6-Benzyloxy-4-methoxymethyl-9H-beta-carboline-3-carboxylic acid isopropyl ester

ID: ALA454095

Chembl Id: CHEMBL454095

Max Phase: Phase

Molecular Formula: C24H24N2O4

Molecular Weight: 404.47

Molecule Type: Small molecule

Names and Identifiers

Synonyms: ZK-112119

Canonical SMILES:  COCc1c(C(=O)OC(C)C)ncc2[nH]c3ccc(OCc4ccccc4)cc3c12

Standard InChI:  InChI=1S/C24H24N2O4/c1-15(2)30-24(27)23-19(14-28-3)22-18-11-17(29-13-16-7-5-4-6-8-16)9-10-20(18)26-21(22)12-25-23/h4-12,15,26H,13-14H2,1-3H3

Standard InChI Key:  RLFKILXOLJVUNF-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA454095

   ABECARNIL

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: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 404.47

Molecular Weight (Monoisotopic): 404.1736

AlogP: 5.01

#Rotatable Bonds: 7

Polar Surface Area: 73.44

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.72

CX Basic pKa: 2.08

CX LogP: 4.28

CX LogD: 4.28

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.44

Np Likeness Score: -0.32

References

1. Cox ED, Diaz-Arauzo H, Huang Q, Reddy MS, Ma C, Harris B, McKernan R, Skolnick P, Cook JM..  (1998)  Synthesis and evaluation of analogues of the partial agonist 6-(propyloxy)-4-(methoxymethyl)-beta-carboline-3-carboxylic acid ethyl ester (6-PBC) and the full agonist 6-(benzyloxy)-4-(methoxymethyl)-beta-carboline-3-carboxylic acid ethyl ester (Zk 93423) at wild type and recombinant GABAA receptors.,  41  (14): [PMID:9651158] [10.1021/jm970460b]

2. Huang Q, He X, Ma C, Liu R, Yu S, Dayer CA, Wenger GR, McKernan R, Cook JM..  (2000)  Pharmacophore/receptor models for GABA(A)/BzR subtypes (alpha1beta3gamma2, alpha5beta3gamma2, and alpha6beta3gamma2) via a comprehensive ligand-mapping approach.,  43  (1): [PMID:10633039] [10.1021/jm990341r]

3. Harris D, Clayton T, Cook J, Sahbaie P, Halliwell RF, Furtmüller R, Huck S, Sieghart W, DeLorey TM..  (2008)  Selective influence on contextual memory: physiochemical properties associated with selectivity of benzodiazepine ligands at GABAA receptors containing the alpha5 subunit.,  51  (13): [PMID:18537233] [10.1021/jm701433b]

4. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

5. Biour M, Ben Salem C, Chazouillères O, Grangé JD, Serfaty L, Poupon R..  (2004)  [Drug-induced liver injury; fourteenth updated edition of the bibliographic database of liver injuries and related drugs].,  28  (8-9): [PMID:15646539] [10.1016/s0399-8320(04)95062-2]

6. Beato A, Gori A, Boucherle B, Peuchmaur M, Haudecoeur R..  (2021)  β-Carboline as a Privileged Scaffold for Multitarget Strategies in Alzheimer's Disease Therapy.,  64  (3.0): [PMID:33528252] [10.1021/acs.jmedchem.0c01887]

Source

Source(2):

• Scientific Literature
• USP Dictionary of USAN and International Drug Names