6-methoxypaeoniflorigenone

ID: ALA1081885

PubChem CID: 46883192

Max Phase: Preclinical

Molecular Formula: C18H20O6

Molecular Weight: 332.35

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 6-Methoxypaeoniflorigenone | 6-methoxypaeoniflorigenone|CHEMBL1081885|BDBM50310717

Canonical SMILES:  CO[C@@]12C[C@@H]3C(=O)[C@@](C)(C1)OC(O2)[C@H]3COC(=O)c1ccccc1

Standard InChI:  InChI=1S/C18H20O6/c1-17-10-18(21-2)8-12(14(17)19)13(16(23-17)24-18)9-22-15(20)11-6-4-3-5-7-11/h3-7,12-13,16H,8-10H2,1-2H3/t12-,13-,16?,17+,18+/m0/s1

Standard InChI Key:  BCPSDKWCITVQOP-IDNXCJIVSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   17.7501  -22.3898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4654  -21.9769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0349  -21.9769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7501  -23.2158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1774  -22.3937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8921  -21.9814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8926  -21.1546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1723  -20.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4605  -21.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5060  -21.3995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3029  -21.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3625  -20.0968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6893  -20.0233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1531  -20.7067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7054  -20.7865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3667  -20.6802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7842  -20.0188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9978  -19.4078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1476  -19.4022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1410  -20.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3204  -20.6272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5301  -20.8301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1182  -22.0132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2970  -22.3059    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.9780  -19.9514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 10 14  1  0
 11 15  1  0
 15 12  1  0
 12 13  1  0
 13 14  1  0
  1  4  2  0
  7  8  1  0
 14 16  1  6
 14 17  1  0
  8  9  2  0
 12 18  1  0
  9  2  1  0
 17 19  1  0
 19 18  1  0
  2  5  2  0
 12 20  1  6
 10 11  1  0
 11 21  1  0
 19 21  1  0
  1  3  1  0
 15 22  2  0
  5  6  1  0
 21 23  1  1
 23  3  1  0
  1  2  1  0
 11 24  1  6
  6  7  2  0
 16 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1081885

   6-Methoxypaeoniflorigenone

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: 332.35

Molecular Weight (Monoisotopic): 332.1260

AlogP: 1.93

#Rotatable Bonds: 4

Polar Surface Area: 71.06

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.11

CX LogD: 3.11

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.78

Np Likeness Score: 1.73

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