otophylloside B (CHEBI:139305)

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CHEBI:139305 - otophylloside B

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ChEBI ID	CHEBI:139305
ChEBI Name	otophylloside B
Stars
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.
Last Modified	7 February 2018
Submitter	KYook
Downloads	Molfile

Formula	C49H78O16
Net Charge	0
Average Mass	923.147
Monoisotopic Mass	922.52899
SMILES	[H][C@]12C[C@@H](OC(=O)/C=C(\C)C(C)C)[C@@]3(C)[C@](O)(CC[C@@]3(O)C(C)=O)[C@]1(O)CC=C1C[C@@H](O[C@H]3C[C@H](OC)[C@H](O[C@H]4C[C@H](OC)[C@H](O[C@H]5C[C@@H](OC)[C@H](O)[C@@H](C)O5)[C@@H](C)O4)[C@@H](C)O3)CC[C@@]12C
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

Species of Metabolite	Component	Source	Comments
Cynanchum otophyllum (ncbitaxon:765270)	root (BTO:0001188)	PubMed (3764407)

Roles Classification

Biological Roles:	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.
Application:	anticonvulsant A drug used to prevent seizures or reduce their severity.

ChEBI Ontology

Outgoing Relation(s)
	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	Source
Ot B	SUBMITTER
(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

Citations