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

ID: ALA2368118

Chembl Id: CHEMBL2368118

PubChem CID: 10319729

Max Phase: Preclinical

Molecular Formula: C24H32O6

Molecular Weight: 416.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H]1[C@@H](CCc2ccc(C(=O)O)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/C24H32O6/c1-14-4-10-19-15(2)20(11-7-16-5-8-17(9-6-16)21(25)26)27-22-24(19)18(14)12-13-23(3,28-22)29-30-24/h5-6,8-9,14-15,18-20,22H,4,7,10-13H2,1-3H3,(H,25,26)/t14-,15-,18+,19+,20-,22-,23+,24-/m1/s1

Standard InChI Key:  ULFXMPVBUZAXFP-PTBRYTJWSA-N

Alternative Forms

1. Parent:

   

   ALA2368118

   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]benzoic acid

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: 416.51

Molecular Weight (Monoisotopic): 416.2199

AlogP: 4.57

#Rotatable Bonds: 4

Polar Surface Area: 74.22

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.24

CX Basic pKa: ┄

CX LogP: 5.49

CX LogD: 2.49

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.73

Np Likeness Score: 2.38

References

1. Jung M, Lee K, Kendrick H, Robinson BL, Croft SL..  (2002)  Synthesis, stability, and antimalarial activity of new hydrolytically stable and water-soluble (+)-deoxoartelinic acid.,  45  (22): [PMID:12383020] [10.1021/jm020244p]

2. Jung M, Tak J, Chung WY, Park KK..  (2006)  Antiangiogenic activity of deoxoartemisinin derivatives on chorioallantoic membrane.,  16  (5): [PMID:16380253] [10.1016/j.bmcl.2005.11.074]

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

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