4-O-butylpaeoniflorin

ID: ALA1078184

PubChem CID: 44253994

Max Phase: Preclinical

Molecular Formula: C27H36O11

Molecular Weight: 536.57

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 4-O-Butylpaeoniflorin | 4-O-butylpaeoniflorin|CHEMBL1078184|BDBM50310708

Canonical SMILES:  CCCCO[C@]12C[C@]3(C)OC(O1)[C@]1(COC(=O)c4ccccc4)[C@@H]2C[C@@]31O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

Standard InChI:  InChI=1S/C27H36O11/c1-3-4-10-34-26-13-24(2)27(36-22-20(31)19(30)18(29)16(12-28)35-22)11-17(26)25(27,23(37-24)38-26)14-33-21(32)15-8-6-5-7-9-15/h5-9,16-20,22-23,28-31H,3-4,10-14H2,1-2H3/t16-,17+,18-,19+,20-,22+,23?,24+,25+,26-,27-/m1/s1

Standard InChI Key:  WZGDJBIFNLWZEF-POZPPLBNSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA1078184

   4-O-butylpaeoniflorin

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: 536.57

Molecular Weight (Monoisotopic): 536.2258

AlogP: 0.47

#Rotatable Bonds: 10

Polar Surface Area: 153.37

Molecular Species: NEUTRAL

HBA: 11

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.21

CX Basic pKa: ┄

CX LogP: 1.58

CX LogD: 1.58

Aromatic Rings: 1

Heavy Atoms: 38

QED Weighted: 0.24

Np Likeness Score: 2.10

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. 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]

Source

Source(1):

• Scientific Literature