| Record Information |
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| Version | 2.0 |
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| Created at | 2022-04-29 05:03:47 UTC |
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| Updated at | 2022-04-29 05:03:47 UTC |
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| NP-MRD ID | NP0084279 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Nymphayol |
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| Description | NYMPHAYOL belongs to the class of organic compounds known as 3-beta-hydroxysteroids. These are steroids carrying a beta-hydroxyl group at the 3-position of the steroid backbone. Nymphayol is found in Nymphaea stellata . Nymphayol was first documented in 2010 (PMID: 22247863). Based on a literature review a small amount of articles have been published on NYMPHAYOL (PMID: 32650545) (PMID: 25499137) (PMID: 25289771) (PMID: 24244827). |
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| Structure | [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC InChI=1S/C25H42O/c1-5-6-7-17(2)21-10-11-22-20-9-8-18-16-19(26)12-14-24(18,3)23(20)13-15-25(21,22)4/h8,17,19-23,26H,5-7,9-16H2,1-4H3/t17-,19+,20+,21-,22+,23+,24+,25-/m1/s1 |
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| Synonyms | Not Available |
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| Chemical Formula | C25H42O |
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| Average Mass | 358.6100 Da |
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| Monoisotopic Mass | 358.32357 Da |
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| IUPAC Name | (1S,2R,5S,10S,11S,14R,15R)-14-[(2R)-hexan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol |
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| Traditional Name | (1S,2R,5S,10S,11S,14R,15R)-14-[(2R)-hexan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol |
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| CAS Registry Number | Not Available |
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| SMILES | [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC |
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| InChI Identifier | InChI=1S/C25H42O/c1-5-6-7-17(2)21-10-11-22-20-9-8-18-16-19(26)12-14-24(18,3)23(20)13-15-25(21,22)4/h8,17,19-23,26H,5-7,9-16H2,1-4H3/t17-,19+,20+,21-,22+,23+,24+,25-/m1/s1 |
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| InChI Key | YDLVZJHEMPUSFL-NMQWMWRVSA-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, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, 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 | | Species Name | Source | Reference |
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| Nymphaea stellata | Plant | |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as 3-beta-hydroxysteroids. These are steroids carrying a beta-hydroxyl group at the 3-position of the steroid backbone. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Steroids and steroid derivatives |
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| Sub Class | Hydroxysteroids |
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| Direct Parent | 3-beta-hydroxysteroids |
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| Alternative Parents | |
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| Substituents | - 3-beta-hydroxysteroid
- 3-beta-hydroxy-delta-5-steroid
- 3-hydroxy-delta-5-steroid
- Delta-5-steroid
- Cyclic alcohol
- Secondary alcohol
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Alcohol
- Aliphatic homopolycyclic compound
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| Molecular Framework | Aliphatic homopolycyclic 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 | - Al-Harbi LN, Subash-Babu P, Binobead MA, Alhussain MH, AlSedairy SA, Aloud AA, Alshatwi AA: Potential Metabolite Nymphayol Isolated from Water Lily (Nymphaea stellata) Flower Inhibits MCF-7 Human Breast Cancer Cell Growth via Upregulation of Cdkn2a, pRb2, p53 and Downregulation of PCNA mRNA Expressions. Metabolites. 2020 Jul 8;10(7). pii: metabo10070280. doi: 10.3390/metabo10070280. [PubMed:32650545 ]
- Subash-Babu P, Ignacimuthu S, Alshatwi AA: Nymphayol increases glucose-stimulated insulin secretion by RIN-5F cells and GLUT4-mediated insulin sensitization in type 2 diabetic rat liver. Chem Biol Interact. 2015 Jan 25;226:72-81. doi: 10.1016/j.cbi.2014.12.011. Epub 2014 Dec 12. [PubMed:25499137 ]
- Antonisamy P, Subash-Babu P, Alshatwi AA, Aravinthan A, Ignacimuthu S, Choi KC, Kim JH: Gastroprotective effect of nymphayol isolated from Nymphaea stellata (Willd.) flowers: contribution of antioxidant, anti-inflammatory and anti-apoptotic activities. Chem Biol Interact. 2014 Dec 5;224:157-63. doi: 10.1016/j.cbi.2014.09.020. Epub 2014 Oct 5. [PubMed:25289771 ]
- Pandurangan SB, Paul AS, Savarimuthu I, Ali AA: Antinociceptive, Immunomodulatory and Antipyretic Activity of Nymphayol Isolated from Nymphaea stellata (Willd.) Flowers. Biomol Ther (Seoul). 2013 Sep 30;21(5):391-7. doi: 10.4062/biomolther.2013.022. [PubMed:24244827 ]
- Raja MK, Sethiya NK, Mishra SH: A comprehensive review on Nymphaea stellata: A traditionally used bitter. J Adv Pharm Technol Res. 2010 Jul;1(3):311-9. doi: 10.4103/0110-5558.72424. [PubMed:22247863 ]
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