Record Information |
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Version | 1.0 |
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Created at | 2022-09-03 19:39:01 UTC |
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Updated at | 2022-09-03 19:39:01 UTC |
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NP-MRD ID | NP0181177 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | β-d-gentiobiosyl crocetin |
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Description | Beta-D-gentiobiosyl crocetin belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. β-d-gentiobiosyl crocetin is found in Apis cerana, Crocus sativus and Gardenia jasminoides. It was first documented in 2014 (PMID: 25075549). Based on a literature review a significant number of articles have been published on beta-D-gentiobiosyl crocetin (PMID: 35669709) (PMID: 29502833) (PMID: 34215950) (PMID: 26340688). |
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Structure | C\C(\C=C\C=C(/C)C(O)=O)=C/C=C/C=C(\C)/C=C/C=C(\C)C(=O)O[C@@H]1O[C@H](CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O InChI=1S/C32H44O14/c1-17(11-7-13-19(3)29(40)41)9-5-6-10-18(2)12-8-14-20(4)30(42)46-32-28(39)26(37)24(35)22(45-32)16-43-31-27(38)25(36)23(34)21(15-33)44-31/h5-14,21-28,31-39H,15-16H2,1-4H3,(H,40,41)/b6-5+,11-7+,12-8+,17-9+,18-10+,19-13+,20-14+/t21-,22-,23-,24-,25+,26+,27-,28-,31-,32+/m1/s1 |
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Synonyms | Value | Source |
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all-trans-Crocetin mono(beta-D-gentiobiosyl) ester | ChEBI | Crocetin mono(beta-gentiobiosyl) ester | ChEBI | trans-Crocetin beta-D-gentiobiosyl ester | ChEBI | all-trans-Crocetin mono(b-D-gentiobiosyl) ester | Generator | all-trans-Crocetin mono(β-D-gentiobiosyl) ester | Generator | Crocetin mono(b-gentiobiosyl) ester | Generator | Crocetin mono(β-gentiobiosyl) ester | Generator | trans-Crocetin b-D-gentiobiosyl ester | Generator | trans-Crocetin β-D-gentiobiosyl ester | Generator | b-D-Gentiobiosyl crocetin | Generator | Β-D-gentiobiosyl crocetin | Generator |
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Chemical Formula | C32H44O14 |
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Average Mass | 652.6900 Da |
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Monoisotopic Mass | 652.27311 Da |
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IUPAC Name | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | Not Available |
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SMILES | C\C(\C=C\C=C(/C)C(O)=O)=C/C=C/C=C(\C)/C=C/C=C(\C)C(=O)O[C@@H]1O[C@H](CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O |
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InChI Identifier | InChI=1S/C32H44O14/c1-17(11-7-13-19(3)29(40)41)9-5-6-10-18(2)12-8-14-20(4)30(42)46-32-28(39)26(37)24(35)22(45-32)16-43-31-27(38)25(36)23(34)21(15-33)44-31/h5-14,21-28,31-39H,15-16H2,1-4H3,(H,40,41)/b6-5+,11-7+,12-8+,17-9+,18-10+,19-13+,20-14+/t21-,22-,23-,24-,25+,26+,27-,28-,31-,32+/m1/s1 |
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InChI Key | VULLCGFNYWDRHL-YJOFKXFJSA-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 diterpenoids. These are terpene compounds formed by four 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 | Diterpenoids |
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Direct Parent | Diterpenoids |
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Alternative Parents | |
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Substituents | - Diterpenoid
- Saccharolipid
- Long-chain fatty acid
- Disaccharide
- Glycosyl compound
- O-glycosyl compound
- Branched fatty acid
- Fatty acid ester
- Heterocyclic fatty acid
- Hydroxy fatty acid
- Methyl-branched fatty acid
- Dicarboxylic acid or derivatives
- Fatty acyl
- Unsaturated fatty acid
- Oxane
- Enoate ester
- Alpha,beta-unsaturated carboxylic ester
- Secondary alcohol
- Carboxylic acid ester
- Polyol
- Organoheterocyclic compound
- Carboxylic acid derivative
- Oxacycle
- Carboxylic acid
- Acetal
- Organooxygen compound
- Organic oxide
- Hydrocarbon derivative
- Alcohol
- Carbonyl group
- Organic oxygen compound
- Primary alcohol
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic 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 | - Ahrazem O, Diretto G, Rambla JL, Rubio-Moraga A, Lobato-Gomez M, Frusciante S, Argandona J, Presa S, Granell A, Gomez-Gomez L: Engineering high levels of saffron apocarotenoids in tomato. Hortic Res. 2022 Mar 23;9:uhac074. doi: 10.1093/hr/uhac074. eCollection 2022. [PubMed:35669709 ]
- Liu J, Chen N, Yang J, Yang B, Ouyang Z, Wu C, Yuan Y, Wang W, Chen M: An integrated approach combining HPLC, GC/MS, NIRS, and chemometrics for the geographical discrimination and commercial categorization of saffron. Food Chem. 2018 Jul 1;253:284-292. doi: 10.1016/j.foodchem.2018.01.140. Epub 2018 Feb 2. [PubMed:29502833 ]
- Valle Garcia-Rodriguez M, Serrano-Diaz J, Tarantilis PA, Lopez-Corcoles H, Carmona M, Alonso GL: Determination of saffron quality by high-performance liquid chromatography. J Agric Food Chem. 2014 Aug 13;62(32):8068-74. doi: 10.1021/jf5019356. Epub 2014 Aug 5. [PubMed:25075549 ]
- Mykhailenko O, Bezruk I, Ivanauskas L, Georgiyants V: Comparative Analysis of the Major Metabolites of Ukrainian Saffron Samples by HPLC. Plant Foods Hum Nutr. 2021 Sep;76(3):394-396. doi: 10.1007/s11130-020-00873-5. Epub 2021 Jul 3. [PubMed:34215950 ]
- Kyriakoudi A, O'Callaghan YC, Galvin K, Tsimidou MZ, O'Brien NM: Cellular Transport and Bioactivity of a Major Saffron Apocarotenoid, Picrocrocin (4-(beta-D-Glucopyranosyloxy)-2,6,6-trimethyl-1-cyclohexene-1-carboxaldehyde). J Agric Food Chem. 2015 Oct 7;63(39):8662-8. doi: 10.1021/acs.jafc.5b03363. Epub 2015 Sep 23. [PubMed:26340688 ]
- LOTUS database [Link]
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