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Record Information
Version2.0
Created at2024-05-01 17:55:04 UTC
Updated at2024-09-03 04:20:33 UTC
NP-MRD IDNP0332878
Natural Product DOIhttps://doi.org/10.57994/2157
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-Dehydroxymelleolide F
Description4-Dehydroxymelleolide F belongs to the class of organic compounds known as melleolides and analogues. Melleolides and analogues are compounds with a structure characterized by the presence of a 2-hydroxy-4-methoxy-6-methylbenzoic acid derivative linked to a 3,6,6,7b-tetramethyl-cyclobuta[e]indene moiety. 4-Dehydroxymelleolide F was first documented in 2024 (PMID: 38390787). Based on a literature review very few articles have been published on 4-Dehydroxymelleolide F.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC23H30O5
Average Mass386.4880 Da
Monoisotopic Mass386.20932 Da
IUPAC Name(2R,2aR,4aS,7aS,7bR)-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,2aH,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate
Traditional Name(2R,2aR,4aS,7aS,7bR)-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,2aH,4aH,5H,7H,7aH-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate
CAS Registry NumberNot Available
SMILES
[H][C@@]12[C@@H](C[C@]1(C)[C@@]1([H])CC(C)(C)C[C@@]1([H])C=C2CO)OC(=O)C1=C(C)C=C(O)C=C1O
InChI Identifier
InChI=1S/C23H30O5/c1-12-5-15(25)7-17(26)19(12)21(27)28-18-10-23(4)16-9-22(2,3)8-13(16)6-14(11-24)20(18)23/h5-7,13,16,18,20,24-26H,8-11H2,1-4H3/t13-,16+,18-,20-,23-/m1/s1
InChI KeyGXPYMWBOQVLJGA-JQISRXLJSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HSQC NMR[1H, 13C] NMR Spectrum (2D, 500 MHz, C3D6O, experimental)sebastian.pfuetze@helmholtz-hzi.deHelmholtz-centre for infection researchSebastian Pfütze2024-05-01View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 500 MHz, C3D6O, experimental)sebastian.pfuetze@helmholtz-hzi.deHelmholtz-centre for infection researchSebastian Pfütze2024-05-01View Spectrum
ROESY NMR[1H, 1H] NMR Spectrum (2D, 500 MHz, C3D6O, experimental)sebastian.pfuetze@helmholtz-hzi.deHelmholtz-centre for infection researchSebastian Pfütze2024-05-01View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 500 MHz, C3D6O, experimental)sebastian.pfuetze@helmholtz-hzi.deHelmholtz-centre for infection researchSebastian Pfütze2024-05-01View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, C3D6O, experimental)sebastian.pfuetze@helmholtz-hzi.deHelmholtz-centre for infection researchSebastian Pfütze2024-05-01View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, C3D6O, experimental)sebastian.pfuetze@helmholtz-hzi.deHelmholtz-centre for infection researchSebastian Pfütze2024-05-01View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Armillaria ostoyae
      Not Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as melleolides and analogues. Melleolides and analogues are compounds with a structure characterized by the presence of a 2-hydroxy-4-methoxy-6-methylbenzoic acid derivative linked to a 3,6,6,7b-tetramethyl-cyclobuta[e]indene moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentMelleolides and analogues
Alternative Parents
Substituents
  • Melleolide-skeleton
  • P-hydroxybenzoic acid alkyl ester
  • P-hydroxybenzoic acid ester
  • O-hydroxybenzoic acid ester
  • Dihydroxybenzoic acid
  • Benzoate ester
  • Salicylic acid or derivatives
  • Benzoic acid or derivatives
  • M-cresol
  • Resorcinol
  • Benzoyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Toluene
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Alcohol
  • Organooxygen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic 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
logP4.56ChemAxon
pKa (Strongest Acidic)8.7ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity107.89 m³·mol⁻¹ChemAxon
Polarizability42.82 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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Pfutze S, Charria-Giron E, Schulzke E, Toshe R, Khonsanit A, Franke R, Surup F, Bronstrup M, Stadler M: Depicting the Chemical Diversity of Bioactive Meroterpenoids Produced by the Largest Organism on Earth. Angew Chem Int Ed Engl. 2024 Apr 15;63(16):e202318505. doi: 10.1002/anie.202318505. Epub 2024 Mar 14. [PubMed:38390787 ]
  2. DOI: 10.1002/anie.202318505