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Qingyangshengenin B

CAT: 0931-TMS1461-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0931-TMS1461-01Size:1 mg
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CAS Number
106758-54-7
Target
Beta Amyloid
Related Pathways
Neuroscience
Purity
0.9951
Bioactivity
Qingyangshengenin B (Otophylloside B) is a C-21 steroidal glycoside isolated from Qingyangshen. Qingyangshengenin B protects against Aβ toxicity, which decreases Aβ deposition by decreasing the expression of Aβ at the mRNA level. Qingyangshengenin B has antiepileptic and anti-aging effects, it can extend lifespan, increase heat stress-resistance, delay body paralysis, and increase the chemotaxis response in C. elegans models of Alzheimer's disease. Otophylloside B can suppress the seizure-like locomotor activity caused by pentylenetetrazole in zebrafish.
Smiles
O[C@]12[C@](C)([C@H](OC(/C=C(/C(C)C)\C)=O)C[C@]3([C@@]1(O)CC=C4[C@]3(C)CC[C@H](O[C@H]5C[C@H](OC)[C@H](O[C@H]6C[C@H](OC)[C@H](O[C@H]7C[C@@H](OC)[C@H](O)[C@@H](C)O7)[C@@H](C)O6)[C@@H](C)O5)C4)[H])[C@@](C(C)=O)(O)CC2
Molecular Formula
C49H78O16
Molecular Weight
923.13
Shipping Conditions
Ice Packs
Storage Temperature
-20°C

Chemical Information

otophylloside B

Otophylloside B is a steroid saponin that is 17alpha-pregnenolone which is substituted by hydroxy groups at positions 8, 12beta, 14beta and 17beta, in which the 14beta-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-beta-D-arabino-hexopyranosyl-(14)-2,6-dideoxy-3-O-methyl-beta-D-ribo-hexopyranosyl-(14)-2,6-dideoxy-3-O-methyl-beta-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. It has a role as an anticonvulsant and a plant metabolite. It is an 8-hydroxy steroid, a tertiary alpha-hydroxy ketone, a 17beta-hydroxy steroid, a 14beta-hydroxy steroid, a steroid saponin and a trisaccharide derivative.

CAS Number106758-54-7
PubChem CID10079485
IUPAC Name[(3S,8S,9R,10R,12R,13S,14R,17S)-17-acetyl-8,14,17-trihydroxy-3-[(2R,4S,5R,6R)-5-[(2S,4S,5R,6R)-5-[(2S,4R,5R,6R)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-10,13-dimethyl-1,2,3,4,7,9,11,12,15,16-decahydrocyclopenta[a]phenanthren-12-yl] (E)-3,4-dimethylpent-2-enoate
Molecular FormulaC49H78O16
Molecular Weight923.1
XLogP3.7
Topological Polar Surface Area207
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count16
Rotatable Bond Count14
Heavy Atom Count65
Formal Charge0
Complexity1790
SMILES
C[C@@H]1[C@H]([C@@H](C[C@@H](O1)O[C@@H]2[C@H](O[C@H](C[C@@H]2OC)O[C@@H]3[C@H](O[C@H](C[C@@H]3OC)O[C@H]4CC[C@@]5([C@H]6C[C@H]([C@@]7([C@@](CC[C@@]7([C@@]6(CC=C5C4)O)O)(C(=O)C)O)C)OC(=O)/C=C(\C)/C(C)C)C)C)C)OC)O
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
Chemical Structure
2D Structure
2D structure of otophylloside B
CAS: 106758-54-7
CID: 10079485
Formula: C49H78O16
MW: 923.1
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight923.1
XLogP33.7
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count16
Rotatable Bond Count14
Exact Mass922.52898640
Monoisotopic Mass922.52898640
Topological Polar Surface Area207 Ų
Heavy Atom Count65
Formal Charge0
Complexity1790
Isotope Atom Count0
Defined Atom Stereocenter Count20
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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GTR19180407Qingyangshengenin 3-O-α-L-cymaropyranosyl- (1→4) -β-D-oleandropyranosyl- (1→4) -β-D-cymaropyranosyl- (1→4) -β-D-cymaropyranoside
MBS5787429Qingyangshengenin 3-O-beta-D-oleandropyranosyl-(1-->4)-beta-D-cymaropyranosyl-(1-->4)-beta-D-digitoxopyranoside
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