(1R,3S,4S,5S)-3-((E)-3-(3,4-dihydroxyphenyl)acryloyloxy)-1,4,5-trihydroxycyclohexanecarboxylic acid

ID: ALA366760

Chembl Id: CHEMBL366760

PubChem CID: 12310830

Max Phase: Preclinical

Molecular Formula: C16H18O9

Molecular Weight: 354.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1ccc(O)c(O)c1)O[C@H]1C[C@@](O)(C(=O)O)C[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23)/b4-2+/t11-,12-,14-,16+/m0/s1

Standard InChI Key:  CWVRJTMFETXNAD-KJOPMHRFSA-N

Alternative Forms

1. Parent:

   

   ALA366760

   Chlorogensaure

Molecule Features

Natural Product: No

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: 354.31

Molecular Weight (Monoisotopic): 354.0951

AlogP: -0.65

#Rotatable Bonds: 4

Polar Surface Area: 164.75

Molecular Species: ACID

HBA: 8

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.33

CX Basic pKa: ┄

CX LogP: -0.27

CX LogD: -3.69

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.23

Np Likeness Score: 2.25

References

1. Chen HZ, Chen YB, Lv YP, Zeng F, Zhang J, Zhou YL, Li HB, Chen LF, Zhou BJ, Gao JR, Xia CN..  (2014)  Synthesis and antitumor activity of feruloyl and caffeoyl derivatives.,  24  (18): [PMID:25160837] [10.1016/j.bmcl.2014.08.024]

2. Chen T, Li Q, Liu Z, Chen Y, Feng F, Sun H..  (2019)  Peptide-based and small synthetic molecule inhibitors on PD-1/PD-L1 pathway: A new choice for immunotherapy?,  161  [PMID:30384043] [10.1016/j.ejmech.2018.10.044]

Source

Source(1):

• Scientific Literature