseph B..  (2007)  Synthesis and antiproliferative activity of clausine E, mukonine, and koenoline bioisosteres.,  15  (16): [PMID:17548198] [10.1016/j.bmc.2007.05.033]

2. Ito C, Katsuno S, Itoigawa M, Ruangrungsi N, Mukainaka T, Okuda M, Kitagawa Y, Tokuda H, Nishino H, Furukawa H..  (2000)  New carbazole alkaloids from Clausena anisata with antitumor promoting activity.,  63  (1): [PMID:10650093] [10.1021/np990285x]

3. Songsiang U, Thongthoom T, Boonyarat C, Yenjai C..  (2011)  Claurailas A-D, cytotoxic carbazole alkaloids from the roots of Clausena harmandiana.,  74  (2): [PMID:21302964] [10.1021/np100654m]

4. Lin W, Wang Y, Lin S, Li C, Zhou C, Wang S, Huang H, Liu P, Ye G, Shen X..  (2012)  Induction of cell cycle arrest by the carbazole alkaloid Clauszoline-I from Clausena vestita D. D. Tao via inhibition of the PKCδ phosphorylation.,  47  [PMID:22093759] [10.1016/j.ejmech.2011.10.047]

5. Perry GS, Das M, Woon ECY..  (2021)  Inhibition of AlkB Nucleic Acid Demethylases: Promising New Epigenetic Targets.,  64  (23.0): [PMID:34792334] [10.1021/acs.jmedchem.1c01694]

Source

Source(1):

• Scientific Literature