kipukasin C

ID: ALA5316183

Max Phase: Preclinical

Molecular Formula: C20H22N2O10

Molecular Weight: 450.40

Names and Identifiers

Canonical SMILES:  COc1cc(C)c(C(=O)O[C@H]2[C@@H](OC(C)=O)[C@H](n3ccc(=O)[nH]c3=O)O[C@@H]2CO)c(O)c1

Standard InChI:  InChI=1S/C20H22N2O10/c1-9-6-11(29-3)7-12(25)15(9)19(27)32-16-13(8-23)31-18(17(16)30-10(2)24)22-5-4-14(26)21-20(22)28/h4-7,13,16-18,23,25H,8H2,1-3H3,(H,21,26,28)/t13-,16-,17-,18-/m1/s1

Standard InChI Key:  HAQMHDBEEOMBGX-BNEJOLLZSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  1  0  0  0  0  0999 V2000
   14.0292   -1.6317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8366   -1.4622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9249   -0.6420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1721   -0.3045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6185   -0.9162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7983   -0.8279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6918   -2.3845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4483   -2.0158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6405   -0.2313    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4646   -0.0733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3539   -0.6456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0694   -0.2349    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.0715    0.5901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3581    1.0044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6425    0.5937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8711   -2.4687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5336   -3.2215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3878   -1.8000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7129   -3.3057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3754   -4.0585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8587   -4.7271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6794   -4.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0168   -3.8902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2297   -2.6370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5212   -5.4800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8375   -3.8060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2748   -2.8223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4895   -3.0753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8864   -3.3759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7870    1.0008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3518   -1.4706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7005   -5.5641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  2  0
  1  7  1  6
  7 16  1  0
  3  4  1  0
 16 17  1  0
  2  8  1  6
 16 18  2  0
  4  5  1  0
 17 19  2  0
 19 20  1  0
  5  1  1  0
 20 21  2  0
  6 10  1  0
 21 22  1  0
  9 11  1  0
 22 23  2  0
 23 17  1  0
  1  2  1  0
 19 24  1  0
 21 25  1  0
 23 26  1  0
  5  6  1  1
  8 27  1  0
  2  3  1  0
 27 28  1  0
  9 15  1  0
 27 29  2  0
 11 12  1  0
 13 30  2  0
 12 13  1  0
 11 31  2  0
 13 14  1  0
 25 32  1  0
  3  9  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA5316183

   ---

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 450.40

Molecular Weight (Monoisotopic): 450.1274

AlogP: -0.39

#Rotatable Bonds: 6

Polar Surface Area: 166.38

Molecular Species: NEUTRAL

HBA: 11

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.43

CX Basic pKa: ┄

CX LogP: 1.22

CX LogD: 1.22

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.49

Np Likeness Score: 1.32

References

1. Jiao P, Mudur SV, Gloer JB, Wicklow DT..  (2007)  Kipukasins, nucleoside derivatives from Aspergillus versicolor.,  70  (8): [PMID:17608440] [10.1021/np070241l]

Source

Source(1):

• Scientific Literature