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

ID: ALA3326041

PubChem CID: 71753792

Max Phase: Preclinical

Molecular Formula: C19H25NO10

Molecular Weight: 427.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1c(O)c(CN2CCOCC2)c2c(c1O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1OC2=O

Standard InChI:  InChI=1S/C19H25NO10/c1-27-17-12(22)8(6-20-2-4-28-5-3-20)10-11(14(17)24)16-18(30-19(10)26)15(25)13(23)9(7-21)29-16/h9,13,15-16,18,21-25H,2-7H2,1H3/t9-,13-,15+,16+,18-/m1/s1

Standard InChI Key:  QFEBOYFUONTMTM-HBPTYVBASA-N

Molfile:  

     RDKit          2D

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    9.0180   -1.4198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0180   -2.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4368   -1.4198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7274   -1.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4368   -2.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7277   -2.6460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7258   -3.4587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4315   -3.8725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1441   -2.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1369   -3.4609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8396   -3.8756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5500   -3.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5533   -2.6517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8500   -2.2448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2626   -2.2457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9728   -2.6570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2552   -3.8880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8537   -1.4235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4306   -4.6939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7274   -0.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4392    0.2353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3050   -1.0091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3067   -2.6506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0097   -3.0541    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0156   -1.6550    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8333   -4.6927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5378   -5.1068    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5258   -5.9233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2263   -6.3372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9395   -5.9376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9478   -5.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2428   -4.7010    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
  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
 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:

   

   ALA3326041

   (2R,3S,4S,4aR,10bS)-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-7-(morpholin-4-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: 427.41

Molecular Weight (Monoisotopic): 427.1478

AlogP: -1.37

#Rotatable Bonds: 4

Polar Surface Area: 158.38

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: 5.37

CX LogP: -1.50

CX LogD: -1.57

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.36

Np Likeness Score: 1.26

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