| Record Information |
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| Version | 2.0 |
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| Created at | 2022-04-28 17:09:51 UTC |
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| Updated at | 2022-04-28 17:09:51 UTC |
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| NP-MRD ID | NP0071815 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Scillascillin |
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| Description | Scillascillin belongs to the class of organic compounds known as isoflavanones. These are polycyclic compounds containing an isoflavan skeleton which bears a ketone at position C4. Scillascillin is found in Merwilla plumbea, Muscari neglectum and Scilla scilloides DRUCE. Scillascillin was first documented in 2004 (PMID: 15165167). Based on a literature review a small amount of articles have been published on Scillascillin (PMID: 25612441) (PMID: 25632469) (PMID: 25276067) (PMID: 25153098). |
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| Structure | OC1=CC(O)=C2C(=O)[C@@]3(CC4=C3C=C3OCOC3=C4)COC2=C1 InChI=1S/C17H12O6/c18-9-2-11(19)15-14(3-9)21-6-17(16(15)20)5-8-1-12-13(4-10(8)17)23-7-22-12/h1-4,18-19H,5-7H2/t17-/m0/s1 |
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| Synonyms | Not Available |
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| Chemical Formula | C17H12O6 |
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| Average Mass | 312.2770 Da |
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| Monoisotopic Mass | 312.06339 Da |
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| IUPAC Name | (3R)-5,7-dihydroxy-2,4-dihydro-9',11'-dioxaspiro[1-benzopyran-3,4'-tricyclo[6.3.0.0^{3,6}]undecane]-1',3'(6'),7'-trien-4-one |
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| Traditional Name | (3R)-5,7-dihydroxy-2H-9',11'-dioxaspiro[1-benzopyran-3,4'-tricyclo[6.3.0.0^{3,6}]undecane]-1',3'(6'),7'-trien-4-one |
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| CAS Registry Number | Not Available |
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| SMILES | OC1=CC(O)=C2C(=O)[C@@]3(CC4=C3C=C3OCOC3=C4)COC2=C1 |
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| InChI Identifier | InChI=1S/C17H12O6/c18-9-2-11(19)15-14(3-9)21-6-17(16(15)20)5-8-1-12-13(4-10(8)17)23-7-22-12/h1-4,18-19H,5-7H2/t17-/m0/s1 |
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| InChI Key | SAXOGBBWXWKZKR-KRWDZBQOSA-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 | |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as isoflavanones. These are polycyclic compounds containing an isoflavan skeleton which bears a ketone at position C4. |
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| Kingdom | Organic compounds |
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| Super Class | Phenylpropanoids and polyketides |
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| Class | Isoflavonoids |
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| Sub Class | Isoflavans |
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| Direct Parent | Isoflavanones |
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| Alternative Parents | |
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| Substituents | - Isoflavanol
- Isoflavanone
- Chromone
- Chromane
- Benzopyran
- 1-benzopyran
- Benzodioxole
- Aryl alkyl ketone
- Aryl ketone
- Alkyl aryl ether
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Benzenoid
- Vinylogous acid
- Ketone
- Oxacycle
- Organoheterocyclic compound
- Acetal
- Ether
- Organic oxide
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxygen compound
- 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 | - Wang YM, Fan MY, Li J, Wang ZM, Gao HM: [Homoisoflavanones and stilbenes from fresh bulb of Scilla scilloides]. Zhongguo Zhong Yao Za Zhi. 2014 Oct;39(19):3788-93. [PubMed:25612441 ]
- Moodley N, Mulholland DA, Crouch NR: Eucosterol-type nortriterpenoids from Merwilla natalensis. J Nat Prod. 2004 May;67(5):918-20. doi: 10.1021/np0204803. [PubMed:15165167 ]
- Matsuo Y, Kurihara R, Akagi N, Mimaki Y: Two new homoisoflavonoids from the bulbs of Bessera elegans. Nat Prod Commun. 2014 Dec;9(12):1725-7. [PubMed:25632469 ]
- Chinthala Y, Chinde S, Kumar AN, Srinivas KV, Kumar JK, Sastry KP, Grover P, Ramana MV: Anticancer Active Homoisoflavone from the Underground Bulbs of Ledebouria hyderabadensis. Pharmacognosy Res. 2014 Oct;6(4):303-5. doi: 10.4103/0974-8490.138272. [PubMed:25276067 ]
- Lin LG, Liu QY, Ye Y: Naturally occurring homoisoflavonoids and their pharmacological activities. Planta Med. 2014 Aug;80(13):1053-66. doi: 10.1055/s-0034-1383026. Epub 2014 Aug 25. [PubMed:25153098 ]
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