3-(3-Phenoxybenzyl)-amino-beta-carboline

ID: ALA1808759

Chembl Id: CHEMBL1808759

Cas Number: 1327080-54-5

PubChem CID: 56666556

Max Phase: Preclinical

Molecular Formula: C24H19N3O

Molecular Weight: 365.44

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  c1ccc(Oc2cccc(CNc3cc4c(cn3)[nH]c3ccccc34)c2)cc1

Standard InChI:  InChI=1S/C24H19N3O/c1-2-8-18(9-3-1)28-19-10-6-7-17(13-19)15-25-24-14-21-20-11-4-5-12-22(20)27-23(21)16-26-24/h1-14,16,27H,15H2,(H,25,26)

Standard InChI Key:  DMCDUELFWCRWHE-UHFFFAOYSA-N

Alternative Forms

Associated Targets(Human)

HeLa S3 (477 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MCF7 (126967 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HeLa (62764 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Raji (5516 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NCI-H460 (60772 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A2780S (286 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HCT-116 (91556 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TUBB4B Tclin Tubulin beta (167 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TUBA3C Tchem Tubulin alpha (84 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TUBB4B Tclin Tubulin (5180 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Tubulin (1327 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ALB Serum albumin (1163 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: 365.44Molecular Weight (Monoisotopic): 365.1528AlogP: 6.12#Rotatable Bonds: 5
Polar Surface Area: 49.94Molecular Species: NEUTRALHBA: 3HBD: 2
#RO5 Violations: 1HBA (Lipinski): 4HBD (Lipinski): 2#RO5 Violations (Lipinski): 1
CX Acidic pKa: CX Basic pKa: 6.30CX LogP: 5.17CX LogD: 5.13
Aromatic Rings: 5Heavy Atoms: 28QED Weighted: 0.39Np Likeness Score: -0.53

References

1. Ikeda R, Kurosawa M, Okabayashi T, Takei A, Yoshiwara M, Kumakura T, Sakai N, Funatsu O, Morita A, Ikekita M, Nakaike Y, Konakahara T..  (2011)  3-(3-Phenoxybenzyl)amino-β-carboline: a novel antitumor drug targeting α-tubulin.,  21  (16): [PMID:21752645] [10.1016/j.bmcl.2011.06.061]
2. Ikeda R, Kimura T, Tsutsumi T, Tamura S, Sakai N, Konakahara T..  (2012)  Structure-activity relationship in the antitumor activity of 6-, 8- or 6,8-substituted 3-benzylamino-β-carboline derivatives.,  22  (10): [PMID:22520257] [10.1016/j.bmcl.2012.03.077]
3. Li Y, Liu Y, Zhu Z, Yan W, Zhang C, Yang Z, Bai P, Tang M, Shi M, He W, Fu S, Liu J, Han K, Li J, Xie L, Ye H, Yang J, Chen L..  (2022)  Structure-Based Design and Synthesis of N-Substituted 3-Amino-β-Carboline Derivatives as Potent αβ-Tubulin Degradation Agents.,  65  (3.0): [PMID:35084853] [10.1021/acs.jmedchem.1c02159]
4. Yang J, Li Y, Qiu Q, Wang R, Yan W, Yu Y, Niu L, Pei H, Wei H, Ouyang L, Ye H, Xu D, Wei Y, Chen Q, Chen L..  (2022)  Small Molecules Promote Selective Denaturation and Degradation of Tubulin Heterodimers through a Low-Barrier Hydrogen Bond.,  65  (13.0): [PMID:35762925] [10.1021/acs.jmedchem.2c00379]

Source