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Record Information
Version2.0
Created at2022-09-04 18:51:00 UTC
Updated at2022-09-04 18:51:00 UTC
NP-MRD IDNP0200081
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1'r,2'r,3r,3ar,4s,5's,6r,6ar,9's,9ar,9br,10's,11'r)-2',6-dihydroxy-2',6,9,11'-tetramethyl-6'-methylidene-2,7'-dioxo-4,5,6a,7,9a,9b-hexahydro-3ah-8'-oxaspiro[azuleno[4,5-b]furan-3,12'-tetracyclo[9.2.2.0¹,¹⁰.0⁵,⁹]pentadecan]-14'-en-4-yl acetate
DescriptionHandelin, also known as yejuhua lactone or ye ju-hua, belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units. (1'r,2'r,3r,3ar,4s,5's,6r,6ar,9's,9ar,9br,10's,11'r)-2',6-dihydroxy-2',6,9,11'-tetramethyl-6'-methylidene-2,7'-dioxo-4,5,6a,7,9a,9b-hexahydro-3ah-8'-oxaspiro[azuleno[4,5-b]furan-3,12'-tetracyclo[9.2.2.0¹,¹⁰.0⁵,⁹]pentadecan]-14'-en-4-yl acetate is found in Chrysanthemum boreale. (1'r,2'r,3r,3ar,4s,5's,6r,6ar,9's,9ar,9br,10's,11'r)-2',6-dihydroxy-2',6,9,11'-tetramethyl-6'-methylidene-2,7'-dioxo-4,5,6a,7,9a,9b-hexahydro-3ah-8'-oxaspiro[azuleno[4,5-b]furan-3,12'-tetracyclo[9.2.2.0¹,¹⁰.0⁵,⁹]pentadecan]-14'-en-4-yl acetate was first documented in 2014 (PMID: 24689881). Based on a literature review a small amount of articles have been published on Handelin (PMID: 35038074) (PMID: 31975220) (PMID: 28807514).
Structure
Thumb
Synonyms
ValueSource
Yejuhua lactoneMeSH
Ye ju-huaMeSH
Chemical FormulaC32H40O8
Average Mass552.6640 Da
Monoisotopic Mass552.27232 Da
IUPAC Name(1'R,2'R,3R,3aR,4S,5'S,6R,6aR,9'S,9aR,9bR,10'S,11'R)-2',6-dihydroxy-2',6,9,11'-tetramethyl-6'-methylidene-2,7'-dioxo-3a,4,5,6,6a,7,9a,9b-octahydro-2H-8'-oxaspiro[azuleno[4,5-b]furan-3,12'-tetracyclo[9.2.2.0^{1,10}.0^{5,9}]pentadecan]-14'-en-4-yl acetate
Traditional Name(1'R,2'R,3R,3aR,4S,5'S,6R,6aR,9'S,9aR,9bR,10'S,11'R)-2',6-dihydroxy-2',6,9,11'-tetramethyl-6'-methylidene-2,7'-dioxo-4,5,6a,7,9a,9b-hexahydro-3aH-8'-oxaspiro[azuleno[4,5-b]furan-3,12'-tetracyclo[9.2.2.0^{1,10}.0^{5,9}]pentadecan]-14'-en-4-yl acetate
CAS Registry NumberNot Available
SMILES
CC(=O)O[C@H]1C[C@@](C)(O)[C@@H]2CC=C(C)[C@@H]2[C@H]2OC(=O)[C@]3(C[C@@]45C=C[C@]3(C)[C@@H]4[C@H]3OC(=O)C(=C)[C@@H]3CC[C@@]5(C)O)[C@H]12
InChI Identifier
InChI=1S/C32H40O8/c1-15-7-8-19-21(15)24-22(20(38-17(3)33)13-29(19,5)36)32(27(35)40-24)14-31-12-11-28(32,4)25(31)23-18(9-10-30(31,6)37)16(2)26(34)39-23/h7,11-12,18-25,36-37H,2,8-10,13-14H2,1,3-6H3/t18-,19+,20-,21-,22+,23-,24+,25-,28+,29+,30+,31-,32-/m0/s1
InChI KeySZQWAXGDCUONOB-QKARTHDOSA-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 Origin
Species NameSourceReference
Chrysanthemum borealeLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesterterpenoids
Direct ParentSesterterpenoids
Alternative Parents
Substituents
  • Sesterterpenoid
  • Guaianolide-skeleton
  • Tricarboxylic acid or derivatives
  • Gamma butyrolactone
  • Cyclic alcohol
  • Tertiary alcohol
  • Tetrahydrofuran
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • 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
logP2ChemAxon
pKa (Strongest Acidic)14.27ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area119.36 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity145.01 m³·mol⁻¹ChemAxon
Polarizability58.99 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00020977
Chemspider ID34257850
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound90474153
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Zhang H, Qin J, Lan X, Zeng W, Zhou J, Huang TE, Xiao WL, Wang QQ, Sun S, Su W, Nie W, Yang S, Yang J, Gao Q, Xiang Y: Handelin extends lifespan and healthspan of Caenorhabditis elegans by reducing ROS generation and improving motor function. Biogerontology. 2022 Feb;23(1):115-128. doi: 10.1007/s10522-022-09950-5. Epub 2022 Jan 17. [PubMed:35038074 ]
  2. Yang J, Zhang H, Sun S, Wang X, Guan Y, Mi Q, Zeng W, Xiang H, Zhu H, Zou X, You Y, Xiang Y, Gao Q: Autophagy and Hsp70 activation alleviate oral epithelial cell death induced by food-derived hypertonicity. Cell Stress Chaperones. 2020 Mar;25(2):253-264. doi: 10.1007/s12192-020-01068-2. Epub 2020 Jan 23. [PubMed:31975220 ]
  3. Wang LC, Liao LX, Lv HN, Liu D, Dong W, Zhu J, Chen JF, Shi ML, Fu G, Song XM, Jiang Y, Zeng KW, Tu PF: Highly Selective Activation of Heat Shock Protein 70 by Allosteric Regulation Provides an Insight into Efficient Neuroinflammation Inhibition. EBioMedicine. 2017 Sep;23:160-172. doi: 10.1016/j.ebiom.2017.08.011. Epub 2017 Aug 9. [PubMed:28807514 ]
  4. Pyee Y, Chung HJ, Choi TJ, Park HJ, Hong JY, Kim JS, Kang SS, Lee SK: Suppression of inflammatory responses by handelin, a guaianolide dimer from Chrysanthemum boreale, via downregulation of NF-kappaB signaling and pro-inflammatory cytokine production. J Nat Prod. 2014 Apr 25;77(4):917-24. doi: 10.1021/np4009877. Epub 2014 Apr 1. [PubMed:24689881 ]
  5. LOTUS database [Link]