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Record Information
Version2.0
Created at2022-09-09 00:13:16 UTC
Updated at2022-09-09 00:13:16 UTC
NP-MRD IDNP0276216
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1r,4s,6r,7r,17r)-4,7-dihydroxy-4-[(1r)-1-hydroxyethyl]-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione
DescriptionJacoline belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. Jacoline is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (1r,4s,6r,7r,17r)-4,7-dihydroxy-4-[(1r)-1-hydroxyethyl]-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione is found in Crassocephalum crepidioides, Crotalaria micans, Jacobaea minuta, Jacobaea vulgaris and Senecio vulgaris. (1r,4s,6r,7r,17r)-4,7-dihydroxy-4-[(1r)-1-hydroxyethyl]-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione was first documented in 2006 (PMID: 16826978). Based on a literature review a significant number of articles have been published on jacoline (PMID: 21969251) (PMID: 35948427) (PMID: 21506416) (PMID: 17913058) (PMID: 21159354) (PMID: 32870736).
Structure
Thumb
Synonyms
ValueSource
(15alpha,20R)-12,15,20-Trihydroxy-15,20-dihydrosenecionan-11,16-dioneChEBI
(15a,20R)-12,15,20-Trihydroxy-15,20-dihydrosenecionan-11,16-dioneGenerator
(15Α,20R)-12,15,20-trihydroxy-15,20-dihydrosenecionan-11,16-dioneGenerator
Chemical FormulaC18H27NO7
Average Mass369.4140 Da
Monoisotopic Mass369.17875 Da
IUPAC Name(1R,4S,6R,7R,17R)-4,7-dihydroxy-4-[(1R)-1-hydroxyethyl]-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0^{14,17}]heptadec-11-ene-3,8-dione
Traditional Name(1R,4S,6R,7R,17R)-4,7-dihydroxy-4-[(1R)-1-hydroxyethyl]-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0^{14,17}]heptadec-11-ene-3,8-dione
CAS Registry NumberNot Available
SMILES
C[C@@H](O)[C@@]1(O)C[C@@H](C)[C@@](C)(O)C(=O)OCC2=CCN3CC[C@@H](OC1=O)[C@@H]23
InChI Identifier
InChI=1S/C18H27NO7/c1-10-8-18(24,11(2)20)16(22)26-13-5-7-19-6-4-12(14(13)19)9-25-15(21)17(10,3)23/h4,10-11,13-14,20,23-24H,5-9H2,1-3H3/t10-,11-,13-,14-,17-,18+/m1/s1
InChI KeyFMWJEBGSMAOQNN-YLFNNMARSA-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
Crassocephalum crepidioidesLOTUS Database
Crotalaria micansLOTUS Database
Jacobaea minutaLOTUS Database
Senecio jacobaeaLOTUS Database
Senecio vulgarisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassMacrolides and analogues
Sub ClassNot Available
Direct ParentMacrolides and analogues
Alternative Parents
Substituents
  • Senecionan-skeleton
  • Macrolide
  • Alkaloid or derivatives
  • Pyrrolizine
  • Dicarboxylic acid or derivatives
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Pyrroline
  • Tertiary alcohol
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Lactone
  • Secondary alcohol
  • Tertiary amine
  • Tertiary aliphatic amine
  • Carboxylic acid derivative
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Organic oxygen compound
  • Amine
  • 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
logP-0.5ChemAxon
pKa (Strongest Acidic)11.42ChemAxon
pKa (Strongest Basic)6.92ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area116.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity91.52 m³·mol⁻¹ChemAxon
Polarizability37.32 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00026209
Chemspider ID57259878
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound78358487
PDB IDNot Available
ChEBI ID136452
Good Scents IDNot Available
References
General References
  1. Cheng D, Kirk H, Vrieling K, Mulder PP, Klinkhamer PG: The relationship between structurally different pyrrolizidine alkaloids and western flower thrips resistance in F(2) hybrids of Jacobaea vulgaris and Jacobaea aquatica. J Chem Ecol. 2011 Oct;37(10):1071-80. doi: 10.1007/s10886-011-0021-6. Epub 2011 Oct 4. [PubMed:21969251 ]
  2. Taenzer J, Gehling M, Klevenhusen F, Saltzmann J, Danicke S, These A: Rumen Metabolism of Senecio Pyrrolizidine Alkaloids May Explain Why Cattle Tolerate Higher Doses Than Monogastric Species. J Agric Food Chem. 2022 Aug 24;70(33):10111-10120. doi: 10.1021/acs.jafc.2c01332. Epub 2022 Aug 10. [PubMed:35948427 ]
  3. Ma H, Yang L, Wang C, Wang Z: [Pyrrolizidine alkaloids of Senecio cannabifolius var. integrilifolius]. Zhongguo Zhong Yao Za Zhi. 2011 Jan;36(2):166-8. [PubMed:21506416 ]
  4. Tundis R, Loizzo MR, Statti GA, Passalacqua NG, Peruzzi L, Menichini F: Pyrrolizidine alkaloid profiles of the Senecio cineraria group (Asteraceae). Z Naturforsch C J Biosci. 2007 Jul-Aug;62(7-8):467-72. doi: 10.1515/znc-2007-7-802. [PubMed:17913058 ]
  5. Joosten L, Cheng D, Mulder PP, Vrieling K, van Veen JA, Klinkhamer PG: The genotype dependent presence of pyrrolizidine alkaloids as tertiary amine in Jacobaea vulgaris. Phytochemistry. 2011 Feb;72(2-3):214-22. doi: 10.1016/j.phytochem.2010.11.013. Epub 2010 Dec 13. [PubMed:21159354 ]
  6. Mulder PPJ, Klijnstra MD, Goselink RMA, van Vuuren AM, Cone JW, Stoopen G, Hoogenboom RLAP: Transfer of pyrrolizidine alkaloids from ragwort, common groundsel and viper's bugloss to milk from dairy cows. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2020 Nov;37(11):1906-1921. doi: 10.1080/19440049.2020.1798028. Epub 2020 Sep 1. [PubMed:32870736 ]
  7. Hoogenboom LA, Mulder PP, Zeilmaker MJ, van den Top HJ, Remmelink GJ, Brandon EF, Klijnstra M, Meijer GA, Schothorst R, Van Egmond HP: Carry-over of pyrrolizidine alkaloids from feed to milk in dairy cows. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2011 Mar;28(3):359-72. doi: 10.1080/19440049.2010.547521. [PubMed:21360378 ]
  8. Wiedenfeld H, Montes C, Tawil B, Contin A, Wynsma R: Pyrrolizidine alkaloid level in Senecio bicolor (Wilid.) Tod, ssp. cineraria (DC.) from middle Europe. Pharmazie. 2006 Jun;61(6):559-61. [PubMed:16826978 ]
  9. LOTUS database [Link]