Record Information |
---|
Version | 2.0 |
---|
Created at | 2022-09-12 08:16:33 UTC |
---|
Updated at | 2022-09-12 08:16:34 UTC |
---|
NP-MRD ID | NP0326585 |
---|
Secondary Accession Numbers | None |
---|
Natural Product Identification |
---|
Common Name | (2r,3r)-2-(2,4-dihydroxyphenyl)-3,5,7-trihydroxy-6,8-bis(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzopyran-4-one |
---|
Description | Kushenol L belongs to the class of organic compounds known as 8-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 8-position. (2r,3r)-2-(2,4-dihydroxyphenyl)-3,5,7-trihydroxy-6,8-bis(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzopyran-4-one is found in Sophora flavescens. It was first documented in 2009 (PMID: 19350824). Based on a literature review a significant number of articles have been published on Kushenol L (PMID: 36130844) (PMID: 36130843) (PMID: 36130842) (PMID: 36130841) (PMID: 36130840) (PMID: 36130836). |
---|
Structure | CC(C)=CCC1=C(O)C(CC=C(C)C)=C2O[C@@H]([C@@H](O)C(=O)C2=C1O)C1=CC=C(O)C=C1O InChI=1S/C25H28O7/c1-12(2)5-8-16-20(28)17(9-6-13(3)4)24-19(21(16)29)22(30)23(31)25(32-24)15-10-7-14(26)11-18(15)27/h5-7,10-11,23,25-29,31H,8-9H2,1-4H3/t23-,25+/m0/s1 |
---|
Synonyms | Not Available |
---|
Chemical Formula | C25H28O7 |
---|
Average Mass | 440.4920 Da |
---|
Monoisotopic Mass | 440.18350 Da |
---|
IUPAC Name | (2R,3R)-2-(2,4-dihydroxyphenyl)-3,5,7-trihydroxy-6,8-bis(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-4-one |
---|
Traditional Name | (2R,3R)-2-(2,4-dihydroxyphenyl)-3,5,7-trihydroxy-6,8-bis(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzopyran-4-one |
---|
CAS Registry Number | Not Available |
---|
SMILES | CC(C)=CCC1=C(O)C(CC=C(C)C)=C2O[C@@H]([C@@H](O)C(=O)C2=C1O)C1=CC=C(O)C=C1O |
---|
InChI Identifier | InChI=1S/C25H28O7/c1-12(2)5-8-16-20(28)17(9-6-13(3)4)24-19(21(16)29)22(30)23(31)25(32-24)15-10-7-14(26)11-18(15)27/h5-7,10-11,23,25-29,31H,8-9H2,1-4H3/t23-,25+/m0/s1 |
---|
InChI Key | GKENRJIRKFSNED-UKILVPOCSA-N |
---|
Experimental Spectra |
---|
|
| Not Available | Predicted Spectra |
---|
|
| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
---|
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 |
---|
|
| Not Available | Species |
---|
Species of Origin | |
---|
Chemical Taxonomy |
---|
Description | Belongs to the class of organic compounds known as 8-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 8-position. |
---|
Kingdom | Organic compounds |
---|
Super Class | Phenylpropanoids and polyketides |
---|
Class | Flavonoids |
---|
Sub Class | Flavans |
---|
Direct Parent | 8-prenylated flavanones |
---|
Alternative Parents | |
---|
Substituents | - 8-prenylated flavanone
- 6-prenylated flavanone
- 6-prenylated flavan
- 3-hydroxyflavonoid
- 4'-hydroxyflavonoid
- 5-hydroxyflavonoid
- 7-hydroxyflavonoid
- Flavanone
- Flavanonol
- Hydroxyflavonoid
- Chromone
- Chromane
- Benzopyran
- 1-benzopyran
- Aryl alkyl ketone
- Aryl ketone
- Resorcinol
- Phenol
- 1-hydroxy-2-unsubstituted benzenoid
- 1-hydroxy-4-unsubstituted benzenoid
- Alkyl aryl ether
- Benzenoid
- Monocyclic benzene moiety
- Vinylogous acid
- Secondary alcohol
- Ketone
- Polyol
- Ether
- Organoheterocyclic compound
- Oxacycle
- Organooxygen compound
- Alcohol
- Organic oxygen compound
- Hydrocarbon derivative
- Organic oxide
- Aromatic heteropolycyclic compound
|
---|
Molecular Framework | Aromatic heteropolycyclic compounds |
---|
External Descriptors | Not Available |
---|
Physical Properties |
---|
State | Not Available |
---|
Experimental Properties | Property | Value | Reference |
---|
Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
|
---|
Predicted Properties | |
---|
General References | - Cani I, Righini M, Cenni P, Foschi M: Teaching NeuroImage: Partially Reversible Widespread Leukoencephalopathy Associated With Atypical Hemolytic Uremic Syndrome. Neurology. 2022 Sep 21. pii: WNL.0000000000201378. doi: 10.1212/WNL.0000000000201378. [PubMed:36130844 ]
- Sasaki R, Morimoto S, Ozawa F, Okano H, Yoshida M, Ishiura H, Tsuji S, Kuzuhara S, Kokubo Y: APOE Alleles With Tau and Abeta Pathology In Patients With Amyotrophic Lateral Sclerosis and Parkinsonism-Dementia Complex in the Kii Peninsula. Neurology. 2022 Sep 21. pii: WNL.0000000000201156. doi: 10.1212/WNL.0000000000201156. [PubMed:36130843 ]
- Zhang Z, Wang M, Gill D, Liu X: Genetically Predicted Smoking and Alcohol Consumption and Functional Outcome After Ischemic Stroke. Neurology. 2022 Sep 21. pii: WNL.0000000000201291. doi: 10.1212/WNL.0000000000201291. [PubMed:36130842 ]
- Khamis S, Mitakidou MR, Champion M, Goyal S, Jones RL, Siddiqui A, Sabanathan S, Hedderly T, Lin JP, Jungbluth H, Papandreou A: Clinical Reasoning: A Teenage Girl With Progressive Hyperkinetic Movements, Seizures, and Encephalopathy. Neurology. 2022 Sep 21. pii: WNL.0000000000201385. doi: 10.1212/WNL.0000000000201385. [PubMed:36130841 ]
- Rosenberg A, Ohlund-Wistbacka U, Hall A, Bonnard A, Hagman G, Ryden M, Thunborg C, Wiggenraad F, Sandebring-Matton A, Solomon A, Kivipelto M: beta-Amyloid, Tau, Neurodegeneration Classification and Eligibility for Anti-amyloid Treatment in a Memory Clinic Population. Neurology. 2022 Sep 21. pii: WNL.0000000000201043. doi: 10.1212/WNL.0000000000201043. [PubMed:36130840 ]
- Yu H, Cai G, Wu J, Li Q: Clinical Phenotypic Variability and Significance of Pneumolabyrinth After Tympanum-Penetrating Injury. Ear Nose Throat J. 2022 Sep 21:1455613221128132. doi: 10.1177/01455613221128132. [PubMed:36130836 ]
- Bedford J, Martin P, Crowe S, Wagstaff D, Santos C, Singleton G, Baumber R, Vindrola-Padros C, Vohra R, Swart M, Oliver CM, Dorey J, Leeman I, Moonesinghe SR: Development and internal validation of a model for postoperative morbidity in adults undergoing major elective colorectal surgery: the peri-operative quality improvement programme (PQIP) colorectal risk model. Anaesthesia. 2022 Sep 21. doi: 10.1111/anae.15858. [PubMed:36130834 ]
- Kim JH, Cho IS, So YK, Kim HH, Kim YH: Kushenol A and 8-prenylkaempferol, tyrosinase inhibitors, derived from Sophora flavescens. J Enzyme Inhib Med Chem. 2018 Dec;33(1):1048-1054. doi: 10.1080/14756366.2018.1477776. [PubMed:29873272 ]
- Silverman A, Beres S: Child Neurology: Horner Syndrome in an Otherwise Well-Appearing Infant. Neurology. 2022 Sep 21. pii: WNL.0000000000201377. doi: 10.1212/WNL.0000000000201377. [PubMed:36130839 ]
- Harada Y, Wang SH, Juel VC: Clinical Reasoning: A 36-Year-Old Man With Asymmetric Muscle Weakness. Neurology. 2022 Sep 21. pii: WNL.0000000000201379. doi: 10.1212/WNL.0000000000201379. [PubMed:36130838 ]
- Guest O, Memon AA, Chukweubuka A, Zaheer M, Siddiqi N: Robotic low anterior resection for locally advanced rectal cancer - A video vignette. Colorectal Dis. 2022 Sep 21. doi: 10.1111/codi.16345. [PubMed:36130837 ]
- Pellicori P, Kalra PR, Clark AL, Friday JM, Cleland JGF: Chronic kidney disease (CKD) and CKD-ism in heart failure - what a mess! Eur J Heart Fail. 2022 Sep 21. doi: 10.1002/ejhf.2696. [PubMed:36130835 ]
- Yuan X, Su Q, Wang H, Shi S, Liu L, Lv J, Wang S, Zhu L, Zhang H: Genetic Variants of the COL4A3 , COL4A4 , and COL4A5 Genes Contribute to Thinned Glomerular Basement Membrane Lesions in Sporadic IgA Nephropathy Patients. J Am Soc Nephrol. 2023 Jan 1;34(1):132-144. doi: 10.1681/ASN.2021111447. Epub 2022 Oct 5. [PubMed:36130833 ]
- Wu C, O'Keeffe C, Sanford J, Hagel J, Childs S, Evers G, Melbourne J, West C, Koch M, Cornia PB: Simple signature/countersignature shared-accountability quality improvement initiative to improve reliability of blood sample collection: an essential clinical task. BMJ Open Qual. 2022 Sep;11(3):e001765. doi: 10.1136/bmjoq-2021-001765. [PubMed:36130832 ]
- Li X, Li JF, Wang D, Wang WN, Cui Z: [Isoflavone glycosides from the bark of Maackia amurensis]. Yao Xue Xue Bao. 2009 Jan;44(1):63-8. [PubMed:19350824 ]
- LOTUS database [Link]
|
---|