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Record Information
Version1.0
Created at2022-09-05 21:34:11 UTC
Updated at2022-09-05 21:34:11 UTC
NP-MRD IDNP0220299
Secondary Accession NumbersNone
Natural Product Identification
Common Name(5s,7s,10as,13s,13as,14s,16ar)-5,16-dihydroxy-7,9,12,13-tetramethyl-14-(2-methylpropyl)-5h,6h,7h,8h,10ah,13h,13ah,14h-oxacyclododeca[2,3-d]isoindol-2-one
Description16Alpha-methylaspochalasin J belongs to the class of organic compounds known as aspochalasins. These are cytochalasans with a structure in which the hydrogenated isoindole bears a 2-methylpropyl group. (5s,7s,10as,13s,13as,14s,16ar)-5,16-dihydroxy-7,9,12,13-tetramethyl-14-(2-methylpropyl)-5h,6h,7h,8h,10ah,13h,13ah,14h-oxacyclododeca[2,3-d]isoindol-2-one is found in Westerdykella dispersa. It was first documented in 2022 (PMID: 36075521). Based on a literature review a significant number of articles have been published on 16alpha-methylaspochalasin J (PMID: 36075137) (PMID: 36075073) (PMID: 36075009) (PMID: 36075008).
Structure
Thumb
Synonyms
ValueSource
16a-Methylaspochalasin JGenerator
16Α-methylaspochalasin JGenerator
Chemical FormulaC25H37NO4
Average Mass415.5740 Da
Monoisotopic Mass415.27226 Da
IUPAC Name(5S,7S,13S,13aS,14S,16aR,16bS)-5,16-dihydroxy-7,9,12,13-tetramethyl-14-(2-methylpropyl)-2H,5H,6H,7H,8H,13H,13aH,14H,16bH-oxacyclododeca[3,2-e]isoindol-2-one
Traditional Name(5S,7S,13S,13aS,14S,16aR,16bS)-5,16-dihydroxy-7,9,12,13-tetramethyl-14-(2-methylpropyl)-5H,6H,7H,8H,13H,13aH,14H,16bH-oxacyclododeca[3,2-e]isoindol-2-one
CAS Registry NumberNot Available
SMILES
CC(C)C[C@@H]1N=C(O)[C@@]23OC(=O)C=C[C@@H](O)C[C@@H](C)CC(C)=C[C@H]2C=C(C)[C@@H](C)[C@@H]13
InChI Identifier
InChI=1S/C25H37NO4/c1-14(2)9-21-23-18(6)17(5)13-19-11-15(3)10-16(4)12-20(27)7-8-22(28)30-25(19,23)24(29)26-21/h7-8,11,13-14,16,18-21,23,27H,9-10,12H2,1-6H3,(H,26,29)/t16-,18+,19-,20+,21-,23-,25+/m0/s1
InChI KeyORYHRHGVSOQILB-BAFAARCQSA-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
Westerdykella dispersaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aspochalasins. These are cytochalasans with a structure in which the hydrogenated isoindole bears a 2-methylpropyl group.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassCytochalasans
Sub ClassAspochalasins
Direct ParentAspochalasins
Alternative Parents
Substituents
  • Lactone aspochalasin skeleton
  • Isoindolone
  • Isoindole or derivatives
  • Isoindole
  • Isoindoline
  • 2-pyrrolidone
  • Pyrrolidone
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Pyrrolidine
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Lactone
  • Lactam
  • Carboxylic acid ester
  • Carboxamide group
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • 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
logP3.47ChemAxon
pKa (Strongest Acidic)2.07ChemAxon
pKa (Strongest Basic)5.08ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area79.12 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity120.73 m³·mol⁻¹ChemAxon
Polarizability47.56 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound146682507
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Ozlem-Caliskan S, Ilikci-Sagkan R, Karakas H, Sever S, Yildirim C, Balikci M, Ertabaklar H: Efficacy of Malachite green mediated Photodynamic therapy on treatment of Cutaneous Leishmaniasis: in vitro study. Photodiagnosis Photodyn Ther. 2022 Sep 5:103111. doi: 10.1016/j.pdpdt.2022.103111. [PubMed:36075521 ]
  2. Bloch E, Sikorski EL, Pontoriero D, Day EK, Berger BW, Lazzara MJ, Thevenin D: Correction: Disrupting the transmembrane domain-mediated oligomerization of protein tyrosine phosphatase receptor J inhibits EGFR-driven cancer cell phenotypes. J Biol Chem. 2022 Sep;298(9):102416. doi: 10.1016/j.jbc.2022.102416. Epub 2022 Sep 5. [PubMed:36075137 ]
  3. Yoshida N, Ishikawa H, Otani T, Goto C, Matsuda T, Takeuchi Y, Sano Y, Itoh Y, Suzuki S, Mutoh M: Aspirin-Mediated Prevention of Colorectal Adenomas Recurrence is Affected by Blood Biochemistry and Nutritional Intake. Cancer Prev Res (Phila). 2022 Dec 1;15(12):837-846. doi: 10.1158/1940-6207.CAPR-22-0144. [PubMed:36075073 ]
  4. Matthay EC, Mousli LM, Fu C, Zhang S, Ponicki WR, Gruenewald P, Apollonio DE, Schmidt LA: Equity in Coverage of Local Cannabis Control Policies in California, 2020‒2021. Am J Public Health. 2022 Nov;112(11):1640-1650. doi: 10.2105/AJPH.2022.307041. Epub 2022 Sep 8. [PubMed:36075009 ]
  5. Garcia-Grossman IR, Gransee L, Williams B: Strategies for Addressing Vaccine Hesitancy Within California State Prisons in 2021 and Beyond. Am J Public Health. 2022 Nov;112(11):1543-1545. doi: 10.2105/AJPH.2022.307042. Epub 2022 Sep 8. [PubMed:36075008 ]
  6. LOTUS database [Link]