zoanthenol analogue

ID: ALA91194

PubChem CID: 44323278

Max Phase: Preclinical

Molecular Formula: C22H27NO4

Molecular Weight: 369.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCC1=C(C)C(=O)[C@](C)(CN2c3ccccc3[C@]3(O)CCOC23)C1=O

Standard InChI:  InChI=1S/C22H27NO4/c1-4-5-8-15-14(2)18(24)21(3,19(15)25)13-23-17-10-7-6-9-16(17)22(26)11-12-27-20(22)23/h6-7,9-10,20,26H,4-5,8,11-13H2,1-3H3/t20?,21-,22+/m0/s1

Standard InChI Key:  XPVQXXLKOCZMGG-JTGIGXABSA-N

Molfile:  

     RDKit          2D

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   -0.8500   -2.1125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3583   -1.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8500   -0.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5500   -3.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -2.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3667   -3.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5417   -2.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6375   -1.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5958   -2.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6375   -1.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4375   -1.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1417   -4.5292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7375   -1.6917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3583   -0.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2708   -0.0500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2042   -2.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4375   -0.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2917   -2.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9250   -4.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3583   -0.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3583   -2.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9625   -3.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -2.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0708   -1.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0708   -1.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3792   -3.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2 10  1  0
  3  2  1  0
  4  3  1  0
  5  1  1  0
  6  1  1  0
  7  5  1  0
  8  6  1  0
  9 11  1  0
 10  1  1  0
 11  2  1  0
 12  3  1  0
 13  5  2  0
 14  6  2  0
 15  4  1  0
  4 16  1  1
  1 17  1  1
 18 12  1  0
 19  8  1  0
 20  7  1  0
 21  9  2  0
 22 11  2  0
 23 19  1  0
 24 23  1  0
 25 26  2  0
 26 22  1  0
 27 24  1  0
  8  7  2  0
  9  4  1  0
 15 18  1  0
 25 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA91194

   MADINDOLINE A

Molecule Features

Natural Product: Yes

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: 369.46

Molecular Weight (Monoisotopic): 369.1940

AlogP: 3.11

#Rotatable Bonds: 5

Polar Surface Area: 66.84

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.65

CX Basic pKa: ┄

CX LogP: 4.49

CX LogD: 4.49

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.81

Np Likeness Score: 1.17

References

1. Hirai G, Oguri H, Hayashi M, Koyama K, Koizumi Y, Moharram SM, Hirama M..  (2004)  Synthesis and preliminary biological evaluation of truncated zoanthenol analogues.,  14  (10): [PMID:15109670] [10.1016/j.bmcl.2004.02.064]

2. Li H, Xiao H, Lin L, Jou D, Kumari V, Lin J, Li C..  (2014)  Drug design targeting protein-protein interactions (PPIs) using multiple ligand simultaneous docking (MLSD) and drug repositioning: discovery of raloxifene and bazedoxifene as novel inhibitors of IL-6/GP130 interface.,  57  (3): [PMID:24456369] [10.1021/jm401144z]

Source

Source(1):

• Scientific Literature