ID: ALA1923413

Max Phase: Preclinical

Molecular Formula: C20H35NO13

Molecular Weight: 497.49

Molecule Type: Small molecule

Representations

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

Canonical SMILES:  OCC1=C[C@H](N[C@H]2C[C@H](CO)[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C20H35NO13/c22-3-6-1-8(12(26)15(29)11(6)25)21-9-2-7(4-23)19(17(31)13(9)27)34-20-18(32)16(30)14(28)10(5-24)33-20/h1,7-32H,2-5H2/t7-,8+,9+,10-,11-,12+,13+,14-,15+,16+,17-,18-,19-,20+/m1/s1

Standard InChI Key:  JARYYMUOCXVXNK-CSLFJTBJSA-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: 497.49

Molecular Weight (Monoisotopic): 497.2108

AlogP: -6.75

#Rotatable Bonds: 7

Polar Surface Area: 253.02

Molecular Species: NEUTRAL

HBA: 14

HBD: 12

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 12

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.07

CX Basic pKa: 7.41

CX LogP: -6.93

CX LogD: -7.24

Aromatic Rings: 0

Heavy Atoms: 34

QED Weighted: 0.15

Np Likeness Score: 2.26

References

1. Cui Z, Yang X, Shi Y, Uzawa H, Cui J, Dohi H, Nishida Y..  (2011)  Molecular design, synthesis and bioactivity of glycosyl hydrazine and hydrazone derivatives: notable effects of the sugar moiety.,  21  (23): [PMID:22004723] [10.1016/j.bmcl.2011.09.068]

2. Dang QL, Kim WK, Nguyen CM, Choi YH, Choi GJ, Jang KS, Park MS, Lim CH, Luu NH, Kim JC..  (2011)  Nematicidal and antifungal activities of annonaceous acetogenins from Annona squamosa against various plant pathogens.,  59  (20): [PMID:21910504] [10.1021/jf203017f]

3. Lee YM, Moon JS, Yun BS, Park KD, Choi GJ, Kim JC, Lee SH, Kim SU..  (2009)  Antifungal activity of CHE-23C, a dimeric sesquiterpene from Chloranthus henryi.,  57  (13): [PMID:19566082] [10.1021/jf900674y]

4. Cui ZN, Shi YX, Zhang L, Ling Y, Li BJ, Nishida Y, Yang XL..  (2012)  Synthesis and fungicidal activity of novel 2,5-disubstituted-1,3,4-oxadiazole derivatives.,  60  (47): [PMID:23134289] [10.1021/jf303807a]

5. Duan G, Zhang Z, Zhang J, Zhou Y, Yu L, Yuan Q..  (2007)  Evaluation of crude toxin and metabolite produced by Helminthosporium gramineum Rabenh for the control of rice sheath blight in paddy fields,  26  (7): [10.1016/j.cropro.2006.09.014]

6. Zhang CQ, Liu YH, Ma XY, Feng Z, Ma ZH..  (2009)  Characterization of sensitivity of Rhizoctonia solani, causing rice sheath blight, to mepronil and boscalid,  28  (5): [10.1016/j.cropro.2008.12.004]

7. Luo Y, Zhang S, Liu ZJ, Chen W, Fu J, Zeng QF, Zhu HL..  (2013)  Synthesis and antimicrobical evaluation of a novel class of 1,3,4-thiadiazole: derivatives bearing 1,2,4-triazolo[1,5-a]pyrimidine moiety.,  64  [PMID:23644188] [10.1016/j.ejmech.2013.04.014]

8. Dai JK, Dan WJ, Wan JB..  (2022)  Natural and synthetic β-carboline as a privileged antifungal scaffolds.,  229  [PMID:34954591] [10.1016/j.ejmech.2021.114057]

Source

Source(1):

• Scientific Literature