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Record Information
Version1.0
Created at2022-09-05 21:12:03 UTC
Updated at2022-09-05 21:12:04 UTC
NP-MRD IDNP0220009
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1s,3e,6r,7e,9s,11e,13r,14s,16r,17s,18r,19s)-17-ethyl-6,21-dihydroxy-19-[(1r)-1-(1h-indol-3-yl)ethyl]-7,9,16-trimethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-3,7,11,20-tetraene-2,5-dione
DescriptionChaetoglobosin K, 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,3e,6r,7e,9s,11e,13r,14s,16r,17s,18r,19s)-17-ethyl-6,21-dihydroxy-19-[(1r)-1-(1h-indol-3-yl)ethyl]-7,9,16-trimethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-3,7,11,20-tetraene-2,5-dione is found in Stenocarpella macrospora. It was first documented in 2013 (PMID: 23695013). Based on a literature review a significant number of articles have been published on Chaetoglobosin K (PMID: 24504633) (PMID: 30542835) (PMID: 25304379) (PMID: 25404879).
Structure
Thumb
Synonyms
ValueSource
Chaetoglobosin aMeSH
Chaetoglobosin bMeSH
Chaetoglobosin CMeSH
Chaetoglobosin DMeSH
Chaetoglobosin eMeSH
Chaetoglobosin FMeSH
Chaetoglobosin QMeSH
Chaetoglobosin RMeSH
Chaetoglobosin TMeSH
Chaetoglobosin uMeSH
Chaetoglobosin VMeSH
Chaetoglobosin WMeSH
Chaetoglobosin yMeSH
ChaetoglobosinsMeSH
Penochalasin KMeSH
Chemical FormulaC34H40N2O5
Average Mass556.7030 Da
Monoisotopic Mass556.29372 Da
IUPAC Name(1R,3E,6R,7E,9S,11E,13R,14S,16R,17S,18R,19S)-17-ethyl-6-hydroxy-19-[(1R)-1-(1H-indol-3-yl)ethyl]-7,9,16-trimethyl-15-oxa-20-azatetracyclo[11.8.0.0^{1,18}.0^{14,16}]henicosa-3,7,11-triene-2,5,21-trione
Traditional Name(1R,3E,6R,7E,9S,11E,13R,14S,16R,17S,18R,19S)-17-ethyl-6-hydroxy-19-[(1R)-1-(1H-indol-3-yl)ethyl]-7,9,16-trimethyl-15-oxa-20-azatetracyclo[11.8.0.0^{1,18}.0^{14,16}]henicosa-3,7,11-triene-2,5,21-trione
CAS Registry NumberNot Available
SMILES
CC[C@H]1[C@H]2[C@@H](NC(=O)[C@@]22[C@@H](\C=C/C[C@H](C)\C=C(C)/[C@@H](O)C(=O)\C=C/C2=O)[C@@H]2O[C@]12C)[C@H](C)C1=CNC2=CC=CC=C12
InChI Identifier
InChI=1S/C34H40N2O5/c1-6-23-28-29(20(4)22-17-35-25-13-8-7-11-21(22)25)36-32(40)34(28)24(31-33(23,5)41-31)12-9-10-18(2)16-19(3)30(39)26(37)14-15-27(34)38/h7-9,11-18,20,23-24,28-31,35,39H,6,10H2,1-5H3,(H,36,40)/b12-9-,15-14-,19-16-/t18-,20+,23-,24-,28-,29-,30+,31-,33+,34+/m0/s1
InChI KeyRSYKJHLWNMXRKZ-RYYZKKQRSA-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
Stenocarpella macrosporaLOTUS 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
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Oxirane
  • Dialkyl ether
  • Azacycle
  • Carboxylic acid derivative
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Alcohol
  • 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
logP4.49ALOGPS
logP5.14ChemAxon
logS-5.7ALOGPS
pKa (Strongest Acidic)12.81ChemAxon
pKa (Strongest Basic)-2.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area111.79 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity159.92 m³·mol⁻¹ChemAxon
Polarizability60.31 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
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 IDC00011318
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound102093923
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Rogers KD, Cannistra JC, Gloer JB, Wicklow DT: Diplodiatoxin, chaetoglobosins, and diplonine associated with a field outbreak of Stenocarpella ear rot in Illinois. Mycotoxin Res. 2014 May;30(2):61-70. doi: 10.1007/s12550-014-0188-0. Epub 2014 Feb 7. [PubMed:24504633 ]
  2. Curless BP, Uko NE, Matesic DF: Modulator of the PI3K/Akt oncogenic pathway affects mTOR complex 2 in human adenocarcinoma cells. Invest New Drugs. 2019 Oct;37(5):902-911. doi: 10.1007/s10637-018-0705-7. Epub 2018 Dec 13. [PubMed:30542835 ]
  3. Li B, Gao Y, Rankin GO, Rojanasakul Y, Cutler SJ, Tu Y, Chen YC: Chaetoglobosin K induces apoptosis and G2 cell cycle arrest through p53-dependent pathway in cisplatin-resistant ovarian cancer cells. Cancer Lett. 2015 Jan 28;356(2 Pt B):418-33. doi: 10.1016/j.canlet.2014.09.023. Epub 2014 Oct 7. [PubMed:25304379 ]
  4. Luo H, Li B, Li Z, Cutler SJ, Rankin GO, Chen YC: Chaetoglobosin K inhibits tumor angiogenesis through downregulation of vascular epithelial growth factor-binding hypoxia-inducible factor 1alpha. Anticancer Drugs. 2013 Aug;24(7):715-24. doi: 10.1097/CAD.0b013e3283627a0b. [PubMed:23695013 ]
  5. Matesic DF, Ali A, Sidorova TS, Burns TJ: A Cell-Cell Communication Marker for Identifying Targeted Tumor Therapies. Curr Bioact Compd. 2013;9(3):255-262. doi: 10.2174/157340720903140119155322. [PubMed:25404879 ]
  6. LOTUS database [Link]