| Record Information |
|---|
| Version | 1.0 |
|---|
| Creation date | 2010-04-08 22:14:02 UTC |
|---|
| Update date | 2019-11-26 03:16:54 UTC |
|---|
| Primary ID | FDB018931 |
|---|
| Secondary Accession Numbers | Not Available |
|---|
| Chemical Information |
|---|
| FooDB Name | Castalagin |
|---|
| Description | Castalagin belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. Castalagin is an extremely weak basic (essentially neutral) compound (based on its pKa). Castalagin has been detected, but not quantified in, a few different foods, such as european chestnuts, nuts, and pomegranates. This could make castalagin a potential biomarker for the consumption of these foods. |
|---|
| CAS Number | 36001-47-5 |
|---|
| Structure | |
|---|
| Synonyms | | Synonym | Source |
|---|
| Vescalagin, (33beta)-isomer | MeSH | | Vescalene | MeSH | | Vescalagin | MeSH | | Vescalin | MeSH | | Castalagin | db_source |
|
|---|
| Predicted Properties | |
|---|
| Chemical Formula | C41H26O26 |
|---|
| IUPAC name | (1R,2R,20R,42S,46R)-7,8,9,12,13,14,25,26,27,30,31,32,35,36,37,46-hexadecahydroxy-3,18,21,41,43-pentaoxanonacyclo[27.13.3.1^{38,42}.0^{2,20}.0^{5,10}.0^{11,16}.0^{23,28}.0^{33,45}.0^{34,39}]hexatetraconta-5,7,9,11,13,15,23,25,27,29(45),30,32,34(39),35,37-pentadecaene-4,17,22,40,44-pentone |
|---|
| InChI Identifier | InChI=1S/C41H26O26/c42-8-1-5-12(24(48)21(8)45)13-6(2-9(43)22(46)25(13)49)39(60)65-34-11(4-63-37(5)58)64-38(59)7-3-10(44)23(47)26(50)14(7)15-18-16(28(52)32(56)27(15)51)17-19-20(30(54)33(57)29(17)53)31(55)35(66-41(19)62)36(34)67-40(18)61/h1-3,11,31,34-36,42-57H,4H2/t11-,31-,34-,35+,36+/m1/s1 |
|---|
| InChI Key | UDYKDZHZAKSYCO-JLQXGYSZSA-N |
|---|
| Isomeric SMILES | O[C@H]1[C@@H]2OC(=O)C3=C1C(O)=C(O)C(O)=C3C1=C(O)C(O)=C(O)C3=C1C(=O)O[C@H]2[C@@H]1OC(=O)C2=C(C(O)=C(O)C(O)=C2)C2=C(O)C(O)=C(O)C=C2C(=O)OC[C@H]1OC(=O)C1=C3C(O)=C(O)C(O)=C1 |
|---|
| Average Molecular Weight | 934.6295 |
|---|
| Monoisotopic Molecular Weight | 934.071231004 |
|---|
| Classification |
|---|
| Description | Belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. |
|---|
| Kingdom | Organic compounds |
|---|
| Super Class | Phenylpropanoids and polyketides |
|---|
| Class | Tannins |
|---|
| Sub Class | Hydrolyzable tannins |
|---|
| Direct Parent | Hydrolyzable tannins |
|---|
| Alternative Parents | |
|---|
| Substituents | - Hydrolyzable tannin
- Pentacarboxylic acid or derivatives
- Gallic acid or derivatives
- Benzopyran
- Isochromane
- 2-benzopyran
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Benzenoid
- Carboxylic acid ester
- Secondary alcohol
- Lactone
- Carboxylic acid derivative
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Hydrocarbon derivative
- Alcohol
- Organic oxygen compound
- Organic oxide
- Organooxygen compound
- Aromatic heteropolycyclic compound
|
|---|
| Molecular Framework | Aromatic heteropolycyclic compounds |
|---|
| External Descriptors | Not Available |
|---|
| Ontology |
|---|
| Ontology | No ontology term |
|---|
| Physico-Chemical Properties |
|---|
| Physico-Chemical Properties - Experimental | | Property | Value | Reference |
|---|
| Physical state | Not Available | |
|---|
| Physical Description | Not Available | |
|---|
| Mass Composition | C 52.69%; H 2.80%; O 44.51% | DFC |
|---|
| Melting Point | Not Available | |
|---|
| Boiling Point | Not Available | |
|---|
| Experimental Water Solubility | Not Available | |
|---|
| Experimental logP | Not Available | |
|---|
| Experimental pKa | Not Available | |
|---|
| Isoelectric point | Not Available | |
|---|
| Charge | Not Available | |
|---|
| Optical Rotation | [a]26D -99.9 (c, 0.52 in MeOH) | DFC |
|---|
| Spectroscopic UV Data | Not Available | |
|---|
| Density | Not Available | |
|---|
| Refractive Index | Not Available | |
|---|
|
|---|
| Spectra |
|---|
| Spectra | Not Available |
|---|
| External Links |
|---|
| ChemSpider ID | 147097 |
|---|
| ChEMBL ID | CHEMBL607711 |
|---|
| KEGG Compound ID | Not Available |
|---|
| Pubchem Compound ID | 168165 |
|---|
| Pubchem Substance ID | Not Available |
|---|
| ChEBI ID | Not Available |
|---|
| Phenol-Explorer ID | Not Available |
|---|
| DrugBank ID | Not Available |
|---|
| HMDB ID | HMDB30602 |
|---|
| CRC / DFC (Dictionary of Food Compounds) ID | LNJ53-M:LNH45-B |
|---|
| EAFUS ID | Not Available |
|---|
| Dr. Duke ID | CASTALAGIN |
|---|
| BIGG ID | Not Available |
|---|
| KNApSAcK ID | Not Available |
|---|
| HET ID | Not Available |
|---|
| Food Biomarker Ontology | Not Available |
|---|
| VMH ID | Not Available |
|---|
| Flavornet ID | Not Available |
|---|
| GoodScent ID | Not Available |
|---|
| SuperScent ID | Not Available |
|---|
| Wikipedia ID | Castalagin |
|---|
| Phenol-Explorer Metabolite ID | Not Available |
|---|
| Duplicate IDS | Not Available |
|---|
| Old DFC IDS | Not Available |
|---|
| Associated Foods |
|---|
| Food | Content Range | Average | Reference |
|---|
| Food | | | Reference |
|---|
|
| Biological Effects and Interactions |
|---|
| Health Effects / Bioactivities | | Descriptor | ID | Definition | Reference |
|---|
| Topoisomerase-II inhibitor | 50750 | An agent that blocks the activity of topoisomerase-II, an enzyme involved in DNA replication. It prevents cancer cell growth by disrupting DNA structure, commonly used in chemotherapy to treat various types of cancer, including leukemia and lymphoma. | DUKE |
|
|---|
| Enzymes | Not Available |
|---|
| Pathways | Not Available |
|---|
| Metabolism | Not Available |
|---|
| Biosynthesis | Not Available |
|---|
| Organoleptic Properties |
|---|
| Flavours | Not Available |
|---|
| Files |
|---|
| MSDS | Not Available |
|---|
| References |
|---|
| Synthesis Reference | Not Available |
|---|
| General Reference |
- Shuaibu MN, Pandey K, Wuyep PA, Yanagi T, Hirayama K, Ichinose A, et al. Castalagin from Anogeissus leiocarpus mediates the killing of Leishmania in vitro. Parasitol Res. 2008 Nov;103(6):1333–8. Pubmed [Structure]
|
|---|
| Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
|
|---|
