CAS 19057-60-4|Collettiside III|dioscin|Dioscin(Collettiside III)|CCRIS 4123|(2S,3R,4R,5R,6S)-2-{[(2R,3S,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-6-[(1'S,2R,2'S,4'S,5R,7'S,8'R,9'S,12'S,13'R,16'S)-5,7',...

General Information

Structure

Molecular Formula

C₄₅H₇₂O₁₆

Molecular Mass

869.04358

Exact Mass

868.48203622

Charge

InChI

InChI=1S/C45H72O16/c1-19-9-14-45(54-18-19)20(2)30-28(61-45)16-27-25-8-7-23-15-24(10-12-43(23,5)26(25)11-13-44(27,30)6)57-42-39(60-41-36(52)34(50)32(48)22(4)56-41)37(53)38(29(17-46)58-42)59-40-35(51)33(49)31(47)21(3)55-40/h7,19-22,24-42,46-53H,8-18H2,1-6H3/t19-,20+,21+,22+,24+,25-,26+,27+,28+,29-,30+,31+,32+,33-,34-,35-,36-,37+,38-,39-,40+,41+,42-,43+,44+,45-/m1/s1

InChIKey

VNONINPVFQTJOC-ZGXDEBHDSA-N

Canonic Smiles

OC[C@H]1O[C@@H](O[C@H]2CC[C@]3(C(=CC[C@@H]4[C@@H]3CC[C@]3([C@H]4C[C@H]4[C@@H]3[C@H](C)[C@]3(O4)CC[C@H](CO3)C)C)C2)C)[C@@H]([C@H]([C@@H]1O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O

Isomeric Smiles

[C@H]1([C@H]([C@@H](O[C@H]([C@@H]1O)O[C@H]1[C@H](O)[C@H]([C@@H](O[C@@H]1CO)O[C@@H]1CC2=CC[C@@H]3[C@@H]([C@]2(CC1)C)CC[C@]1([C@H]3C[C@H]2[C@@H]1[C@@H]([C@@]1(O2)OC[C@@H](CC1)C)C)C)O[C@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)C)O)O)O)C)O)O

Calculated Properties

JChem

LogD (pH = 7.4)

1.71

LogD (pH = 5.5)

1.71

Log P

1.71

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

false

Acid pKa

11.88

Polar Surface Area

235.68

Polarizability

96.28

Molar Refractivity

214.42

LOG S

-4.34

Data Source

Commercial Catalog

Academic Data

Data Source

Names and Identifiers

Synonyms

Collettiside IIIDioscin(Collettiside III)CCRIS 41233-O-(Rhaalpha1-4(Rhaalpha1-2)Glcbeta)-(25R)-spirost-5-en-3beta-ol3-O-[alpha-L-Rha-(1->4)-[alpha-L-Rha-(1->2)]-beta-D-Glc]-diosgeninCollettiside III3-O-[alpha-L-Rhap-(1->4)-[alpha-L-Rhap-(1->2)]-beta-D-Glcp]-diosgeninDioscinedioscindioscin

IUPAC Traditional name

dioscin (2S,3R,4R,5R,6S)-2-{[(2R,3S,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-6-[(1'S,2R,2'S,4'S,5R,7'S,8'R,9'S,12'S,13'R,16'S)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosan]-18'-eneoxy]-5-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol

IUPAC name

(2S,3R,4R,5R,6S)-2-{[(2R,3S,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-6-[(1'S,2R,2'S,4'S,5R,7'S,8'R,9'S,12'S,13'R,16'S)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosan]-18'-eneoxy]-5-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol (2S,3R,4R,5R,6S)-2-{[(2R,3S,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-6-[(1'S,2R,2'S,4'S,5R,7'S,8'R,9'S,12'S,13'R,16'S)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-18'-eneoxy]-5-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol

Names and Identifiers

Registration numbers

PubChem SID

PubChem CID

CAS Number

BKMS React Database

MetaboLights Database

MTBLS3750MTBLS591MTBLS1918

PubMed Citation Links

2339641923467827232621922238681623621869231077412289565523552851232380772223140616079518225160572367880023193420206225012293991522334414

IntEnz Database

EC 3.2.1.190EC 3.2.1.189

BRENDA Database

3.2.1.1903.2.1.189

CHEMBL

CHEMBL507001

CHEBI ID

CHEBI:4627CHEBI:74023

KEGG ID

KNApSAcK Database

Reaxys Registry

ACToR Database

SureChEMBL Database

Rhea Database

LIPID MAPS Instance

BRENDA Ligand Database

19055

Registration numbers

Properties

Product Information

Salt Data

Free Base

Safety Information

Storage Condition

-20°C

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

Selleck Chemicals

S2379

Research Area: Cancer
Biological Activity:
Dioscin(Collettiside III) is extracted and isolated from Polygonatum Zanlanscianense Pamp with IC50 of 2.6, 0.8, 7.5, and 4.5 μM for the inhibition of the growth of the MDA-MB-435, H14, HL60, and HeLa cell lines, respectively. Hela cells underwent apoptosis in dose- and time-dependent manners when treated with Dioscin. Caspase-3, -8 and -9 activities were also detected. The low enzymatic activity of caspase-8 and high activity of caspase-9 showed that the mitochondrial pathway was activated in apoptosis. [1] [2]

ChEBI

CHEBI:74023

A spirostanyl glycoside that consists of the trisaccharide alpha-L-Rha-(1->4)-[alpha-L-Rha-(1->2)]-beta-D-Glc attached to position 3 of diosgenin via a glycosidic linkage.

Molecule Details

References

PubChem Literature

From Data Sources

• Cai J et al. Biol Pharm Bull. 2002 Feb;25(2):193-6.

References

Bioactivity

PubChem BioAssay

Bioactivity

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Calculated Properties