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

ID: ALA3326040

PubChem CID: 118711321

Max Phase: Preclinical

Molecular Formula: C20H27NO10

Molecular Weight: 441.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1c(O)c(CN2CCC[C@H]2CO)c2c(c1O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1OC2=O

Standard InChI:  InChI=1S/C20H27NO10/c1-29-18-13(24)9(5-21-4-2-3-8(21)6-22)11-12(15(18)26)17-19(31-20(11)28)16(27)14(25)10(7-23)30-17/h8,10,14,16-17,19,22-27H,2-7H2,1H3/t8-,10+,14+,16-,17-,19+/m0/s1

Standard InChI Key:  BZEKYOMYVVCWIZ-LOLNYDFYSA-N

Molfile:  

     RDKit          2D

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    1.3125   -0.7016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3125   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7313   -0.7016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0219   -0.2848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7313   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0203   -2.7405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7260   -3.1544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4386   -1.9266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4313   -2.7428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1340   -3.1574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8444   -2.7529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8478   -1.9335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1445   -1.5267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5570   -1.5276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2673   -1.9389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5497   -3.1698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7250   -3.9757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7337    0.9534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5994   -0.2910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6012   -1.9325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3042   -2.3360    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3100   -0.9369    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1277   -3.9746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8323   -4.3887    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9085   -5.2030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7065   -5.3791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1206   -4.6745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5784   -4.0631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2960   -5.7440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5213   -5.4841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  6  1  0
  5  3  1  0
  3  4  1  0
  5  6  1  0
  5  9  1  0
  6  7  1  0
  7  8  1  0
  8 10  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
 13 15  1  0
 15 16  1  0
 12 17  1  0
 14 18  1  0
  8 19  2  0
  4 20  1  1
 20 21  1  0
  1 22  1  6
  2 23  1  1
  6 24  1  1
  5 25  1  6
 11 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 27  1  0
 28 32  1  1
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3326040

   ---

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: 441.43

Molecular Weight (Monoisotopic): 441.1635

AlogP: -1.24

#Rotatable Bonds: 5

Polar Surface Area: 169.38

Molecular Species: NEUTRAL

HBA: 11

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 8.21

CX Basic pKa: 7.34

CX LogP: -1.86

CX LogD: -1.93

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.30

Np Likeness Score: 1.43

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