paeonoside

ID: ALA1079882

PubChem CID: 46883331

Max Phase: Preclinical

Molecular Formula: C20H28O12

Molecular Weight: 460.43

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Paeonoside | CHEMBL1079882|BDBM50310720|AKOS037514888

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

Standard InChI:  InChI=1S/C20H28O12/c1-9(22)11-4-3-10(28-2)5-12(11)31-18-16(25)15(24)14(23)13(32-18)6-29-19-17(26)20(27,7-21)8-30-19/h3-5,13-19,21,23-27H,6-8H2,1-2H3/t13-,14-,15+,16-,17+,18-,19-,20-/m1/s1

Standard InChI Key:  IRLNKOAURQPXIQ-LTRJMQNCSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
    9.4362  -28.7731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4362  -29.5793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1334  -29.9801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8353  -29.5793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8353  -28.7731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1334  -28.3677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7630  -28.3812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7611  -27.6033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5078  -28.3803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5068  -29.9693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1323  -30.7627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7641  -29.9683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7948  -26.3168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7935  -27.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5081  -27.5552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2244  -27.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2211  -26.3128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5060  -25.9063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0807  -25.9037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0814  -25.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9392  -27.5561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9398  -28.3812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6534  -27.1431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0456  -27.1926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9540  -26.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1466  -26.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7358  -26.9212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2896  -27.5328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1207  -28.3404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9155  -27.0096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7277  -26.0953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0092  -25.6898    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
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 24  1  0
  1  7  1  1
 28 29  1  6
 14 15  1  0
 27 30  1  0
  1  2  1  0
 27 31  1  1
 15 16  2  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1079882

   PAEONOSIDE

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: 8

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: 11.70

CX Basic pKa: ┄

CX LogP: -2.47

CX LogD: -2.47

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.23

Np Likeness Score: 1.87

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]

2. Marín C, Ramírez-Macías I, López-Céspedes A, Olmo F, Villegas N, Díaz JG, Rosales MJ, Gutiérrez-Sánchez R, Sánchez-Moreno M..  (2011)  In vitro and in vivo trypanocidal activity of flavonoids from Delphinium staphisagria against Chagas disease.,  74  (4): [PMID:21466157] [10.1021/np1008043]

Source

Source(1):

• Scientific Literature