ID: ALA601773

Max Phase: Unknown

Molecular Formula: C35H41N5O5

Molecular Weight: 611.74

Molecule Type: Small molecule

Representations

Synonyms (2): 9,10-dihydroergocristine | GNF-PF-3462
Synonyms from Alternative Forms(2):

Canonical SMILES:  CC(C)[C@@]1(NC(=O)[C@@H]2C[C@@H]3c4cccc5[nH]cc(c45)C[C@H]3N(C)C2)O[C@@]2(O)[C@@H]3CCCN3C(=O)[C@H](Cc3ccccc3)N2C1=O

Standard InChI:  InChI=1S/C35H41N5O5/c1-20(2)34(37-31(41)23-16-25-24-11-7-12-26-30(24)22(18-36-26)17-27(25)38(3)19-23)33(43)40-28(15-21-9-5-4-6-10-21)32(42)39-14-8-13-29(39)35(40,44)45-34/h4-7,9-12,18,20,23,25,27-29,36,44H,8,13-17,19H2,1-3H3,(H,37,41)/t23-,25-,27-,28+,29+,34-,35+/m1/s1

Standard InChI Key:  DEQITUUQPICUMR-HJPBWRTMSA-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: Yes

Availability: No

Prodrug: No

Properties

Molecular Weight: 611.74

Molecular Weight (Monoisotopic): 611.3108

AlogP: 2.72

#Rotatable Bonds: 5

Polar Surface Area: 118.21

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.69

CX Basic pKa: 8.39

CX LogP: 3.83

CX LogD: 2.95

Aromatic Rings: 3

Heavy Atoms: 45

QED Weighted: 0.41

Np Likeness Score: 1.05

References

1. Plouffe D, Brinker A, McNamara C, Henson K, Kato N, Kuhen K, Nagle A, Adrián F, Matzen JT, Anderson P, Nam TG, Gray NS, Chatterjee A, Janes J, Yan SF, Trager R, Caldwell JS, Schultz PG, Zhou Y, Winzeler EA..  (2008)  In silico activity profiling reveals the mechanism of action of antimalarials discovered in a high-throughput screen.,  105  (26): [PMID:18579783] [10.1073/pnas.0802982105]

2. PubChem BioAssay data set, 

3. PubChem BioAssay data set, 

4. PubChem BioAssay data set, 

5. PubChem BioAssay data set, 

6. Ekins S, Kim RB, Leake BF, Dantzig AH, Schuetz EG, Lan LB, Yasuda K, Shepard RL, Winter MA, Schuetz JD, Wikel JH, Wrighton SA..  (2002)  Three-dimensional quantitative structure-activity relationships of inhibitors of P-glycoprotein.,  61  (1): [PMID:11961113] [10.1124/mol.61.5.964]

7. Yasuda K, Lan LB, Sanglard D, Furuya K, Schuetz JD, Schuetz EG..  (2002)  Interaction of cytochrome P450 3A inhibitors with P-glycoprotein.,  303  (1): [PMID:12235267] [10.1124/jpet.102.037549]

8. PubChem BioAssay data set, 

9. PubChem BioAssay data set, 

10. PubChem BioAssay data set, 

11. PubChem BioAssay data set, 

12. WHO Anatomical Therapeutic Chemical Classification, 

13. 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]

14. 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]

15. 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]

16. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

17. 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]

18. Hügel HM, de Silva NH, Siddiqui A, Blanch E, Lingham A..  (2021)  Natural spirocyclic alkaloids and polyphenols as multi target dementia leads.,  43  [PMID:34153839] [10.1016/j.bmc.2021.116270]

Source

Source(8):

• Scientific Literature
• Novartis Malaria Screening
• PubChem BioAssays
• TP-search Transporter Database
• WHO Anatomical Therapeutic Chemical Classification
• SARS-CoV-2 Screening Data 2020-21
• IMI-CARE SARS-CoV-2 Data
• Fraunhofer HDAC6