Lyoniside

ID: ALA583884

Cas Number: 34425-25-7

PubChem CID: 14521039

Max Phase: Preclinical

Molecular Formula: C27H36O12

Molecular Weight: 552.57

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Lyoniside | Lyoniside|34425-25-7|(2R,3R,4S,5R)-2-[[(1S,2R,3R)-7-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-6,8-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl]methoxy]oxane-3,4,5-triol|CHEMBL583884|DTXSID001318597|HY-N3348|BDBM50378458|AKOS032962464|FS-9782|CID 14521039|CS-0023957|Lyoniresinol, -D-xyloside ; -D-Xylopyranoside, [1,2,3,4-tetrahydro-7-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-6,8-dimethoxy-2-naphthalenyl]methyl, [1S-(1,2,3)]-

Canonical SMILES:  COc1cc([C@H]2c3c(cc(OC)c(O)c3OC)C[C@@H](CO)[C@@H]2CO[C@@H]2OC[C@@H](O)[C@H](O)[C@H]2O)cc(OC)c1O

Standard InChI:  InChI=1S/C27H36O12/c1-34-17-7-13(8-18(35-2)23(17)31)20-15(10-38-27-25(33)22(30)16(29)11-39-27)14(9-28)5-12-6-19(36-3)24(32)26(37-4)21(12)20/h6-8,14-16,20,22,25,27-33H,5,9-11H2,1-4H3/t14-,15-,16+,20+,22-,25+,27+/m0/s1

Standard InChI Key:  GWDZRGQRNHELQM-VEKSOEEBSA-N

Molfile:  

     RDKit          2D

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    6.6996  -11.4790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  5  6  1  0
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  3 11  1  0
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  2  3  1  0
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  2 13  1  0
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  3  6  2  0
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  1 14  1  0
 29 30  1  0
  1  2  2  0
 31 30  1  1
 31 32  1  0
 14 15  1  0
  5  4  2  0
  9 16  1  1
  4  1  1  0
 16 17  1  0
 31 36  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
  5 10  1  0
 36 37  1  6
  7 18  1  1
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  6  7  1  0
 34 39  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA583884

   LYONISIDE

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: 552.57

Molecular Weight (Monoisotopic): 552.2207

AlogP: 0.50

#Rotatable Bonds: 9

Polar Surface Area: 176.76

Molecular Species: NEUTRAL

HBA: 12

HBD: 6

#RO5 Violations: 3

HBA (Lipinski): 12

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 9.24

CX Basic pKa: ┄

CX LogP: 0.32

CX LogD: 0.32

Aromatic Rings: 2

Heavy Atoms: 39

QED Weighted: 0.25

Np Likeness Score: 1.95

References

1. Arai MA, Masada A, Ohtsuka T, Kageyama R, Ishibashi M..  (2009)  The first Hes1 dimer inhibitors from natural products.,  19  (19): [PMID:19716294] [10.1016/j.bmcl.2009.07.146]

2. Cai YH, Guo Y, Li Z, Wu D, Li X, Zhang H, Yang J, Lu H, Sun Z, Luo HB, Yin S, Wu Y..  (2016)  Discovery and modelling studies of natural ingredients from Gaultheria yunnanensis (FRANCH.) against phosphodiesterase-4.,  114  [PMID:26978121] [10.1016/j.ejmech.2015.12.002]

Source

Source(1):

• Scientific Literature