[6-(5,6-dihydro-9-methoxy-7H-furo[3,2-g]-1-benzopyran-7-yl)-N-(2-methyl-propyl)-2(E),4(E)-hexadienamide

ID: ALA470770

PubChem CID: 10547077

Max Phase: Preclinical

Molecular Formula: C22H27NO4

Molecular Weight: 369.46

Molecule Type: Small molecule

Names and Identifiers

Synonyms: erythrococcamide C | ERYTHROCOCCAMIDE C|CHEMBL470770

Canonical SMILES:  COc1c2c(cc3ccoc13)CCC(C/C=C/C=C/C(=O)NCC(C)C)O2

Standard InChI:  InChI=1S/C22H27NO4/c1-15(2)14-23-19(24)8-6-4-5-7-18-10-9-16-13-17-11-12-26-20(17)22(25-3)21(16)27-18/h4-6,8,11-13,15,18H,7,9-10,14H2,1-3H3,(H,23,24)/b5-4+,8-6+

Standard InChI Key:  QXUGXSMOZSERHH-DVBIZMGNSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   -3.0204  -11.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0224   -9.5503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3042   -9.9590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3006  -10.7926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5809  -11.2038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8602  -10.7862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8639   -9.9525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5882   -9.5367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7334  -10.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7319   -9.9614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5199   -9.7040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0084  -10.3739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5221  -11.0454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1445  -11.1965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5686  -10.7818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0230  -12.0282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7387  -12.4385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2842  -11.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9974  -10.7774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7129  -11.1877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4261  -10.7730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1418  -11.1834    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4236   -9.9481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8549  -10.7687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5705  -11.1790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5730  -12.0038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2837  -10.7643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0
 13  9  1  0
  3  4  1  0
  6 14  1  0
  3  8  1  0
 14 15  1  0
  4  5  1  0
  1 16  1  0
  5  6  1  0
 16 17  1  0
  6  7  1  0
 15 18  2  0
  7  8  1  0
 18 19  1  0
  9 10  2  0
 19 20  2  0
  9  1  1  0
 20 21  1  0
  1  4  2  0
 21 22  1  0
 21 23  2  0
  3  2  2  0
 22 24  1  0
  2 10  1  0
 24 25  1  0
 10 11  1  0
 25 26  1  0
 11 12  2  0
 25 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA470770

   ERYTHROCOCCAMIDE C

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: 369.46

Molecular Weight (Monoisotopic): 369.1940

AlogP: 4.41

#Rotatable Bonds: 7

Polar Surface Area: 60.70

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.00

CX LogD: 4.00

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.58

Np Likeness Score: 1.54

References

1. Latif Z, Hartley TG, Rice MJ, Waigh RD, Waterman PG..  (1998)  Novel and insecticidal isobutylamides from dinosperma erythrococca,  61  (5): [PMID:9599259] [10.1021/np9705569]

Source

Source(1):

• Scientific Literature