(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-((1S,4aS,7aS)-7-(acetoxymethyl)-4-(oxazol-2-ylcarbamoyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yloxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

ID: ALA5195751

PubChem CID: 168284327

Max Phase: Preclinical

Molecular Formula: C29H34N2O15

Molecular Weight: 650.59

Names and Identifiers

Canonical SMILES:  CC(=O)OCC1=CC[C@@H]2C(C(=O)Nc3ncco3)=CO[C@@H](O[C@@H]3O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]3OC(C)=O)[C@H]12

Standard InChI:  InChI=1S/C29H34N2O15/c1-13(32)39-10-18-6-7-19-20(26(37)31-29-30-8-9-38-29)11-41-27(22(18)19)46-28-25(44-17(5)36)24(43-16(4)35)23(42-15(3)34)21(45-28)12-40-14(2)33/h6,8-9,11,19,21-25,27-28H,7,10,12H2,1-5H3,(H,30,31,37)/t19-,21-,22-,23-,24+,25-,27+,28+/m1/s1

Standard InChI Key:  ZRGTVTKQKKMZRG-RVLABJBRSA-N

Molfile:  

 
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M  END

Alternative Forms

1. Parent:

   

   ALA5195751

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 650.59

Molecular Weight (Monoisotopic): 650.1959

AlogP: 1.08

#Rotatable Bonds: 11

Polar Surface Area: 214.32

Molecular Species: NEUTRAL

HBA: 16

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 17

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 7.75

CX Basic pKa: ┄

CX LogP: -0.33

CX LogD: -0.48

Aromatic Rings: 1

Heavy Atoms: 46

QED Weighted: 0.20

Np Likeness Score: 1.42

References

1. Chen JS, Wang MX, Wang MM, Zhang YK, Guo X, Chen YY, Zhang MQ, Sun JY, Liu YF, Liu C..  (2022)  Synthesis and biological evaluation of geniposide derivatives as inhibitors of hyperuricemia, inflammatory and fibrosis.,  237  [PMID:35468514] [10.1016/j.ejmech.2022.114379]

Source

Source(1):

• Scientific Literature