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Record Information
Version1.0
Created at2022-09-04 23:33:10 UTC
Updated at2022-09-04 23:33:10 UTC
NP-MRD IDNP0203965
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3s,8s,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 C 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,8s,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: 36070879). Based on a literature review a significant number of articles have been published on Hamigeromycin C (PMID: 36070862) (PMID: 36070861) (PMID: 36070818) (PMID: 36070817) (PMID: 36070688) (PMID: 36070805).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC20H26O8
Average Mass394.4200 Da
Monoisotopic Mass394.16277 Da
IUPAC Name(3S,8S,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,8S,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-YARXNDSESA-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
logP2.42ChemAxon
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
Polarizability40.31 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 ID78438508
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound45140074
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Premalatha A, Vijayalakshmi K, Shanmugavel M, Rajakumar GS: Optimization of culture conditions for enhanced production of extracellular alpha-amylase using solid-state and submerged fermentation from Aspergillus tamarii MTCC5152. Biotechnol Appl Biochem. 2022 Sep 7. doi: 10.1002/bab.2403. [PubMed:36070879 ]
  2. Huang W, Le S, Sun Y, Lin DJ, Yao M, Shi Y, Yan J: Mechanical Stabilization of a Bacterial Adhesion Complex. J Am Chem Soc. 2022 Sep 21;144(37):16808-16818. doi: 10.1021/jacs.2c03961. Epub 2022 Sep 7. [PubMed:36070862 ]
  3. Byrne C, Cosnefroy A, Eston R, Lee JKW, Noakes T: Continuous Thermoregulatory Responses to a Mass-Participation 89-km Ultramarathon Road Race. Int J Sports Physiol Perform. 2022 Sep 6:1-9. doi: 10.1123/ijspp.2022-0043. [PubMed:36070861 ]
  4. Wang B, Qi J, Xie M, Wang X, Xu J, Yu Z, Zhao W, Xiao Y, Wei W: Enhancement of sugar release from sugarcane bagasse through NaOH-catalyzed ethylene glycol pretreatment and water-soluble sulfonated lignin. Int J Biol Macromol. 2022 Sep 5;221:38-47. doi: 10.1016/j.ijbiomac.2022.08.193. [PubMed:36070818 ]
  5. Balog M, Anderson A, Gurumurthy CB, Quadros RM, Korade Z, Mirnics K: Knock-in mouse models for studying somatostatin and cholecystokinin expressing cells. J Neurosci Methods. 2022 Nov 1;381:109704. doi: 10.1016/j.jneumeth.2022.109704. Epub 2022 Sep 5. [PubMed:36070817 ]
  6. Caires R, Garrud TAC, Romero LO, Fernandez-Pena C, Vasquez V, Jaggar JH, Cordero-Morales JF: Genetic- and diet-induced omega-3 fatty acid enrichment enhances TRPV4-mediated vasodilation in mice. Cell Rep. 2022 Sep 6;40(10):111306. doi: 10.1016/j.celrep.2022.111306. [PubMed:36070688 ]
  7. Vudriko P, Echodu R, Tashiro M, Oka N, Hayashi K, Ichikawa-Seki M: Population structure, molecular characterization, and phylogenetic analysis of Fasciola gigantica from two locations in Uganda. Infect Genet Evol. 2022 Oct;104:105359. doi: 10.1016/j.meegid.2022.105359. Epub 2022 Sep 5. [PubMed:36070805 ]
  8. Pergialiotis V, Psarris A, Antsaklis P, Theodora M, Papapanagiotou A, Rodolakis A, Daskalakis G: Cervical Cerclage vs. Pessary in Women with a Short Cervix on Ultrasound. Ultraschall Med. 2023 Mar 7. doi: 10.1055/a-1938-6042. [PubMed:36070802 ]
  9. Halder S, Sanchez A, Ranjha L, Reginato G, Ceppi I, Acharya A, Anand R, Cejka P: Double-stranded DNA binding function of RAD51 in DNA protection and its regulation by BRCA2. Mol Cell. 2022 Oct 6;82(19):3553-3565.e5. doi: 10.1016/j.molcel.2022.08.014. Epub 2022 Sep 6. [PubMed:36070766 ]
  10. Dai S, Tang X, Li L, Ishidate T, Ozturk AR, Chen H, Dude AL, Yan YH, Dong MQ, Shen EZ, Mello CC: A family of C. elegans VASA homologs control Argonaute pathway specificity and promote transgenerational silencing. Cell Rep. 2022 Sep 6;40(10):111265. doi: 10.1016/j.celrep.2022.111265. [PubMed:36070689 ]
  11. LOTUS database [Link]