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Record Information
Version2.0
Created at2021-01-06 01:42:04 UTC
Updated at2024-09-03 04:18:14 UTC
NP-MRD IDNP0016811
Natural Product DOIhttps://doi.org/10.57994/1328
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-epi-microsphaeropsisin
Provided ByNPAtlasNPAtlas Logo
Description 4-epi-microsphaeropsisin is found in Didymosphaeria variabile and Paraconiothyrium. 4-epi-microsphaeropsisin was first documented in 2017 (PMID: 28737947). Based on a literature review very few articles have been published on 4-epi-microsphaeropsisin (PMID: 37159940).
Structure
Data?1624506285
SynonymsNot Available
Chemical FormulaC16H22O4
Average Mass278.3480 Da
Monoisotopic Mass278.15181 Da
IUPAC Name(3S,3aS,4aS,5S,9aR)-3a-hydroxy-9a-methoxy-3,4a,5-trimethyl-2H,3H,3aH,4H,4aH,5H,6H,9aH-naphtho[2,3-b]furan-6-one
Traditional Name(3S,3aS,4aS,5S,9aR)-3a-hydroxy-9a-methoxy-3,4a,5-trimethyl-2H,3H,4H,5H-naphtho[2,3-b]furan-6-one
CAS Registry NumberNot Available
SMILES
CO[C@]12OC[C@H](C)[C@@]1(O)C[C@@]1(C)[C@H](C)C(=O)C=CC1=C2
InChI Identifier
InChI=1S/C16H22O4/c1-10-8-20-16(19-4)7-12-5-6-13(17)11(2)14(12,3)9-15(10,16)18/h5-7,10-11,18H,8-9H2,1-4H3/t10-,11+,14-,15-,16+/m0/s1
InChI KeySFCGEIHSBRXLDW-DCIASYOESA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HMBC NMR[1H, 13C] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental)dongdong.wang@nih.govNCI-FrederickDong Wang2024-05-11View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, C2D6OS, experimental)dongdong.wang@nih.govNCI-FrederickDong Wang2024-05-11View Spectrum
HSQC NMR[1H, 13C] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental)dongdong.wang@nih.govNCI-FrederickDong Wang2024-05-11View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental)dongdong.wang@nih.govNCI-FrederickDong Wang2024-05-11View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, C2D6OS, experimental)dongdong.wang@nih.govNCI-FrederickDong Wang2024-05-11View Spectrum
ROESY NMR[1H, 1H] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental)dongdong.wang@nih.govNCI-FrederickDong Wang2024-05-11View Spectrum
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
Didymosphaeria variabileLOTUS Database
ParaconiothyriumNPAtlas
Paraconiothyrium sporulosum
      Not Available
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
logP1.38ALOGPS
logP2.01ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)12.61ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity76.79 m³·mol⁻¹ChemAxon
Polarizability29.78 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
NPAtlas IDNPA023843
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID78439321
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound139591066
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Amand S, Vallet M, Guedon L, Genta-Jouve G, Wien F, Mann S, Dupont J, Prado S, Nay B: A Reactive Eremophilane and Its Antibacterial 2(1H)-Naphthalenone Rearrangement Product, Witnesses of a Microbial Chemical Warfare. Org Lett. 2017 Aug 4;19(15):4038-4041. doi: 10.1021/acs.orglett.7b01788. Epub 2017 Jul 24. [PubMed:28737947 ]
  2. Sun B, Wang D, Ren J, Wang C, Yan P, Gustafson KR, Jiang W: Paraconulones A-G: Eremophilane Sesquiterpenoids from the Marine-Derived Fungus Paraconiothyrium sporulosum DL-16. J Nat Prod. 2023 May 26;86(5):1360-1369. doi: 10.1021/acs.jnatprod.3c00221. Epub 2023 May 9. [PubMed:37159940 ]