2-phenylsulfonylethyl 21-oxa-13-azapentacyclo[10.9.0.01,20.05,20.014,19]henicosa-8,14(19),15,17-tetraen-6,10-diyne-13-carboxylate

ID: ALA15924

PubChem CID: 44270653

Max Phase: Preclinical

Molecular Formula: C28H23NO5S

Molecular Weight: 485.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(OCCS(=O)(=O)c1ccccc1)N1c2ccccc2[C@@]23O[C@]24CCC[C@@H]3C#C/C=C\C#C[C@H]14

Standard InChI:  InChI=1S/C28H23NO5S/c30-26(33-19-20-35(31,32)22-13-5-3-6-14-22)29-24-16-9-8-15-23(24)28-21-11-4-1-2-7-17-25(29)27(28,34-28)18-10-12-21/h1-3,5-6,8-9,13-16,21,25H,10,12,18-20H2/b2-1-/t21-,25-,27-,28+/m0/s1

Standard InChI Key:  VNDPXXUJXJOMBG-MBSKNNGPSA-N

Molfile:  

     RDKit          2D

 37 42  0  0  1  0  0  0  0  0999 V2000
    4.3292   -3.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3000   -4.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6125   -3.8917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9000   -3.4417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6250   -3.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5792   -4.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8792   -4.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5500   -2.8417    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.1792   -3.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6500   -2.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0000   -4.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6292   -3.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6417   -1.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6292   -2.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1625   -3.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5458   -2.0167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2708   -3.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0292   -2.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1792   -2.2042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2292   -0.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6375   -1.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0542   -3.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4667   -3.4375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5625   -5.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8792   -2.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1500   -4.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7625   -3.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7292   -4.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8292   -2.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1833   -1.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8292   -5.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1292   -5.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4042   -0.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4125   -1.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2042   -1.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9667   -5.5667    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8375   -2.8125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  1  3  1  6
  4  5  1  0
  5  1  1  0
  6  2  1  0
  7  4  1  0
  8 15  1  0
  9  4  1  0
  5 10  1  0
 11  2  1  0
 12 11  1  0
 13 10  3  0
 14 12  3  0
 15 25  1  0
 16  8  2  0
 17  8  2  0
 18  8  1  0
 19  9  2  0
 20 13  1  0
 21 20  2  0
 22  1  1  0
 23  9  1  0
 24  6  1  0
 25 23  1  0
 26  7  1  0
 27 22  1  0
 28 27  1  0
 29 18  2  0
 30 18  1  0
 31 24  2  0
 32 26  2  0
 33 30  2  0
 34 29  1  0
 35 33  1  0
 11 36  1  6
  5 37  1  6
  2  3  1  6
 28 11  1  0
  6  7  2  0
 14 21  1  0
 31 32  1  0
 35 34  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA15924

   2-(benzenesulfonyl)ethyl (1S,5R,8Z,12S,20R)-21-oxa-13-azapentacyclo[10.9.0.01,20.05,20.014,19]henicosa-8,14,16,18-tetraen-6,10-diyne-13-carboxylate

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: 485.56

Molecular Weight (Monoisotopic): 485.1297

AlogP: 3.83

#Rotatable Bonds: 4

Polar Surface Area: 76.21

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.65

CX Basic pKa: ┄

CX LogP: 4.42

CX LogD: 4.42

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.49

Np Likeness Score: 0.62

References

1. Nicolaou K, Dai W, Tsay S, Wrasidlo W.  (1992)  On the mechanism of activation of designed enediynes with selective cytotoxicity,  2  (9): [10.1016/S0960-894X(00)80638-1]

Source

Source(1):

• Scientific Literature