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Record Information
Version2.0
Created at2022-04-28 16:32:28 UTC
Updated at2022-04-28 16:32:28 UTC
NP-MRD IDNP0071138
Secondary Accession NumbersNone
Natural Product Identification
Common Name(-)-Dihydroartemisinic acid
DescriptionDihydroartemisinic acid, also known as dihydroarteannuate, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (-)-Dihydroartemisinic acid is found in Artemisia annua . (-)-Dihydroartemisinic acid was first documented in 2021 (PMID: 34023721). Based on a literature review a small amount of articles have been published on dihydroartemisinic acid (PMID: 35357832) (PMID: 35344268) (PMID: 34137611) (PMID: 33664720).
Structure
Thumb
Synonyms
ValueSource
(-)-Dihydroartemisinic acidChEBI
(2R)-2-[(1R)-4beta,7-Dimethyl-1,2,3,4,4abeta,5,6,8abeta-octahydronaphthalen-1alpha-yl]propionic acidChEBI
Dihydroarteannuic acidChEBI
(-)-DihydroartemisinateGenerator
(2R)-2-[(1R)-4b,7-Dimethyl-1,2,3,4,4abeta,5,6,8abeta-octahydronaphthalen-1a-yl]propionateGenerator
(2R)-2-[(1R)-4b,7-Dimethyl-1,2,3,4,4abeta,5,6,8abeta-octahydronaphthalen-1a-yl]propionic acidGenerator
(2R)-2-[(1R)-4beta,7-Dimethyl-1,2,3,4,4abeta,5,6,8abeta-octahydronaphthalen-1alpha-yl]propionateGenerator
(2R)-2-[(1R)-4Β,7-dimethyl-1,2,3,4,4abeta,5,6,8abeta-octahydronaphthalen-1α-yl]propionateGenerator
(2R)-2-[(1R)-4Β,7-dimethyl-1,2,3,4,4abeta,5,6,8abeta-octahydronaphthalen-1α-yl]propionic acidGenerator
DihydroarteannuateGenerator
DihydroartemisinateGenerator
Chemical FormulaC15H24O2
Average Mass236.3550 Da
Monoisotopic Mass236.17763 Da
IUPAC Name(2R)-2-[(1R,4R,4aS,8aS)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl]propanoic acid
Traditional Name(2R)-2-[(1R,4R,4aS,8aS)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl]propanoic acid
CAS Registry NumberNot Available
SMILES
C[C@H]([C@@H]1CC[C@@H](C)[C@@H]2CCC(C)=C[C@H]12)C(O)=O
InChI Identifier
InChI=1S/C15H24O2/c1-9-4-6-12-10(2)5-7-13(14(12)8-9)11(3)15(16)17/h8,10-14H,4-7H2,1-3H3,(H,16,17)/t10-,11-,12+,13+,14+/m1/s1
InChI KeyJYGAZEJXUVDYHI-DGTMBMJNSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Artemisia annuaPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Sesquiterpenoid
  • Cadinane sesquiterpenoid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic 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
logP3.15ALOGPS
logP3.79ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)4.98ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity69.44 m³·mol⁻¹ChemAxon
Polarizability27.89 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00030130
Chemspider ID9196075
KEGG Compound IDNot Available
BioCyc IDCPD-7559
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11020893
PDB IDNot Available
ChEBI ID144078
Good Scents IDNot Available
References
General References
  1. Nagy C, Pesti A, Andrasi M, Vasas G, Gaspar A: Determination of artemisinin and its analogs in Artemisia annua extracts by capillary electrophoresis - Mass spectrometry. J Pharm Biomed Anal. 2021 Aug 5;202:114131. doi: 10.1016/j.jpba.2021.114131. Epub 2021 May 12. [PubMed:34023721 ]
  2. Varela K, Al Mahmud H, Arman HD, Martinez LR, Wakeman CA, Yoshimoto FK: Autoxidation of a C2-Olefinated Dihydroartemisinic Acid Analogue to Form an Aromatic Ring: Application to Serrulatene Biosynthesis. J Nat Prod. 2022 Apr 22;85(4):951-962. doi: 10.1021/acs.jnatprod.1c01101. Epub 2022 Mar 31. [PubMed:35357832 ]
  3. Wang D, Li M, Yuan C, Fang Y, Zhang Z: Bioassay-Guided Isolation of Nematicidal Artemisinic Acid and Dihydroartemisinic Acid from Artemisia annua L. and Evaluation of Their Activity against Meloidogyne incognita. Chem Biodivers. 2022 May;19(5):e202200083. doi: 10.1002/cbdv.202200083. Epub 2022 Apr 5. [PubMed:35344268 ]
  4. Varela K, Arman HD, Yoshimoto FK: Synthesis of [15,15,15-(2)H(3)]-Dihydroartemisinic Acid and Isotope Studies Support a Mixed Mechanism in the Endoperoxide Formation to Artemisinin. J Nat Prod. 2021 Jul 23;84(7):1967-1984. doi: 10.1021/acs.jnatprod.1c00246. Epub 2021 Jun 17. [PubMed:34137611 ]
  5. Zeng BX, Yao MD, Xiao WH, Luo YZ, Wang Y, Yuan YJ: Endogenous 2mu Plasmid Editing for Pathway Engineering in Saccharomyces cerevisiae. Front Microbiol. 2021 Feb 16;12:631462. doi: 10.3389/fmicb.2021.631462. eCollection 2021. [PubMed:33664720 ]