ID: ALA47482

Max Phase: Preclinical

Molecular Formula: C15H15N

Molecular Weight: 209.29

Molecule Type: Small molecule

Representations

Canonical SMILES:  NCC1c2ccccc2Cc2ccccc21

Standard InChI:  InChI=1S/C15H15N/c16-10-15-13-7-3-1-5-11(13)9-12-6-2-4-8-14(12)15/h1-8,15H,9-10,16H2

Standard InChI Key:  GEICAQNIOJFRQN-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: 209.29

Molecular Weight (Monoisotopic): 209.1204

AlogP: 2.68

#Rotatable Bonds: 1

Polar Surface Area: 26.02

Molecular Species: BASE

HBA: 1

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 1

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 9.70

CX LogP: 3.01

CX LogD: 0.77

Aromatic Rings: 2

Heavy Atoms: 16

QED Weighted: 0.77

Np Likeness Score: 0.08

References

1. Runyon SP, Peddi S, Savage JE, Roth BL, Glennon RA, Westkaemper RB..  (2002)  Geometry-affinity relationships of the selective serotonin receptor ligand 9-(aminomethyl)-9,10-dihydroanthracene.,  45  (8): [PMID:11931619] [10.1021/jm010354g]

2. Peddi S, Roth BL, Glennon RA, Westkaemper RB..  (2004)  Structural determinants for high 5-HT(2A) receptor affinity of spiro[9,10-dihydroanthracene]-9,3(')-pyrrolidine (SpAMDA).,  14  (9): [PMID:15081025] [10.1016/j.bmcl.2004.02.014]

3. Peddi S, Roth BL, Glennon RA, Westkaemper RB..  (2003)  Ring substituted analogues of 5-aminomethyl-10,11-dihydro-dibenzo[a,d]cycloheptene (AMDH): potential modes of binding to the 5-HT(2A) receptor.,  13  (15): [PMID:12852967] [10.1016/s0960-894x(03)00504-3]

4. Westkaemper RB, Runyon SP, Savage JE, Roth BL, Glennon RA..  (2001)  Exploring the relationship between binding modes of 9-(aminomethyl)-9,10-dihydroanthracene and cyproheptadine analogues at the 5-HT2A serotonin receptor.,  11  (4): [PMID:11229772] [10.1016/s0960-894x(01)00010-5]

5. Runyon SP, Savage JE, Taroua M, Roth BL, Glennon RA, Westkaemper RB..  (2001)  Influence of chain length and N-alkylation on the selective serotonin receptor ligand 9-(aminomethyl)-9,10-dihydroanthracene.,  11  (5): [PMID:11266163] [10.1016/s0960-894x(01)00023-3]

6. Dewkar GK, Peddi S, Mosier PD, Roth BL, Westkaemper RB..  (2008)  Methoxy-substituted 9-aminomethyl-9,10-dihydroanthracene (AMDA) derivatives exhibit differential binding affinities at the 5-HT(2A) receptor.,  18  (19): [PMID:18774714] [10.1016/j.bmcl.2008.08.059]

7. Runyon SP, Mosier PD, Roth BL, Glennon RA, Westkaemper RB..  (2008)  Potential modes of interaction of 9-aminomethyl-9,10-dihydroanthracene (AMDA) derivatives with the 5-HT2A receptor: a ligand structure-affinity relationship, receptor mutagenesis and receptor modeling investigation.,  51  (21): [PMID:18847250] [10.1021/jm800771x]

8. Shah JR, Mosier PD, Roth BL, Kellogg GE, Westkaemper RB..  (2009)  Synthesis, structure-affinity relationships, and modeling of AMDA analogs at 5-HT2A and H1 receptors: structural factors contributing to selectivity.,  17  (18): [PMID:19700330] [10.1016/j.bmc.2009.08.016]

Source

Source(1):

• Scientific Literature