(2R,3R,4S,5R)-2-(((2S,3R)-2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydrobenzofuran-3-yl)methoxy)tetrahydro-2H-pyran-3,4,5-triol

ID: ALA3793756

PubChem CID: 127053189

Max Phase: Preclinical

Molecular Formula: C25H32O10

Molecular Weight: 492.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc([C@H]2Oc3c(OC)cc(CCCO)cc3[C@@H]2CO[C@@H]2OC[C@@H](O)[C@H](O)[C@H]2O)ccc1O

Standard InChI:  InChI=1S/C25H32O10/c1-31-19-10-14(5-6-17(19)27)23-16(11-33-25-22(30)21(29)18(28)12-34-25)15-8-13(4-3-7-26)9-20(32-2)24(15)35-23/h5-6,8-10,16,18,21-23,25-30H,3-4,7,11-12H2,1-2H3/t16-,18+,21-,22+,23+,25+/m0/s1

Standard InChI Key:  GZLTWCGHVQYMHT-PBSLLFOFSA-N

Molfile:  

     RDKit          2D

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   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6267   -2.9927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9300   -3.7369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9364   -4.9369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0896    0.0290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9234    1.2700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4199    1.1671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0791   -0.1803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2418   -1.4248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7453   -1.3220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2762   -0.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.2273   -3.7690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3153   -8.6101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9585   -9.1610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  5  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  5  1  0
  3 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  1 14  1  0
 14 15  1  0
  7 16  1  1
 16 17  1  0
 18 17  1  6
 18 19  1  0
 18 23  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
  8 24  1  6
 27 30  1  0
 28 31  1  0
 31 32  1  0
 22 33  1  6
 21 34  1  1
 23 35  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA3793756

   ---

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: 492.52

Molecular Weight (Monoisotopic): 492.1995

AlogP: 1.01

#Rotatable Bonds: 9

Polar Surface Area: 147.30

Molecular Species: NEUTRAL

HBA: 10

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.91

CX Basic pKa: ┄

CX LogP: 0.82

CX LogD: 0.81

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.34

Np Likeness Score: 1.96

References

1. 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