27-Acetyl-4-dehydrowithaferin A

ID: ALA3234486

Chembl Id: CHEMBL3234486

PubChem CID: 90670453

Max Phase: Preclinical

Molecular Formula: C30H38O7

Molecular Weight: 510.63

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  CC(=O)OCC1=C(C)C[C@H]([C@@H](C)[C@H]2CC[C@H]3[C@@H]4C[C@H]5O[C@]56C(=O)C=CC(=O)[C@]6(C)[C@H]4CC[C@]23C)OC1=O

Standard InChI:  InChI=1S/C30H38O7/c1-15-12-23(36-27(34)19(15)14-35-17(3)31)16(2)20-6-7-21-18-13-26-30(37-26)25(33)9-8-24(32)29(30,5)22(18)10-11-28(20,21)4/h8-9,16,18,20-23,26H,6-7,10-14H2,1-5H3/t16-,18-,20+,21-,22-,23+,26+,28+,29-,30+/m0/s1

Standard InChI Key:  YTFZKBQQXHQMDQ-SPUPQYEPSA-N

Associated Targets(Human)

HSPA6 Tbio Heat shock 70 kDa protein 6 (44 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HeLa (62764 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A549 (127892 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MCF7 (126967 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RPMI-8226 (44974 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MM1.S (1111 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Vero (26788 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: 510.63Molecular Weight (Monoisotopic): 510.2618AlogP: 4.13#Rotatable Bonds: 4
Polar Surface Area: 99.27Molecular Species: NEUTRALHBA: 7HBD:
#RO5 Violations: 1HBA (Lipinski): 7HBD (Lipinski): #RO5 Violations (Lipinski): 1
CX Acidic pKa: CX Basic pKa: CX LogP: 4.79CX LogD: 4.79
Aromatic Rings: Heavy Atoms: 37QED Weighted: 0.41Np Likeness Score: 3.00

References

1. Wijeratne EM, Xu YM, Scherz-Shouval R, Marron MT, Rocha DD, Liu MX, Costa-Lotufo LV, Santagata S, Lindquist S, Whitesell L, Gunatilaka AA..  (2014)  Structure-activity relationships for withanolides as inducers of the cellular heat-shock response.,  57  (7): [PMID:24625088] [10.1021/jm401279n]
2. Llanos GG, Araujo LM, Jiménez IA, Moujir LM, Rodríguez J, Jiménez C, Bazzocchi IL..  (2017)  Structure-based design, synthesis, and biological evaluation of withaferin A-analogues as potent apoptotic inducers.,  140  [PMID:28923386] [10.1016/j.ejmech.2017.09.004]
3. Freitas Misakyan MF, Wijeratne EMK, Issa ME, Xu YM, Monteillier A, Gunatilaka AAL, Cuendet M..  (2021)  Structure-Activity Relationships of Withanolides as Antiproliferative Agents for Multiple Myeloma: Comparison of Activity in 2D Models and a 3D Coculture Model.,  84  (8.0): [PMID:34445874] [10.1021/acs.jnatprod.1c00446]

Source