N-[2-(5-Methoxy-1-methyl-1H-indol-3-yl)-ethyl]-acetamide

ID: ALA33700

Chembl Id: CHEMBL33700

PubChem CID: 11776674

Max Phase: Preclinical

Molecular Formula: C14H18N2O2

Molecular Weight: 246.31

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

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

Associated Targets(Human)

MTNR1A Tclin Melatonin receptor (989 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MTNR1A Tclin Melatonin receptor 1A (2519 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MTNR1B Tclin Melatonin receptor 1B (2168 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NQO2 Tchem Quinone reductase 2 (885 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Melatonin receptor (571 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Melatonin receptor 1C (17 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Rattus norvegicus (775804 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Oryctolagus cuniculus (11301 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 246.31Molecular Weight (Monoisotopic): 246.1368AlogP: 1.87#Rotatable Bonds: 4
Polar Surface Area: 43.26Molecular Species: NEUTRALHBA: 3HBD: 1
#RO5 Violations: HBA (Lipinski): 4HBD (Lipinski): 1#RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: CX LogP: 1.37CX LogD: 1.37
Aromatic Rings: 2Heavy Atoms: 18QED Weighted: 0.89Np 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,  (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