paeonolide

ID: ALA1079881

Cas Number: 20309-70-0

PubChem CID: 442924

Max Phase: Preclinical

Molecular Formula: C15H20O8

Molecular Weight: 328.32

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Paeonolide | 20309-70-0|CHEMBL1079881|CHEBI:7892|C10717|1-[4-methoxy-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]ethanone|Ethanone, 1-[2-(beta-D-glucopyranosyloxy)-4-methoxyphenyl]-|2-Acetyl-5-methoxyphenyl beta-D-Glucopyranoside|AC1L9DNQ|DTXSID60942452|CHEBI:718638|C15H20O8|HY-N2351|BDBM50310719|AKOS040763747|2-Acetyl-5-methoxyphenyl hexopyranoside|CS-0022158|2-Acetyl-5-methoxyphenyl ??-D-Glucopyranoside|Q27107607|1-(4-Methoxy-2-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-Show More⌵

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

Standard InChI:  InChI=1S/C15H20O8/c1-7(17)9-4-3-8(21-2)5-10(9)22-15-14(20)13(19)12(18)11(6-16)23-15/h3-5,11-16,18-20H,6H2,1-2H3/t11-,12-,13+,14-,15-/m1/s1

Standard InChI Key:  AVIUTYMRHHBXPB-UXXRCYHCSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    0.7494  -28.6747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7494  -29.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4487  -29.8853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1527  -29.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1527  -28.6747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4487  -28.2681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0743  -28.2816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0723  -27.5014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8272  -28.2807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8262  -29.8745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4475  -30.6703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0752  -29.8735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1121  -26.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1108  -27.0413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8275  -27.4531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5460  -27.0408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5427  -26.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8254  -25.7994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3958  -25.7968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3965  -24.9692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2629  -27.4540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2634  -28.2816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9793  -27.0398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
  2 12  1  6
  5  6  1  0
 13 14  2  0
  1  7  1  1
 14 15  1  0
  1  2  1  0
 15 16  2  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
M  END

Alternative Forms

1. Parent:

   

   ALA1079881

   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: 328.32

Molecular Weight (Monoisotopic): 328.1158

AlogP: -0.92

#Rotatable Bonds: 5

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: 12.20

CX Basic pKa: ┄

CX LogP: -1.20

CX LogD: -1.20

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.51

Np Likeness Score: 1.38

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