Salinosporamide A

ID: ALA5283576

Max Phase: Preclinical

Molecular Formula: C14H18ClNO4

Molecular Weight: 299.75

Names and Identifiers

Canonical SMILES:  O=C1NC2([C@@H](O)[C@@H]3C=CCCC3)C(=O)O[C@H]2[C@H]1CCCl

Standard InChI:  InChI=1S/C14H18ClNO4/c15-7-6-9-11-14(13(19)20-11,16-12(9)18)10(17)8-4-2-1-3-5-8/h2,4,8-11,17H,1,3,5-7H2,(H,16,18)/t8-,9-,10+,11+,14?/m1/s1

Standard InChI Key:  OLSLVDNVMYYZGX-CAMXFFFOSA-N

Molfile:  

 
     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   -1.8313    0.2168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0344    0.0033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3863    0.5208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3063    0.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4313    0.8961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2282    1.1097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0927   -0.7163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7488   -0.7163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1613   -1.4308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1208   -1.5132    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9033   -0.9335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1168   -0.1364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8313    0.2760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1520    1.4795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9488    1.2660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5322    1.8493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3186    2.6462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5218    2.8597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0614    2.2764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6448    1.6930    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7488   -2.1452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1613   -2.8597    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  1  0
  4  5  1  0
  5  6  1  6
  4  7  1  0
  7  8  1  0
  8  2  1  0
  8  9  1  1
  7 10  1  6
  7 11  1  0
 12 11  1  0
  4 12  1  0
 12 13  2  0
  5 14  1  0
 15 14  1  0
 16 15  2  0
 17 16  1  0
 18 17  1  0
 19 18  1  0
 14 19  1  0
 14 20  1  1
  9 21  1  0
 21 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5283576

   ---

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: 299.75

Molecular Weight (Monoisotopic): 299.0924

AlogP: 0.74

#Rotatable Bonds: 4

Polar Surface Area: 75.63

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.26

CX Basic pKa: ┄

CX LogP: 0.96

CX LogD: 0.96

Aromatic Rings: ┄

Heavy Atoms: 20

QED Weighted: 0.46

Np Likeness Score: 1.90

References

1. Song R, Qiao W, He J, Huang J, Luo Y, Yang T..  (2021)  Proteases and Their Modulators in Cancer Therapy: Challenges and Opportunities.,  64  (6.0): [PMID:33656892] [10.1021/acs.jmedchem.0c01640]

Source

Source(1):

• Scientific Literature