(2R,3S,4S,4aR,10bS)-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-7-((4-methylpiperazin-1-yl)methyl)-2,3,4,4a-tetrahydropyrano[3,2-c]isochromen-6(10bH)-one

ID: ALA3326045

PubChem CID: 118711324

Max Phase: Preclinical

Molecular Formula: C20H28N2O9

Molecular Weight: 440.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1c(O)c(CN2CCN(C)CC2)c2c(c1O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1OC2=O

Standard InChI:  InChI=1S/C20H28N2O9/c1-21-3-5-22(6-4-21)7-9-11-12(15(26)18(29-2)13(9)24)17-19(31-20(11)28)16(27)14(25)10(8-23)30-17/h10,14,16-17,19,23-27H,3-8H2,1-2H3/t10-,14-,16+,17+,19-/m1/s1

Standard InChI Key:  PVEHVIJJHCJSIY-DGOWFPMBSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
    7.5532   -0.9081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2598   -2.1396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5478   -2.5551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8372   -1.3168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4057   -0.9128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4010    0.3413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6898   -1.3226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4028   -1.3215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1209   -0.9081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2672   -1.3155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5532   -0.0790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1125   -1.7289    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5468   -3.3842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8370    1.1733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6742   -3.8011    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3984   -2.5707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.5556    1.5862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.1374   -0.3164    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9835   -0.0827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9628   -3.3831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9692   -2.5581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8370    0.3432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8354   -2.1373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9798   -0.9118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1209   -0.0790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6614   -4.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3686   -5.0449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0886   -4.6414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0969   -3.8155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3851   -3.3930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7916   -5.0580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0
 14 18  1  0
 25  3  1  0
 22 15  1  0
  1 10  1  0
 26 21  1  0
  4 25  1  0
 27  6  1  6
  3  2  1  0
  9  4  1  0
  7 26  2  0
  2 23  1  0
 27 24  1  0
  3 13  2  0
  5 19  1  0
 27  9  1  0
 17  7  1  0
 17 16  1  0
 11 24  1  0
 26 10  1  0
  1 20  1  6
 10  2  2  0
 24 14  1  1
  1 11  1  0
 23 17  2  0
 23 22  1  0
  9  8  1  1
  7  5  1  0
  4 12  1  1
 15 28  1  0
 15 32  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 30 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3326045

   ---

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: 440.45

Molecular Weight (Monoisotopic): 440.1795

AlogP: -1.45

#Rotatable Bonds: 4

Polar Surface Area: 152.39

Molecular Species: NEUTRAL

HBA: 11

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.21

CX Basic pKa: 7.35

CX LogP: -1.76

CX LogD: -1.82

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.35

Np Likeness Score: 1.30

References

1. Jain SK, Singh S, Khajuria A, Guru SK, Joshi P, Meena S, Nadkarni JR, Singh A, Bharate SS, Bhushan S, Bharate SB, Vishwakarma RA..  (2014)  Pyrano-isochromanones as IL-6 inhibitors: synthesis, in vitro and in vivo antiarthritic activity.,  57  (16): [PMID:25111439] [10.1021/jm500901e]

Source

Source(1):

• Scientific Literature