ID: ALA444067

Max Phase: Preclinical

Molecular Formula: C14H9NO2

Molecular Weight: 223.23

Molecule Type: Small molecule

Representations

Synonyms (1): Cleistopholine
Synonyms from Alternative Forms(1):

Canonical SMILES:  Cc1ccnc2c1C(=O)c1ccccc1C2=O

Standard InChI:  InChI=1S/C14H9NO2/c1-8-6-7-15-12-11(8)13(16)9-4-2-3-5-10(9)14(12)17/h2-7H,1H3

Standard InChI Key:  GVRYUHXXENMGEV-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: 223.23

Molecular Weight (Monoisotopic): 223.0633

AlogP: 2.17

#Rotatable Bonds: 0

Polar Surface Area: 47.03

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: 2.38

CX LogP: 2.60

CX LogD: 2.60

Aromatic Rings: 2

Heavy Atoms: 17

QED Weighted: 0.59

Np Likeness Score: 0.59

References

1. Peterson JR, Zjawiony JK, Liu S, Hufford CD, Clark AM, Rogers RD..  (1992)  Copyrine alkaloids: synthesis, spectroscopic characterization, and antimycotic/antimycobacterial activity of A- and B-ring-functionalized sampangines.,  35  (22): [PMID:1433213] [10.1021/jm00100a012]

2. Koyama J, Morita I, Kobayashi N, Osakai T, Usuki Y, Taniguchi M..  (2005)  Structure-activity relations of azafluorenone and azaanthraquinone as antimicrobial compounds.,  15  (4): [PMID:15686916] [10.1016/j.bmcl.2004.12.059]

3. Konoshima T, Kozuka M, Koyama J, Okatani T, Tagahara K, Tokuda H..  (1989)  Studies on inhibitors of skin tumor promotion, VI. Inhibitory effects of quinones on Epstein-Barr virus activation.,  52  (5): [PMID:2558164] [10.1021/np50065a012]

4. Hsieh TJ, Chang FR, Chia YC, Chen CY, Chiu HF, Wu YC..  (2001)  Cytotoxic constituents of the fruits of Cananga odorata.,  64  (5): [PMID:11374955] [10.1021/np0005208]

5. Claes P, Cappoen D, Mbala BM, Jacobs J, Mertens B, Mathys V, Verschaeve L, Huygen K, De Kimpe N..  (2013)  Synthesis and antimycobacterial activity of analogues of the bioactive natural products sampangine and cleistopholine.,  67  [PMID:23850570] [10.1016/j.ejmech.2013.06.010]

6. Suthiphasilp V, Maneerat W, Rujanapun N, Duangyod T, Charoensup R, Deachathai S, Andersen RJ, Patrick BO, Pyne SG, Laphookhieo S..  (2020)  α-Glucosidase inhibitory and nitric oxide production inhibitory activities of alkaloids isolated from a twig extract of Polyalthia cinnamomea.,  28  (10): [PMID:32247751] [10.1016/j.bmc.2020.115462]

7. Swain SS, Pati S, Hussain T..  (2022)  Quinoline heterocyclic containing plant and marine candidates against drug-resistant Mycobacterium tuberculosis: A systematic drug-ability investigation.,  232  [PMID:35168150] [10.1016/j.ejmech.2022.114173]

8. Mishra SK, Tripathi G, Kishore N, Singh RK, Singh A, Tiwari VK..  (2017)  Drug development against tuberculosis: Impact of alkaloids.,  137  [PMID:28628823] [10.1016/j.ejmech.2017.06.005]

Source

Source(1):

• Scientific Literature