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Record Information
Version2.0
Created at2022-05-30 16:43:11 UTC
Updated at2022-05-30 16:43:11 UTC
NP-MRD IDNP0137150
Secondary Accession NumbersNone
Natural Product Identification
Common NameDihydroartemisinin
DescriptionDihydroartemisinin, 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).
Structure
Thumb
Synonyms
ValueSource
9alpha-HydroxydeoxyartemisininHMDB
DihydroartemisinineHMDB
DihydroqinghaosuHMDB
DihydroquinghaosuHMDB
Dihydroquinghaosu, (3R-(3alpha,5abeta,6beta,8abeta,9alpha,10alpha,12alpha,12ar*))-isomerHMDB
Dihydroquinghaosu, (3R-(3alpha,5abeta,6beta,8abeta,9alpha,10beta,12alpha,12ar*))-isomerHMDB
3alpha-HydroxydeoxydihydroartemisininHMDB
8alpha-HydroxydeoxyartemisininHMDB
AlaxinMeSH
SalaxinMeSH
SantecxinMeSH
(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-olMeSH
CotecxinMeSH
CotexinMeSH
ArtenimolMeSH
Chemical FormulaC15H24O5
Average Mass284.3520 Da
Monoisotopic Mass284.16237 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILES
CC1CCC2C(C)C(O)OC3OC4(C)CCC1C23OO4
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
InChI KeyBJDCWCLMFKKGEE-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentArtemisinins
Alternative Parents
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
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
HMDB IDHMDB0242686
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID470515
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDihydroartemisinin
METLIN IDNot Available
PubChem Compound540327
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]