forsythoside B   Click here for help

GtoPdb Ligand ID: 10303

Immunopharmacology Ligand
Comment: Forsythoside B is a naturallt occurring compound found in Lamiophlomis rotata Kudo plants. It has demonstrated in vivo antipruritic activity via inhibition of the thermosensitive TRPV3 ion channel in the skin [1]. Chemically it is a phenylethanoid glycoside.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 15
Hydrogen bond donors 11
Rotatable bonds 14
Topological polar surface area 304.21
Molecular weight 756.25
XLogP -0.64
No. Lipinski's rules broken 3
SMILES / InChI / InChIKey
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Canonical SMILES OCC1(O)COC(C1O)OCC1OC(OCCc2ccc(c(c2)O)O)C(C(C1OC(=O)C=Cc1ccc(c(c1)O)O)OC1OC(C)C(C(C1O)O)O)O
Isomeric SMILES OC[C@@]1(O)CO[C@H]([C@@H]1O)OC[C@H]1O[C@@H](OCCc2ccc(c(c2)O)O)[C@@H]([C@H]([C@@H]1OC(=O)/C=C/c1ccc(c(c1)O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O
InChI InChI=1S/C34H44O19/c1-15-24(41)25(42)26(43)32(50-15)53-29-27(44)31(47-9-8-17-3-6-19(37)21(39)11-17)51-22(12-48-33-30(45)34(46,13-35)14-49-33)28(29)52-23(40)7-4-16-2-5-18(36)20(38)10-16/h2-7,10-11,15,22,24-33,35-39,41-46H,8-9,12-14H2,1H3/b7-4+/t15-,22+,24-,25+,26+,27+,28+,29+,30-,31+,32-,33+,34+/m0/s1
InChI Key JMBINOWGIHWPJI-UNSOMVRXSA-N
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Compound class Natural product or derivative
IUPAC Name Click here for help
[(2R,3R,4R,5R,6R)-2-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Database Links Click here for help
CAS Registry No. 81525-13-5 (source: PubChem)
GtoPdb PubChem SID 381744984
PubChem CID 23928102
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