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Record Information
Version2.0
Created at2022-04-27 23:11:14 UTC
Updated at2022-04-27 23:11:14 UTC
NP-MRD IDNP0051986
Secondary Accession NumbersNone
Natural Product Identification
Common NameZaluzanin C
DescriptionZaluzanin C belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. Zaluzanin C is found in Ainsliaea acerifolia, Ainsliaea fragrans, Arctotis revoluta, Chaetanthera chilensis, Cheirolophus sempervirens, Conocephalum conicum, Cynara cornigera, Gochnatia vernonioides, Ixeris dentata Nakai, Laurus nobilis, Laurus nobilis L. , Onopordon laconicum, Podachaenium eminens, Saussurea lappa , Urospermum dalechampii, Urospermum dalechampii (L.) F.W.Schmidt , Vernonia spp. , Youngia japonica, Youngia japonica (L.) DC., Zaluzania angusta, Zaluzania spp. and Zinnia acerosa. Zaluzanin C was first documented in 2016 (PMID: 28920380). Zaluzanin C is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 32738593) (PMID: 31294342) (PMID: 29017788).
Structure
Thumb
Synonyms
ValueSource
3beta-Hydroxy-4(15),10(14),11(13)-guaiatrien-12,6-olideChEBI
3b-Hydroxy-4(15),10(14),11(13)-guaiatrien-12,6-olideGenerator
3Β-hydroxy-4(15),10(14),11(13)-guaiatrien-12,6-olideGenerator
Chemical FormulaC15H18O3
Average Mass246.3060 Da
Monoisotopic Mass246.12559 Da
IUPAC Name(3aS,6aR,8S,9aR,9bS)-8-hydroxy-3,6,9-trimethylidene-dodecahydroazuleno[4,5-b]furan-2-one
Traditional Namezaluzanin c
CAS Registry NumberNot Available
SMILES
[H][C@@]12CCC(=C)[C@]3([H])C[C@H](O)C(=C)[C@]3([H])[C@@]1([H])OC(=O)C2=C
InChI Identifier
InChI=1S/C15H18O3/c1-7-4-5-10-8(2)15(17)18-14(10)13-9(3)12(16)6-11(7)13/h10-14,16H,1-6H2/t10-,11-,12-,13-,14-/m0/s1
InChI KeyXFVLNEYIZGZDHP-PEDHHIEDSA-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
Ainsliaea acerifoliaLOTUS Database
Ainsliaea fragransPlant
Arctotis revolutaLOTUS Database
Chaetanthera chilensisLOTUS Database
Cheirolophus sempervirensLOTUS Database
Conocephalum conicumPlant
Cynara cornigeraLOTUS Database
Gochnatia vernonioidesLOTUS Database
Ixeris dentata NakaiPlant
Laurus nobilisLOTUS Database
Laurus nobilis L.Plant
Onopordon laconicumPlant
Podachaenium eminensPlant
Saussurea costusPlant
Urospermum dalechampiiLOTUS Database
Urospermum dalechampii (L.) F.W.SchmidtPlant
Vernonia spp.Plant
Youngia japonicaLOTUS Database
Youngia japonica (L.) DC.Plant
Zaluzania angustaPlant
Zaluzania spp.Plant
Zinnia acerosaPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentGuaianolides and derivatives
Alternative Parents
Substituents
  • Guaianolide-skeleton
  • Guaiane sesquiterpenoid
  • Sesquiterpenoid
  • Gamma butyrolactone
  • Cyclic alcohol
  • Tetrahydrofuran
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Secondary alcohol
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
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
logP1.6ALOGPS
logP1.84ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)14.6ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity67.49 m³·mol⁻¹ChemAxon
Polarizability26.33 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00003397
Chemspider ID65509
KEGG Compound IDC09606
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound72646
PDB IDNot Available
ChEBI ID10103
Good Scents IDNot Available
References
General References
  1. Cheeran V, Munuswamy-Ramanujam G: Sesquiterpene lactone Zaluzanin D alters MMP-9 promoter methylation in differentiated THP-1 monocytic cells and down regulates inflammatory cytokines IL-1beta and TNF-alpha. Int Immunopharmacol. 2020 Oct;87:106803. doi: 10.1016/j.intimp.2020.106803. Epub 2020 Jul 29. [PubMed:32738593 ]
  2. Kwak SH, Kim YH: Zaluzanin C Inhibits Differentiation of 3T3-L1 Preadipocytes into Mature Adipocytes. J Obes Metab Syndr. 2019 Jun;28(2):105-111. doi: 10.7570/jomes.2019.28.2.105. Epub 2019 Jun 30. [PubMed:31294342 ]
  3. Kim KM, Jang WG: Zaluzanin C (ZC) induces osteoblast differentiation through regulating of osteogenic genes expressions in early stage of differentiation. Bioorg Med Chem Lett. 2017 Nov 1;27(21):4789-4793. doi: 10.1016/j.bmcl.2017.09.061. Epub 2017 Sep 30. [PubMed:29017788 ]
  4. Liu B, Xie YZ, Li XX, Sun YY, Xu F, Ji TF: [Chemical constituents of Myripnois dioica]. Zhongguo Zhong Yao Za Zhi. 2016 Sep;41(17):3260-3264. doi: 10.4268/cjcmm20161723. [PubMed:28920380 ]