1,4-Dihydroxy-2-((E)-1-hydroxy-4-(4-methoxyphenyl)but-3-enyl)anthracene-9,10-dione

ID: ALA3798767

Chembl Id: CHEMBL3798767

PubChem CID: 127046891

Max Phase: Preclinical

Molecular Formula: C25H20O6

Molecular Weight: 416.43

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  COc1ccc(/C=C/CC(O)c2cc(O)c3c(c2O)C(=O)c2ccccc2C3=O)cc1

Standard InChI:  InChI=1S/C25H20O6/c1-31-15-11-9-14(10-12-15)5-4-8-19(26)18-13-20(27)21-22(25(18)30)24(29)17-7-3-2-6-16(17)23(21)28/h2-7,9-13,19,26-27,30H,8H2,1H3/b5-4+

Standard InChI Key:  ZDOWULZBUGHTCU-SNAWJCMRSA-N

Alternative Forms

  1. Parent:

    ALA3798767

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Associated Targets(Human)

MDA-MB-231 (73002 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HeLa (62764 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MCF7 (126967 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MCF10 (107 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: 416.43Molecular Weight (Monoisotopic): 416.1260AlogP: 4.02#Rotatable Bonds: 5
Polar Surface Area: 104.06Molecular Species: NEUTRALHBA: 6HBD: 3
#RO5 Violations: HBA (Lipinski): 6HBD (Lipinski): 3#RO5 Violations (Lipinski):
CX Acidic pKa: 8.51CX Basic pKa: CX LogP: 5.37CX LogD: 5.34
Aromatic Rings: 3Heavy Atoms: 31QED Weighted: 0.42Np Likeness Score: 0.90

References

1. Zhao LM, Cao FX, Jin HS, Zhang JH, Szwaya J, Wang G..  (2016)  One-pot synthesis of 1,4-dihydroxy-2-((E)-1-hydroxy-4-phenylbut-3-enyl)anthracene-9,10-diones as novel shikonin analogs and evaluation of their antiproliferative activities.,  26  (11): [PMID:27080175] [10.1016/j.bmcl.2016.04.006]

Source