ID: ALA2228796

Max Phase: Preclinical

Molecular Formula: C17H25N5O13

Molecular Weight: 507.41

Molecule Type: Small molecule

Representations

Canonical SMILES:  NC(=O)OC[C@H](O)[C@@H](O)[C@H](N)C(=O)N[C@H](C(=O)O)[C@H]1O[C@@H](n2cc(CO)c(=O)[nH]c2=O)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C17H25N5O13/c18-6(8(25)5(24)3-34-16(19)32)13(29)20-7(15(30)31)11-9(26)10(27)14(35-11)22-1-4(2-23)12(28)21-17(22)33/h1,5-11,14,23-27H,2-3,18H2,(H2,19,32)(H,20,29)(H,30,31)(H,21,28,33)/t5-,6-,7-,8+,9-,10+,11+,14+/m0/s1

Standard InChI Key:  YFZNSPMAOIVQRP-YVKGXWRCSA-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: 507.41

Molecular Weight (Monoisotopic): 507.1449

AlogP: -6.64

#Rotatable Bonds: 10

Polar Surface Area: 309.98

Molecular Species: ACID

HBA: 14

HBD: 10

#RO5 Violations: 3

HBA (Lipinski): 18

HBD (Lipinski): 12

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.30

CX Basic pKa: 7.53

CX LogP: -8.72

CX LogD: -8.94

Aromatic Rings: 1

Heavy Atoms: 35

QED Weighted: 0.14

Np Likeness Score: 1.02

References

1. Krainer E, Becker JM, Naider F..  (1991)  Synthesis and biological evaluation of dipeptidyl and tripeptidyl polyoxin and nikkomycin analogues as anticandidal prodrugs.,  34  (1): [PMID:1992114] [10.1021/jm00105a026]

2. Yoon MY, Choi NH, Min BS, Choi GJ, Choi YH, Jang KS, Han SS, Cha B, Kim JC..  (2011)  Potent in vivo antifungal activity against powdery mildews of pregnane glycosides from the roots of Cynanchum wilfordii.,  59  (22): [PMID:21992072] [10.1021/jf2039185]

3. Ji Q, Yang D, Wang X, Chen C, Deng Q, Ge Z, Yuan L, Yang X, Liao F..  (2014)  Design, synthesis and evaluation of novel quinazoline-2,4-dione derivatives as chitin synthase inhibitors and antifungal agents.,  22  (13): [PMID:24856180] [10.1016/j.bmc.2014.04.042]

4. Ji Q, Ge Z, Ge Z, Chen K, Wu H, Liu X, Huang Y, Yuan L, Yang X, Liao F..  (2016)  Synthesis and biological evaluation of novel phosphoramidate derivatives of coumarin as chitin synthase inhibitors and antifungal agents.,  108  [PMID:26647304] [10.1016/j.ejmech.2015.11.027]

5. Ji Q, Deng Q, Li B, Li B, Shen Y..  (2019)  Design, synthesis and biological evaluation of novel 5-(piperazin-1-yl)quinolin-2(1H)-one derivatives as potential chitin synthase inhibitors and antifungal agents.,  180  [PMID:31306907] [10.1016/j.ejmech.2019.07.035]

6. Li B, Wang K, Zhang R, Li B, Shen Y, Ji Q..  (2019)  Design, synthesis and biological evaluation of novel diazaspiro[4.5]decan-1-one derivatives as potential chitin synthase inhibitors and antifungal agents.,  182  [PMID:31494473] [10.1016/j.ejmech.2019.111669]

7. Wang LL,Battini N,Bheemanaboina RRY,Zhang SL,Zhou CH.  (2019)  Design and synthesis of aminothiazolyl norfloxacin analogues as potential antimicrobial agents and their biological evaluation.,  167  [PMID:30769240] [10.1016/j.ejmech.2019.01.072]

8. Li B,Shen Y,Wu H,Wu X,Yuan L,Ji Q.  (2020)  Design, synthesis and biological evaluation of novel 3,4-dihydro-2(1H)-quinolinone derivatives as potential chitin synthase inhibitors and antifungal agents.,  195  [PMID:32283299] [10.1016/j.ejmech.2020.112278]

9. Wu H, Du C, Xu Y, Liu L, Zhou X, Ji Q..  (2022)  Design, synthesis, and biological evaluation of novel spiro[pyrrolidine-2,3'-quinolin]-2'-one derivatives as potential chitin synthase inhibitors and antifungal agents.,  233  [PMID:35220015] [10.1016/j.ejmech.2022.114208]

Source

Source(1):

• Scientific Literature