6'-O-Caffeoyldihydrosyringin

ID: ALA3933639

Chembl Id: CHEMBL3933639

PubChem CID: 92135955

Max Phase: Preclinical

Molecular Formula: C26H32O12

Molecular Weight: 536.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(CCCO)cc(OC)c1O[C@@H]1O[C@H](COC(=O)/C=C/c2ccc(O)c(O)c2)[C@@H](O)[C@H](O)[C@H]1O

Standard InChI:  InChI=1S/C26H32O12/c1-34-18-11-15(4-3-9-27)12-19(35-2)25(18)38-26-24(33)23(32)22(31)20(37-26)13-36-21(30)8-6-14-5-7-16(28)17(29)10-14/h5-8,10-12,20,22-24,26-29,31-33H,3-4,9,13H2,1-2H3/b8-6+/t20-,22-,23+,24-,26+/m1/s1

Standard InChI Key:  IJQFQHJDNDTAOI-BWSLIHEESA-N

Alternative Forms

1. Parent:

   

   ALA3933639

   [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[4-(3-hydroxypropyl)-2,6-dimethoxyphenoxy]oxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

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: 536.53

Molecular Weight (Monoisotopic): 536.1894

AlogP: 0.48

#Rotatable Bonds: 11

Polar Surface Area: 184.60

Molecular Species: NEUTRAL

HBA: 12

HBD: 6

#RO5 Violations: 3

HBA (Lipinski): 12

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 9.21

CX Basic pKa: ┄

CX LogP: 1.48

CX LogD: 1.47

Aromatic Rings: 2

Heavy Atoms: 38

QED Weighted: 0.13

Np Likeness Score: 1.52

References

1. Seo S, Lee KG, Shin JS, Chung EK, Lee JY, Kim HJ, Lee KT..  (2016)  6'-O-Caffeoyldihydrosyringin isolated from Aster glehni suppresses lipopolysaccharide-induced iNOS, COX-2, TNF-α, IL-1β and IL-6 expression via NF-κB and AP-1 inactivation in RAW 264.7 macrophages.,  26  (19): [PMID:27590705] [10.1016/j.bmcl.2016.08.074]

Source

Source(1):

• Scientific Literature