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3,5-bis(3-hydroxybenzylidene)piperidin-4-one

ID: ALA2386416

Chembl Id: CHEMBL2386416

PubChem CID: 66554458

Max Phase: Preclinical

Molecular Formula: C19H17NO3

Molecular Weight: 307.35

Molecule Type: Small molecule

Associated Items:

Bioactivity Summary Target Summary Assay Summary

Names and Identifiers

Canonical SMILES: O=C1/C(=C/c2cccc(O)c2)CNC/C1=C\c1cccc(O)c1

Standard InChI: InChI=1S/C19H17NO3/c21-17-5-1-3-13(9-17)7-15-11-20-12-16(19(15)23)8-14-4-2-6-18(22)10-14/h1-10,20-22H,11-12H2/b15-7+,16-8+

Standard InChI Key: VAQPUHTZPOQXOC-BGPOSVGRSA-N

Parent:

ALA2386416
(3E,5E)-3,5-bis[(3-hydroxyphenyl)methylidene]piperidin-4-one

Caco-2 (12174 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

L1210 (27553 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

B16 (5829 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

RAW264.7 (28094 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MDCK (10148 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

MESH ID	MESH Heading	EFO IDs	EFO Terms	Max Phase for Indication	References

Mechanism of Action	Action Type	target ID	Target Name	Target Type	Target Organism	Binding Site Name	References

Molecular Weight: 307.35	Molecular Weight (Monoisotopic): 307.1208	AlogP: 2.74	#Rotatable Bonds: 2
Polar Surface Area: 69.56	Molecular Species: NEUTRAL	HBA: 4	HBD: 3
#RO5 Violations: 0	HBA (Lipinski): 4	HBD (Lipinski): 3	#RO5 Violations (Lipinski): 0
CX Acidic pKa: 9.09	CX Basic pKa: 6.40	CX LogP: 3.29	CX LogD: 3.24
Aromatic Rings: 2	Heavy Atoms: 23	QED Weighted: 0.75	Np Likeness Score: 0.16

1. Gregory M, Dandavati A, Lee M, Tzou S, Savagian M, Brien KA, Satam V, Patil P, Lee M. (2013) Synthesis, cytotoxicity, and structureactivity insight of NH- and N-methyl-3,5-bis-(arylidenyl)-4-piperidones, 22 (11): [10.1007/s00044-013-0557-9]
2. Wu J, Zhang Y, Cai Y, Wang J, Weng B, Tang Q, Chen X, Pan Z, Liang G, Yang S.. (2013) Discovery and evaluation of piperid-4-one-containing mono-carbonyl analogs of curcumin as anti-inflammatory agents., 21 (11): [PMID:23611769] [10.1016/j.bmc.2013.03.057]
3. Tan KL, Ali A, Du Y, Fu H, Jin HX, Chin TM, Khan M, Go ML.. (2014) Synthesis and evaluation of bisbenzylidenedioxotetrahydrothiopranones as activators of endoplasmic reticulum (ER) stress signaling pathways and apoptotic cell death in acute promyelocytic leukemic cells., 57 (14): [PMID:24960549] [10.1021/jm401352a]
4. Singh RS, Michel D, Das U, Dimmock JR, Alcorn J.. (2014) Cytotoxic 1,5-diaryl-3-oxo-1,5-pentadienes: an assessment and comparison of membrane permeability using Caco-2 and MDCK monolayers., 24 (22): [PMID:25442312] [10.1016/j.bmcl.2014.09.074]
5. Moreira J, Saraiva L, Pinto MM, Cidade H.. (2020) Diarylpentanoids with antitumor activity: A critical review of structure-activity relationship studies., 192 [PMID:32172081] [10.1016/j.ejmech.2020.112177]

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