oxypaeoniflorin

ID: ALA1078550

PubChem CID: 46882883

Max Phase: Preclinical

Molecular Formula: C23H28O12

Molecular Weight: 496.47

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Oxypaeoniflorin | CHEMBL1078550|BDBM50378696

Canonical SMILES:  C[C@@]12C[C@@]3(O)O[C@@H](O1)[C@]1(COC(=O)c4ccc(O)cc4)[C@@H]3C[C@]12O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

Standard InChI:  InChI=1S/C23H28O12/c1-20-8-22(30)13-6-23(20,33-18-16(28)15(27)14(26)12(7-24)32-18)21(13,19(34-20)35-22)9-31-17(29)10-2-4-11(25)5-3-10/h2-5,12-16,18-19,24-28,30H,6-9H2,1H3/t12-,13+,14-,15+,16-,18+,19-,20+,21+,22-,23-/m1/s1

Standard InChI Key:  FCHVXNVDFYXLIL-QYDSDWLYSA-N

Molfile:  

     RDKit          2D

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   20.3498  -23.1365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0809  -23.5530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8022  -23.1340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8008  -22.2940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0780  -21.8731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0765  -21.0331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   16.7537  -21.1327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   18.9230  -22.3103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1975  -21.9172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   19.6688  -23.5306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   21.3133  -25.7155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   22.9690  -21.9950    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.5695  -27.5779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  6
 17 22  1  0
 18 19  1  0
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 20 21  1  0
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  6  8  1  0
 18 23  1  6
  1  9  1  0
 19 24  1  1
  3  9  1  0
 20 25  1  6
 21 11  1  1
  9 10  1  0
 13 26  1  0
  8 10  1  0
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  1 11  1  6
 26 28  2  0
  9 12  1  1
 27 29  2  0
 12 13  1  0
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  3 14  1  6
 30 31  2  0
 31 32  1  0
  1  2  1  0
 32 33  2  0
 33 27  1  0
 15 16  1  0
  4 34  1  6
  1  6  1  0
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 17 16  1  1
 10 36  1  1
 17 18  1  0
 31 37  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1078550

   OXYPAEONIFLORIN

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: 496.47

Molecular Weight (Monoisotopic): 496.1581

AlogP: -1.65

#Rotatable Bonds: 6

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: 8.50

CX Basic pKa: ┄

CX LogP: -0.69

CX LogD: -0.72

Aromatic Rings: 1

Heavy Atoms: 35

QED Weighted: 0.25

Np Likeness Score: 2.37

References

1. Duan WJ, Yang JY, Chen LX, Zhang LJ, Jiang ZH, Cai XD, Zhang X, Qiu F..  (2009)  Monoterpenes from Paeonia albiflora and their inhibitory activity on nitric oxide production by lipopolysaccharide-activated microglia.,  72  (9): [PMID:19691309] [10.1021/np9001898]

2. 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]

3. Ding L, Zhao F, Chen L, Jiang Z, Liu Y, Li Z, Qiu F, Yao X..  (2012)  New monoterpene glycosides from Paeonia suffruticosa Andrews and their inhibition on NO production in LPS-induced RAW 264.7 cells.,  22  (23): [PMID:23067550] [10.1016/j.bmcl.2012.09.034]

4. Song WH, Cheng ZH, Chen DF..  (2014)  Anticomplement monoterpenoid glucosides from the root bark of Paeonia suffruticosa.,  77  (1): [PMID:24377852] [10.1021/np400571x]

Source

Source(1):

• Scientific Literature