((2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(4-hydroxyphenethoxy)tetrahydro-2H-pyran-2-yl)methyl acetate

ID: ALA4743378

PubChem CID: 101844777

Max Phase: Preclinical

Molecular Formula: C16H22O8

Molecular Weight: 342.34

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(=O)OC[C@H]1O[C@@H](OCCc2ccc(O)cc2)[C@H](O)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C16H22O8/c1-9(17)23-8-12-13(19)14(20)15(21)16(24-12)22-7-6-10-2-4-11(18)5-3-10/h2-5,12-16,18-21H,6-8H2,1H3/t12-,13-,14+,15-,16-/m1/s1

Standard InChI Key:  KYMAFSUPPGDNQZ-IBEHDNSVSA-N

Molfile:  

 
     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
   27.7185   -8.0357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7185   -8.8529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4237   -9.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1290   -8.8529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1290   -8.0357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4237   -7.6230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0096   -7.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0072   -6.8120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0114   -9.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.8361   -9.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.4237  -10.0746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.8379   -7.6292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.5444   -8.0399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2533   -7.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9598   -8.0440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9561   -8.8622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6618   -9.2728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3717   -8.8662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3714   -8.0448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6652   -7.6379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0770   -9.2772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7137   -6.4013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4226   -6.8079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7113   -5.5842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  1  7  1  1
  7  8  1  0
  2  9  1  6
  4 10  1  6
  3 11  1  1
  5 12  1  1
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 18 21  1  0
  8 22  1  0
 22 23  2  0
 22 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4743378

   [(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]oxan-2-yl]methyl acetate

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 342.34

Molecular Weight (Monoisotopic): 342.1315

AlogP: -0.68

#Rotatable Bonds: 6

Polar Surface Area: 125.68

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.20

CX Basic pKa: ┄

CX LogP: -0.14

CX LogD: -0.14

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.50

Np Likeness Score: 1.86

References

1. Yang Z,Huang X,Lai W,Tang Y,Liu J,Wang Y,Chu K,Brown J,Hong G.  (2021)  Synthesis and identification of a novel derivative of salidroside as a selective, competitive inhibitor of monoamine oxidase B with enhanced neuroprotective properties.,  209  [PMID:33097301] [10.1016/j.ejmech.2020.112935]

Source

Source(1):

• Scientific Literature