Np mrd loader

Record Information
Version2.0
Created at2022-09-03 21:35:52 UTC
Updated at2022-09-03 21:35:52 UTC
NP-MRD IDNP0182802
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1s,7e,9s,11e,13r,14s,16r,17s,18r,19s)-21-hydroxy-19-(1h-indol-3-ylmethyl)-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-7,11,20-triene-2,5,6-trione
DescriptionChaetoglobosin C, also known as penochalasin K, belongs to the class of organic compounds known as chaetoglobosins. These are cytochalasans with a structure in which the hydrogenated isoindole bears an (indol-3-yl)methyl group. (1s,7e,9s,11e,13r,14s,16r,17s,18r,19s)-21-hydroxy-19-(1h-indol-3-ylmethyl)-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-7,11,20-triene-2,5,6-trione is found in Calonectria kyotensis. (1s,7e,9s,11e,13r,14s,16r,17s,18r,19s)-21-hydroxy-19-(1h-indol-3-ylmethyl)-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-7,11,20-triene-2,5,6-trione was first documented in 2011 (PMID: 21196335). Based on a literature review a small amount of articles have been published on chaetoglobosin C (PMID: 24689437) (PMID: 30343206) (PMID: 28958956) (PMID: 22732319).
Structure
Thumb
Synonyms
ValueSource
Chaetoglobosin DMeSH
Chaetoglobosin TMeSH
Chaetoglobosin VMeSH
Chaetoglobosin yMeSH
ChaetoglobosinsMeSH
Penochalasin KMeSH
Chaetoglobosin aMeSH
Chaetoglobosin QMeSH
Chaetoglobosin RMeSH
Chaetoglobosin WMeSH
Chaetoglobosin bMeSH
Chaetoglobosin eMeSH
Chaetoglobosin FMeSH
Chaetoglobosin KMeSH
Chaetoglobosin uMeSH
Chemical FormulaC32H36N2O5
Average Mass528.6490 Da
Monoisotopic Mass528.26242 Da
IUPAC Name(1S,7E,9S,11E,13R,14S,16R,17S,18R,19S)-21-hydroxy-19-[(1H-indol-3-yl)methyl]-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.0^{1,18}.0^{14,16}]henicosa-7,11,20-triene-2,5,6-trione
Traditional Name(1S,7E,9S,11E,13R,14S,16R,17S,18R,19S)-21-hydroxy-19-(1H-indol-3-ylmethyl)-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.0^{1,18}.0^{14,16}]henicosa-7,11,20-triene-2,5,6-trione
CAS Registry NumberNot Available
SMILES
C[C@H]1[C@H]2[C@H](CC3=CNC4=CC=CC=C34)N=C(O)[C@@]22[C@@H](\C=C\C[C@H](C)\C=C(C)\C(=O)C(=O)CCC2=O)[C@@H]2O[C@]12C
InChI Identifier
InChI=1S/C32H36N2O5/c1-17-8-7-10-22-29-31(4,39-29)19(3)27-24(15-20-16-33-23-11-6-5-9-21(20)23)34-30(38)32(22,27)26(36)13-12-25(35)28(37)18(2)14-17/h5-7,9-11,14,16-17,19,22,24,27,29,33H,8,12-13,15H2,1-4H3,(H,34,38)/b10-7+,18-14+/t17-,19-,22-,24-,27-,29-,31+,32+/m0/s1
InChI KeyRIZAHVBYKWUPHQ-GNNSKLCBSA-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
Calonectria kyotensisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as chaetoglobosins. These are cytochalasans with a structure in which the hydrogenated isoindole bears an (indol-3-yl)methyl group.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassCytochalasans
Sub ClassChaetoglobosins
Direct ParentChaetoglobosins
Alternative Parents
Substituents
  • Chaetoglobosin skeleton
  • Macrolactam
  • Isoindolone
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Isoindoline
  • Isoindole or derivatives
  • Oxepane
  • Benzenoid
  • Substituted pyrrole
  • 2-pyrrolidone
  • Pyrrolidone
  • Heteroaromatic compound
  • Pyrrole
  • Pyrrolidine
  • Cyclic ketone
  • Carboxamide group
  • Ketone
  • Lactam
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Oxirane
  • Dialkyl ether
  • Azacycle
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic 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
logP4.73ChemAxon
pKa (Strongest Acidic)2.75ChemAxon
pKa (Strongest Basic)5.41ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area112.12 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity149.76 m³·mol⁻¹ChemAxon
Polarizability57.23 ųChemAxon
Number of Rings6ChemAxon
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 IDC00011309
Chemspider ID10235105
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound21603251
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Xiao J, Zhang Q, Gao YQ, Tang JJ, Zhang AL, Gao JM: Secondary metabolites from the endophytic Botryosphaeria dothidea of Melia azedarach and their antifungal, antibacterial, antioxidant, and cytotoxic activities. J Agric Food Chem. 2014 Apr 23;62(16):3584-90. doi: 10.1021/jf500054f. Epub 2014 Apr 9. [PubMed:24689437 ]
  2. Gao W, He Y, Li F, Chai C, Zhang J, Guo J, Chen C, Wang J, Zhu H, Hu Z, Zhang Y: Antibacterial activity against drug-resistant microbial pathogens of cytochalasan alkaloids from the arthropod-associated fungus Chaetomium globosum TW1-1. Bioorg Chem. 2019 Mar;83:98-104. doi: 10.1016/j.bioorg.2018.10.020. Epub 2018 Oct 10. [PubMed:30343206 ]
  3. Zhu X, Zhou D, Liang F, Wu Z, She Z, Li C: Penochalasin K, a new unusual chaetoglobosin from the mangrove endophytic fungus Penicillium chrysogenum V11 and its effective semi-synthesis. Fitoterapia. 2017 Nov;123:23-28. doi: 10.1016/j.fitote.2017.09.016. Epub 2017 Sep 27. [PubMed:28958956 ]
  4. Kim HY, Park HM, Lee CH: Mass spectrometry-based chemotaxonomic classification of Penicillium species (P. echinulatum, P. expansum, P. solitum, and P. oxalicum) and its correlation with antioxidant activity. J Microbiol Methods. 2012 Sep;90(3):327-35. doi: 10.1016/j.mimet.2012.06.006. Epub 2012 Jun 23. [PubMed:22732319 ]
  5. Straus DC: The possible role of fungal contamination in sick building syndrome. Front Biosci (Elite Ed). 2011 Jan 1;3(2):562-80. doi: 10.2741/e270. [PubMed:21196335 ]
  6. LOTUS database [Link]