ID: ALA2112186

Max Phase: Preclinical

Molecular Formula: C25H35NO9

Molecular Weight: 493.55

Molecule Type: Small molecule

Representations

Synonyms (1): Ryanodine
Synonyms from Alternative Forms(1):

Canonical SMILES:  CC(C)[C@@]1(O)[C@@H](OC(=O)c2cc[nH]c2)[C@@]2(O)[C@]3(C)C[C@@]4(O)O[C@@]5([C@H](O)[C@@H](C)CC[C@]35O)[C@@]2(O)[C@@]41C

Standard InChI:  InChI=1S/C25H35NO9/c1-12(2)22(31)17(34-16(28)14-7-9-26-10-14)23(32)18(4)11-21(30)19(22,5)25(23,33)24(35-21)15(27)13(3)6-8-20(18,24)29/h7,9-10,12-13,15,17,26-27,29-33H,6,8,11H2,1-5H3/t13-,15+,17+,18+,19-,20-,21+,22+,23+,24+,25+/m0/s1

Standard InChI Key:  URVDQZDQPQVIGE-ZORYXUITSA-N

Molecule Features

Natural Product: No

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: 493.55

Molecular Weight (Monoisotopic): 493.2312

AlogP: -0.19

#Rotatable Bonds: 3

Polar Surface Area: 172.70

Molecular Species: NEUTRAL

HBA: 9

HBD: 7

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.24

CX Basic pKa:

CX LogP: 0.18

CX LogD: 0.18

Aromatic Rings: 1

Heavy Atoms: 35

QED Weighted: 0.28

Np Likeness Score: 2.58

References

1. Gerzon K, Humerickhouse RA, Besch HR, Bidasee KR, Emmick JT, Roeske RW, Tian Z, Ruest L, Sutko JL..  (1993)  Amino- and guanidinoacylryanodines: basic ryanodine esters with enhanced affinity for the sarcoplasmic reticulum Ca(2+)-release channel.,  36  (10): [PMID:8388466] [10.1021/jm00062a003]

2. Jefferies PR, Gengo PJ, Watson MJ, Casida JE..  (1996)  Ryanodine action at calcium release channels. 2. relation to substituents of the cyclohexane ring.,  39  (12): [PMID:8691428] [10.1021/jm950712d]

3. McNeal ET, Lewandowski GA, Daly JW, Creveling CR..  (1985)  [3H]Batrachotoxinin A 20 alpha-benzoate binding to voltage-sensitive sodium channels: a rapid and quantitative assay for local anesthetic activity in a variety of drugs.,  28  (3): [PMID:2579237] [10.1021/jm00381a019]

4. Fraga BM, Gonzalez-Coloma A, Gutierrez C, Terrero D.  (1997)  Insect Antifeedant Isoryanodane Diterpenes from Persea indica ,  60  (9): [10.1021/np970167e]

5. Jefferies PR, Toia RF, Casida JE..  (1991)  Ryanodyl 3-(pyridine-3-carboxylate): a novel ryanoid from Ryania insecticide.,  54  (4): [PMID:1791479] [10.1021/np50076a043]

6. Achenbach H, Hübner H, Vierling W, Brandt W, Reiter M..  (1995)  Spiganthine, the cardioactive principle of Spigelia anthelmia.,  58  (7): [PMID:7561902] [10.1021/np50121a019]

7. 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]

8. Masaki T, Yasokawa N, Fujioka S, Motoba K, Tohnishi M, Hirooka T.  (2009)  Quantitative relationship between insecticidal activity and Ca2+ pump stimulation by flubendiamide and its related compounds,  34  (1): [10.1584/jpestics.G08-29]

9. Sandoval-Mojica AF, Capinera JL..  (2011)  Antifeedant effect of commercial chemicals and plant extracts against Schistocerca americana (Orthoptera: Acrididae) and Diaprepes abbreviatus (Coleoptera: Curculionidae).,  67  (7): [PMID:21370392] [10.1002/ps.2125]

10. Waterhouse AL, Pessah IN, Francini AO, Casida JE..  (1987)  Structural aspects of ryanodine action and selectivity.,  30  (4): [PMID:2435905] [10.1021/jm00387a022]

11. Waterhouse AL, Pessah IN, Francini AO, Casida JE..  (1987)  Structural aspects of ryanodine action and selectivity.,  30  (4): [PMID:2435905] [10.1021/jm00387a022]

12. Jefferies PR, Lehmberg E, Lam WW, Casida JE..  (1993)  Bioactive ryanoids from nucleophilic additions to 4,12-seco-4,12-dioxoryanodine.,  36  (9): [PMID:8387597] [10.1021/jm00061a003]

13. Tohnishi M, Nakao H, Furuya T, Seo A, Kodama H, Tsubata K, Fujioka S, Kodama H, Hirooka T, Nishimatsu T.  (2005)  Flubendiamide, a Novel Insecticide Highly Active against Lepidopterous Insect Pests,  30  (4): [10.1584/jpestics.30.354]

14. Kirby RW, Martelli A, Calderone V, McKay NG, Lawson K..  (2013)  Large conductance Ca(2+)-activated K(+) channel (BKCa) activating properties of a series of novel N-arylbenzamides: Channel subunit dependent effects.,  21  (14): [PMID:23707646] [10.1016/j.bmc.2013.05.003]

Source

Source(1):

• Scientific Literature