3-Methyl-butyric acid 6-{6-[4-acetoxy-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxo-ethyl)-oxacyclohexadeca-11,13-dien-6-yloxy]-4-dimethylamino-5-hydroxy-2-methyl-tetrahydro-pyran-3-yloxy}-4-hydroxy-2,4-dimethyl-tetrahydro-pyran-3-yl ester (leucomycin A3)

ID: ALA329011

Chembl Id: CHEMBL329011

Cas Number: 16846-24-5

PubChem CID: 6419972

Max Phase: Preclinical

Molecular Formula: C42H69NO15

Molecular Weight: 828.01

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO[C@@H]1[C@@H](OC2OC(C)C(OC3CC(C)(O)C(OC(=O)CC(C)C)C(C)O3)C(N(C)C)C2O)[C@@H](CC=O)C[C@@H](C)[C@@H](O)/C=C/C=C/C[C@@H](C)OC(=O)C[C@H]1OC(C)=O

Standard InChI:  InChI=1S/C42H69NO15/c1-23(2)19-32(47)56-40-27(6)53-34(22-42(40,8)50)57-37-26(5)54-41(36(49)35(37)43(9)10)58-38-29(17-18-44)20-24(3)30(46)16-14-12-13-15-25(4)52-33(48)21-31(39(38)51-11)55-28(7)45/h12-14,16,18,23-27,29-31,34-41,46,49-50H,15,17,19-22H2,1-11H3/b13-12+,16-14+/t24-,25-,26?,27?,29+,30+,31-,34?,35?,36?,37?,38+,39+,40?,41?,42?/m1/s1

Standard InChI Key:  XJSFLOJWULLJQS-ZQXIYRAGSA-N

Alternative Forms

1. Parent:

   

   ALA329011

   [6-[6-[[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-4-acetyloxy-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy]-4-(dimethylamino)-5-hydroxy-2-methyloxan-3-yl]oxy-4-hydroxy-2,4-dimethyloxan-3-yl] 3-methylbutanoate

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: 828.01

Molecular Weight (Monoisotopic): 827.4667

AlogP: 3.01

#Rotatable Bonds: 12

Polar Surface Area: 206.05

Molecular Species: NEUTRAL

HBA: 16

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 16

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.71

CX Basic pKa: 7.90

CX LogP: 3.22

CX LogD: 2.60

Aromatic Rings: ┄

Heavy Atoms: 58

QED Weighted: 0.15

Np Likeness Score: 2.14

References

1. Omura S, Miyano K, Matsubara H, Nakagawa A..  (1982)  Novel dimeric derivatives of leucomycins and tylosin, sixteen-membered macrolides.,  25  (3): [PMID:7040661] [10.1021/jm00345a014]

2. Agouridas C, Denis A, Auger JM, Benedetti Y, Bonnefoy A, Bretin F, Chantot JF, Dussarat A, Fromentin C, D'Ambrières SG, Lachaud S, Laurin P, Le Martret O, Loyau V, Tessot N..  (1998)  Synthesis and antibacterial activity of ketolides (6-O-methyl-3-oxoerythromycin derivatives): a new class of antibacterials highly potent against macrolide-resistant and -susceptible respiratory pathogens.,  41  (21): [PMID:9767644] [10.1021/jm980240d]

Source

Source(1):

• Scientific Literature