ID: ALA375563

Max Phase: Preclinical

Molecular Formula: C30H52O3

Molecular Weight: 460.74

Molecule Type: Small molecule

Representations

Synonyms (1): 20(S)-Protopanaxadiol
Synonyms from Alternative Forms(1):

Canonical SMILES:  CC(C)=CCC[C@](C)(O)[C@H]1CC[C@]2(C)[C@@H]1[C@H](O)C[C@@H]1[C@@]3(C)CC[C@H](O)C(C)(C)[C@@H]3CC[C@]12C

Standard InChI:  InChI=1S/C30H52O3/c1-19(2)10-9-14-30(8,33)20-11-16-29(7)25(20)21(31)18-23-27(5)15-13-24(32)26(3,4)22(27)12-17-28(23,29)6/h10,20-25,31-33H,9,11-18H2,1-8H3/t20-,21+,22-,23+,24-,25-,27-,28+,29+,30-/m0/s1

Standard InChI Key:  PYXFVCFISTUSOO-HKUCOEKDSA-N

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

Properties

Molecular Weight: 460.74

Molecular Weight (Monoisotopic): 460.3916

AlogP: 6.50

#Rotatable Bonds: 4

Polar Surface Area: 60.69

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa:

CX Basic pKa:

CX LogP: 5.53

CX LogD: 5.53

Aromatic Rings: 0

Heavy Atoms: 33

QED Weighted: 0.42

Np Likeness Score: 3.15

References

1. Kwon BM, Kim MK, Baek NI, Kim DS, Park JD, Kim YK, Lee HK, Kim SI..  (1999)  Acyl-CoA: cholesterol acyltransferase inhibitory activity of ginseng sapogenins, produced from the ginseng saponins.,  9  (10): [PMID:10360739] [10.1016/s0960-894x(99)00208-5]

2. Kwon B, Lee S, Kim K, Lee I, Lee UC, Hong S, Bok S.  (1997)  Rhombenone: farnesyl protein transferase inhibitor from the leaves of Hedera rhombea Bean,  7  (8): [10.1016/S0960-894X(97)00139-X]

3. Liu GY, Bu X, Yan H, Jia WW..  (2007)  20S-protopanaxadiol-induced programmed cell death in glioma cells through caspase-dependent and -independent pathways.,  70  (2): [PMID:17261067] [10.1021/np060313t]

4. Usami Y, Liu YN, Lin AS, Shibano M, Akiyama T, Itokawa H, Morris-Natschke SL, Bastow K, Kasai R, Lee KH..  (2008)  Antitumor agents. 261. 20(S)-protopanaxadiol and 20(s)-protopanaxatriol as antiangiogenic agents and total assignment of (1)H NMR spectra.,  71  (3): [PMID:18271556] [10.1021/np070613q]

5. Zhao JM, Li N, Zhang H, Wu CF, Piao HR, Zhao YQ..  (2011)  Novel dammarane-type sapogenins from Panax ginseng berry and their biological activities.,  21  (3): [PMID:21216145] [10.1016/j.bmcl.2010.12.035]

6. Kang KS, Kim HY, Yoo HH, Piao XL, Ham J, Yang HO, Park JH..  (2012)  Protective effect of ginseng sapogenins against 2,2'-azobis (1-aminopropane) dihydrochloride (AAPH)-induced LLC-PK₁ cell damage.,  22  (1): [PMID:22113113] [10.1016/j.bmcl.2011.10.063]

7. Li N, Wu CF, Xu XY, Liu ZY, Li X, Zhao YQ..  (2012)  Triterpenes possessing an unprecedented skeleton isolated from hydrolyzate of total saponins from Gynostemma pentaphyllum.,  50  [PMID:22342101] [10.1016/j.ejmech.2012.01.052]

8. Zhang XS, Bi XL, Wan-Xiao, Cao JQ, Xia XC, Diao YP, Zhao YQ..  (2013)  Protein tyrosine phosphatase 1B inhibitory effect by dammarane-type triterpenes from hydrolyzate of total Gynostemma pentaphyllum saponins.,  23  (1): [PMID:23177789] [10.1016/j.bmcl.2012.10.097]

9. Liu J, Wang X, Liu P, Deng R, Lei M, Chen W, Hu L..  (2013)  20(S)-Protopanaxadiol (PPD) analogues chemosensitize multidrug-resistant cancer cells to clinical anticancer drugs.,  21  (14): [PMID:23683834] [10.1016/j.bmc.2013.04.067]

10. Zhou Z, Ma C, Zhang H, Bi Y, Chen X, Tian H, Xie X, Meng Q, Lewis PJ, Xu J..  (2013)  Synthesis and biological evaluation of novel ocotillol-type triterpenoid derivatives as antibacterial agents.,  68  [PMID:23994872] [10.1016/j.ejmech.2013.07.041]

11. Kwak JH, Park JY, Lee D, Kwak JY, Park EH, Kim KH, Park HJ, Kim HY, Jang HJ, Ham J, Hwang GS, Yamabe N, Kang KS..  (2014)  Inhibitory effects of ginseng sapogenins on the proliferation of triple negative breast cancer MDA-MB-231 cells.,  24  (23): [PMID:25453798] [10.1016/j.bmcl.2014.10.041]

12. Li L, Chen X, Li D, Zhong D..  (2011)  Identification of 20(S)-protopanaxadiol metabolites in human liver microsomes and human hepatocytes.,  39  (3): [PMID:21139039] [10.1124/dmd.110.036723]

13. Li L, Chen X, Li D, Zhong D..  (2011)  Identification of 20(S)-protopanaxadiol metabolites in human liver microsomes and human hepatocytes.,  39  (3): [PMID:21139039] [10.1124/dmd.110.036723]

14. Ma LY, Zhou QL, Yang XW..  (2015)  New SIRT1 activator from alkaline hydrolysate of total saponins in the stems-leaves of Panax ginseng.,  25  (22): [PMID:26420067] [10.1016/j.bmcl.2015.09.039]

15. Yang XW, Ma LY, Zhou QL, Xu W, Zhang YB..  (2018)  SIRT1 activator isolated from artificial gastric juice incubate of total saponins in stems and leaves of Panax ginseng.,  28  (3): [PMID:29317167] [10.1016/j.bmcl.2017.12.067]

16. Bernhard Ellinger, Denisa Bojkova, Andrea Zaliani, Jindrich Cinatl, Carsten Claussen, Sandra Westhaus, Jeanette Reinshagen, Maria Kuzikov, Markus Wolf, Gerd Geisslinger, Philip Gribbon, Sandra Ciesek.  (2020)  Identification of inhibitors of SARS-CoV-2 in-vitro cellular toxicity in human (Caco-2) cells using a large scale drug repurposing collection,  [10.21203/rs.3.rs-23951/v1]

17. Maria Kuzikov, Elisa Costanzi, Jeanette Reinshagen, Francesca Esposito, Laura Vangeel, Markus Wolf, Bernhard Ellinger, Carsten Claussen, Gerd Geisslinger, Angela Corona, Daniela Iaconis, Carmine Talarico, Candida Manelfi, Rolando Cannalire, Giulia Rossetti, Jonas Gossen, Simone Albani, Francesco Musiani, Katja Herzog, Yang Ye, Barbara Giabbai, Nicola Demitri, Dirk Jochmans, Steven De Jonghe, Jasper Rymenants, Vincenzo Summa, Enzo Tramontano, Andrea R. Beccari, Pieter Leyssen, Paola Storici, Johan Neyts, Philip Gribbon, and Andrea Zaliani.  (2020)  Identification of inhibitors of SARS-Cov2 M-Pro enzymatic activity using a small molecule repurposing screen,  [10.6019/CHEMBL4495564]

18. Andrea Zaliani, Laura Vangeel, Jeanette Reinshagen, Daniela Iaconis, Maria Kuzikov, Oliver Keminer, Markus Wolf, Bernhard Ellinger, Francesca Esposito, Angela Corona, Enzo Tramontano, Candida Manelfi, Katja Herzog, Dirk Jochmans, Steven De Jonghe, Winston Chiu, Thibault Francken, Joost Schepers, Caroline Collard, Kayvan Abbasi, Carsten Claussen , Vincenzo Summa, Andrea R. Beccari, Johan Neyts, Philip Gribbon and Pieter Leyssen.  (2020)  Cytopathic SARS-Cov2 screening on VERO-E6 cells in a large repurposing effort,  [10.6019/CHEMBL4495565]

19. Cheng Y,Li R,Lin Z,Chen F,Dai J,Zhu Z,Chen L,Zhao Y.  (2020)  Structure-activity relationship analysis of dammarane-type natural products as muscle-type creatine kinase activators.,  30  (17.0): [PMID:32738969] [10.1016/j.bmcl.2020.127364]

20. Bernhard Ellinger, Justus Dick, Vanessa Lage-Rupprecht, Bruce Schultz, Andrea Zaliani, Marcin Namysl, Stephan Gebel, Ole Pless, Jeanette Reinshagen, Christian Ebeling, Alexander Esser, Marc Jacobs, Carsten Claussen, and Martin Hofmann-Apitius.  (2021)  HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators,  [10.6019/CHEMBL4808148]

21. Ha S, Luo G, Xiang H..  (2022)  A Comprehensive Overview of Small-Molecule Androgen Receptor Degraders: Recent Progress and Future Perspectives.,  65  (24.0): [PMID:36459083] [10.1021/acs.jmedchem.2c01487]

Source

Source(3):

• Scientific Literature
• SARS-CoV-2 Screening Data 2020-21
• Fraunhofer HDAC6