CHEBI:139305 - otophylloside B

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ChEBI Name otophylloside B
ChEBI ID CHEBI:139305
Definition A steroid saponin that is 17α-pregnenolone which is substituted by hydroxy groups at positions 8, 12β, 14β and 17β, in which the 14β-hydrocy group has been acylated by formal condensation with the carboxy group of (2E)-3,4-dimethylpent-2-enoic acid, and in which the hydroxy group at position 3 has been glycosylated with 2,6-dideoxy-3-O-methyl-β-D-arabino-hexopyranosyl-(1→4)-2,6-dideoxy-3-O-methyl-β-D-ribo-hexopyranosyl-(1→4)-2,6-dideoxy-3-O-methyl-β-D-ribo-hexopyranos. A C-21 steroidal glycoside, it is the essential active ingredient of the traditional Chinese medicine Qingyangshen, isolated from Cynanchum otophyllum and used to treat epilepsy and rheumatic pain.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter KYook
Supplier Information
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Formula C49H78O16
Net Charge 0
Average Mass 923.136
Monoisotopic Mass 922.52899
InChI InChI=1S/C49H78O16/c1-25(2)26(3)19-38(51)63-37-24-36-45(8)15-14-32(20-31(45)13-16-48(36,54)49(55)18-17-47(53,30(7)50)46(37,49)9)62-39-22-34(57-11)43(28(5)60-39)65-41-23-35(58-12)44(29(6)61-41)64-40-21-33(56-10)42(52)27(4)59-40/h13,19,25,27-29,32-37,39-44,52-55H,14-18,20-24H2,1-12H3/b26-19+/t27-,28-,29-,32+,33-,34+,35+,36-,37-,39+,40+,41+,42-,43-,44-,45+,46-,47-,48+,49-/m1/s1
InChIKey YLHXSKZGPASTOD-ZMZOTGGVSA-N
SMILES [C@]12(CC=C3[C@@]([C@]1(C[C@H]([C@]4([C@@]2(CC[C@]4(C(=O)C)O)O)C)OC(=O)/C=C(\C)/C(C)C)[H])(CC[C@@H](C3)O[C@@H]5O[C@@H]([C@@H](O[C@H]6C[C@H](OC)[C@@H]([C@H](O6)C)O[C@@H]7O[C@@H]([C@H]([C@@H](C7)OC)O)C)[C@H](C5)OC)C)C)O
Metabolite of Species Details
Cynanchum otophyllum (NCBI:txid765270) Found in root (BTO:0001188). See: PubMed
Roles Classification
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via saponin )
Application(s): anticonvulsant
A drug used to prevent seizures or reduce their severity.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing otophylloside B (CHEBI:139305) has role anticonvulsant (CHEBI:35623)
otophylloside B (CHEBI:139305) has role plant metabolite (CHEBI:76924)
otophylloside B (CHEBI:139305) is a 14β-hydroxy steroid (CHEBI:36862)
otophylloside B (CHEBI:139305) is a 17β-hydroxy steroid (CHEBI:35343)
otophylloside B (CHEBI:139305) is a 8-hydroxy steroid (CHEBI:139333)
otophylloside B (CHEBI:139305) is a steroid saponin (CHEBI:61655)
otophylloside B (CHEBI:139305) is a tertiary α-hydroxy ketone (CHEBI:139592)
otophylloside B (CHEBI:139305) is a trisaccharide derivative (CHEBI:63571)
IUPAC Name
3β-{[2,6-dideoxy-3-O-methyl-β-D-arabino-hexopyranosyl-(1→4)-2,6-dideoxy-3-O-methyl-β-D-ribo-hexopyranosyl-(1→4)-2,6-dideoxy-3-O-methyl-β-D-ribo-hexopyranosyl]oxy}-8,14β,17β-trihydroxy-20-oxo-17α-pregn-5-en-12β-yl (2E)-3,4-dimethylpent-2-enoate
Synonyms Sources
(3β,12β,14β,17α)-3-{[2,6-dideoxy-3-O-methyl-β-D-arabino-hexopyranosyl-(1→4)-2,6-dideoxy-3-O-methyl-β-D-ribo-hexopyranosyl-(1→4)-2,6-dideoxy-3-O-methyl-β-D-ribo-hexopyranosyl]oxy}-8,14,17-trihydroxy-20-oxopregn-5-en-12-yl (2E)-3,4-dimethylpent-2-enoate IUPAC
Ot B SUBMITTER
Citations Waiting for Citations Types Sources
21513722 PubMed citation Europe PMC
25039181 PubMed citation Europe PMC
25579837 PubMed citation Europe PMC
26112394 PubMed citation Europe PMC
26135914 PubMed citation Europe PMC
28194725 PubMed citation Europe PMC
28845649 PubMed citation Europe PMC
3764407 PubMed citation Europe PMC
Last Modified
07 February 2018