ID: ALA173530

Max Phase: Preclinical

Molecular Formula: C19H14O9

Molecular Weight: 386.31

Molecule Type: Small molecule

Representations

Synonyms (1): NSC-87511
Synonyms from Alternative Forms(1):

Canonical SMILES:  COc1cc(C)c2c(c1C=O)Oc1c(c(C)c(O)c3c1C(O)OC3=O)OC2=O

Standard InChI:  InChI=1S/C19H14O9/c1-6-4-9(25-3)8(5-20)15-10(6)17(22)27-14-7(2)13(21)11-12(16(14)26-15)19(24)28-18(11)23/h4-5,19,21,24H,1-3H3

Standard InChI Key:  SKCUFZLDTAYNBZ-UHFFFAOYSA-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: 386.31

Molecular Weight (Monoisotopic): 386.0638

AlogP: 2.32

#Rotatable Bonds: 2

Polar Surface Area: 128.59

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 9.59

CX Basic pKa:

CX LogP: 3.08

CX LogD: 3.08

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.45

Np Likeness Score: 2.04

References

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2. PubChem BioAssay data set, 

3. PubChem BioAssay data set, 

4. PubChem BioAssay data set, 

5. PubChem BioAssay data set, 

6. Giez I, Lange OL, Proksch P.  (1994)  Growth retarding activity of lichen substances against the polyphagous herbivorous insect Spodoptera littoralis,  22  (2): [10.1016/0305-1978(94)90001-9]

7. De Bruyn T, van Westen GJ, Ijzerman AP, Stieger B, de Witte P, Augustijns PF, Annaert PP..  (2013)  Structure-based identification of OATP1B1/3 inhibitors.,  83  (6): [PMID:23571415] [10.1124/mol.112.084152]

8. Schinkovitz A, Kaur A, Urban E, Zehl M, Páchniková G, Wang Y, Kretschmer N, Slaninová I, Pauli GF, Franzblau SG, Krupitza G, Bauer R, Kopp B..  (2014)  Cytotoxic constituents from Lobaria scrobiculata and a comparison of two bioassays for their evaluation.,  77  (4): [PMID:24725159] [10.1021/np4008574]

9. Asada K, Canestrari E, Paroo Z..  (2016)  A druggable target for rescuing microRNA defects.,  26  (20): [PMID:27641467] [10.1016/j.bmcl.2016.09.019]

10. Olivon F, Nothias LF, Dumontet V, Retailleau P, Berger S, Ferry G, Cohen W, Pfeiffer B, Boutin JA, Scalbert E, Roussi F, Litaudon M..  (2018)  Natural Inhibitors of the RhoA-p115 Complex from the Bark of Meiogyne baillonii.,  81  (7): [PMID:29969260] [10.1021/acs.jnatprod.8b00209]

11. Johannes Zuegg, Alysha Elliott, Maite Amado, Emma Cowie, Ali Hinton, Geraldine Kaeslin, Angela Kavanagh, Anne Kunert, Gabriell Lowe, Soumya Ramu, Janet Reid, Robin Trauer, Mathilde Desselle, Ruth Neale, Karl Hansford, Mark Blascovich, Matthew Cooper. CO-ADD screening of NIH NCI Natural Product Set III,  [10.6019/CHEMBL4296183]

12. 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]

13. 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]

14. Petrova ON,Lamarre I,Fasani F,Grillon C,Negrerie M.  (2020)  Soluble Guanylate Cyclase Inhibitors Discovered among Natural Compounds.,  83  (12.0): [PMID:33290062] [10.1021/acs.jnatprod.0c00854]

15. Linciano P, Cavalloro V, Martino E, Kirchmair J, Listro R, Rossi D, Collina S..  (2020)  Tackling Antimicrobial Resistance with Small Molecules Targeting LsrK: Challenges and Opportunities.,  63  (24.0): [PMID:33152241] [10.1021/acs.jmedchem.0c01282]

16. McCullough BS, Wang H, Barrios AM..  (2022)  Inhibitor Screen Identifies Covalent Inhibitors of the Protein Histidine Phosphatase PHPT1.,  13  (7.0): [PMID:35859860] [10.1021/acsmedchemlett.2c00053]

Source

Source(4):

• Scientific Literature
• PubChem BioAssays
• CO-ADD antimicrobial screening data
• SARS-CoV-2 Screening Data 2020-21