3β,16β,17α-Trihydroxycholest-5-en-22-one 3-O-β-D-glucopyranoside 16-O-{O-(2-E-cinnamoyl-β-D-xyopyranosyl)-(1→3)-2-O-acetyl-α-L-arabinopyranoside}

SANC00618

Entry name:

3β,16β,17α-Trihydroxycholest-5-en-22-one 3-O-β-D-glucopyranoside 16-O-{O-(2-E-cinnamoyl-β-D-xyopyranosyl)-(1→3)-2-O-acetyl-α-L-arabinopyranoside}

Formula:

C₅₄H₇₈O₁₉

Molecular mass:

1031.18

ChemSpider ID:

8504151

CAS No.

183729-13-7

2D Image 3D View

SMILES:

[H][C@@]8(O[C@H]5C[C@@]4([H])[C@]3([H])CC=C2C[C@@H](O[C@]1([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)CC[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@]5(O)[C@H](C)C(=O)CCC(C)C)OC[C@H](O)[C@H](O[C@]6([H])OC[C@@H](O)[C@H](O)[C@H]6OC(=O)/C=C/c7ccccc7)[C@H]8OC(C)=O

Scaffold SMILES:

c1ccccc1
C1=C2CCCCC2C2CCC3CCCC3C2C1
C1=CCCCC1
C1=CCC2CCCCC2C1
C1=C2CCCCC2C2CCC3CC(OC4CCCCO4)CC3C2C1
C1CCOCC1
C1=C2CC(OC3CCCCO3)CCC2C2CCC3CCCC3C2C1
C1=C2CC(OC3CCCCO3)CCC2C2CCC3CC(OC4CCCCO4)CC3C2C1
C1CCCCC1
O=C(C=Cc1ccccc1)OC1CCCOC1OC1CCOC(OC2CC3CCC4C5CCC(OC6CCCCO6)CC5=CCC4C3C2)C1
C1=C2CCCCC2C2CCC3CC(OC4CC(OC5CCCCO5)CCO4)CC3C2C1
C1=C2CCCCC2CCC1
C1=C2CC(OC3CCCCO3)CCC2C2CCC3CC(OC4CC(OC5CCCCO5)CCO4)CC3C2C1
O=C(C=Cc1ccccc1)OC1CCCOC1OC1CCOC(OC2CC3CCC4C5CCCCC5=CCC4C3C2)C1

References

Mimaki et al. (1997) Cholestane glycosides with potent cytostatic activities on various tumor cells from Ornithogalum saundersiae bulbs

Kuroda et al. (2001) Cholestane Glycosides from the Bulbs of Galtonia candicans and Their Cytotoxicity

Classifications

Cholestane

Glycoside

Steroids and steroid derivatives (Classyfire)

Other Names

Cholest-5-En-22-One, 16-[[2-O-Acetyl-3-O-[2-O-[(2E)-1-Oxo-3-Phenyl-2-Propenyl]-[Beta]-D-Xylopyranosyl]-[Alpha]-L-Arabinopyranosyl]Oxy]-3-([Beta]-D-Glucopyranosyloxy)-17-Hydroxy-, (3[Beta],16[Beta])

Cholest-5-En-22-One, 16-[[2-O-Acetyl-3-O-[2-O-[(2E)-1-Oxo-3-Phenyl-2-Propen-1-Yl]-[Beta]-D-Xylopyranosyl]-[Alpha]-L-Arabinopyranosyl]Oxy]-3-([Beta]-D-Glucopyranosyloxy)-17-Hydroxy-, (3[Beta],16[Beta])-

3[Beta],16[Beta],17[Alpha]-Trihydroxycholest-5-En-22-One 3-O-[Beta]-D-Glucopyranoside 16-O-{O-(2-E-Cinnamoyl-[Beta]-D-Xyopyranosyl)-(1[To]3)-2-O-Acetyl-[Alpha]-L-Arabinopyranoside}

16[Beta]-[(O-(2-O-(E)-Cinnamoyl-[Beta]-D-Xylopyranosyl)-(1[To]2)-2-O-Acetyl-[Alpha]-L-Arabinopyranosyl)Oxy]-3[Beta]-[([Beta]-D-Glucopyranosyl)Oxy]-17[Alpha]-Hydroxycholest-5-En-22-One

Source Organisms

Ornithogalum saundersiae

Galtonia candicans

Compound Uses

Cytostatic activity against HL-60 leukemia cells

Cytotoxic activity on HL-60 leukemia cells

SANC00618

Entry name:

3β,16β,17α-Trihydroxycholest-5-en-22-one 3-O-β-D-glucopyranoside 16-O-{O-(2-E-cinnamoyl-β-D-xyopyranosyl)-(1→3)-2-O-acetyl-α-L-arabinopyranoside}

Formula:

C₅₄H₇₈O₁₉

Molecular mass:

1031.18

ChemSpider ID:

8504151

CAS No.

183729-13-7

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SMILES:

[H][C@@]8(O[C@H]5C[C@@]4([H])[C@]3([H])CC=C2C[C@@H](O[C@]1([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)CC[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@]5(O)[C@H](C)C(=O)CCC(C)C)OC[C@H](O)[C@H](O[C@]6([H])OC[C@@H](O)[C@H](O)[C@H]6OC(=O)/C=C/c7ccccc7)[C@H]8OC(C)=O

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Classifications

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SANC00618

Entry name:

3β,16β,17α-Trihydroxycholest-5-en-22-one 3-O-β-D-glucopyranoside 16-O-{O-(2-E-cinnamoyl-β-D-xyopyranosyl)-(1→3)-2-O-acetyl-α-L-arabinopyranoside}

Formula:

C54H78O19

Molecular mass:

1031.18

ChemSpider ID:

8504151

CAS No.

183729-13-7

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SMILES:

[H][C@@]8(O[C@H]5C[C@@]4([H])[C@]3([H])CC=C2C[C@@H](O[C@]1([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)CC[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@]5(O)[C@H](C)C(=O)CCC(C)C)OC[C@H](O)[C@H](O[C@]6([H])OC[C@@H](O)[C@H](O)[C@H]6OC(=O)/C=C/c7ccccc7)[C@H]8OC(C)=O Search PubChem SMILES

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C₅₄H₇₈O₁₉

[H][C@@]8(O[C@H]5C[C@@]4([H])[C@]3([H])CC=C2C[C@@H](O[C@]1([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)CC[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@]5(O)[C@H](C)C(=O)CCC(C)C)OC[C@H](O)[C@H](O[C@]6([H])OC[C@@H](O)[C@H](O)[C@H]6OC(=O)/C=C/c7ccccc7)[C@H]8OC(C)=O