(2S,3R,4S,5R)-2-((S)-4-(2,4-dihydroxyphenyl)butan-2-yloxy)tetrahydro-2H-pyran-3,4,5-triol

ID: ALA3100133

PubChem CID: 71768558

Max Phase: Preclinical

Molecular Formula: C15H22O7

Molecular Weight: 314.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H](CCc1ccc(O)cc1O)O[C@@H]1OC[C@@H](O)[C@H](O)[C@H]1O

Standard InChI:  InChI=1S/C15H22O7/c1-8(2-3-9-4-5-10(16)6-11(9)17)22-15-14(20)13(19)12(18)7-21-15/h4-6,8,12-20H,2-3,7H2,1H3/t8-,12+,13-,14+,15-/m0/s1

Standard InChI Key:  SSQDSAFOXKKNBY-BGXOLSLGSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   22.0110   -7.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2958   -7.6015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2856   -8.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9899   -8.8376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7060   -8.4326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7126   -7.6163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4102   -8.8471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4033   -9.6643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1075  -10.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1006  -10.8960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8186   -9.6763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5934   -7.1837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5229  -10.0909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5113  -10.9110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.2114  -11.3255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9249  -10.9264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9338  -10.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2292   -9.6893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5187   -9.2698    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   26.2372   -8.8722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.6276  -11.3437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.6464   -9.7082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4241   -7.2142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  1
  2 12  1  0
 11 13  1  0
 13 14  1  0
 13 18  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 13 19  1  6
 18 20  1  6
 16 21  1  6
 17 22  1  1
  6 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3100133

   (2S,3R,4S,5R)-2-[(2S)-4-(2,4-dihydroxyphenyl)butan-2-yl]oxyoxane-3,4,5-triol

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: 314.33

Molecular Weight (Monoisotopic): 314.1366

AlogP: -0.13

#Rotatable Bonds: 5

Polar Surface Area: 119.61

Molecular Species: NEUTRAL

HBA: 7

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.54

CX Basic pKa: ┄

CX LogP: 0.61

CX LogD: 0.60

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.51

Np Likeness Score: 1.78

References

1. Iwadate T, Kashiwakura Y, Masuoka N, Yamada Y, Nihei K..  (2014)  Chemical synthesis and tyrosinase inhibitory activity of rhododendrol glycosides.,  24  (1): [PMID:24332496] [10.1016/j.bmcl.2013.11.063]

2. Iwadate T, Nihei K..  (2015)  Rhododendrol glycosides as stereospecific tyrosinase inhibitors.,  23  (20): [PMID:26386819] [10.1016/j.bmc.2015.09.014]

Source

Source(1):

• Scientific Literature