hederagenin 3-O-arabinoside (Q27106835)

(4aS,6aS,6bR,8aR,9R,12aR,12bR,14bS)-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-10-{[(2S)-3,4,5-trihydroxyoxan-2-yl]oxy}-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid

inferred from SMILES

1 reference

inferred from SMILES

mass

604.397519±0 dalton

1 reference

Cauloside A (English)

(4aR,6aR,6aS,6bR,8aR,9S,10R,12aR,14bR)-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-10-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid

5 October 2016

stereoisomer of

2 references

2 references

Hederagenin alpha-L-arabinoside

2 references

(4aS,6aR,6aS,6bR,8aS,9R,10S,12aR,14bS)-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-10-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid

2 references

(4aS,6aS,6aR,6bR,8aR,9R,10S,12aR,14bR)-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-10-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid

1 reference

(4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-10-[(2R,3S,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid

1 reference

(4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-10-[(2R,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid

1 reference

(4aS,6aR,6aS,6bR,8aR,9R,10R,12aR,14bS)-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-10-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid

1 reference

(4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-10-[(2S,3S,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid

1 reference

(4aS,6aR,6aS,6bR,8aR,9S,10S,12aR,14bS)-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-10-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid

1 reference

chemical formula

C₃₅H₅₆O₈

1 reference

Cauloside A (English)

5 October 2016

canonical SMILES

CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)CO)OC6C(C(C(CO6)O)O)O)C)C)C2C1)C)C(=O)O)C

1 reference

Cauloside A (English)

5 October 2016

isomeric SMILES

C[C@]12CC[C@@H]([C@@]([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(CC[C@@]5([C@H]4CC(CC5)(C)C)C(=O)O)C)C)(C)CO)O[C@H]6[C@@H]([C@H]([C@H](CO6)O)O)O

1 reference

High-performance liquid chromatographic determination of saponins fromHedera helix L. using a light-scattering detector

Cauloside A (English)

5 October 2016

5 references

Saponins of the ivy plant, Hedera helix, and their leishmanicidic activity

Triterpene glycosides ofHedera canariensis. I. Structures of glycosides L-A, L-B1, L-B2, L-C, L-D, L-E1 1, L-G1, L-G2, L-G3, L-G4, L-H1, L-H2, AND L-I1 from the leaves ofHedera canariensis

Triterpene glycosides ofHedera canariensis. V. Structure of glycosides from canary ivy stems

Triterpene glycosides ofHedera helix I. The structures of glycosides L-1, L-2a, L-2b, L-3, L-4a, L-4b, L-6a, L-6b, L-6c, L-7a, and L7-b from the leaves of common ivy

Lonicera japonica

1 reference

Studies on the saponins of Lonicera japonica THUNB

Stauntonia hexaphylla

2 references

Triterpenoid glycosides from Stauntonia hexaphylla

Bioactive triterpene glycosides from the fruit of Stauntonia hexaphylla and insights into the molecular mechanism of its inflammatory effects

Anemoclema glaucifolium

1 reference

Triterpenoid glycosides from Anemoclema glaucifolium

Bongardia chrysogonum

1 reference

Triterpenoid saponins from Bongardia chrysogonum

Hedera colchica

2 references

Triterpenoid saponins from berries of Hedera colchica

Triterpenoid saponins from berries of Hedera colchica

Caulophyllum robustum

2 references

Triterpene glycosides of Caulophyllum robustum

Use of centrifugal column chromatography for the analytical separation of the caulosides from the roots ofCaulophyllum robustum

Caulophyllum thalictroides

4 references

Alkaloids and saponins from blue cohosh.

Characterization of the triterpene saponins of the roots and rhizomes of blue cohosh (Caulophyllum thalictroides).

Characterization of the triterpene saponins of the roots and rhizomes of blue cohosh (Caulophyllum thalictroides).

Triterpene glycosides from the underground parts of Caulophyllum thalictroides.

Kalopanax septemlobus

2 references

In vitro antiinflammatory activity of kalopanaxsaponin A isolated from Kalopanax pictus in murine macrophage RAW 264.7 cells

Saponins from leaves of Kalopanax septemlobus (Thunb.) Koidz.: Structures of Kalopanax-saponins La, Lb and Lc.

Polyscias fulva

1 reference

Constituents isolated from Polyscias fulva

Symphytum officinale

1 reference

A new triterpene glycoside from the roots of Symphytum officinale

Phyllanthus polyphyllus

2 references

Bioactive constituents of the leaves of Phyllanthus polyphyllus var. siamensis

Bioactive constituents of the leaves of Phyllanthus polyphyllus var. siamensis

Akebia quinata

1 reference

Triterpene glycosides from the stems of Akebia quinata

Anemone coronaria

1 reference

Triterpene glycosides from the tubers of Anemone coronaria

Cussonia paniculata

1 reference

Triterpene Glycosides from Cussonia paniculata. II. Acetylated Glycosides from Leaves

Dipsacus azureus

1 reference

Triterpene glycosides ofDipsacus azureus

Fatsia japonica

3 references

Triterpene glycosides ofFatsia japonica. I. Isolation and structure of glycosides fromFatsia japonica seeds

Triterpene glycosides of the leaves ofFatsia japonica

Triterpene saponins and other constituents from Fatsia japonica

Hedera canariensis

2 references

Triterpene glycosides ofHedera canariensis. I. Structures of glycosides L-A, L-B1, L-B2, L-C, L-D, L-E1 1, L-G1, L-G2, L-G3, L-G4, L-H1, L-H2, AND L-I1 from the leaves ofHedera canariensis

Triterpene glycosides ofHedera canariensis. V. Structure of glycosides from canary ivy stems

Hedera caucasigena

1 reference

Triterpene glycosides fromHedera caucasignena leaves

Hedera nepalensis

1 reference

Studies on nepalese crude drugs. III. On the saponins of Hedera nepalensis K. Koch.

Medicago arabica

2 references

Triterpene saponins from aerial parts of Medicago arabica L.

New triterpenic saponins from the aerial parts of Medicago arabica (L.) huds

Medicago polymorpha

1 reference

Triterpenoid glycosides from the leaves of two cultivars of Medicago polymorpha L

Pometia eximia

1 reference

Hederagenin glycosides from Pometia eximia

Pulsatilla cernua

1 reference

A new triterpenoid saponin from Pulsatilla cernua.

Sapindus mukorossi

1 reference

Molluscicidal saponins from Sapindus mukorossi, inhibitory agents of golden apple snails, Pomacea canaliculata.

Anemone taipaiensis

1 reference

Bioactive oleanane-type saponins from the rhizomes of Anemone taipaiensis

Dipsacus dipsacoides

1 reference

Triterpene glycosides ofDipsacus azureus

Allophylus cobbe

1 reference

Hederagenin glycosides from Pometia eximia

Pometia pinnata

1 reference

Hederagenin glycosides from Pometia eximia

Acer pictum

1 reference

In vitro antiinflammatory activity of kalopanaxsaponin A isolated from Kalopanax pictus in murine macrophage RAW 264.7 cells

subject has role

topoisomerase I inhibitor

1 reference

Medical Subject Headings

MeSH descriptor ID

C036411

InChI=1S/C35H56O8/c1-30(2)13-15-35(29(40)41)16-14-33(5)20(21(35)17-30)7-8-24-31(3)11-10-25(43-28-27(39)26(38)22(37)18-42-28)32(4,19-36)23(31)9-12-34(24,33)6/h7,21-28,36-39H,8-19H2,1-6H3,(H,40,41)/t21-,22-,23 ,24 ,25-,26-,27 ,28-,31-,32-,33 ,34 ,35-/m0/s1

15 March 2018

Identifiers

InChI

1 reference

Cauloside A (English)

5 October 2016

2 references

Cauloside A (English)

5 October 2016

ChEBI release 2020-09-01

2 references

hederagenin 3-O-arabinoside (English)

5 October 2016

https://commonchemistry.cas.org/detail?cas_rn=17184-21-3

9 April 2021

1 reference

(3beta)-3-(alpha-L-Arabinopyranosyloxy)-23-hydroxyolean-12-en-28-oic acid (English)

5 October 2016

2 references

Cauloside A (English)

5 October 2016

Reaxys registry number

4241078

1 reference

hederagenin 3-O-arabinoside (English)

5 October 2016

ChEBI ID

5634

mapping relation type

2 references

hederagenin 3-O-arabinoside (English)

5 October 2016

International Chemical Identifier

InChI

InChI=1S/C35H56O8/c1-30(2)13-15-35(29(40)41)16-14-33(5)20(21(35)17-30)7-8-24-31(3)11-10-25(43-28-27(39)26(38)22(37)18-42-28)32(4,19-36)23(31)9-12-34(24,33)6/h7,21-28,36-39H,8-19H2,1-6H3,(H,40,41)/t21-,22-,23 ,24 ,25-,26-,27 ,28-,31-,32-,33 ,34 ,35-/m0/s1

1 reference

CHEMBL452911 (English)

5 October 2016

1 reference

1 reference

DSSTOX compound identifier

0 references

1 reference

Medical Subject Headings

14 March 2018

1 reference

hederagenin 3-O-arabinoside (English)

5 October 2016

UNII

QW2X5B5L5W

1 reference

0 references

1 reference

hederagenin 3-O-arabinoside (English)