[6-(4-Dimethylamino-3,5-dihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-16-ethyl-4-hydroxy-15-hydroxymethyl-5,9,13-trimethyl-2,10-dioxo-oxacyclohexadeca-11,13-dien-7-yl]-acetaldehyde

ID: ALA44949

Chembl Id: CHEMBL44949

Cas Number: 61257-02-1

PubChem CID: 6437420

Max Phase: Preclinical

Molecular Formula: C31H51NO10

Molecular Weight: 597.75

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@H]1OC(=O)C[C@@H](O)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)[C@@H](O)[C@H](N(C)C)[C@H]2O)[C@@H](CC=O)C[C@@H](C)C(=O)/C=C/C(C)=C/[C@@H]1CO

Standard InChI:  InChI=1S/C31H51NO10/c1-8-25-22(16-34)13-17(2)9-10-23(35)18(3)14-21(11-12-33)30(19(4)24(36)15-26(37)41-25)42-31-29(39)27(32(6)7)28(38)20(5)40-31/h9-10,12-13,18-22,24-25,27-31,34,36,38-39H,8,11,14-16H2,1-7H3/b10-9+,17-13+/t18-,19+,20-,21+,22-,24-,25-,27+,28-,29-,30-,31+/m1/s1

Standard InChI Key:  WGUJDBLMJBJUQU-VKRLOHBMSA-N

Alternative Forms

1. Parent:

   

   ALA44949

   Mycaminosyltylonolide

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: 597.75

Molecular Weight (Monoisotopic): 597.3513

AlogP: 1.40

#Rotatable Bonds: 7

Polar Surface Area: 163.06

Molecular Species: NEUTRAL

HBA: 11

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.67

CX Basic pKa: 7.24

CX LogP: 1.30

CX LogD: 1.07

Aromatic Rings: 0

Heavy Atoms: 42

QED Weighted: 0.25

Np Likeness Score: 2.16

References

1. Kirst HA, Toth JE, Debono M, Willard KE, Truedell BA, Ott JL, Counter FT, Felty-Duckworth AM, Pekarek RS..  (1988)  Synthesis and evaluation of tylosin-related macrolides modified at the aldehyde function: a new series of orally effective antibiotics.,  31  (8): [PMID:3398001] [10.1021/jm00403a025]

2. Zhai H, Luo C, Yang P, Zhang S, Wang H, Cao Y, Yang Y, Liu H, Kong X, Arhema Frejat FO, Ren C, Shi X, Wu C..  (2022)  Design, synthesis and activity against drug-resistant bacteria evaluation of C-20, C-23 modified 5-O-mycaminosyltylonolide derivatives.,  238  [PMID:35675753] [10.1016/j.ejmech.2022.114495]

Source

Source(1):

• Scientific Literature