Cauloside A
PubChem CID
441928
Structure
Molecular Formula
Synonyms
- Cauloside A
- 17184-21-3
- Leontoside A
- Delta-Hederin
- Hederagenin 3-O-arabinoside
Molecular Weight
604.8 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
- Create:2005-06-24
- Modify:2024-12-28
Description
Hederagenin 3-O-arabinoside is a triterpenoid saponin that is hederagenin attached to an alpha-L-arabinopyranosyl residue at position 3 via a glycosidic linkage. It has a role as a plant metabolite. It is a triterpenoid saponin, a monosaccharide derivative, a pentacyclic triterpenoid, a hydroxy monocarboxylic acid and an alpha-L-arabinopyranoside. It is functionally related to a hederagenin. It derives from a hydride of an oleanane.
Cauloside A has been reported in Anemone taipaiensis, Caulophyllum thalictroides, and other organisms with data available.
See also: Caulophyllum robustum Root (part of).
Chemical Structure Depiction
(4aS,6aR,6aS,6bR,8aR,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
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)
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
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
QUBNLZCADIYAFW-RITZIESXSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
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
Computed by OEChem 2.3.0 (PubChem release 2021.10.14)
C35H56O8
Computed by PubChem 2.2 (PubChem release 2021.10.14)
- 3-(alpha-L-arabinopyransoyloxy)-23-hydroxy-olean-12-en-28-oic acid
- 3-O-(alpha-L-arabinopyranosyl)hederagenin
- 3-O-arabinopyranosylhederagenin
- cauloside A
- FJ-2 acid
- leontoside A
- Cauloside A
- 17184-21-3
- Leontoside A
- Delta-Hederin
- Hederagenin 3-O-arabinoside
- FJ-2 Acid
- Scabioside A
- 3-O-Arabinopyranosylhederagenin
- AKEBOSIDE STB
- TAUROSIDE B
- 3-O-(alpha-L-Arabinopyranosyl)hederagenin
- FATSIASIDE B1
- HEDEROSIDE A3
- PROSAPOGENIN CP1
- SAPONIN K3
- GLYCOSIDE L-B2
- NEPALIN 1
- KIZUTA SAPONIN K3
- QW2X5B5L5W
- CHEBI:5634
- (4aS,6aR,6aS,6bR,8aR,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
- .delta.-Hederin
- (4AS,6AR,6AS,6BR,8AR,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
- 3-(alpha-L-Arabinopyransoyloxy)-23-hydroxy-olean-12-en-28-oic acid
- CHEMBL452911
- beta2-FATSIN
- AKEBIA SAPONIN PA
- .BETA.2-FATSIN
- DTXSID80938054
- Olean-12-en-28-oic acid, 3-(alpha-L-arabinopyranosyloxy)-23-hydroxy-, (3beta,4alpha)-
- HY-N3557
- AKOS032949072
- DA-71963
- MS-30661
- 3beta-O-alpha-L-arabinopyranosyl hederagenin
- CS-0023837
- C08953
- E88796
- HEDERAGENIN 3-O-.ALPHA.-L-ARABINOPYRANOSIDE
- Q27106835
- 23-Hydroxy-3-(pentopyranosyloxy)olean-12-en-28-oic acid
- 3beta-(alpha-L-arabinopyranosyloxy)-23-hydroxyolean-12-en-28-oic acid
- 3.BETA.-(.ALPHA.-L-ARABINOPYRANOSYLOXY)-23-HYDROXYOLEAN-12-EN-28-OIC ACID
- OLEAN-12-EN-28-OIC ACID, 3-(ALPHA-L-ARABINOPYRANOSYLOXY)-23-HYDROXY-, (3.BETA.,4.ALPHA.)-
Property Name
Property Value
Reference
Property Name
Molecular Weight
Property Value
604.8 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
4.7
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
8
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
604.39751874 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
604.39751874 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
137Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
43
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
1150
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
13
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)
Follow these links to do a live 2D search or do a live 3D search for this compound, sorted by annotation score. This section is deprecated (see here for details), but these live search links provide equivalent functionality to the table that was previously shown here.
Same Connectivity Count
Same Parent, Connectivity Count
Similar Compounds (2D)
Similar Conformers (3D)
Same Count
Caulophyllum robustum Root (part of)
Topoisomerase I Inhibitors
Compounds that inhibit the activity of DNA TOPOISOMERASE I. (See all compounds classified as Topoisomerase I Inhibitors.)
The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106
- CAS Common ChemistryLICENSEThe data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.https://creativecommons.org/licenses/by-nc/4.0/
- EPA DSSTox23-Hydroxy-3-(pentopyranosyloxy)olean-12-en-28-oic acidhttps://comptox.epa.gov/dashboard/DTXSID80938054CompTox Chemicals Dashboard Chemical Listshttps://comptox.epa.gov/dashboard/chemical-lists/
- FDA Global Substance Registration System (GSRS)LICENSEUnless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.https://www.fda.gov/about-fda/about-website/website-policies#linking
- ChEBIHederagenin 3-O-arabinosidehttps://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:5634
- LOTUS - the natural products occurrence databaseLICENSEThe code for LOTUS is released under the GNU General Public License v3.0.https://lotus.nprod.net/Cauloside Ahttps://www.wikidata.org/wiki/Q27106835LOTUS Treehttps://lotus.naturalproducts.net/
- ChEMBLLICENSEAccess to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).http://www.ebi.ac.uk/Information/termsofuse.html
- Japan Chemical Substance Dictionary (Nikkaji)
- KEGGLICENSEAcademic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial licensehttps://www.kegg.jp/kegg/legal.htmlPhytochemical compoundshttp://www.genome.jp/kegg-bin/get_htext?br08003.keg
- Natural Product Activity and Species Source (NPASS)
- Metabolomics Workbench
- SpectraBase3-O-ALPHA-L-ARABINOPYRANOSYL-HEDERAGENIN;3-O-ALPHA-L-ARABINOPYRANOSYL-23-HYDROXYOLEAN-12-EN-28-OIC-ACIDhttps://spectrabase.com/spectrum/JVdOQ5pKjtBHEDERAGENIN-3-O-ALPHA-L-ARABINOPYRANOSIDEhttps://spectrabase.com/spectrum/9VNjoeOdgli
- Springer Nature
- Wikidatahederagenin 3-O-arabinosidehttps://www.wikidata.org/wiki/Q27106835
- PubChem
- Medical Subject Headings (MeSH)LICENSEWorks produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.https://www.nlm.nih.gov/copyright.htmlcauloside Ahttps://www.ncbi.nlm.nih.gov/mesh/67036411Topoisomerase I Inhibitorshttps://www.ncbi.nlm.nih.gov/mesh/68059004
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
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