Aurantiamide acetate

ID: ALA4071910

Cas Number: 56121-42-7

PubChem CID: 10026486

Product Number: A651241, Order Now?

Max Phase: Preclinical

Molecular Formula: C27H28N2O4

Molecular Weight: 444.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)OC[C@H](Cc1ccccc1)NC(=O)[C@H](Cc1ccccc1)NC(=O)c1ccccc1

Standard InChI:  InChI=1S/C27H28N2O4/c1-20(30)33-19-24(17-21-11-5-2-6-12-21)28-27(32)25(18-22-13-7-3-8-14-22)29-26(31)23-15-9-4-10-16-23/h2-16,24-25H,17-19H2,1H3,(H,28,32)(H,29,31)/t24-,25-/m0/s1

Standard InChI Key:  VZPAURMDJZOGHU-DQEYMECFSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
    9.0934   -5.6225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0603   -4.8063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7520   -4.3676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4768   -4.7493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5099   -5.5655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8182   -6.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1596   -7.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4389   -6.8732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4058   -6.0570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1927   -8.0711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8513   -6.8162    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5760   -7.1979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6091   -8.0141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3298   -8.3916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3629   -9.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0877   -9.5894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7793   -9.1549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7463   -8.3387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0215   -7.9570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2636   -6.7592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9884   -7.1408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7473   -7.3119    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7804   -8.1281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0887   -8.5627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1218   -9.3789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4301   -9.8175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7053   -9.4359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6722   -8.6197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3639   -8.1852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5010   -8.5098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6912   -6.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4022   -7.1302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6846   -5.9102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  1  6  2  0
  7  8  1  0
  8  9  1  0
  7 10  2  0
  7 11  1  0
  1  9  1  0
 12 13  1  6
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 14 19  2  0
 13 14  1  0
 20 21  1  0
 12 20  1  0
 11 12  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 24 29  2  0
 23 30  2  0
 22 23  1  0
  8 22  1  1
 21 31  1  0
 31 32  1  0
 31 33  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4071910

   Aurantiamide acetate

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: 444.53

Molecular Weight (Monoisotopic): 444.2049

AlogP: 3.32

#Rotatable Bonds: 10

Polar Surface Area: 84.50

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.82

CX Basic pKa: ┄

CX LogP: 3.99

CX LogD: 3.99

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.47

Np Likeness Score: 0.01

References

1. Zhou D, Wei H, Jiang Z, Li X, Jiao K, Jia X, Hou Y, Li N..  (2017)  Natural potential neuroinflammatory inhibitors from Alhagi sparsifolia Shap.,  27  (4): [PMID:28073678] [10.1016/j.bmcl.2016.12.075]

2. Qiu J, Gong Q, Gao J, Chen W, Zhang Y, Gu X, Tang D..  (2018)  Design, synthesis and evaluation of novel phenyl propionamide derivatives as non-nucleoside hepatitis B virus inhibitors.,  144  [PMID:29288943] [10.1016/j.ejmech.2017.12.042]

Source

Source(1):

• Scientific Literature