apiopaeonoside

ID: ALA1080061

Cas Number: 72520-92-4

PubChem CID: 442923

Product Number: P160234, Order Now?

Max Phase: Preclinical

Molecular Formula: C20H28O12

Molecular Weight: 460.43

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Apiopaeonoside | Paeonolide|72520-92-4|CHEMBL1080061|C10715|CHEBI:7891|1-[4-methoxy-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxyphenyl]ethanone|AC1L9DNN|DTXSID20993369|CHEBI:718640|HY-N2156|XCA52092|BDBM50310721|MFCD20265600|AKOS030573577|CS-0019456|Q27107606|2-Acetyl-5-methoxyphenyl 6-O-pentopyranosylhexopyranoside|1-[4-methoxy-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5S)-3,4,5-trihydroxytetrahydropyran-2-yl]oxymethyl]tetrahyShow More⌵

Canonical SMILES:  COc1ccc(C(C)=O)c(O[C@@H]2O[C@H](CO[C@@H]3OC[C@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H](O)[C@H]2O)c1

Standard InChI:  InChI=1S/C20H28O12/c1-8(21)10-4-3-9(28-2)5-12(10)31-20-18(27)16(25)15(24)13(32-20)7-30-19-17(26)14(23)11(22)6-29-19/h3-5,11,13-20,22-27H,6-7H2,1-2H3/t11-,13+,14-,15+,16-,17+,18+,19-,20+/m0/s1

Standard InChI Key:  IDZZECHGWAZTIB-NYBIBFQCSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
   18.8489  -28.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8489  -29.0133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5469  -29.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2496  -29.0133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2496  -28.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5469  -27.8002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1750  -27.8138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1731  -27.0350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9229  -27.8128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9219  -29.4037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5458  -30.1980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1760  -29.4027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2090  -25.7471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2078  -26.5758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9231  -26.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6403  -26.5752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6370  -25.7430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9211  -25.3362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4941  -25.3335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4948  -24.5075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3559  -26.9878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3564  -27.8137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0709  -26.5743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4567  -26.6238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4589  -25.8003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7467  -25.3892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0300  -25.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0301  -26.6275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7469  -27.0431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7502  -27.8691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3144  -27.0398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3151  -25.3866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0
 16 17  1  0
  1  6  1  0
 17 18  2  0
 18 13  1  0
  5  9  1  1
 13 19  1  0
  2  3  1  0
 19 20  1  0
  4 10  1  6
 16 21  1  0
  3  4  1  0
 21 22  2  0
  3 11  1  1
 21 23  1  0
 15  9  1  0
  4  5  1  0
 24  8  1  1
 24 25  1  0
  2 12  1  6
  5  6  1  0
 13 14  2  0
  1  7  1  1
 24 29  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 14 15  1  0
 29 30  1  6
  1  2  1  0
 28 31  1  1
 15 16  2  0
 27 32  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA1080061

   Paeonolide

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: 460.43

Molecular Weight (Monoisotopic): 460.1581

AlogP: -2.46

#Rotatable Bonds: 7

Polar Surface Area: 184.60

Molecular Species: NEUTRAL

HBA: 12

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.92

CX Basic pKa: ┄

CX LogP: -2.34

CX LogD: -2.34

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.24

Np Likeness Score: 1.44

References

1. Ha do T, Ngoc TM, Lee I, Lee YM, Kim JS, Jung H, Lee S, Na M, Bae K..  (2009)  Inhibitors of aldose reductase and formation of advanced glycation end-products in moutan cortex (Paeonia suffruticosa).,  72  (8): [PMID:19670875] [10.1021/np9002004]

Source

Source(1):

• Scientific Literature