kipukasin G

ID: ALA5316187

Max Phase: Preclinical

Molecular Formula: C19H22N2O9

Molecular Weight: 422.39

Names and Identifiers

Canonical SMILES:  COc1cc(O)cc(C)c1C(=O)O[C@H]1[C@@H](O)[C@H](n2ccc(=O)n(C)c2=O)O[C@@H]1CO

Standard InChI:  InChI=1S/C19H22N2O9/c1-9-6-10(23)7-11(28-3)14(9)18(26)30-16-12(8-22)29-17(15(16)25)21-5-4-13(24)20(2)19(21)27/h4-7,12,15-17,22-23,25H,8H2,1-3H3/t12-,15-,16-,17-/m1/s1

Standard InChI Key:  CIJRLBYKDKLPQB-BASLNEPJSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  1  0  0  0  0  0999 V2000
   -0.8267  -19.0761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0201  -18.9026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0660  -18.0820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6907  -17.7469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2385  -18.3627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0592  -18.2788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1613  -19.8302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5937  -19.4539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7800  -17.6687    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3970  -17.5261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4976  -18.0844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2085  -17.6730    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2098  -16.8476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4941  -16.4354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7770  -16.8486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9817  -19.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3164  -20.6715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4674  -19.2505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1375  -20.7557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4722  -21.5089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9863  -22.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1620  -22.0865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8311  -21.3331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6219  -20.0878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3200  -22.9313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0110  -21.2429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9244  -16.4353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4975  -18.9094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2856  -19.3345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9228  -18.0856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  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
 13 27  2  0
  2  3  1  0
 11 28  2  0
  9 15  1  0
 24 29  1  0
 11 12  1  0
 12 13  1  0
 12 30  1  0
  3  9  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA5316187

   ---

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: 422.39

Molecular Weight (Monoisotopic): 422.1325

AlogP: -0.95

#Rotatable Bonds: 5

Polar Surface Area: 149.45

Molecular Species: NEUTRAL

HBA: 11

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.66

CX Basic pKa: ┄

CX LogP: 0.36

CX LogD: 0.33

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.52

Np Likeness Score: 1.28

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