(S)-5-(((2R,3R,5S,6S)-6-((5-((3R,4R,5R,7R)-4-hydroxy-7-methyl-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: ALA5192042

PubChem CID: 153313489

Max Phase: Preclinical

Molecular Formula: C27H41NO7

Molecular Weight: 491.63

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](C)C[C@@]3(CO3)[C@@H]2O)O[C@@H]1C

Standard InChI:  InChI=1S/C27H41NO7/c1-16(8-11-24-26(31)27(15-32-27)14-19(4)34-24)7-10-23-17(2)13-22(20(5)35-23)28-25(30)12-9-18(3)33-21(6)29/h7-9,11-12,17-20,22-24,26,31H,10,13-15H2,1-6H3,(H,28,30)/b11-8+,12-9-,16-7+/t17-,18-,19+,20+,22+,23-,24+,26+,27+/m0/s1

Standard InChI Key:  MXISVNOQTGJKDU-KTCJIYLQSA-N

Molfile:  

 
     RDKit          2D

 35 37  0  0  0  0  0  0  0  0999 V2000
   -4.5885    1.5957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4135    1.5957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0017    0.8798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7165    0.4672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7165   -0.3581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0017   -0.7708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2870   -0.3581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2870    0.4672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    0.8797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.3581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.3581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7143   -0.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0002   -0.3581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0002    0.4669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7147    0.8794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4293    0.4668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1438    0.8794    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8583    0.4668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5728    0.8794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2874    0.4668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2874   -0.3582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0019   -0.7707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7165   -0.3582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7165    0.4668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4311   -0.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5728   -0.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8583   -0.3582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4293   -0.3582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1438   -0.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7147   -0.7707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7143    0.8794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.5957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4311   -0.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  0
  3  1  1  6
  4  3  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  3  1  0
  8  9  1  6
  7 10  1  1
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 15 14  1  1
 16 15  1  0
 17 16  1  0
 18 17  1  0
 18 19  1  1
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  1
 24 25  1  0
 25 26  2  0
 25 27  1  0
 23 28  1  0
 20 29  2  0
 30 18  1  0
 30 31  1  1
 32 30  1  0
 15 32  1  0
 16 33  1  1
 12 34  1  0
  5 35  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA5192042

   ---

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: 491.63

Molecular Weight (Monoisotopic): 491.2883

AlogP: 2.99

#Rotatable Bonds: 8

Polar Surface Area: 106.62

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.92

CX Basic pKa: ┄

CX LogP: 2.21

CX LogD: 2.21

Aromatic Rings: ┄

Heavy Atoms: 35

QED Weighted: 0.23

Np Likeness Score: 2.47

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