5-(8,9-methylenedioxy)-2-trans-4-cis-pentadienyl-N-(2'-methylpropyl)amide

ID: ALA249652

PubChem CID: 24763329

Max Phase: Preclinical

Molecular Formula: C16H19NO3

Molecular Weight: 273.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)CNC(=O)/C=C/C=C\c1ccc2c(c1)OCO2

Standard InChI:  InChI=1S/C16H19NO3/c1-12(2)10-17-16(18)6-4-3-5-13-7-8-14-15(9-13)20-11-19-14/h3-9,12H,10-11H2,1-2H3,(H,17,18)/b5-3-,6-4+

Standard InChI Key:  WHAAPCGHVWVUEX-CIIODKQPSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
   -2.0711    0.6348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3547    1.0481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3575    1.8787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0729    2.2878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7859    1.0477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7847    1.8766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5727    2.1339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0609    1.4640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5747    0.7928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6446    2.2939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0714    1.8841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0745    1.0591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7905    0.6493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7936   -0.1757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5097   -0.5855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0807   -0.5909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2226   -0.1704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9386   -0.5802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6515   -0.1650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9417   -1.4052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  6  1  0
  3 10  1  0
  5  6  2  0
 10 11  2  0
  1  2  2  0
 11 12  1  0
  5  1  1  0
 12 13  2  0
  2  3  1  0
 13 14  1  0
 14 15  1  0
  3  4  2  0
 14 16  2  0
  6  7  1  0
 15 17  1  0
  7  8  1  0
 17 18  1  0
  8  9  1  0
 18 19  1  0
  9  5  1  0
 18 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA249652

   SCUTIFOLAMIDE A

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: 273.33

Molecular Weight (Monoisotopic): 273.1365

AlogP: 2.76

#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: 2.95

CX LogD: 2.95

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.66

Np Likeness Score: 0.36

References

1. Marques JV, Kitamura RO, Lago JH, Young MC, Guimarães EF, Kato MJ..  (2007)  Antifungal amides from Piper scutifolium and Piper hoffmanseggianum.,  70  (12): [PMID:18031016] [10.1021/np070347g]

Source

Source(1):

• Scientific Literature