ID: ALA476894

Max Phase: Preclinical

Molecular Formula: C17H26N8O5

Molecular Weight: 422.45

Molecule Type: Small molecule

Representations

Synonyms (1): Blasticidin S
Synonyms from Alternative Forms(1):

Canonical SMILES:  CN(CC[C@H](N)CC(=O)N[C@H]1C=C[C@H](n2ccc(N)nc2=O)O[C@@H]1C(=O)O)C(=N)N

Standard InChI:  InChI=1S/C17H26N8O5/c1-24(16(20)21)6-4-9(18)8-12(26)22-10-2-3-13(30-14(10)15(27)28)25-7-5-11(19)23-17(25)29/h2-3,5,7,9-10,13-14H,4,6,8,18H2,1H3,(H3,20,21)(H,22,26)(H,27,28)(H2,19,23,29)/t9-,10-,13+,14-/m0/s1

Standard InChI Key:  CXNPLSGKWMLZPZ-ZNIXKSQXSA-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: 422.45

Molecular Weight (Monoisotopic): 422.2026

AlogP: -2.22

#Rotatable Bonds: 8

Polar Surface Area: 215.67

Molecular Species: ZWITTERION

HBA: 9

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.71

CX Basic pKa: 12.19

CX LogP: -4.70

CX LogD: -5.62

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.15

Np Likeness Score: 1.05

References

1. Engelmeier D, Hadacek F, Hofer O, Lutz-Kutschera G, Nagl M, Wurz G, Greger H..  (2004)  Antifungal 3-butylisocoumarins from Asteraceae-Anthemideae.,  67  (1): [PMID:14738379] [10.1021/np0301339]

2. McCarthy PJ, Pitts TP, Gunawardana GP, Kelly-Borges M, Pomponi SA..  (1992)  Antifungal activity of meridine, a natural product from the marine sponge Corticium sp.,  55  (11): [PMID:1479383] [10.1021/np50089a016]

3. Lisk G, Pain M, Gluzman IY, Kambhampati S, Furuya T, Su XZ, Fay MP, Goldberg DE, Desai SA..  (2008)  Changes in the plasmodial surface anion channel reduce leupeptin uptake and can confer drug resistance in Plasmodium falciparum-infected erythrocytes.,  52  (7): [PMID:18443109] [10.1128/aac.00057-08]

4. Engelmeier D, Hadacek F, Pacher T, Vajrodaya S, Greger H..  (2000)  Cyclopenta[b]benzofurans from Aglaia species with pronounced antifungal activity against rice blast fungus (Pyricularia grisea).,  48  (4): [PMID:10775404] [10.1021/jf990509h]

5. KIM HT, MIN JY, CHOI GJ, KIM J, KIM BS, CHUNG YR, KIM BT, KIM YS, YAMAGUCHI I, CHO KY.  (2002)  Synthesis of a New 1, 2, 4-Oxadiazol-5-one Derivative, KC10017, and Its Controlling Activity against Rice Blast Disease Caused by Magnaporthe grisea,  27  (3): [10.1584/jpestics.27.229]

6. Kumar G, Kiran Tudu A..  (2023)  Tackling multidrug-resistant Staphylococcus aureus by natural products and their analogues acting as NorA efflux pump inhibitors.,  80  [PMID:36731248] [10.1016/j.bmc.2023.117187]

Source

Source(1):

• Scientific Literature