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Record Information
Version2.0
Created at2022-09-10 01:27:24 UTC
Updated at2022-09-10 01:27:24 UTC
NP-MRD IDNP0293450
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1s,3s,4r,9r,12r)-9-methyl-10-oxo-7-[(1s)-1,3,3-trimethylcyclohexyl]-2,11-dioxatricyclo[6.3.1.0⁴,¹²]dodec-7-en-3-yl acetate
DescriptionTetrahydroaplysulphurin belongs to the class of organic compounds known as furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds. (1s,3s,4r,9r,12r)-9-methyl-10-oxo-7-[(1s)-1,3,3-trimethylcyclohexyl]-2,11-dioxatricyclo[6.3.1.0⁴,¹²]dodec-7-en-3-yl acetate is found in Cadlina luteomarginata. (1s,3s,4r,9r,12r)-9-methyl-10-oxo-7-[(1s)-1,3,3-trimethylcyclohexyl]-2,11-dioxatricyclo[6.3.1.0⁴,¹²]dodec-7-en-3-yl acetate was first documented in 2009 (PMID: 19601607). Based on a literature review a significant number of articles have been published on Tetrahydroaplysulphurin (PMID: 27822214) (PMID: 26356268) (PMID: 32586020) (PMID: 27041481) (PMID: 25724081) (PMID: 32281798).
Structure
Thumb
Synonyms
ValueSource
TetrahydroaplysulfurinGenerator
Chemical FormulaC22H32O5
Average Mass376.4930 Da
Monoisotopic Mass376.22497 Da
IUPAC Name(1S,3S,4R,9R,12R)-9-methyl-10-oxo-7-[(1S)-1,3,3-trimethylcyclohexyl]-2,11-dioxatricyclo[6.3.1.0^{4,12}]dodec-7-en-3-yl acetate
Traditional Name(1S,3S,4R,9R,12R)-9-methyl-10-oxo-7-[(1S)-1,3,3-trimethylcyclohexyl]-2,11-dioxatricyclo[6.3.1.0^{4,12}]dodec-7-en-3-yl acetate
CAS Registry NumberNot Available
SMILES
C[C@H]1C(=O)O[C@@H]2O[C@@H](OC(C)=O)[C@@H]3CCC(=C1[C@H]23)[C@@]1(C)CCCC(C)(C)C1
InChI Identifier
InChI=1S/C22H32O5/c1-12-16-15(22(5)10-6-9-21(3,4)11-22)8-7-14-17(16)20(26-18(12)24)27-19(14)25-13(2)23/h12,14,17,19-20H,6-11H2,1-5H3/t12-,14-,17-,19-,20-,22+/m1/s1
InChI KeyLYEXPFKXURJWNG-MEYBLWIUSA-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
Cadlina luteomarginataLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassFuropyrans
Sub ClassNot Available
Direct ParentFuropyrans
Alternative Parents
Substituents
  • Furopyran
  • Delta valerolactone
  • Delta_valerolactone
  • Dicarboxylic acid or derivatives
  • Oxane
  • Pyran
  • Furan
  • Tetrahydrofuran
  • Lactone
  • Carboxylic acid ester
  • Acetal
  • Carboxylic acid derivative
  • Oxacycle
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • 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
logP4.11ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area61.83 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity99.9 m³·mol⁻¹ChemAxon
Polarizability42.08 ųChemAxon
Number of Rings4ChemAxon
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 ID10356648
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound23247763
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Rateb ME, Houssen WE, Schumacher M, Harrison WT, Diederich M, Ebel R, Jaspars M: Bioactive diterpene derivatives from the marine sponge Spongionella sp. J Nat Prod. 2009 Aug;72(8):1471-6. doi: 10.1021/np900233c. [PubMed:19601607 ]
  2. Sanchez JA, Alfonso A, Rodriguez I, Alonso E, Cifuentes JM, Bermudez R, Rateb ME, Jaspars M, Houssen WE, Ebel R, Tabudravu J, Botana LM: Spongionella Secondary Metabolites, Promising Modulators of Immune Response through CD147 Receptor Modulation. Front Immunol. 2016 Oct 24;7:452. doi: 10.3389/fimmu.2016.00452. eCollection 2016. [PubMed:27822214 ]
  3. Sanchez JA, Alfonso A, Leiros M, Alonso E, Rateb ME, Jaspars M, Houssen WE, Ebel R, Botana LM: Spongionella Secondary Metabolites Regulate Store Operated Calcium Entry Modulating Mitochondrial Functioning in SH-SY5Y Neuroblastoma Cells. Cell Physiol Biochem. 2015;37(2):779-92. doi: 10.1159/000430395. Epub 2015 Sep 11. [PubMed:26356268 ]
  4. Bory A, Shilling AJ, Allen J, Azhari A, Roth A, Shaw LN, Kyle DE, Adams JH, Amsler CD, McClintock JB, Baker BJ: Bioactivity of Spongian Diterpenoid Scaffolds from the Antarctic Sponge Dendrilla antarctica. Mar Drugs. 2020 Jun 23;18(6). pii: md18060327. doi: 10.3390/md18060327. [PubMed:32586020 ]
  5. Sanchez JA, Alfonso A, Leiros M, Alonso E, Rateb ME, Jaspars M, Houssen WE, Ebel R, Tabudravu J, Botana LM: Identification of Spongionella compounds as cyclosporine A mimics. Pharmacol Res. 2016 May;107:407-414. doi: 10.1016/j.phrs.2016.03.029. Epub 2016 Apr 1. [PubMed:27041481 ]
  6. Leiros M, Alonso E, Rateb ME, Houssen WE, Ebel R, Jaspars M, Alfonso A, Botana LM: Gracilins: Spongionella-derived promising compounds for Alzheimer disease. Neuropharmacology. 2015 Jun;93:285-93. doi: 10.1016/j.neuropharm.2015.02.015. Epub 2015 Feb 24. [PubMed:25724081 ]
  7. Shilling AJ, Witowski CG, Maschek JA, Azhari A, Vesely BA, Kyle DE, Amsler CD, McClintock JB, Baker BJ: Spongian Diterpenoids Derived from the Antarctic Sponge Dendrilla antarctica Are Potent Inhibitors of the Leishmania Parasite. J Nat Prod. 2020 May 22;83(5):1553-1562. doi: 10.1021/acs.jnatprod.0c00025. Epub 2020 Apr 13. [PubMed:32281798 ]
  8. White AM, Pierens GK, Forster LC, Winters AE, Cheney KL, Garson MJ: Rearranged Diterpenes and Norditerpenes from Three Australian Goniobranchus Mollusks. J Nat Prod. 2016 Mar 25;79(3):477-83. doi: 10.1021/acs.jnatprod.5b00866. Epub 2015 Dec 23. [PubMed:26698272 ]
  9. Leiros M, Sanchez JA, Alonso E, Rateb ME, Houssen WE, Ebel R, Jaspars M, Alfonso A, Botana LM: Spongionella secondary metabolites protect mitochondrial function in cortical neurons against oxidative stress. Mar Drugs. 2014 Jan 27;12(2):700-18. doi: 10.3390/md12020700. [PubMed:24473170 ]
  10. LOTUS database [Link]