kipukasin A

ID: ALA5316181

Max Phase: Preclinical

Molecular Formula: C21H24N2O10

Molecular Weight: 464.43

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(OC)c1

Standard InChI:  InChI=1S/C21H24N2O10/c1-10-7-12(29-3)8-13(30-4)16(10)20(27)33-17-14(9-24)32-19(18(17)31-11(2)25)23-6-5-15(26)22-21(23)28/h5-8,14,17-19,24H,9H2,1-4H3,(H,22,26,28)/t14-,17-,18-,19-/m1/s1

Standard InChI Key:  MAWCJLLSYLMLHT-UTRMSSBJSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  1  0  0  0  0  0999 V2000
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   -1.6864   -1.0155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9530   -0.2347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7779   -0.2470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0211   -1.0354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3342   -2.3352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8980   -1.2587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4781    0.4399    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4231   -0.7592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1815    1.0405    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5283    1.7891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8249    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.7261   -4.8312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0055   -5.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2973   -4.8099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3096   -3.9850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4589   -3.6045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9932   -6.0579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6013   -3.5619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3193   -2.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0738   -2.3062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0534    2.4637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3097   -0.3827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1671   -4.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7014   -6.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
 24 32  1  0
 14 15  2  0
 25 33  1  0
  3  9  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA5316181

   ---

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: 464.43

Molecular Weight (Monoisotopic): 464.1431

AlogP: -0.09

#Rotatable Bonds: 7

Polar Surface Area: 155.38

Molecular Species: NEUTRAL

HBA: 11

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.70

CX Basic pKa: ┄

CX LogP: 0.72

CX LogD: 0.72

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.53

Np Likeness Score: 1.15

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