4beta-hydroxywithanolide

ID: ALA502563

Chembl Id: CHEMBL502563

Cas Number: 54334-04-2

PubChem CID: 73621

Max Phase: Preclinical

Molecular Formula: C28H38O8

Molecular Weight: 502.60

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 4Beta-Hydroxywithanolide | 4Beta-Hydroxywithanolide E | 4beta-Hydroxywithanolide E|54334-04-2|4beta-hydroxywithanolide|4-beta-Hydroxywithanolide E|CHEMBL502563|NSC212509|(1S,2R,6S,7R,9R,11R,12R,15S,16S)-15-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-6,12,15-trihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-en-3-one|5beta,6beta-epoxy-4beta,14,17alpha,20,22R-pentahydroxy-1-oxo-ergosta-2,24-dien-26-oic acid, -lactone|Withanolide E, 4-beta-hydroxy-Show More⌵

Canonical SMILES:  CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O)CC[C@@]3(O)[C@@H]4C[C@H]5O[C@]56[C@@H](O)C=CC(=O)[C@]6(C)[C@H]4CC[C@]23C)C1

Standard InChI:  InChI=1S/C28H38O8/c1-14-12-20(35-22(31)15(14)2)25(5,32)27(34)11-10-26(33)17-13-21-28(36-21)19(30)7-6-18(29)24(28,4)16(17)8-9-23(26,27)3/h6-7,16-17,19-21,30,32-34H,8-13H2,1-5H3/t16-,17+,19-,20+,21+,23-,24-,25-,26+,27-,28+/m0/s1

Standard InChI Key:  UPBUGICUKQIKTJ-KABTZXSUSA-N

Alternative Forms

1. Parent:

   

   ALA502563

   4beta-Hydroxywithanolide E

Molecule Features

Natural Product: Yes

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

Calculated Properties

Molecular Weight: 502.60

Molecular Weight (Monoisotopic): 502.2567

AlogP: 1.73

#Rotatable Bonds: 2

Polar Surface Area: 136.82

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.64

CX Basic pKa: ┄

CX LogP: 1.77

CX LogD: 1.77

Aromatic Rings: ┄

Heavy Atoms: 36

QED Weighted: 0.33

Np Likeness Score: 3.65

References

1. Tan GT, Pezzuto JM, Kinghorn AD, Hughes SH..  (1991)  Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.,  54  (1): [PMID:1710653] [10.1021/np50073a012]

2. Machin RP, Veleiro AS, Nicotra VE, Oberti JC, M Padrón J..  (2010)  Antiproliferative activity of withanolides against human breast cancer cell lines.,  73  (5): [PMID:20438092] [10.1021/np9006734]

3. PubChem BioAssay data set, 

4. Sang-Ngern M, Youn UJ, Park EJ, Kondratyuk TP, Simmons CJ, Wall MM, Ruf M, Lorch SE, Leong E, Pezzuto JM, Chang LC..  (2016)  Withanolides derived from Physalis peruviana (Poha) with potential anti-inflammatory activity.,  26  (12): [PMID:27210437] [10.1016/j.bmcl.2016.04.077]

5. Xu YM, Brooks AD, Wijeratne EM, Henrich CJ, Tewary P, Sayers TJ, Gunatilaka AA..  (2017)  17β-Hydroxywithanolides as Sensitizers of Renal Carcinoma Cells to Tumor Necrosis Factor-α Related Apoptosis Inducing Ligand (TRAIL) Mediated Apoptosis: Structure-Activity Relationships.,  60  (7): [PMID:28257574] [10.1021/acs.jmedchem.7b00069]

6. Xu YM, Wijeratne EMK, Babyak AL, Marks HR, Brooks AD, Tewary P, Xuan LJ, Wang WQ, Sayers TJ, Gunatilaka AAL..  (2017)  Withanolides from Aeroponically Grown Physalis peruviana and Their Selective Cytotoxicity to Prostate Cancer and Renal Carcinoma Cells.,  80  (7): [PMID:28617598] [10.1021/acs.jnatprod.6b01129]

7. Park EJ, Sang-Ngern M, Chang LC, Pezzuto JM..  (2019)  Physalactone and 4β-Hydroxywithanolide E Isolated from Physalis peruviana Inhibit LPS-Induced Expression of COX-2 and iNOS Accompanied by Abatement of Akt and STAT1.,  82  (3): [PMID:30649869] [10.1021/acs.jnatprod.8b00861]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays