homoazadiradione

ID: ALA2288870

PubChem CID: 76316560

Max Phase: Preclinical

Molecular Formula: C29H38O4

Molecular Weight: 450.62

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)O[C@@H]1C[C@H]2C(C)(C)CC(=O)C=C[C@]2(C)[C@H]2CC[C@]3(C)C(=CC[C@H]3c3ccoc3)[C@@]21C

Standard InChI:  InChI=1S/C29H38O4/c1-18(30)33-25-15-24-26(2,3)16-20(31)9-12-28(24,5)23-10-13-27(4)21(19-11-14-32-17-19)7-8-22(27)29(23,25)6/h8-9,11-12,14,17,21,23-25H,7,10,13,15-16H2,1-6H3/t21-,23+,24-,25+,27-,28+,29-/m0/s1

Standard InChI Key:  OOHAWVHDVDYZNN-YZSKNTCUSA-N

Molfile:  

     RDKit          2D

 33 37  0  0  0  0  0  0  0  0999 V2000
    3.1634   -8.5810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1678   -9.4088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8879   -9.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5990   -9.4140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8945   -8.1589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5990   -8.6010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6093   -6.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8945   -7.3626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3107   -7.3547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3168   -8.2103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1547   -8.3773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6080   -7.6856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0932   -7.0415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3109   -6.2477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0836   -5.9563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0424   -5.1344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2486   -4.9186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7975   -5.6058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1634   -7.7579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5990   -7.7780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3308   -9.8365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3798   -6.5109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3373  -10.6796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0502  -11.0912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6246  -11.0912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5134   -8.0685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7073   -8.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3523   -9.0048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7073   -9.7487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5134   -9.9285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5292   -9.0057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3003  -10.7235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0953  -10.5105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  5  1  0
  2  3  1  1
  3  4  1  0
  4  6  1  0
  5  6  1  0
  5  8  1  1
  6 10  1  0
  9  7  1  0
  7  8  1  0
  9 10  1  0
  9 13  1  0
 11 12  1  0
 12 13  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 14  1  0
 13 14  1  6
  1 19  1  1
  6 20  1  1
  4 21  1  6
  9 22  1  6
 10 11  2  0
 21 23  1  0
 23 24  1  0
 23 25  2  0
  1 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30  2  1  0
 28 31  2  0
 30 32  1  0
 30 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2288870

   HOMOAZADIRADIONE

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: 450.62

Molecular Weight (Monoisotopic): 450.2770

AlogP: 6.63

#Rotatable Bonds: 2

Polar Surface Area: 56.51

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.34

CX LogD: 5.34

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.37

Np Likeness Score: 3.33

References

1. Suresh G, Gopalakrishnan G, Wesley SD, Pradeep Singh ND, Malathi R, Rajan SS..  (2002)  Insect antifeedant activity of tetranortriterpenoids from the Rutales. A perusal of structural relations.,  50  (16): [PMID:12137465] [10.1021/jf025534t]

Source

Source(1):

• Scientific Literature