ID: ALA33700

Max Phase: Preclinical

Molecular Formula: C14H18N2O2

Molecular Weight: 246.31

Molecule Type: Small molecule

Representations

Canonical SMILES:  COc1ccc2c(c1)c(CCNC(C)=O)cn2C

Standard InChI:  InChI=1S/C14H18N2O2/c1-10(17)15-7-6-11-9-16(2)14-5-4-12(18-3)8-13(11)14/h4-5,8-9H,6-7H2,1-3H3,(H,15,17)

Standard InChI Key:  GSMWHFKFNGUYRN-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: 246.31

Molecular Weight (Monoisotopic): 246.1368

AlogP: 1.87

#Rotatable Bonds: 4

Polar Surface Area: 43.26

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 1.37

CX LogD: 1.37

Aromatic Rings: 2

Heavy Atoms: 18

QED Weighted: 0.89

Np Likeness Score: -0.87

References

1. Rivara S, Mor M, Silva C, Zuliani V, Vacondio F, Spadoni G, Bedini A, Tarzia G, Lucini V, Pannacci M, Fraschini F, Plazzi PV..  (2003)  Three-dimensional quantitative structure-activity relationship studies on selected MT1 and MT2 melatonin receptor ligands: requirements for subtype selectivity and intrinsic activity modulation.,  46  (8): [PMID:12672242] [10.1021/jm020982d]

2. Garratt PJ, Vonhoff S, Rowe SJ, Sugden D.  (1994)  Mapping the melatonin receptor. 2. synthesis and biological activity of indole derived melatonin analogues with restricted conformations of the C-3 amidoethane side chain,  4  (13): [10.1016/S0960-894X(01)80566-7]

3. Leclerc V, Yous S, Delagrange P, Boutin JA, Renard P, Lesieur D..  (2002)  Synthesis of nitroindole derivatives with high affinity and selectivity for melatoninergic binding sites MT(3).,  45  (9): [PMID:11960497] [10.1021/jm011053+]

4. Mor M, Rivara S, Silva C, Bordi F, Plazzi PV, Spadoni G, Diamantini G, Balsamini C, Tarzia G, Fraschini F, Lucini V, Nonno R, Stankov BM..  (1998)  Melatonin receptor ligands: synthesis of new melatonin derivatives and comprehensive comparative molecular field analysis (CoMFA) study.,  41  (20): [PMID:9748358] [10.1021/jm9810093]

5. Du H, Wang J, Zhang X, Hu Z..  (2008)  A novel quantitative structure-activity relationship method to predict the affinities of MT3 melatonin binding site.,  43  (12): [PMID:18400335] [10.1016/j.ejmech.2008.02.012]

6. Flaugh ME, Crowell TA, Clemens JA, Sawyer BD..  (1979)  Synthesis and evaluation of the antiovulatory activity of a variety of melatonin analogues.,  22  (1): [PMID:423184] [10.1021/jm00187a015]

7. Zaryanova EV, Lozinskaya NA, Beznos OV, Volkova MS, Chesnokova NB, Zefirov NS..  (2017)  Oxindole-based intraocular pressure reducing agents.,  27  (16): [PMID:28687205] [10.1016/j.bmcl.2017.06.065]

Source

Source(1):

• Scientific Literature