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

ID: ALA3326042

PubChem CID: 71754011

Max Phase: Preclinical

Molecular Formula: C20H27NO9

Molecular Weight: 425.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1c(O)c(CN2CCCCC2)c2c(c1O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1OC2=O

Standard InChI:  InChI=1S/C20H27NO9/c1-28-18-13(23)9(7-21-5-3-2-4-6-21)11-12(15(18)25)17-19(30-20(11)27)16(26)14(24)10(8-22)29-17/h10,14,16-17,19,22-26H,2-8H2,1H3/t10-,14-,16+,17+,19-/m1/s1

Standard InChI Key:  PXKRADMBKLYNQM-DGOWFPMBSA-N

Molfile:  

     RDKit          2D

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   16.4346   -2.4309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8534   -1.6096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1440   -1.1928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8534   -2.4309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1443   -2.8359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1425   -3.6485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8481   -4.0624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5608   -2.8346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5535   -3.6508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2562   -4.0654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9666   -3.6609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9699   -2.8415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2666   -2.4347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6792   -2.4356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3895   -2.8468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6719   -4.0778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2704   -1.6133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8472   -4.8837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1440   -0.3715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8559    0.0454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7216   -1.1990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7233   -2.8404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4264   -3.2440    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.4322   -1.8449    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.2499   -4.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9544   -5.2966    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9424   -6.1132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6429   -6.5271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3561   -6.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3644   -5.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6595   -4.8909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  5  9  1  0
  6  7  1  0
  7  8  1  0
  8 10  1  0
  9 10  2  0
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 11 12  2  0
 12 13  1  0
 13 14  2  0
 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
 26 27  1  0
 27 28  1  0
 27 32  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3326042

   (2R,3S,4S,4aR,10bS)-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-7-(piperidin-1-ylmethyl)-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-6-one

Molecule Features

Natural Product: Yes

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: 425.43

Molecular Weight (Monoisotopic): 425.1686

AlogP: -0.21

#Rotatable Bonds: 4

Polar Surface Area: 149.15

Molecular Species: NEUTRAL

HBA: 10

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.36

CX Basic pKa: 7.33

CX LogP: -0.80

CX LogD: -0.88

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.41

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