ID: ALA256105

Max Phase: Phase

Molecular Formula: C36H62O11

Molecular Weight: 670.88

Molecule Type: Small molecule

Representations

Synonyms (3): Monensin | 67314 | A-3823A
Synonyms from Alternative Forms(3):

Canonical SMILES:  CC[C@@]1([C@@H]2O[C@@H]([C@H]3O[C@@](O)(CO)[C@H](C)C[C@@H]3C)C[C@@H]2C)CC[C@H]([C@]2(C)CC[C@]3(C[C@H](O)[C@@H](C)[C@@H]([C@@H](C)[C@@H](OC)[C@H](C)C(=O)O)O3)O2)O1

Standard InChI:  InChI=1S/C36H62O11/c1-10-34(31-20(3)16-26(43-31)28-19(2)15-21(4)36(41,18-37)46-28)12-11-27(44-34)33(8)13-14-35(47-33)17-25(38)22(5)30(45-35)23(6)29(42-9)24(7)32(39)40/h19-31,37-38,41H,10-18H2,1-9H3,(H,39,40)/t19-,20-,21+,22+,23-,24-,25-,26+,27+,28-,29+,30-,31+,33-,34-,35+,36-/m0/s1

Standard InChI Key:  GAOZTHIDHYLHMS-KEOBGNEYSA-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: 670.88

Molecular Weight (Monoisotopic): 670.4292

AlogP: 4.27

#Rotatable Bonds: 10

Polar Surface Area: 153.37

Molecular Species: ACID

HBA: 10

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.24

CX Basic pKa:

CX LogP: 4.82

CX LogD: 1.81

Aromatic Rings: 0

Heavy Atoms: 47

QED Weighted: 0.26

Np Likeness Score: 2.41

References

1. Bochis RJ, Chabala JC, Harris E, Peterson LH, Barash L, Beattie T, Brown JE, Graham DW, Waksmunski FS, Tischler M..  (1991)  Benzylated 1,2,3-triazoles as anticoccidiostats.,  34  (9): [PMID:1895303] [10.1021/jm00113a024]

2. 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]

3. Huczyński A, Stefańska J, Przybylski P, Brzezinski B, Bartl F..  (2008)  Synthesis and antimicrobial properties of monensin A esters.,  18  (8): [PMID:18375122] [10.1016/j.bmcl.2008.03.038]

4. Imoto M, Umezawa K, Takahashi Y, Naganawa H, Iitaka Y, Nakamura H, Koizumi Y, Sasaki Y, Hamada M, Sawa T, Takeuchi T.  (1990)  Isolation and Structure Determination of Inostamycin, a Novel Inhibitor of Phosphatidylinositol Turnover,  53  (4): [10.1021/np50070a008]

5. Łowicki D, Huczyński A, Stefańska J, Brzezinski B..  (2010)  Structural characterization and antibacterial activity against clinical isolates of Staphylococcus of N-phenylamide of monensin A and its 1:1 complexes with monovalent cations.,  45  (9): [PMID:20580137] [10.1016/j.ejmech.2010.05.064]

6. Mahmoudi N, Garcia-Domenech R, Galvez J, Farhati K, Franetich JF, Sauerwein R, Hannoun L, Derouin F, Danis M, Mazier D..  (2008)  New active drugs against liver stages of Plasmodium predicted by molecular topology.,  52  (4): [PMID:18212104] [10.1128/aac.01043-07]

7. Lamping E, Ranchod A, Nakamura K, Tyndall JD, Niimi K, Holmes AR, Niimi M, Cannon RD..  (2009)  Abc1p is a multidrug efflux transporter that tips the balance in favor of innate azole resistance in Candida krusei.,  53  (2): [PMID:19015352] [10.1128/aac.01095-08]

8. Polli JW, Wring SA, Humphreys JE, Huang L, Morgan JB, Webster LO, Serabjit-Singh CS..  (2001)  Rational use of in vitro P-glycoprotein assays in drug discovery.,  299  (2): [PMID:11602674]

9. Huczyński A, Janczak J, Stefańska J, Antoszczak M, Brzezinski B..  (2012)  Synthesis and antimicrobial activity of amide derivatives of polyether antibiotic-salinomycin.,  22  (14): [PMID:22721714] [10.1016/j.bmcl.2012.05.081]

10. Polli JW, Wring SA, Humphreys JE, Huang L, Morgan JB, Webster LO, Serabjit-Singh CS..  (2001)  Rational use of in vitro P-glycoprotein assays in drug discovery.,  299  (2): [PMID:11602674]

11. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

12. Huczyński A..  (2012)  Polyether ionophores-promising bioactive molecules for cancer therapy.,  22  (23): [PMID:23063400] [10.1016/j.bmcl.2012.09.046]

13. Dadgar S, Ramjan Z, Floriano WB..  (2013)  Paclitaxel is an inhibitor and its boron dipyrromethene derivative is a fluorescent recognition agent for botulinum neurotoxin subtype A.,  56  (7): [PMID:23484537] [10.1021/jm301829h]

14. Unpublished dataset, 

15. Huczyński A, Klejborowska G, Antoszczak M, Maj E, Wietrzyk J..  (2015)  Anti-proliferative activity of Monensin and its tertiary amide derivatives.,  25  (20): [PMID:26338363] [10.1016/j.bmcl.2015.08.067]

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

Source

Source(5):

• Scientific Literature
• USP Dictionary of USAN and International Drug Names
• TP-search Transporter Database
• Gene Expression Atlas Compounds
• IMI-CARE SARS-CoV-2 Data