| Record Information |
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| Version | 2.0 |
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| Created at | 2022-05-30 16:43:11 UTC |
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| Updated at | 2022-05-30 16:43:11 UTC |
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| NP-MRD ID | NP0137150 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Dihydroartemisinin |
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| Description | Dihydroartemisinin, also known as dihydroqinghaosu or alaxin, belongs to the class of organic compounds known as artemisinins. These are sesquiterpenoids originally isolated from the herb Artemisia annua. Their structure is based on artemisinin, a tetracyclic compound that contains a 1,2-dioxepane fused to an octahydrobenzopyran moiety. The internal peroxide bridge is believed to be a key to the mode of action of artemisinins. In humans, dihydroartemisinin is involved in the artemether metabolism pathway. Dihydroartemisinin is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Dihydroartemisinin was first documented in 2022 (PMID: 35624465). Based on a literature review a small amount of articles have been published on Dihydroartemisinin (PMID: 35617818) (PMID: 35604186) (PMID: 35569552) (PMID: 35568865). |
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| Structure | CC1CCC2C(C)C(O)OC3OC4(C)CCC1C23OO4 InChI=1S/C15H24O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-13,16H,4-7H2,1-3H3 |
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| Synonyms | | Value | Source |
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| 9alpha-Hydroxydeoxyartemisinin | HMDB | | Dihydroartemisinine | HMDB | | Dihydroqinghaosu | HMDB | | Dihydroquinghaosu | HMDB | | Dihydroquinghaosu, (3R-(3alpha,5abeta,6beta,8abeta,9alpha,10alpha,12alpha,12ar*))-isomer | HMDB | | Dihydroquinghaosu, (3R-(3alpha,5abeta,6beta,8abeta,9alpha,10beta,12alpha,12ar*))-isomer | HMDB | | 3alpha-Hydroxydeoxydihydroartemisinin | HMDB | | 8alpha-Hydroxydeoxyartemisinin | HMDB | | Alaxin | MeSH | | Salaxin | MeSH | | Santecxin | MeSH | | (3R,5AS,6R,8as,9R,10S,12R,12ar)-decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano(4,3-J)-1,2-benzodioxepin-10-ol | MeSH | | Cotecxin | MeSH | | Cotexin | MeSH | | Artenimol | MeSH |
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| Chemical Formula | C15H24O5 |
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| Average Mass | 284.3520 Da |
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| Monoisotopic Mass | 284.16237 Da |
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| IUPAC Name | Not Available |
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| Traditional Name | Not Available |
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| CAS Registry Number | Not Available |
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| SMILES | CC1CCC2C(C)C(O)OC3OC4(C)CCC1C23OO4 |
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| InChI Identifier | InChI=1S/C15H24O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-13,16H,4-7H2,1-3H3 |
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| InChI Key | BJDCWCLMFKKGEE-UHFFFAOYSA-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 | Not Available |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as artemisinins. These are sesquiterpenoids originally isolated from the herb Artemisia annua. Their structure is based on artemisinin, a tetracyclic compound that contains a 1,2-dioxepane fused to an octahydrobenzopyran moiety. The internal peroxide bridge is believed to be a key to the mode of action of artemisinins. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Prenol lipids |
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| Sub Class | Sesquiterpenoids |
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| Direct Parent | Artemisinins |
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| Alternative Parents | |
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| Substituents | - Artemisinin skeleton
- Oxepane
- 1,2,4-trioxane
- Oxane
- Dialkyl peroxide
- Hemiacetal
- Oxacycle
- Organoheterocyclic compound
- Acetal
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Aliphatic heteropolycyclic compound
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| Molecular Framework | Aliphatic 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 Y, Chen J, Yang Y, Gao S, Wang Z, Liu Y, Zhang X, Hua L, Guo Y, Yang Y: Oil-water partition coefficient preparation and detection in the dihydroartemisinin self-emulsifying drug delivery system. BMC Biotechnol. 2022 May 27;22(1):16. doi: 10.1186/s12896-022-00746-6. [PubMed:35624465 ]
- Sugiarto SR, Bwire GM, Moore BR, Page-Sharp M, Manning L, Batty KT, Minzi OMS, Ngasala B, Davis TME, Makani J, Salman S: The effect of sickle cell genotype on the pharmacokinetic properties of artemether-lumefantrine in Tanzanian children. Int J Parasitol Drugs Drug Resist. 2022 May 20;19:31-39. doi: 10.1016/j.ijpddr.2022.05.002. [PubMed:35617818 ]
- Siahaan L: Observation of Malaria Treatment with Dihydroartemisinin-Piperaquine Combination at Primary Health Care Turkiye Parazitol Derg. 2022 May 23;46(2):102-107. doi: 10.4274/tpd.galenos.2021.54264. [PubMed:35604186 ]
- Zhang H, Zhuo Y, Li D, Zhang L, Gao Q, Yang L, Yuan X: Dihydroartemisinin inhibits the growth of pancreatic cells by inducing ferroptosis and activating antitumor immunity. Eur J Pharmacol. 2022 Jul 5;926:175028. doi: 10.1016/j.ejphar.2022.175028. Epub 2022 May 13. [PubMed:35569552 ]
- Yang XX, Xu X, Wang MF, Xu HZ, Peng XC, Han N, Yu TT, Li LG, Li QR, Chen X, Wen Y, Li TF: A nanoreactor boosts chemodynamic therapy and ferroptosis for synergistic cancer therapy using molecular amplifier dihydroartemisinin. J Nanobiotechnology. 2022 May 14;20(1):230. doi: 10.1186/s12951-022-01455-0. [PubMed:35568865 ]
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