(S)-5-(((2R,3R,5S,6S)-6-((5-((3R,4R,5R,7R)-7-(2-((tert-butoxycarbonyl)amino)ethyl)-4-hydroxy-1,6-dioxaspiro[2.5]octan-5-yl)-3-methylpenta-2,4-dien-1-yl)-2,5-dimethyltetrahydro-2H-pyran-3-yl)amino)-5-oxopent-3-en-2-yl acetate

ID: ALA5206108

PubChem CID: 168294878

Max Phase: Preclinical

Molecular Formula: C33H52N2O9

Molecular Weight: 620.78

Names and Identifiers

Canonical SMILES:  CC(=O)O[C@@H](C)/C=C\C(=O)N[C@@H]1C[C@H](C)[C@H](C/C=C(C)/C=C/[C@H]2O[C@H](CCNC(=O)OC(C)(C)C)C[C@@]3(CO3)[C@@H]2O)O[C@@H]1C

Standard InChI:  InChI=1S/C33H52N2O9/c1-20(9-12-27-21(2)17-26(23(4)42-27)35-29(37)14-11-22(3)41-24(5)36)10-13-28-30(38)33(19-40-33)18-25(43-28)15-16-34-31(39)44-32(6,7)8/h9-11,13-14,21-23,25-28,30,38H,12,15-19H2,1-8H3,(H,34,39)(H,35,37)/b13-10+,14-11-,20-9+/t21-,22-,23+,25+,26+,27-,28+,30+,33+/m0/s1

Standard InChI Key:  XBVZTXDANPJEPT-IGMWFBRCSA-N

Molfile:  

 
     RDKit          2D

 44 46  0  0  0  0  0  0  0  0999 V2000
    0.0002   -1.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0002   -0.7706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7147   -0.3581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4291   -0.7706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1436   -0.3581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8581   -0.7706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5726   -0.3581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2870   -0.7706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5726    0.4668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2870    0.8793    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0016    0.4668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0016   -0.3581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7160    0.8793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4305    0.4668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4305   -0.3581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1450   -0.7706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8595   -0.3581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5739   -0.7706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8595    0.4668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7160   -0.7706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8581    0.8793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1436    0.4668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4291    0.8793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7142   -0.3581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4287   -0.7706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1432   -0.3581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1432    0.4671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4287    0.8796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2696    1.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4446    1.5956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5726    0.4671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5726   -0.3581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2870   -0.7706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0016   -0.3581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7160   -0.7706    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4305   -0.3581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1450   -0.7706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8595   -0.3581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5739   -0.7706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8595    0.4669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5739    0.0543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4305    0.4669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.7707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  2  0
  3  4  1  0
  5  4  1  1
  5  6  1  0
  6  7  1  0
  7  8  1  1
  7  9  1  0
  9 10  1  1
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  1
 16 17  1  0
 17 18  1  0
 17 19  2  0
 15 20  1  0
  9 21  1  0
 21 22  1  0
 22  5  1  0
 22 23  1  1
 24  2  1  0
 25 24  2  0
 26 25  1  1
 26 27  1  0
 27 28  1  6
 27 29  1  0
 29 30  1  0
 31 30  1  0
 29 31  1  6
 32 29  1  0
 32 33  1  0
 33 34  1  6
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 39 40  1  0
 39 41  1  0
 39 42  1  0
 37 43  2  0
 33 44  1  0
 44 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5206108

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 620.78

Molecular Weight (Monoisotopic): 620.3673

AlogP: 3.89

#Rotatable Bonds: 11

Polar Surface Area: 144.95

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.91

CX Basic pKa: ┄

CX LogP: 2.61

CX LogD: 2.61

Aromatic Rings: ┄

Heavy Atoms: 44

QED Weighted: 0.14

Np Likeness Score: 1.83

References

1. Ghosh AK, Mishevich JL, Jurica MS..  (2021)  Spliceostatins and Derivatives: Chemical Syntheses and Biological Properties of Potent Splicing Inhibitors.,  84  (5.0): [PMID:33974423] [10.1021/acs.jnatprod.1c00100]

Source

Source(1):

• Scientific Literature