Record Information |
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Version | 2.0 |
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Created at | 2022-03-17 20:40:06 UTC |
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Updated at | 2022-03-17 20:40:06 UTC |
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NP-MRD ID | NP0047432 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Soyacerebroside I |
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Description | Soyacerebroside I, also known as AS 1-4, belongs to the class of organic compounds known as glycosyl-n-acylsphingosines. Glycosyl-N-acylsphingosines are compounds containing a sphingosine linked to a simple glucosyl moiety. Soyacerebroside I is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Soyacerebroside I has been detected, but not quantified in, several different foods, such as garlics, green vegetables, herbs and spices, onion-family vegetables, and pulses. Soyacerebroside I is found in Albizia julibrissin, Allium sativum var. sativum , Allium sativum var.sativum , Allium tuberosum, Cinnamomum zaylanicum, Dimocarpus fumatus, Dimocarpus longan, Dioscorea opposita , Dioscorea oppositifolia, Glycine max and Tetragonia tetragonoides . Soyacerebroside I was first documented in 1999 (PMID: 9891934). This could make soyacerebroside I a potential biomarker for the consumption of these foods (PMID: 18203056) (PMID: 15467243). |
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Structure | CCCCCCCCCCCCCCC(O)C(=O)NC(COC1OC(CO)C(O)C(O)C1O)C(O)\C=C/CC\C=C/CCCCCCCCC InChI=1S/C40H75NO9/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-33(43)32(31-49-40-38(47)37(46)36(45)35(30-42)50-40)41-39(48)34(44)29-27-25-23-21-18-16-14-12-10-8-6-4-2/h19-20,26,28,32-38,40,42-47H,3-18,21-25,27,29-31H2,1-2H3,(H,41,48)/b20-19-,28-26- |
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Synonyms | Value | Source |
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(+)-Soyacerebroside I | HMDB | AS 1-4 | HMDB | Soya-cerebroside I | HMDB | 2-Hydroxy-N-[(4Z,8Z)-3-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadeca-4,8-dien-2-yl]hexadecanimidate | Generator | 1-O-Glucopyranosyl-2-N-(2'-hydroxypalmitoyl)octadecasphinga-4,8-dienine | MeSH |
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Chemical Formula | C40H75NO9 |
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Average Mass | 714.0248 Da |
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Monoisotopic Mass | 713.54418 Da |
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IUPAC Name | 2-hydroxy-N-[(4Z,8Z)-3-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadeca-4,8-dien-2-yl]hexadecanamide |
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Traditional Name | 2-hydroxy-N-[(4Z,8Z)-3-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadeca-4,8-dien-2-yl]hexadecanamide |
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CAS Registry Number | 114297-20-0 |
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SMILES | CCCCCCCCCCCCCCC(O)C(=O)NC(COC1OC(CO)C(O)C(O)C1O)C(O)\C=C/CC\C=C/CCCCCCCCC |
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InChI Identifier | InChI=1S/C40H75NO9/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-33(43)32(31-49-40-38(47)37(46)36(45)35(30-42)50-40)41-39(48)34(44)29-27-25-23-21-18-16-14-12-10-8-6-4-2/h19-20,26,28,32-38,40,42-47H,3-18,21-25,27,29-31H2,1-2H3,(H,41,48)/b20-19-,28-26- |
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InChI Key | HOMYIYLRRDTKAA-UYIJODJPSA-N |
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Experimental Spectra |
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| Not Available | Predicted Spectra |
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| Not Available | 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 glycosyl-n-acylsphingosines. Glycosyl-N-acylsphingosines are compounds containing a sphingosine linked to a simple glucosyl moiety. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Sphingolipids |
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Sub Class | Glycosphingolipids |
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Direct Parent | Glycosyl-N-acylsphingosines |
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Alternative Parents | |
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Substituents | - Glycosyl-n-acylsphingosine
- Fatty acyl glycoside
- Fatty acyl glycoside of mono- or disaccharide
- Alkyl glycoside
- Hexose monosaccharide
- Glycosyl compound
- O-glycosyl compound
- Fatty amide
- Fatty acyl
- Monosaccharide
- N-acyl-amine
- Oxane
- Carboxamide group
- Secondary carboxylic acid amide
- Secondary alcohol
- Acetal
- Carboxylic acid derivative
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Alcohol
- Organic oxygen compound
- Organic nitrogen compound
- Primary alcohol
- Carbonyl group
- Organooxygen compound
- Organonitrogen compound
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | Not Available |
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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 | - Magid AA, Voutquenne-Nazabadioko L, Bontemps G, Litaudon M, Lavaud C: Tyrosinase inhibitors and sesquiterpene diglycosides from Guioa villosa. Planta Med. 2008 Jan;74(1):55-60. doi: 10.1055/s-2007-993780. Epub 2008 Jan 17. [PubMed:18203056 ]
- Voutquenne L, Lavaud C, Massiot G, Sevenet T, Hadi HA: Cytotoxic polyisoprenes and glycosides of long-chain fatty alcohols from Dimocarpus fumatus. Phytochemistry. 1999 Jan;50(1):63-9. doi: 10.1016/s0031-9422(98)00483-x. [PubMed:9891934 ]
- Sautour M, Mitaine-Offer AC, Miyamoto T, Wagner H, Lacaille-Dubois MA: A new phenanthrene glycoside and other constituents from Dioscorea opposita. Chem Pharm Bull (Tokyo). 2004 Oct;52(10):1235-7. doi: 10.1248/cpb.52.1235. [PubMed:15467243 ]
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