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Record Information
Version1.0
Created at2022-09-03 13:31:52 UTC
Updated at2022-09-03 13:31:52 UTC
NP-MRD IDNP0175950
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3s,8r,9r,11e)-8,9,16-trihydroxy-13,14-dimethoxy-3-methyl-4,5,6,8,9,10-hexahydro-3h-2-benzoxacyclotetradecine-1,7-dione
DescriptionHamigeromycin E belongs to the class of organic compounds known as zearalenones. These are macrolides which contains a fourteen-member lactone fused to 1,3-dihydroxybenzene. (3s,8r,9r,11e)-8,9,16-trihydroxy-13,14-dimethoxy-3-methyl-4,5,6,8,9,10-hexahydro-3h-2-benzoxacyclotetradecine-1,7-dione is found in Hamigera avellanea. It was first documented in 2022 (PMID: 36057434). Based on a literature review a significant number of articles have been published on Hamigeromycin E (PMID: 36057292) (PMID: 36057258) (PMID: 36057245) (PMID: 36057242) (PMID: 36057226).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC20H26O8
Average Mass394.4200 Da
Monoisotopic Mass394.16277 Da
IUPAC Name(3S,8R,9R)-8,9,16-trihydroxy-13,14-dimethoxy-3-methyl-3,4,5,6,7,8,9,10-octahydro-1H-2-benzoxacyclotetradecine-1,7-dione
Traditional Name(3S,8R,9R)-8,9,16-trihydroxy-13,14-dimethoxy-3-methyl-4,5,6,8,9,10-hexahydro-3H-2-benzoxacyclotetradecine-1,7-dione
CAS Registry NumberNot Available
SMILES
COC1=CC(O)=C2C(\C=C\C[C@@H](O)[C@@H](O)C(=O)CCC[C@H](C)OC2=O)=C1OC
InChI Identifier
InChI=1S/C20H26O8/c1-11-6-4-8-13(21)18(24)14(22)9-5-7-12-17(20(25)28-11)15(23)10-16(26-2)19(12)27-3/h5,7,10-11,14,18,22-24H,4,6,8-9H2,1-3H3/b7-5+/t11-,14+,18-/m0/s1
InChI KeyINOAIAVUQLBIID-KFRKGIJFSA-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
Hamigera avellaneaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as zearalenones. These are macrolides which contains a fourteen-member lactone fused to 1,3-dihydroxybenzene.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassMacrolides and analogues
Sub ClassZearalenones
Direct ParentZearalenones
Alternative Parents
Substituents
  • Zearalenone-skeleton
  • Anisole
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Benzenoid
  • Vinylogous acid
  • Cyclic ketone
  • 1,2-diol
  • Secondary alcohol
  • Carboxylic acid ester
  • Ketone
  • Lactone
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Polyol
  • Ether
  • Oxacycle
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • 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
logP1.6ALOGPS
logP2.42ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)10.09ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area122.52 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity102.14 m³·mol⁻¹ChemAxon
Polarizability40.47 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 ID78437241
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound45140076
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Kindler J, Koenig J, Lerch S, van der Venne P, Resch F, Kaess M: Increased immunological markers in female adolescents with non-suicidal self-injury. J Affect Disord. 2022 Dec 1;318:191-195. doi: 10.1016/j.jad.2022.08.125. Epub 2022 Aug 31. [PubMed:36057292 ]
  2. Geng S, Li Q, Zhou X, Zheng J, Liu H, Zeng J, Yang R, Fu H, Hao F, Feng Q, Qi B: Gut commensal E. coli outer membrane proteins activate the host food digestive system through neural-immune communication. Cell Host Microbe. 2022 Oct 12;30(10):1401-1416.e8. doi: 10.1016/j.chom.2022.08.004. Epub 2022 Sep 2. [PubMed:36057258 ]
  3. Ma Z, Wang D, Chen XY, Tao Y, Yang Z, Zhang Y, Huang S, Bu L, Wang C, Wu L, Fan F: Network structure of insomnia and depressive symptoms among shift workers in China. Sleep Med. 2022 Dec;100:150-156. doi: 10.1016/j.sleep.2022.08.010. Epub 2022 Aug 24. [PubMed:36057245 ]
  4. Dos Anjos Adur M, Chatre P, Metayer V, Drapeau A, Pillonetto M, Penkal ML, Lopes JK, Beirao BCB, Madec JY, de Macedo REF, Haenni M: Escherichia coli ST224 and IncF/bla(CTX-M-55) plasmids drive resistance to extended-spectrum cephalosporins in poultry flocks in Parana, Brazil. Int J Food Microbiol. 2022 Nov 2;380:109885. doi: 10.1016/j.ijfoodmicro.2022.109885. Epub 2022 Aug 27. [PubMed:36057242 ]
  5. Lou J, Xu J, Zhang Y, Sun Y, Fang A, Liu J, Mur LAJ, Ji B: PPsNet: An improved deep learning model for microsatellite instability high prediction in colorectal cancer from whole slide images. Comput Methods Programs Biomed. 2022 Oct;225:107095. doi: 10.1016/j.cmpb.2022.107095. Epub 2022 Aug 28. [PubMed:36057226 ]
  6. LOTUS database [Link]