ID: ALA480627

Max Phase: Preclinical

Molecular Formula: C20H20N2O3

Molecular Weight: 336.39

Molecule Type: Small molecule

Representations

Synonyms (2): Alpha-Cyclopiazonic Acid | Cyclopiazonic Acid
Synonyms from Alternative Forms(2):

Canonical SMILES:  CC(=O)C1=C(O)[C@@H]2[C@H]3c4c[nH]c5cccc(c45)C[C@H]3C(C)(C)N2C1=O

Standard InChI:  InChI=1S/C20H20N2O3/c1-9(23)14-18(24)17-16-11-8-21-13-6-4-5-10(15(11)13)7-12(16)20(2,3)22(17)19(14)25/h4-6,8,12,16-17,21,24H,7H2,1-3H3/t12-,16+,17+/m1/s1

Standard InChI Key:  SZINUGQCTHLQAZ-DQYPLSBCSA-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: 336.39

Molecular Weight (Monoisotopic): 336.1474

AlogP: 2.83

#Rotatable Bonds: 1

Polar Surface Area: 73.40

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 3.84

CX Basic pKa:

CX LogP: 1.77

CX LogD: -1.47

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.79

Np Likeness Score: 1.36

References

1. Zhang L, Yu J, Pan H, Hu P, Hao Y, Cai W, Zhu H, Yu AD, Xie X, Ma D, Yuan J..  (2007)  Small molecule regulators of autophagy identified by an image-based high-throughput screen.,  104  (48): [PMID:18024584] [10.1073/pnas.0709695104]

2. Deye J, Elam C, Lape M, Ratliff R, Evans K, Paula S..  (2009)  Structure-based virtual screening for novel inhibitors of the sarco/endoplasmic reticulum calcium ATPase and their experimental evaluation.,  17  (3): [PMID:19117760] [10.1016/j.bmc.2008.12.010]

3. Schobert R, Schlenk A..  (2008)  Tetramic and tetronic acids: an update on new derivatives and biological aspects.,  16  (8): [PMID:18334299] [10.1016/j.bmc.2008.02.069]

4. Borrelli F, Ascione V, Capasso R, Izzo AA, Fattorusso E, Taglialatela-Scafati O..  (2006)  Spasmolytic effects of nonprenylated rotenoid constituents of Boerhaavia diffusa roots.,  69  (6): [PMID:16792408] [10.1021/np060073h]

5. Rottmann M, McNamara C, Yeung BK, Lee MC, Zou B, Russell B, Seitz P, Plouffe DM, Dharia NV, Tan J, Cohen SB, Spencer KR, González-Páez GE, Lakshminarayana SB, Goh A, Suwanarusk R, Jegla T, Schmitt EK, Beck HP, Brun R, Nosten F, Renia L, Dartois V, Keller TH, Fidock DA, Winzeler EA, Diagana TT..  (2010)  Spiroindolones, a potent compound class for the treatment of malaria.,  329  (5996): [PMID:20813948] [10.1126/science.1193225]

6. PubChem BioAssay data set, 

7. PubChem BioAssay data set, 

8. Yao S, Gallenkamp D, Wölfel K, Lüke B, Schindler M, Scherkenbeck J..  (2011)  Synthesis and SERCA activities of structurally simplified cyclopiazonic acid analogues.,  19  (15): [PMID:21719297] [10.1016/j.bmc.2011.06.001]

9. Brunhofer G, Fallarero A, Karlsson D, Batista-Gonzalez A, Shinde P, Gopi Mohan C, Vuorela P..  (2012)  Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.,  20  (22): [PMID:23062825] [10.1016/j.bmc.2012.09.040]

10. Iwasaki A, Ohno O, Katsuyama S, Morita M, Sasazawa Y, Dan S, Simizu S, Yamori T, Suenaga K..  (2015)  Identification of a molecular target of kurahyne, an apoptosis-inducing lipopeptide from marine cyanobacterial assemblages.,  25  (22): [PMID:26428873] [10.1016/j.bmcl.2015.09.044]

11. Sato E, Morita M, Ogawa H, Iwatsuki M, Hokari R, Ishiyama A, Ōmura S, Iwasaki A, Suenaga K..  (2018)  Design, synthesis and anti-malarial activities of synthetic analogs of biselyngbyolide B, a Ca²⁺ pump inhibitor from marine cyanobacteria.,  28  (3): [PMID:29292225] [10.1016/j.bmcl.2017.12.050]

12. 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]

13. 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]

14. 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]

15. 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]

Source

Source(4):

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