4''-deoxy-4''-Aminoavermectin derivative

ID: ALA268085

Chembl Id: CHEMBL268085

PubChem CID: 44318016

Max Phase: Preclinical

Molecular Formula: C50H77NO15

Molecular Weight: 932.16

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(C)[C@H]1O[C@]2(CC(O)[C@@H]1C)C[C@@H]1C[C@@H](C/C=C(\C)[C@@H](O[C@H]3C[C@H](OC)[C@@H](O[C@H]4C[C@H](OC)[C@H](NC(C)=O)[C@H](C)O4)[C@H](C)O3)[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/C50H77NO15/c1-12-25(2)45-29(6)37(53)23-49(66-45)22-35-19-34(65-49)17-16-27(4)44(26(3)14-13-15-33-24-59-47-43(54)28(5)18-36(48(55)62-35)50(33,47)56)63-41-21-39(58-11)46(31(8)61-41)64-40-20-38(57-10)42(30(7)60-40)51-32(9)52/h13-16,18,25-26,29-31,34-47,53-54,56H,12,17,19-24H2,1-11H3,(H,51,52)/b14-13+,27-16+,33-15+/t25?,26-,29-,30-,31-,34+,35-,36-,37?,38-,39-,40-,41-,42+,43+,44-,45+,46-,47+,49-,50+/m0/s1

Standard InChI Key:  PLWIYFTWTBRGSA-UJIOELJRSA-N

Alternative Forms

1. Parent:

   

   ALA268085

   N-[(2S,3R,4S,6S)-6-[(2S,3S,4S,6R)-6-[(1R,4S,5'S,6R,6'R,8R,10E,12S,13S,14E,16E,20R,21R,24S)-6'-butan-2-yl-4',21,24-trihydroxy-5',11,13,22-tetramethyl-2-oxospiro[3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene-6,2'-oxane]-12-yl]oxy

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: 932.16

Molecular Weight (Monoisotopic): 931.5293

AlogP: 4.72

#Rotatable Bonds: 9

Polar Surface Area: 199.16

Molecular Species: NEUTRAL

HBA: 15

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 16

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.49

CX Basic pKa:

CX LogP: 4.56

CX LogD: 4.56

Aromatic Rings: 0

Heavy Atoms: 66

QED Weighted: 0.18

Np Likeness Score: 2.17

References

1. Mrozik H, Eskola P, Arison BH, Linn BO, Lusi A, Matzuk A, Shih TL, Tischler M, Waksmunski FS, Wyvratt MJ, Blizzard TA, Margiatto GM, Fisher MH, Shoop WL, Egerton JR.  (1995)  4-Deoxy-4-aminoavermectins with potent broad spectrum antiparasitic activities,  5  (20): [10.1016/0960-894X(95)00424-R]

Source

Source(1):

• Scientific Literature