N-(2,3-methylenedioxy-6-methoxyphenanthr-9-ylmethyl)-L-4-piperidinem ethanol

ID: ALA231594

Chembl Id: CHEMBL231594

PubChem CID: 16657823

Max Phase: Preclinical

Molecular Formula: C23H25NO4

Molecular Weight: 379.46

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  COc1ccc2c(CN3CCC(CO)CC3)cc3cc4c(cc3c2c1)OCO4

Standard InChI:  InChI=1S/C23H25NO4/c1-26-18-2-3-19-17(12-24-6-4-15(13-25)5-7-24)8-16-9-22-23(28-14-27-22)11-20(16)21(19)10-18/h2-3,8-11,15,25H,4-7,12-14H2,1H3

Standard InChI Key:  GFBRRLPJNPKOEJ-UHFFFAOYSA-N

Associated Targets(Human)

A549 (127892 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KB (17409 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DU-145 (51482 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ZR-75-1 (953 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NCI-H460 (60772 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PC-9 (1037 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CL1-0 (56 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AKT1 Tchem Serine/threonine-protein kinase AKT (9192 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CHUK Tchem Inhibitor of nuclear factor kappa B kinase alpha subunit (3170 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
IKBKB Tchem Inhibitor of nuclear factor kappa B kinase beta subunit (5554 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HSP90AB1 Tchem HSP90 and hnRNPA2/B1 (10 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MDA-MB-231 (73002 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MCF7 (126967 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Mus musculus (284745 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: 379.46Molecular Weight (Monoisotopic): 379.1784AlogP: 3.93#Rotatable Bonds: 4
Polar Surface Area: 51.16Molecular Species: BASEHBA: 5HBD: 1
#RO5 Violations: HBA (Lipinski): 5HBD (Lipinski): 1#RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: 9.20CX LogP: 3.14CX LogD: 1.34
Aromatic Rings: 3Heavy Atoms: 28QED Weighted: 0.70Np Likeness Score: -0.11

References

1. Wei L, Shi Q, Bastow KF, Brossi A, Morris-Natschke SL, Nakagawa-Goto K, Wu TS, Pan SL, Teng CM, Lee KH..  (2007)  Antitumor agents 253. Design, synthesis, and antitumor evaluation of novel 9-substituted phenanthrene-based tylophorine derivatives as potential anticancer agents.,  50  (15): [PMID:17585747] [10.1021/jm061366a]
2. Lin JC, Yang SC, Hong TM, Yu SL, Shi Q, Wei L, Chen HY, Yang PC, Lee KH..  (2009)  Phenanthrene-based tylophorine-1 (PBT-1) inhibits lung cancer cell growth through the Akt and NF-kappaB pathways.,  52  (7): [PMID:19284764] [10.1021/jm801344j]
3. Yang X, Shi Q, Liu YN, Zhao G, Bastow KF, Lin JC, Yang SC, Yang PC, Lee KH..  (2009)  Antitumor agents 268. Design, synthesis, and mechanistic studies of new 9-substituted phenanthrene-based tylophorine analogues as potent cytotoxic agents.,  52  (16): [PMID:19645447] [10.1021/jm9009263]
4. Lee KH..  (2010)  Discovery and development of natural product-derived chemotherapeutic agents based on a medicinal chemistry approach.,  73  (3): [PMID:20187635] [10.1021/np900821e]
5. Chen CY, Yang SC, Lee KH, Yang X, Wei LY, Chow LP, Wang TC, Hong TM, Lin JC, Kuan C, Yang PC..  (2014)  The antitumor agent PBT-1 directly targets HSP90 and hnRNP A2/B1 and inhibits lung adenocarcinoma growth and metastasis.,  57  (3): [PMID:24428777] [10.1021/jm401686b]
6. Xie L, Goto M, Chen X, Morris-Natschke SL, Lee KH..  (2021)  Lead Optimization: Synthesis and Biological Evaluation of PBT-1 Derivatives as Novel Antitumor Agents.,  12  (12.0): [PMID:34917259] [10.1021/acsmedchemlett.1c00505]

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