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Record Information
Version2.0
Created at2022-09-12 00:38:06 UTC
Updated at2022-09-12 00:38:06 UTC
NP-MRD IDNP0322070
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3s)-12,14-dihydroxy-3-methyl-4,5,6,7,8,10-hexahydro-3h-2-benzoxacyclododecine-1,9-dione
DescriptionDihydroresorcylide belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. (3s)-12,14-dihydroxy-3-methyl-4,5,6,7,8,10-hexahydro-3h-2-benzoxacyclododecine-1,9-dione is found in Sarocladium zeae. (3s)-12,14-dihydroxy-3-methyl-4,5,6,7,8,10-hexahydro-3h-2-benzoxacyclododecine-1,9-dione was first documented in 2008 (PMID: 18416554). Based on a literature review a small amount of articles have been published on Dihydroresorcylide (PMID: 27417331) (PMID: 28436691) (PMID: 21425679).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC16H20O5
Average Mass292.3310 Da
Monoisotopic Mass292.13107 Da
IUPAC Name(3S)-12,14-dihydroxy-3-methyl-3,4,5,6,7,8,9,10-octahydro-1H-2-benzoxacyclododecine-1,9-dione
Traditional Name(3S)-12,14-dihydroxy-3-methyl-4,5,6,7,8,10-hexahydro-3H-2-benzoxacyclododecine-1,9-dione
CAS Registry NumberNot Available
SMILES
C[C@H]1CCCCCC(=O)CC2=CC(O)=CC(O)=C2C(=O)O1
InChI Identifier
InChI=1S/C16H20O5/c1-10-5-3-2-4-6-12(17)7-11-8-13(18)9-14(19)15(11)16(20)21-10/h8-10,18-19H,2-7H2,1H3/t10-/m0/s1
InChI KeyZUWLHVBAEWLIDQ-JTQLQIEISA-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
Sarocladium zeaeLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassMacrolides and analogues
Sub ClassNot Available
Direct ParentMacrolides and analogues
Alternative Parents
Substituents
  • Macrolide
  • Dihydroxybenzoic acid
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Vinylogous acid
  • Carboxylic acid ester
  • Ketone
  • Lactone
  • Cyclic ketone
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic 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
logP3.76ChemAxon
pKa (Strongest Acidic)8.5ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.83 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity78.02 m³·mol⁻¹ChemAxon
Polarizability30.59 ųChemAxon
Number of Rings2ChemAxon
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 ID77430115
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound24866778
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. He WJ, Zhou XJ, Qin XC, Mai YX, Lin XP, Liao SR, Yang B, Zhang T, Tu ZC, Wang JF, Liu Y: Quinone/hydroquinone meroterpenoids with antitubercular and cytotoxic activities produced by the sponge-derived fungus Gliomastix sp. ZSDS1-F7. Nat Prod Res. 2017 Mar;31(5):604-609. doi: 10.1080/14786419.2016.1207076. Epub 2016 Jul 15. [PubMed:27417331 ]
  2. Poling SM, Wicklow DT, Rogers KD, Gloer JB: Acremonium zeae, a protective endophyte of maize, produces dihydroresorcylide and 7-hydroxydihydroresorcylides. J Agric Food Chem. 2008 May 14;56(9):3006-9. doi: 10.1021/jf073274f. Epub 2008 Apr 17. [PubMed:18416554 ]
  3. Jiang CS, Zhang L, Gong JX, Li JY, Yao LG, Li J, Guo YW: Concise synthesis and PTP1B inhibitory activity of (R)- and (S)-dihydroresorcylide. J Asian Nat Prod Res. 2017 Dec;19(12):1204-1213. doi: 10.1080/10286020.2017.1317752. Epub 2017 Apr 24. [PubMed:28436691 ]
  4. Zeng J, Valiente J, Zhan J: Generation of two new macrolactones through sequential biotransformation of dihydroresorcylide. Nat Prod Commun. 2011 Feb;6(2):223-6. [PubMed:21425679 ]
  5. LOTUS database [Link]