(3R,4S,5S,6R,7R,9R,10S,11S,12R,13S,14R)-14-ethyl-7,10,12,13-tetrahydroxy-6-((2S,3R,4S,6R)-3-hydroxy-4-((2-hydroxyethyl)(methyl)amino)-6-methyltetrahydro-2H-pyran-2-yloxy)-4-((2S,4S,6S)-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yloxy)-3,5,7,9,11,13-hexamethyloxacyclotetradecan-2-one

ID: ALA1778047

PubChem CID: 54582661

Max Phase: Preclinical

Molecular Formula: C38H71NO13

Molecular Weight: 749.98

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)C[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@H](N(C)CCO)[C@H]2O)[C@](C)(O)C[C@@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@]1(C)O

Standard InChI:  InChI=1S/C38H71NO13/c1-13-27-38(10,46)32(43)23(5)29(41)20(2)17-37(9,45)33(52-35-30(42)26(16-21(3)49-35)39(11)14-15-40)24(6)31(25(7)34(44)50-27)51-28-19-36(8,47-12)18-22(4)48-28/h20-33,35,40-43,45-46H,13-19H2,1-12H3/t20-,21-,22+,23+,24+,25-,26+,27-,28+,29+,30-,31+,32-,33-,35+,36+,37-,38-/m1/s1

Standard InChI Key:  YPNNHAAJVYNNJH-ZYSXJUQQSA-N

Molfile:  

     RDKit          2D

 54 56  0  0  0  0  0  0  0  0999 V2000
   27.9000   -0.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7542   -1.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3167   -1.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6042    0.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0375   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9292    0.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4625   -0.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7417   -0.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3167    1.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3167   -0.9125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3167    0.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0292    1.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1750   -0.9125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.2292   -4.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6542    0.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4625    0.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4792   -2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2042   -3.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6042   -0.9708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7667   -3.4083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6042   -0.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5250   -4.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4542   -2.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.8000   -4.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7417    1.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7417    0.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3542    0.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6875    1.5125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.6125   -2.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.3292   -0.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0292    2.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0917    0.9625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.2605    0.6438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.6792    1.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.0292    0.3167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.2417   -5.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8792   -0.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0417   -2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0292   -0.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6042    1.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9292   -3.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1750   -0.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8917   -0.9208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0917   -4.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4625    1.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9875    1.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4167    1.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0292   -1.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9667   -5.4208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8917   -1.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1917   -2.5583    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   27.8917   -1.3500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   30.1162    1.4627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8447    1.8498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  5  1  0
  4 11  1  0
  5  2  1  0
  6  1  1  0
  7 13  1  6
  8  7  1  0
  9 12  1  0
 10  3  1  0
 11  9  1  0
 12 25  1  0
 13  1  1  0
 14 18  1  0
 15  6  1  0
 16  7  1  0
 17 23  1  0
 18 17  1  0
 19  1  1  0
 20 17  1  0
 21 10  1  0
 22 24  1  0
  2 23  1  6
 24 20  1  0
 25 26  1  0
 26 16  1  0
 27 30  1  0
 15 28  1  1
 29  3  2  0
 30 19  1  0
 12 31  1  1
  4 32  1  1
  6 33  1  6
 16 34  1  1
 11 35  1  1
 14 36  1  1
 37  4  1  0
  5 38  1  1
  8 39  1  6
  9 40  1  1
 41 14  1  0
 42 16  1  0
 21 43  1  6
 24 44  1  6
 25 45  1  6
 46 28  1  0
 47 28  1  0
 30 48  1  1
 49 36  1  0
 50 43  1  0
 17 51  1  6
  1 52  1  6
 27 15  1  0
  4 21  1  0
 22 14  1  0
 47 53  1  0
  2  8  1  0
 53 54  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1778047

   (3R,4S,5S,6R,7R,9R,10S,11S,12R,13S,14R)-14-ethyl-7,10,12,13-tetrahydroxy-6-((2S,3R,4S,6R)-3-hydroxy-4-((2-hydroxyethyl)(methyl)amino)-6-methyltetrahydro-2H-pyran-2-yloxy)-4-((2S,4S,6S)-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yloxy)-3,5,7,9,11,13-hexam

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: 749.98

Molecular Weight (Monoisotopic): 749.4925

AlogP: 1.97

#Rotatable Bonds: 9

Polar Surface Area: 197.07

Molecular Species: BASE

HBA: 14

HBD: 6

#RO5 Violations: 3

HBA (Lipinski): 14

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 12.58

CX Basic pKa: 8.90

CX LogP: 1.92

CX LogD: 0.41

Aromatic Rings: ┄

Heavy Atoms: 52

QED Weighted: 0.19

Np Likeness Score: 1.54

References

1. Liu Y, Carreras CW, Claypool M, Myles DC, Shaw SJ..  (2011)  The role of the 4''-hydroxyl on motilin agonist potency in the 9-dihydroerythromycin series.,  21  (12): [PMID:21570844] [10.1016/j.bmcl.2011.04.078]

Source

Source(1):

• Scientific Literature