(2R,3R,4S,5S,6R)-2-((S)-4-(2,4-dihydroxyphenyl)butan-2-yloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

ID: ALA3100131

PubChem CID: 71769045

Max Phase: Preclinical

Molecular Formula: C16H24O8

Molecular Weight: 344.36

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H24O8/c1-8(2-3-9-4-5-10(18)6-11(9)19)23-16-15(22)14(21)13(20)12(7-17)24-16/h4-6,8,12-22H,2-3,7H2,1H3/t8-,12+,13+,14-,15+,16+/m0/s1

Standard InChI Key:  XNCMTBXGJAVONM-UCYYYPAZSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
    3.0877   -6.3925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3724   -6.7925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3622   -7.6101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0666   -8.0287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7826   -7.6236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7893   -6.8073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4869   -8.0382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4799   -8.8554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1841   -9.2699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1772  -10.0871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8953   -8.8674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6701   -6.3747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5995   -9.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5879  -10.1021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2881  -10.5166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0016  -10.1175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0105   -9.2994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3059   -8.8804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5953   -8.4608    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3139   -8.0632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7042  -10.5347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7230   -8.8992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2781  -11.3337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5654  -11.7336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5008   -6.4053    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
 15 23  1  1
 23 24  1  0
  6 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3100131

   (2R,3R,4S,5S,6R)-2-[(2S)-4-(2,4-dihydroxyphenyl)butan-2-yl]oxy-6-(hydroxymethyl)oxane-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: 344.36

Molecular Weight (Monoisotopic): 344.1471

AlogP: -0.76

#Rotatable Bonds: 6

Polar Surface Area: 139.84

Molecular Species: NEUTRAL

HBA: 8

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.54

CX Basic pKa: ┄

CX LogP: -0.02

CX LogD: -0.03

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.40

Np Likeness Score: 1.90

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