zanthomamide

ID: ALA1081790

PubChem CID: 14237550

Max Phase: Preclinical

Molecular Formula: C18H17NO3

Molecular Weight: 295.34

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Zanthomamide | zanthomamide|CHEMBL1081790|SCHEMBL14148887|(E)-N-[2-(1,3-benzodioxol-5-yl)ethyl]-3-phenyl-prop-2-enamide

Canonical SMILES:  O=C(/C=C/c1ccccc1)NCCc1ccc2c(c1)OCO2

Standard InChI:  InChI=1S/C18H17NO3/c20-18(9-7-14-4-2-1-3-5-14)19-11-10-15-6-8-16-17(12-15)22-13-21-16/h1-9,12H,10-11,13H2,(H,19,20)/b9-7+

Standard InChI Key:  VLYAGIXYMUMJMN-VQHVLOKHSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   20.6256   -5.9192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9097   -5.5071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3456   -5.5107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0538   -5.9233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7733   -5.5071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7696   -4.6821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0571   -4.2707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3446   -4.6809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1980   -5.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2063   -6.7481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4780   -5.5124    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7663   -5.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0463   -5.5177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3263   -5.9387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6136   -5.5251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6103   -7.1735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3269   -6.7633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9020   -6.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9012   -5.9370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1178   -5.6858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6358   -6.3464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1165   -7.0150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9 11  1  0
  5  6  2  0
 11 12  1  0
  1  2  2  0
 12 13  1  0
  6  7  1  0
 13 14  1  0
  3  4  2  0
 14 15  2  0
 15 19  1  0
  7  8  2  0
 18 16  1  0
  8  3  1  0
 16 17  2  0
 17 14  1  0
 18 19  2  0
  2  9  1  0
  4  5  1  0
  9 10  2  0
  1  3  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1081790

   ZANTHOMAMIDE

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: 295.34

Molecular Weight (Monoisotopic): 295.1208

AlogP: 2.79

#Rotatable Bonds: 5

Polar Surface Area: 47.56

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.19

CX LogD: 3.19

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.86

Np Likeness Score: -0.14

References

1. Lenta BN, Tantangmo F, Devkota KP, Wansi JD, Chouna JR, Soh RC, Neumann B, Stammler HG, Tsamo E, Sewald N..  (2009)  Bioactive constituents of the stem bark of Beilschmiedia zenkeri.,  72  (12): [PMID:19904919] [10.1021/np900341f]

Source

Source(1):

• Scientific Literature