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

ID: ALA3326044

PubChem CID: 118711323

Max Phase: Preclinical

Molecular Formula: C19H27NO9

Molecular Weight: 413.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(CC)Cc1c(O)c(OC)c(O)c2c1C(=O)O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]21

Standard InChI:  InChI=1S/C19H27NO9/c1-4-20(5-2)6-8-10-11(14(24)17(27-3)12(8)22)16-18(29-19(10)26)15(25)13(23)9(7-21)28-16/h9,13,15-16,18,21-25H,4-7H2,1-3H3/t9-,13-,15+,16+,18-/m1/s1

Standard InChI Key:  UAFRKQOASLZXGM-HBPTYVBASA-N

Molfile:  

     RDKit          2D

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    0.6883   -8.1430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6883   -8.9643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0268  -10.1819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6830  -10.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3956   -9.3680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3884  -10.1842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0911  -10.5988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8015  -10.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8048   -9.3749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1015   -8.9681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5140   -8.9690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2243   -9.3802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5067  -10.6112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4472   -9.3738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7388   -9.7774    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2671   -8.3783    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0848  -11.4160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7893  -11.8300    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7830  -12.6472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5001  -11.4269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2047  -11.8410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4875  -13.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  6  1  0
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  3  4  1  0
  5  6  1  0
  5  9  1  0
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  8 10  1  0
  9 10  2  0
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 11 12  2  0
 12 13  1  0
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 14  9  1  0
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 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
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 27 28  1  0
 27 29  1  0
 29 30  1  0
 28 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3326044

   ---

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: 413.42

Molecular Weight (Monoisotopic): 413.1686

AlogP: -0.36

#Rotatable Bonds: 6

Polar Surface Area: 149.15

Molecular Species: BASE

HBA: 10

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.36

CX Basic pKa: 8.74

CX LogP: -1.32

CX LogD: -1.46

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.39

Np Likeness Score: 1.48

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