2-phenylsulfonylpropyl 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: ALA15828

PubChem CID: 44270566

Max Phase: Preclinical

Molecular Formula: C29H25NO5S

Molecular Weight: 499.59

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C29H25NO5S/c1-21(36(32,33)23-14-6-4-7-15-23)20-34-27(31)30-25-17-10-9-16-24(25)29-22-12-5-2-3-8-18-26(30)28(29,35-29)19-11-13-22/h2-4,6-7,9-10,14-17,21-22,26H,11,13,19-20H2,1H3/b3-2-/t21-,22-,26-,28-,29+/m0/s1

Standard InChI Key:  RIHYKJIVPKDKGD-BLSRZQDWSA-N

Molfile:  

     RDKit          2D

 38 43  0  0  1  0  0  0  0  0999 V2000
    5.5167   -2.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4917   -3.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8042   -3.0500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0917   -2.6000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8167   -2.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7750   -3.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6417   -2.0000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.0667   -3.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3750   -2.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8417   -1.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3542   -2.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1917   -3.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8167   -2.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8375   -0.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8250   -1.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6542   -2.5917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6417   -1.1750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0750   -2.4042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2250   -1.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3750   -1.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0667   -2.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4167    0.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8292   -0.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2500   -2.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7542   -4.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3417   -3.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3417   -3.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9542   -2.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9250   -3.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0167   -1.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0125   -0.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0250   -5.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3167   -4.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5917   -0.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6042   -1.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3917   -0.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0292   -1.9667    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1625   -4.7292    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 11  1  0
  8  4  1  0
  9  4  1  0
  5 10  1  0
 11 21  1  0
 12  2  1  0
 13 12  1  0
 14 10  3  0
 15 13  3  0
 16  9  1  0
 17  7  2  0
 18  7  2  0
 19  7  1  0
 20  9  2  0
 21 16  1  0
 22 14  1  0
 23 22  2  0
 24  1  1  0
 25  6  1  0
 26  8  1  0
 11 27  1  6
 28 24  1  0
 29 28  1  0
 30 19  2  0
 31 19  1  0
 32 25  2  0
 33 26  2  0
 34 31  2  0
 35 30  1  0
 36 34  1  0
  5 37  1  6
 12 38  1  6
  2  3  1  6
 29 12  1  0
  6  8  2  0
 15 23  1  0
 32 33  1  0
 36 35  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA15828

   [(2S)-2-(benzenesulfonyl)propyl] (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: 499.59

Molecular Weight (Monoisotopic): 499.1453

AlogP: 4.22

#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: 13.68

CX Basic pKa: ┄

CX LogP: 4.99

CX LogD: 4.99

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.47

Np Likeness Score: 0.69

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