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Record Information
Version1.0
Created at2020-12-09 00:10:22 UTC
Updated at2021-07-15 16:45:26 UTC
NP-MRD IDNP0003073
Secondary Accession NumbersNone
Natural Product Identification
Common NameIlludin H
Provided ByNPAtlasNPAtlas Logo
Description(1'R,3'R,4'R,6'S)-1',3',4',6'-tetrahydroxy-2',2',4',6'-tetramethyl-1',2',3',4',6',7'-hexahydrospiro[cyclopropane-1,5'-indene]-7'-one belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. Illudin H is found in Omphalotus nidiformis. It was first documented in 1999 (PMID: 10579869). Based on a literature review very few articles have been published on (1'R,3'R,4'R,6'S)-1',3',4',6'-tetrahydroxy-2',2',4',6'-tetramethyl-1',2',3',4',6',7'-hexahydrospiro[cyclopropane-1,5'-indene]-7'-one.
Structure
Data?1624573717
SynonymsNot Available
Chemical FormulaC15H22O5
Average Mass282.3360 Da
Monoisotopic Mass282.14672 Da
IUPAC Name(1'R,3'R,4'R,6'S)-1',3',4',6'-tetrahydroxy-2',2',4',6'-tetramethyl-1',2',3',4',6',7'-hexahydrospiro[cyclopropane-1,5'-indene]-7'-one
Traditional Name(1'R,3'R,4'R,6'S)-1',3',4',6'-tetrahydroxy-2',2',4',6'-tetramethyl-1',3'-dihydrospiro[cyclopropane-1,5'-indene]-7'-one
CAS Registry NumberNot Available
SMILES
CC1(C)[C@@H](O)C2=C([C@@H]1O)[C@@](C)(O)C1(CC1)[C@](C)(O)C2=O
InChI Identifier
InChI=1S/C15H22O5/c1-12(2)9(16)7-8(11(12)18)13(3,19)15(5-6-15)14(4,20)10(7)17/h9,11,16,18-20H,5-6H2,1-4H3/t9-,11-,13+,14+/m0/s1
InChI KeyMVHBMSFOLKLQJQ-BNQQVVLKSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Omphalotus nidiformis
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentCyclohexenones
Alternative Parents
Substituents
  • Cyclohexenone
  • Acyloin
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Polyol
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic 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
logP0.15ALOGPS
logP-0.41ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)12.64ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity71.8 m³·mol⁻¹ChemAxon
Polarizability29.01 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
NPAtlas IDNPA001040
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID78440011
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound139583384
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Burgess ML, Zhang YL, Barrow KD: Characterization of new illudanes, illudins F, G, and H from the basidiomycete omphalotus nidiformis J Nat Prod. 1999 Nov;62(11):1542-4. doi: 10.1021/np990247d. [PubMed:10579869 ]