(S)-beta-salicyloylamino-alpha-exo-methylene-gamma-butyrolactone

ID: ALA4084402

Cas Number: 1443448-82-5

PubChem CID: 137647276

Product Number: S646776, Order Now?

Max Phase: Preclinical

Molecular Formula: C12H11NO4

Molecular Weight: 233.22

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1C(=O)OC[C@H]1NC(=O)c1ccccc1O

Standard InChI:  InChI=1S/C12H11NO4/c1-7-9(6-17-12(7)16)13-11(15)8-4-2-3-5-10(8)14/h2-5,9,14H,1,6H2,(H,13,15)/t9-/m1/s1

Standard InChI Key:  SBEBFCLNXGMFOQ-SECBINFHSA-N

Molfile:  

     RDKit          2D

 17 18  0  0  0  0  0  0  0  0999 V2000
    6.7978   -2.8538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7967   -3.6810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5114   -4.0939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2278   -3.6806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2249   -2.8502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5095   -2.4411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0833   -2.4415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0819   -4.0930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3679   -3.6799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0813   -4.9179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6531   -4.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8991   -3.7561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3466   -4.3688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7586   -5.0836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5655   -4.9126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4225   -5.8369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1779   -5.4652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  1  7  1  0
  2  8  1  0
  8  9  1  0
  8 10  2  0
 11  9  1  1
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 11  1  0
 14 16  2  0
 15 17  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4084402

   SEMBL

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: 233.22

Molecular Weight (Monoisotopic): 233.0688

AlogP: 0.60

#Rotatable Bonds: 2

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: 8.19

CX Basic pKa: ┄

CX LogP: 1.83

CX LogD: 1.76

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.58

Np Likeness Score: 0.38

References

1. Sidthipong K, Ma J, Yu WL, Wang YF, Kobayashi S, Kishino S, Koide N, Yokochi T, Kato K, Okada S, Umezawa K..  (2017)  Rational design, synthesis and in vitro evaluation of novel exo-methylene butyrolactone salicyloylamide as NF-κB inhibitor.,  27  (3): [PMID:28003138] [10.1016/j.bmcl.2016.12.017]

Source

Source(1):

• Scientific Literature