Record Information |
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Version | 1.0 |
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Created at | 2022-09-08 23:15:58 UTC |
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Updated at | 2022-09-08 23:15:58 UTC |
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NP-MRD ID | NP0275500 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | β-hederin |
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Description | Beta-Hederin, also known as β-hederin, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. β-hederin is found in Akebia quinata, Anemoclema glaucifolium, Anemone chinensis, Anemone coronaria, Clematis tangutica, Eleutherococcus senticosus, Hedera caucasigena, Hedera helix, Hedera hibernica, Hedera nepalensis, Kalopanax septemlobus and Polyscias fulva. It was first documented in 2016 (PMID: 26902407). Based on a literature review a significant number of articles have been published on beta-Hederin (PMID: 30250584) (PMID: 30061173) (PMID: 29146183) (PMID: 28273565). |
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Structure | C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@@H](O)CO[C@H]2O[C@H]2CC[C@@]3(C)[C@@H](CC[C@]4(C)[C@@H]3CC=C3[C@@H]5CC(C)(C)CC[C@@]5(CC[C@@]43C)C(O)=O)C2(C)C)[C@H](O)[C@H](O)[C@H]1O InChI=1S/C41H66O11/c1-21-28(43)30(45)31(46)33(50-21)52-32-29(44)24(42)20-49-34(32)51-27-12-13-38(6)25(37(27,4)5)11-14-40(8)26(38)10-9-22-23-19-36(2,3)15-17-41(23,35(47)48)18-16-39(22,40)7/h9,21,23-34,42-46H,10-20H2,1-8H3,(H,47,48)/t21-,23-,24-,25-,26+,27-,28-,29-,30+,31+,32+,33-,34-,38-,39+,40+,41-/m0/s1 |
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Synonyms | Value | Source |
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b-Hederin | Generator | Β-hederin | Generator | (3beta)-3-((2-O-(6-Deoxy-alpha-L-mannopyranosyl)-alpha-L-arabinopyranosyl)oxy)olean-12-en-28-Oic acid | MeSH |
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Chemical Formula | C41H66O11 |
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Average Mass | 734.9680 Da |
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Monoisotopic Mass | 734.46051 Da |
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IUPAC Name | (4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-{[(2S,3R,4S,5S)-4,5-dihydroxy-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-2,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid |
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Traditional Name | β-hederin |
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CAS Registry Number | Not Available |
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SMILES | C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@@H](O)CO[C@H]2O[C@H]2CC[C@@]3(C)[C@@H](CC[C@]4(C)[C@@H]3CC=C3[C@@H]5CC(C)(C)CC[C@@]5(CC[C@@]43C)C(O)=O)C2(C)C)[C@H](O)[C@H](O)[C@H]1O |
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InChI Identifier | InChI=1S/C41H66O11/c1-21-28(43)30(45)31(46)33(50-21)52-32-29(44)24(42)20-49-34(32)51-27-12-13-38(6)25(37(27,4)5)11-14-40(8)26(38)10-9-22-23-19-36(2,3)15-17-41(23,35(47)48)18-16-39(22,40)7/h9,21,23-34,42-46H,10-20H2,1-8H3,(H,47,48)/t21-,23-,24-,25-,26+,27-,28-,29-,30+,31+,32+,33-,34-,38-,39+,40+,41-/m0/s1 |
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InChI Key | IBAJNOZMACNWJD-HVUPOBLPSA-N |
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Experimental Spectra |
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| Not Available | Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 25 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Triterpenoids |
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Direct Parent | Triterpenoids |
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Alternative Parents | |
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Substituents | - Triterpenoid
- Disaccharide
- Glycosyl compound
- O-glycosyl compound
- Oxane
- Secondary alcohol
- Acetal
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Oxacycle
- Polyol
- Organoheterocyclic compound
- Organic oxide
- Carbonyl group
- Hydrocarbon derivative
- Organooxygen compound
- Alcohol
- Organic oxygen compound
- Aliphatic heteropolycyclic compound
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Molecular Framework | Aliphatic heteropolycyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Not Available |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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General References | - Chen WX, Cheng L, Pan M, Qian Q, Zhu YL, Xu LY, Ding Q: D Rhamnose beta-Hederin against human breast cancer by reducing tumor-derived exosomes. Oncol Lett. 2018 Oct;16(4):5172-5178. doi: 10.3892/ol.2018.9254. Epub 2018 Aug 2. [PubMed:30250584 ]
- Chen WX, Xu LY, Qian Q, He X, Peng WT, Fan WQ, Zhu YL, Tang JH, Cheng L: d Rhamnose beta-hederin reverses chemoresistance of breast cancer cells by regulating exosome-mediated resistance transmission. Biosci Rep. 2018 Sep 28;38(5):BSR20180110. doi: 10.1042/BSR20180110. Print 2018 Oct 31. [PubMed:30061173 ]
- Cheng L, Xia TS, Shi L, Xu L, Chen W, Zhu Y, Ding Q: D Rhamnose beta-hederin inhibits migration and invasion of human breast cancer cell line MDA-MB-231. Biochem Biophys Res Commun. 2018 Jan 1;495(1):775-780. doi: 10.1016/j.bbrc.2017.11.081. Epub 2017 Nov 14. [PubMed:29146183 ]
- Wang L, Wang Z, Su S, Xing Y, Li Y, Li M, Liu J, Yang S: Synthesis and cytotoxicity of oleanolic acid trisaccharide saponins. Carbohydr Res. 2017 Apr 10;442:9-16. doi: 10.1016/j.carres.2017.02.010. Epub 2017 Feb 28. [PubMed:28273565 ]
- Schulte-Michels J, Wolf A, Aatz S, Engelhard K, Sieben A, Martinez-Osuna M, Haberlein F, Haberlein H: alpha-Hederin inhibits G protein-coupled receptor kinase 2-mediated phosphorylation of beta2-adrenergic receptors. Phytomedicine. 2016 Jan 15;23(1):52-7. doi: 10.1016/j.phymed.2015.12.001. Epub 2015 Dec 18. [PubMed:26902407 ]
- LOTUS database [Link]
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