Record Information |
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Version | 2.0 |
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Created at | 2022-09-08 00:24:44 UTC |
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Updated at | 2022-09-08 00:24:44 UTC |
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NP-MRD ID | NP0258786 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | [(2r,3s,4s,5r,6r)-6-{[(3ar,4s,9ar,9br)-6-methyl-3-methylidene-2-oxo-4-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3ah,4h,5h,7h,9ah,9bh-azuleno[4,5-b]furan-9-yl]methoxy}-3,4,5-trihydroxyoxan-2-yl]methyl 2-(4-hydroxyphenyl)acetate |
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Description | Lanceocrepidiaside C belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. [(2r,3s,4s,5r,6r)-6-{[(3ar,4s,9ar,9br)-6-methyl-3-methylidene-2-oxo-4-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3ah,4h,5h,7h,9ah,9bh-azuleno[4,5-b]furan-9-yl]methoxy}-3,4,5-trihydroxyoxan-2-yl]methyl 2-(4-hydroxyphenyl)acetate is found in Crepidiastrum lanceolatum. It was first documented in 2022 (PMID: 36100330). Based on a literature review a significant number of articles have been published on Lanceocrepidiaside C (PMID: 36100310) (PMID: 36100292) (PMID: 36100266) (PMID: 36100248). |
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Structure | CC1=C2CC=C(CO[C@@H]3O[C@H](COC(=O)CC4=CC=C(O)C=C4)[C@@H](O)[C@H](O)[C@H]3O)[C@@H]2[C@H]2OC(=O)C(=C)[C@@H]2[C@H](C1)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O InChI=1S/C35H44O16/c1-14-9-20(48-35-31(44)28(41)26(39)21(11-36)49-35)24-15(2)33(45)51-32(24)25-17(5-8-19(14)25)12-47-34-30(43)29(42)27(40)22(50-34)13-46-23(38)10-16-3-6-18(37)7-4-16/h3-7,20-22,24-32,34-37,39-44H,2,8-13H2,1H3/t20-,21+,22+,24+,25-,26+,27+,28-,29-,30+,31+,32-,34+,35+/m0/s1 |
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Synonyms | Not Available |
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Chemical Formula | C35H44O16 |
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Average Mass | 720.7210 Da |
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Monoisotopic Mass | 720.26294 Da |
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IUPAC Name | [(2R,3S,4S,5R,6R)-6-{[(3aR,4S,9aR,9bR)-6-methyl-3-methylidene-2-oxo-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-9-yl]methoxy}-3,4,5-trihydroxyoxan-2-yl]methyl 2-(4-hydroxyphenyl)acetate |
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Traditional Name | [(2R,3S,4S,5R,6R)-6-{[(3aR,4S,9aR,9bR)-6-methyl-3-methylidene-2-oxo-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-9-yl]methoxy}-3,4,5-trihydroxyoxan-2-yl]methyl (4-hydroxyphenyl)acetate |
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CAS Registry Number | Not Available |
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SMILES | CC1=C2CC=C(CO[C@@H]3O[C@H](COC(=O)CC4=CC=C(O)C=C4)[C@@H](O)[C@H](O)[C@H]3O)[C@@H]2[C@H]2OC(=O)C(=C)[C@@H]2[C@H](C1)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O |
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InChI Identifier | InChI=1S/C35H44O16/c1-14-9-20(48-35-31(44)28(41)26(39)21(11-36)49-35)24-15(2)33(45)51-32(24)25-17(5-8-19(14)25)12-47-34-30(43)29(42)27(40)22(50-34)13-46-23(38)10-16-3-6-18(37)7-4-16/h3-7,20-22,24-32,34-37,39-44H,2,8-13H2,1H3/t20-,21+,22+,24+,25-,26+,27+,28-,29-,30+,31+,32-,34+,35+/m0/s1 |
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InChI Key | NWAICQLPBNMFRL-CFLGGORVSA-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 o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbohydrates and carbohydrate conjugates |
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Direct Parent | O-glycosyl compounds |
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Alternative Parents | |
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Substituents | - O-glycosyl compound
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Benzenoid
- Oxane
- Monosaccharide
- Gamma butyrolactone
- Dicarboxylic acid or derivatives
- Monocyclic benzene moiety
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Tetrahydrofuran
- Secondary alcohol
- Lactone
- Carboxylic acid ester
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Carboxylic acid derivative
- Acetal
- Organic oxide
- Hydrocarbon derivative
- Primary alcohol
- Carbonyl group
- Alcohol
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic 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 | - Qu X, An G, Sui W, Wang T, Zhang X, Yang J, Zhang Y, Zhang L, Zhu D, Huang J, Zhu S, Yao X, Li J, Zheng C, Zhu K, Wei Y, Lv X, Lan L, Yao Y, Zhou D, Lu P, Qiu L, Li J: Phase 1 study of C-CAR088, a novel humanized anti-BCMA CAR T-cell therapy in relapsed/refractory multiple myeloma. J Immunother Cancer. 2022 Sep;10(9). pii: jitc-2022-005145. doi: 10.1136/jitc-2022-005145. [PubMed:36100310 ]
- Liang Z, Chen Y, Wang Z, Wu X, Deng C, Wang C, Yang W, Tian Y, Zhang S, Lu C, Yang Y: Protective effects and mechanisms of psoralidin against adriamycin-induced cardiotoxicity. J Adv Res. 2022 Sep;40:249-261. doi: 10.1016/j.jare.2021.12.007. Epub 2021 Dec 28. [PubMed:36100330 ]
- Prystupa K, Renklint R, Chninou Y, Otten J, Fritsche L, Hoerber S, Peter A, Birkenfeld AL, Fritsche A, Heni M, Wagner R: Comprehensive validation of fasting-based and oral glucose tolerance test-based indices of insulin secretion against gold standard measures. BMJ Open Diabetes Res Care. 2022 Sep;10(5). pii: 10/5/e002909. doi: 10.1136/bmjdrc-2022-002909. [PubMed:36100292 ]
- Rodrigues Wilde MO, Mezadri T, Gouveia PB, Grillo LP, Valete C: Prediction of early-onset neonatal sepsis in umbilical cord blood analysis: an integrative review. J Matern Fetal Neonatal Med. 2022 Sep 13:1-12. doi: 10.1080/14767058.2022.2122798. [PubMed:36100266 ]
- Lu JG, Benet-Martinez V, Wang LC: A Socioecological-Genetic Framework of Culture and Personality: Their Roots, Trends, and Interplay. Annu Rev Psychol. 2022 Sep 13. doi: 10.1146/annurev-psych-032420-032631. [PubMed:36100248 ]
- LOTUS database [Link]
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