physalin B

ID: ALA504404

Chembl Id: CHEMBL504404

Cas Number: 23133-56-4

PubChem CID: 11613161

Max Phase: Preclinical

Molecular Formula: C28H30O9

Molecular Weight: 510.54

Molecule Type: Small molecule

Names and Identifiers

Synonyms: NSC-287088 | Physalin B|CHEMBL504404|NSC-287088|23133-56-4|DTXSID901318463|HY-N7695|BDBM50378034|AKOS040760627|MS-29476|CS-0135227

Canonical SMILES:  C[C@]12C(=O)C=CCC1=CC[C@@H]1[C@@H]2CC[C@]2(O)C(=O)O[C@@]3(C)[C@H]4C[C@]5(C)[C@@H](CO[C@@]16O[C@@]32[C@H]5C6=O)C(=O)O4

Standard InChI:  InChI=1S/C28H30O9/c1-23-11-18-25(3)28-19(23)20(30)27(37-28,34-12-16(23)21(31)35-18)15-8-7-13-5-4-6-17(29)24(13,2)14(15)9-10-26(28,33)22(32)36-25/h4,6-7,14-16,18-19,33H,5,8-12H2,1-3H3/t14-,15+,16-,18+,19-,23+,24-,25-,26-,27+,28-/m0/s1

Standard InChI Key:  HVTFEHJSUSPQBK-DNJDGUCCSA-N

Alternative Forms

1. Parent:

   

   ALA504404

   PHYSALIN B

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: 510.54

Molecular Weight (Monoisotopic): 510.1890

AlogP: 1.56

#Rotatable Bonds: ┄

Polar Surface Area: 125.43

Molecular Species: NEUTRAL

HBA: 9

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.22

CX Basic pKa: ┄

CX LogP: 2.58

CX LogD: 2.58

Aromatic Rings: ┄

Heavy Atoms: 37

QED Weighted: 0.38

Np Likeness Score: 3.95

References

1. Damu AG, Kuo PC, Su CR, Kuo TH, Chen TH, Bastow KF, Lee KH, Wu TS..  (2007)  Isolation, structures, and structure - cytotoxic activity relationships of withanolides and physalins from Physalis angulata.,  70  (7): [PMID:17580910] [10.1021/np0701374]

2. Antoun MD, Abramson D, Tyson RL, Chang CJ, McLaughlin JL, Peck G, Cassady JM..  (1981)  Potential antitumor agents. XVII. physalin B and 25,26-epidihydrophysalin C from Witheringia coccoloboides.,  44  (5): [PMID:7320739] [10.1021/np50017a013]

3. Mahindroo N, Punchihewa C, Fujii N..  (2009)  Hedgehog-Gli signaling pathway inhibitors as anticancer agents.,  52  (13): [PMID:19309080] [10.1021/jm801420y]

4. Jacobo-Herrera NJ, Bremner P, Marquez N, Gupta MP, Gibbons S, Muñoz E, Heinrich M..  (2006)  Physalins from Witheringia solanacea as modulators of the NF-kappaB cascade.,  69  (3): [PMID:16562828] [10.1021/np050225t]

5. Qiu L, Zhao F, Jiang ZH, Chen LX, Zhao Q, Liu HX, Yao XS, Qiu F..  (2008)  Steroids and flavonoids from Physalis alkekengi var. franchetii and their inhibitory effects on nitric oxide production.,  71  (4): [PMID:18348534] [10.1021/np700713r]

6. Sá MS, de Menezes MN, Krettli AU, Ribeiro IM, Tomassini TC, Ribeiro dos Santos R, de Azevedo WF, Soares MB..  (2011)  Antimalarial activity of physalins B, D, F, and G.,  74  (10): [PMID:21954931] [10.1021/np200260f]

7. Beck J, Guminski Y, Long C, Marcourt L, Derguini F, Plisson F, Grondin A, Vandenberghe I, Vispé S, Brel V, Aussagues Y, Ausseil F, Arimondo PB, Massiot G, Sautel F, Cantagrel F..  (2012)  Semisynthetic neoboutomellerone derivatives as ubiquitin-proteasome pathway inhibitors.,  20  (2): [PMID:22206869] [10.1016/j.bmc.2011.11.066]

8. Ozawa M, Morita M, Hirai G, Tamura S, Kawai M, Tsuchiya A, Oonuma K, Maruoka K, Sodeoka M..  (2013)  Contribution of Cage-Shaped Structure of Physalins to Their Mode of Action in Inhibition of NF-κB Activation.,  4  (8): [PMID:24900739] [10.1021/ml400144e]

9. Lima Mda S, Evangelista AF, Santos GG, Ribeiro IM, Tomassini TC, Pereira Soares MB, Villarreal CF..  (2014)  Antinociceptive properties of physalins from Physalis angulata.,  77  (11): [PMID:25396337] [10.1021/np5003093]

10. Yang Y,Xiang K,Sun D,Zheng M,Song Z,Li M,Wang X,Li H,Chen L.  (2021)  Withanolides from dietary tomatillo suppress HT1080 cancer cell growth by targeting mutant IDH1.,  36  [PMID:33735687] [10.1016/j.bmc.2021.116095]

11. Xu GB, Xu YM, Wijeratne EMK, Ranjbar F, Liu MX, Gunatilaka AAL..  (2021)  Cytotoxic Physalins from Aeroponically Grown Physalis acutifolia.,  84  (2.0): [PMID:33586438] [10.1021/acs.jnatprod.0c00380]

12. Wu JP, Li LY, Li JR, Yu M, Zhao J, Xu QM, Gu YC, Zhang T, Zou ZM..  (2022)  Silencing Tautomerization to Isolate Unstable Physalins from Physalis minima.,  85  (6.0): [PMID:35608269] [10.1021/acs.jnatprod.2c00101]

13. Feng Z, Zhu S, Li W, Yao M, Song H, Wang RB..  (2022)  Current approaches and strategies to identify Hedgehog signaling pathway inhibitors for cancer therapy.,  244  [PMID:36332550] [10.1016/j.ejmech.2022.114867]

Source

Source(1):

• Scientific Literature