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Record Information
Version1.0
Created at2021-06-19 16:34:39 UTC
Updated at2021-06-29 23:48:11 UTC
NP-MRD IDNP0024101
Secondary Accession NumbersNone
Natural Product Identification
Common NameAjudazol A
Provided ByJEOL DatabaseJEOL Logo
Description Ajudazol A is found in Chondromyces crocatus. It was first documented in 2005 (PMID: 15760139). Based on a literature review a small amount of articles have been published on Ajudazol A (PMID: 32806171) (PMID: 18517210).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC34H42N2O7
Average Mass590.7170 Da
Monoisotopic Mass590.29920 Da
IUPAC Name(2E)-N-[(2E,6Z,8Z)-11-{4-[(2S)-2-[(3S,4R)-4,8-dihydroxy-7-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-3-yl]propyl]-1,3-oxazol-2-yl}dodeca-2,6,8,11-tetraen-1-yl]-3-methoxy-N-methylbut-2-enamide
Traditional Name(2E)-N-[(2E,6Z,8Z)-11-{4-[(2S)-2-[(3S,4R)-4,8-dihydroxy-7-methyl-1-oxo-3,4-dihydro-2-benzopyran-3-yl]propyl]-1,3-oxazol-2-yl}dodeca-2,6,8,11-tetraen-1-yl]-3-methoxy-N-methylbut-2-enamide
CAS Registry NumberNot Available
SMILES
[H]OC1=C(C([H])=C([H])C2=C1C(=O)O[C@@]([H])([C@@]([H])(C([H])([H])[H])C([H])([H])C1=C([H])OC(=N1)C(=C([H])[H])C([H])([H])C(\[H])=C(\[H])/C(/[H])=C(/[H])C([H])([H])C([H])([H])C(\[H])=C(/[H])C([H])([H])N(C(=O)C(\[H])=C(\OC([H])([H])[H])C([H])([H])[H])C([H])([H])[H])[C@]2([H])O[H])C([H])([H])[H]
InChI Identifier
InChI=1S/C34H42N2O7/c1-22-16-17-27-29(30(22)38)34(40)43-32(31(27)39)24(3)19-26-21-42-33(35-26)23(2)15-13-11-9-7-8-10-12-14-18-36(5)28(37)20-25(4)41-6/h7,9,11-14,16-17,20-21,24,31-32,38-39H,2,8,10,15,18-19H2,1,3-6H3/b9-7-,13-11-,14-12+,25-20+/t24-,31+,32-/m0/s1
InChI KeyCIWQMSHQAVWNOO-OPGPRAPUSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 600 MHz, DMSO-d6/D2O at 80 C, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, DMSO-d6/D2O at 80 C, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, DMSO-d6/D2O at 80 C, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, DMSO-d6/D2O at 80 C, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, DMSO-d6/D2O at 80 C, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, DMSO-d6/D2O at 80 C, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, DMSO-d6/D2O at 80 C, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, DMSO-d6/D2O at 80 C, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, DMSO-d6/D2O at 80 C, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6/D2O at 80 C, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, DMSO-d6/D2O at 80 C, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, DMSO-d6/D2O at 80 C, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, DMSO-d6/D2O at 80 C, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, DMSO-d6/D2O at 80 C, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, DMSO-d6/D2O at 80 C, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, DMSO-d6/D2O at 80 C, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, DMSO-d6/D2O at 80 C, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, DMSO-d6/D2O at 80 C, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, DMSO-d6/D2O at 80 C, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, DMSO-d6/D2O at 80 C, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Chondromyces crocatusJEOL database
    • Jansen, R., et al, Eur. J. Org. Chem. 2002, 917
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
logP5.96ALOGPS
logP5.79ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)9.94ChemAxon
pKa (Strongest Basic)0.27ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area122.33 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity171.19 m³·mol⁻¹ChemAxon
Polarizability64.79 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID8591438
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10416005
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Wollnitzke P, Essig S, Golz JP, von Schwarzenberg K, Menche D: Total Synthesis of Ajudazol A by a Modular Oxazole Diversification Strategy. Org Lett. 2020 Aug 21;22(16):6344-6348. doi: 10.1021/acs.orglett.0c02188. Epub 2020 Aug 6. [PubMed:32806171 ]
  2. Hobson SJ, Parkin A, Marquez R: Oxidative rearrangements of isobenzofurans: studies toward the synthesis of the ajudazols. Org Lett. 2008 Jul 3;10(13):2813-6. doi: 10.1021/ol8009336. Epub 2008 Jun 3. [PubMed:18517210 ]
  3. Krebs O, Taylor RJ: Synthesis of the eastern portion of ajudazol a based on Stille coupling and double acetylene carbocupration. Org Lett. 2005 Mar 17;7(6):1063-6. doi: 10.1021/ol047313+. [PubMed:15760139 ]
  4. Jansen, R., et al. (2002). Jansen, R., et al, Eur. J. Org. Chem. 2002, 917. Eur. J. Org. Chem..