1-(3-trifluoromethylphenyl)-4-{2-[1,5,9-trimethyl-(1R,4R,5R,8S,9R,10R,12R,13R)-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadec-10-yl]ethyl}hexahydropyrazine

ID: ALA2368860

Chembl Id: CHEMBL2368860

PubChem CID: 10929453

Max Phase: Preclinical

Molecular Formula: C28H39F3N2O4

Molecular Weight: 524.62

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H]1[C@@H](CCN2CCN(c3cccc(C(F)(F)F)c3)CC2)O[C@@H]2O[C@]3(C)CC[C@H]4[C@H](C)CC[C@@H]1[C@@]24OO3

Standard InChI:  InChI=1S/C28H39F3N2O4/c1-18-7-8-23-19(2)24(34-25-27(23)22(18)9-11-26(3,35-25)36-37-27)10-12-32-13-15-33(16-14-32)21-6-4-5-20(17-21)28(29,30)31/h4-6,17-19,22-25H,7-16H2,1-3H3/t18-,19-,22+,23+,24-,25-,26+,27-/m1/s1

Standard InChI Key:  ILHLSPYNKOOAAQ-OKGDRXONSA-N

Alternative Forms

1. Parent:

   

   ALA2368860

   1-[3-(trifluoromethyl)phenyl]-4-[2-[(1S,4S,5R,8S,9R,10R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]ethyl]piperazine

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

Calculated Properties

Molecular Weight: 524.62

Molecular Weight (Monoisotopic): 524.2862

AlogP: 5.47

#Rotatable Bonds: 4

Polar Surface Area: 43.40

Molecular Species: NEUTRAL

HBA: 6

HBD: 0

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 2

CX Acidic pKa:

CX Basic pKa: 8.26

CX LogP: 6.07

CX LogD: 5.16

Aromatic Rings: 1

Heavy Atoms: 37

QED Weighted: 0.49

Np Likeness Score: 0.97

References

1. Hindley S, Ward SA, Storr RC, Searle NL, Bray PG, Park BK, Davies J, O'Neill PM..  (2002)  Mechanism-based design of parasite-targeted artemisinin derivatives: synthesis and antimalarial activity of new diamine containing analogues.,  45  (5): [PMID:11855985] [10.1021/jm0109816]

2. Slack RD, Jacobine AM, Posner GH.  (2012)  Antimalarial peroxides: advances in drug discovery and design,  3  (3): [10.1039/C2MD00277A]

3. Kumari A, Karnatak M, Singh D, Shankar R, Jat JL, Sharma S, Yadav D, Shrivastava R, Verma VP..  (2019)  Current scenario of artemisinin and its analogues for antimalarial activity.,  163  [PMID:30579122] [10.1016/j.ejmech.2018.12.007]

4. Patel OPS, Beteck RM, Legoabe LJ..  (2021)  Exploration of artemisinin derivatives and synthetic peroxides in antimalarial drug discovery research.,  213  [PMID:33508479] [10.1016/j.ejmech.2021.113193]

Source

Source(1):

• Scientific Literature