| Record Information |
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| Version | 2.0 |
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| Created at | 2023-12-21 12:02:25 UTC |
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| Updated at | 2024-09-03 04:18:40 UTC |
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| NP-MRD ID | NP0332273 |
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| Natural Product DOI | https://doi.org/10.57994/1468 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Compound 11 |
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| Description | Compound 11 belongs to the class of organic compounds known as 7,9'-epoxylignans. These are lignans that contain the 7,9'-epoxylignan skeleton, which consists of a tetrahydrofuran that carries a phenyl group, a methyl group, and a benzyl group at the 2-, 3-, 4-position, respectively. Compound 11 was first documented in 2024 (PMID: 39273546). Based on a literature review a significant number of articles have been published on Compound 11 (PMID: 39307807) (PMID: 39041085) (PMID: 39298888) (PMID: 39270454) (PMID: 39223706) (PMID: 39208150). |
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| Structure | [H][C@]1(CC#N)[C@@H](OC[C@]1([H])[C@H](OCOC)C1=CC=C(OC)C(OC)=C1)C1=CC(OC)=C(OC)C=C1 InChI=1S/C25H31NO7/c1-27-15-33-25(17-7-9-21(29-3)23(13-17)31-5)19-14-32-24(18(19)10-11-26)16-6-8-20(28-2)22(12-16)30-4/h6-9,12-13,18-19,24-25H,10,14-15H2,1-5H3/t18-,19+,24+,25-/m1/s1 |
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| Synonyms | Not Available |
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| Chemical Formula | C25H31NO7 |
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| Average Mass | 457.5230 Da |
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| Monoisotopic Mass | 457.21005 Da |
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| IUPAC Name | 2-[(2R,3R,4R)-2-(3,4-dimethoxyphenyl)-4-[(S)-(3,4-dimethoxyphenyl)(methoxymethoxy)methyl]oxolan-3-yl]acetonitrile |
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| Traditional Name | 2-[(2R,3R,4R)-2-(3,4-dimethoxyphenyl)-4-[(S)-(3,4-dimethoxyphenyl)(methoxymethoxy)methyl]oxolan-3-yl]acetonitrile |
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| CAS Registry Number | Not Available |
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| SMILES | [H][C@]1(CC#N)[C@@H](OC[C@]1([H])[C@H](OCOC)C1=CC=C(OC)C(OC)=C1)C1=CC(OC)=C(OC)C=C1 |
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| InChI Identifier | InChI=1S/C25H31NO7/c1-27-15-33-25(17-7-9-21(29-3)23(13-17)31-5)19-14-32-24(18(19)10-11-26)16-6-8-20(28-2)22(12-16)30-4/h6-9,12-13,18-19,24-25H,10,14-15H2,1-5H3/t18-,19+,24+,25-/m1/s1 |
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| InChI Key | NFOMCEBQACFSCE-QIMADWELSA-N |
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| Experimental Spectra |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| NOESY NMR | [Proton, Proton] NMR Spectrum (2D, 600 MHz, CDCL3, experimental) | Not Available | Keio University | Haruhisa Kikuchi | 2024-03-06 | View Spectrum | | COSY NMR | [Proton, Proton] NMR Spectrum (2D, 600 MHz, CDCL3, experimental) | Not Available | Keio University | Haruhisa Kikuchi | 2024-03-06 | View Spectrum | | 1D NMR | Proton NMR Spectrum (1D, 600 MHz, CDCL3, experimental) | Not Available | Keio University | Haruhisa Kikuchi | 2024-03-06 | View Spectrum | | 1D NMR | Carbon13 NMR Spectrum (1D, 151 MHz, CDCL3, experimental) | Not Available | Keio University | Haruhisa Kikuchi | 2024-03-06 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CDCL3, experimental) | halkiku@keio.jp | Keio University | Haruhisa Kikuchi | 2024-05-14 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, CDCL3, experimental) | halkiku@keio.jp | Keio University | Haruhisa Kikuchi | 2024-05-14 | View Spectrum |
| | Predicted Spectra |
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| Not Available | | Chemical Shift Submissions |
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| Not Available | | Species |
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| Species of Origin | Not Available |
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| Chemical Taxonomy |
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| Description | This compound belongs to the class of organic compounds known as 7,9'-epoxylignans. These are lignans that contain the 7,9'-epoxylignan skeleton, which consists of a tetrahydrofuran that carries a phenyl group, a methyl group, and a benzyl group at the 2-, 3-, 4-position, respectively. |
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| Kingdom | Organic compounds |
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| Super Class | Lignans, neolignans and related compounds |
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| Class | Furanoid lignans |
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| Sub Class | Tetrahydrofuran lignans |
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| Direct Parent | 7,9'-epoxylignans |
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| Alternative Parents | |
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| Substituents | - 7,9p-epoxylignan
- Phenoxy compound
- Methoxybenzene
- Phenol ether
- Anisole
- Alkyl aryl ether
- Benzenoid
- Monocyclic benzene moiety
- Tetrahydrofuran
- Oxacycle
- Organoheterocyclic compound
- Nitrile
- Carbonitrile
- Ether
- Dialkyl ether
- Acetal
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Aromatic heteromonocyclic compound
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| Molecular Framework | Aromatic heteromonocyclic 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 | - Dai W, Lei M, Yin Q, Nan H, Qian G: Isolation and Characterization of Novel Pueroside B Isomers and Other Bioactive Compounds from Pueraria lobata Roots: Structure Elucidation, alpha-Glucosidase, and alpha-Amylase Inhibition Studies. Int J Mol Sci. 2024 Sep 4;25(17):9602. doi: 10.3390/ijms25179602. [PubMed:39273546 ]
- Long CY, Li QJ, Zhou L, Hu ZX, Yang J: [Chemical constituents of Viburnum utile and their inhibitory activities against alpha-glucosidase]. Zhongguo Zhong Yao Za Zhi. 2024 Sep;49(17):4695-4701. doi: 10.19540/j.cnki.cjcmm.20240607.201. [PubMed:39307807 ]
- Wang ZX, An Z, Liu HW, Xie JY, Wang HR, Yan XT: [Two new glycosides from Hypericum elatoides]. Zhongguo Zhong Yao Za Zhi. 2024 Jun;49(12):3242-3251. doi: 10.19540/j.cnki.cjcmm.20240319.201. [PubMed:39041085 ]
- Akash S, Shanto SKHI, Islam MR, Bayil I, Afolabi SO, Guendouzi A, Abdellattif MH, E A Zaki M: Discovery of novel MLK4 inhibitors against colorectal cancer through computational approaches. Comput Biol Med. 2024 Sep 18;182:109136. doi: 10.1016/j.compbiomed.2024.109136. [PubMed:39298888 ]
- Kim J, Kadayat TM, Lee JE, Kwon S, Jung K, Hwang JS, Kwon OB, Kim YJ, Choi YK, Park KG, Hwang H, Cho SJ, Lee T, Jeon YH, Chin J: Discovery of the therapeutic potential of PPARdelta agonist bearing 1,3,4- thiadiazole in inflammatory disorders. Eur J Med Chem. 2024 Sep 12;279:116856. doi: 10.1016/j.ejmech.2024.116856. [PubMed:39270454 ]
- Dudey AP, Rigby JM, Hughes GR, Stephenson GR, Storr TE, Chantry A, Hemmings AM: Expanding the inhibitor space of the WWP1 and WWP2 HECT E3 ligases. J Enzyme Inhib Med Chem. 2024 Dec;39(1):2394895. doi: 10.1080/14756366.2024.2394895. Epub 2024 Sep 2. [PubMed:39223706 ]
- Alonso de Diego SA, Linares ML, Garcia Molina A, de Lucas AI, Del Cerro A, Alonso JM, Ver Donck L, Cid JM, Trabanco AA, Van Gool M: Discovery of 6,7-Dihydropyrazolo[1,5-a]pyrazin-4(5H)-one Derivatives as mGluR(2) Negative Allosteric Modulators with In Vivo Activity in a Rodent's Model of Cognition. J Med Chem. 2024 Sep 12;67(17):15569-15585. doi: 10.1021/acs.jmedchem.4c01227. Epub 2024 Aug 29. [PubMed:39208150 ]
- Hu X, Kabir M, Lin Y, Xiong Y, Parsons RE, Gu W, Jin J: Design, Synthesis, and Evaluation of p53Y220C Acetylation Targeting Chimeras (AceTACs). J Med Chem. 2024 Aug 22;67(16):14633-14648. doi: 10.1021/acs.jmedchem.4c01497. Epub 2024 Aug 6. [PubMed:39169826 ]
- Kim J, Hwang SJ, Lee GS, Lee JR, An HI, Im HS, Kim M, Lee SS, Lee HJ, Kim CS: Collagenase and Tyrosinase Inhibitory Compounds from Fish Gut Bacteria Ruegeria atlantica and Pseudoalteromonas neustonica. ACS Omega. 2024 Jul 29;9(32):34259-34267. doi: 10.1021/acsomega.3c09585. eCollection 2024 Aug 13. [PubMed:39157099 ]
- Zhao LH, Guo XY, Yan HW, Jiang JS, Zhang X, Yang YN, Yuan X, Sun H, Zhang PC: A class of geranylquinol-derived polycyclic meroterpenoids from Arnebia euchroma against heart failure by reducing excessive autophagy and apoptosis in cardiomyocytes. Bioorg Chem. 2024 Oct;151:107691. doi: 10.1016/j.bioorg.2024.107691. Epub 2024 Aug 3. [PubMed:39116524 ]
- Xu ZY, Hu Z, La CS, Du NN, Bai M, Hao J, Lin B, Huang XX, Song SJ: Hydroxyl-Amide Alkaloids from Pepper Roots: Potential Sources of Natural Antioxidants and Tyrosinase Inhibitors. J Agric Food Chem. 2024 Sep 11;72(36):19800-19811. doi: 10.1021/acs.jafc.4c03650. Epub 2024 Aug 8. [PubMed:39116367 ]
- Tolmacheva I, Eroshenko D, Chernyshova I, Nazarov M, Lavrik O, Grishko V: Synthesis of furanotriterpenoids from betulin and evaluation of Tyrosyl-DNA phosphodiesterase 1 (Tdp1) inhibitory properties of new semi-synthetic triterpenoids. Eur J Med Chem. 2024 Oct 5;276:116724. doi: 10.1016/j.ejmech.2024.116724. Epub 2024 Jul 27. [PubMed:39079310 ]
- Khamees Thabet H, Ammar YA, Imran M, Hamdy Helal M, Ibrahim Alaqel S, Alshehri A, Ash Mohd A, Abusaif MS, Ragab A: Unveiling anti-diabetic potential of new thiazole-sulfonamide derivatives: Design, synthesis, in vitro bio-evaluation targeting DPP-4, alpha-glucosidase, and alpha-amylase with in-silico ADMET and docking simulation. Bioorg Chem. 2024 Oct;151:107671. doi: 10.1016/j.bioorg.2024.107671. Epub 2024 Jul 23. [PubMed:39067419 ]
- Eltahir AOE, Omoruyi SI, Augustine TN, Luckay RC, Hussein AA: Neuroprotective Effects of Glycyrrhiza glabra Total Extract and Isolated Compounds. Pharmaceuticals (Basel). 2024 Jun 28;17(7):852. doi: 10.3390/ph17070852. [PubMed:39065703 ]
- Wang D, Sun D, Wang X, Peng X, Ji Y, Tang L, He Q, Chen D, Yang Y, Zhou X, Xiong B, Ai J: Remodeling tumor-associated macrophage for anti-cancer effects by rational design of irreversible inhibition of mitogen-activated protein kinase-activated protein kinase 2. MedComm (2020). 2024 Jul 10;5(7):e634. doi: 10.1002/mco2.634. eCollection 2024 Jul. [PubMed:38988492 ]
- Huang X, Li D, Long B, Li H, Li J, Wang W, Xu K, Yu X: Activation of a Silent Gene Cluster from the Endophytic Fungus Talaromyces sp. Unearths Cryptic Azaphilone Metabolites. J Agric Food Chem. 2024 Jul 17;72(28):15801-15810. doi: 10.1021/acs.jafc.4c03162. Epub 2024 Jul 4. [PubMed:38962874 ]
- Chen T, Hou A, Guo P, Peng S, Qin G, Ding A, Hu X, Duan Y, Chen J, Gong L, Xuan L: Novel Jatrophane Diterpenoids from Euphorbia esula Promotes Lipid Clearance by Transcriptional Regulation of PCSK9. J Med Chem. 2024 Jul 25;67(14):12055-12067. doi: 10.1021/acs.jmedchem.4c00779. Epub 2024 Jul 3. [PubMed:38959380 ]
- Moncada-Basualto M, Saavedra-Olavarria J, Rivero-Jerez PS, Rojas C, Maya JD, Liempi A, Zuniga-Bustos M, Olea-Azar C, Lapier M, Perez EG, Pozo-Martinez J: Assessment of the Activity of Nitroisoxazole Derivatives against Trypanosoma cruzi. Molecules. 2024 Jun 11;29(12):2762. doi: 10.3390/molecules29122762. [PubMed:38930828 ]
- Khamees Thabet H, Ragab A, Imran M, Helal MH, Ibrahim Alaqel S, Alshehri A, Ash Mohd A, Rakan Alshammari M, S Abusaif M, A Ammar Y: Discovery of new anti-diabetic potential agents based on paracetamol incorporating sulfa-drugs: Design, synthesis, alpha-amylase, and alpha-glucosidase inhibitors with molecular docking simulation. Eur J Med Chem. 2024 Sep 5;275:116589. doi: 10.1016/j.ejmech.2024.116589. Epub 2024 Jun 8. [PubMed:38878516 ]
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