13-substituted 22,23-dihydroavermectin B1a analogue

ID: ALA330828

Chembl Id: CHEMBL330828

Cas Number: 123997-59-1

PubChem CID: 13710870

Max Phase: Preclinical

Molecular Formula: C34H50O8

Molecular Weight: 586.77

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@H](C)[C@H]1O[C@]2(CC[C@@H]1C)C[C@@H]1C[C@@H](C/C=C(\C)[C@@H](O)[C@@H](C)/C=C/C=C3\CO[C@@H]4[C@H](O)C(C)=C[C@@H](C(=O)O1)[C@]34O)O2

Standard InChI:  InChI=1S/C34H50O8/c1-7-19(2)30-22(5)13-14-33(42-30)17-26-16-25(41-33)12-11-21(4)28(35)20(3)9-8-10-24-18-39-31-29(36)23(6)15-27(32(37)40-26)34(24,31)38/h8-11,15,19-20,22,25-31,35-36,38H,7,12-14,16-18H2,1-6H3/b9-8+,21-11+,24-10+/t19-,20-,22-,25+,26-,27-,28-,29+,30+,31+,33+,34+/m0/s1

Standard InChI Key:  XOCXXEYUGYTCNG-AOIHNFKZSA-N

Alternative Forms

1. Parent:

   

   ALA330828

   IVM AGLYCONE

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: 586.77

Molecular Weight (Monoisotopic): 586.3506

AlogP: 4.53

#Rotatable Bonds: 2

Polar Surface Area: 114.68

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.55

CX Basic pKa: ┄

CX LogP: 4.19

CX LogD: 4.19

Aromatic Rings: ┄

Heavy Atoms: 42

QED Weighted: 0.32

Np Likeness Score: 2.85

References

1. Mrozik H, Linn BO, Eskola P, Lusi A, Matzuk A, Preiser FA, Ostlind DA, Schaeffer JM, Fisher MH..  (1989)  Syntheses and biological activities of 13-substituted avermectin aglycons.,  32  (2): [PMID:2913297] [10.1021/jm00122a015]

2. dos Santos AR, Falcão CA, Muzitano MF, Kaiser CR, Rossi-Bergmann B, Férézou JP..  (2009)  Ivermectin-derived leishmanicidal compounds.,  17  (2): [PMID:19114308] [10.1016/j.bmc.2008.12.003]

3. Singh L, Fontinha D, Francisco D, Mendes AM, Prudêncio M, Singh K..  (2020)  Molecular Design and Synthesis of Ivermectin Hybrids Targeting Hepatic and Erythrocytic Stages of Plasmodium Parasites.,  63  (4): [PMID:32011136] [10.1021/acs.jmedchem.0c00033]

Source

Source(1):

• Scientific Literature