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Record Information
Version1.0
Created at2020-10-21 16:06:43 UTC
Updated at2021-07-15 16:45:10 UTC
NP-MRD IDNP0001751
Secondary Accession NumbersNone
Natural Product Identification
Common NameMadangolide
Provided ByNPAtlasNPAtlas Logo
Description Madangolide is found in Lyngbya and Lyngbya bouillonii. It was first documented in 1999 (PMID: 10395526). Based on a literature review very few articles have been published on (12Z)-2-tert-butyl-4,7,9,16-tetramethyl-1-oxa-9-azacycloheptadeca-10,12-diene-8,17-dione.
Structure
Data?1624573696
SynonymsNot Available
Chemical FormulaC23H39NO3
Average Mass377.5690 Da
Monoisotopic Mass377.29299 Da
IUPAC Name(2R,4S,7R,10Z,12Z,16R)-2-tert-butyl-4,7,9,16-tetramethyl-1-oxa-9-azacycloheptadeca-10,12-diene-8,17-dione
Traditional Name(2R,4S,7R,10Z,12Z,16R)-2-tert-butyl-4,7,9,16-tetramethyl-1-oxa-9-azacycloheptadeca-10,12-diene-8,17-dione
CAS Registry NumberNot Available
SMILES
CC1CCC(C)C(=O)N(C)\C=C/C=C\CCC(C)C(=O)OC(C1)C(C)(C)C
InChI Identifier
InChI=1S/C23H39NO3/c1-17-13-14-18(2)21(25)24(7)15-11-9-8-10-12-19(3)22(26)27-20(16-17)23(4,5)6/h8-9,11,15,17-20H,10,12-14,16H2,1-7H3/b9-8-,15-11-
InChI KeyPZISRZRLNYYESW-SCLISBBUSA-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
LyngbyaNPAtlas
Moorea bouillonii-
Chemical Taxonomy
ClassificationNot classified
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
logP5.83ALOGPS
logP5.61ChemAxon
logS-5.7ALOGPS
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area46.61 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity112.39 m³·mol⁻¹ChemAxon
Polarizability44.82 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
NPAtlas IDNPA001207
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10205974
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10547620
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Klein D, Braekman JC, Daloze D, Hoffmann L, Castillo G, Demoulin V V: Madangolide and laingolide A, two novel macrolides from lyngbya bouillonii (Cyanobacteria) J Nat Prod. 1999 Jun;62(6):934-6. doi: 10.1021/np9900324. [PubMed:10395526 ]