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Record Information
Version2.0
Created at2022-09-10 04:56:51 UTC
Updated at2022-09-10 04:56:52 UTC
NP-MRD IDNP0295767
Secondary Accession NumbersNone
Natural Product Identification
Common Nametrichoverritone
DescriptionTrichoverritone belongs to the class of organic compounds known as trichothecenes. These are sesquiterpene mycotoxins structurally characterized by the presence of an epoxide ring and a benzopyran derivative with a variant number of hydroxyl, acetyl, or other substituents. The most important structural features causing the biological activities of trichothecenes are the 12,13-epoxy ring, the presence of hydroxyl or acetyl groups at appropriate positions on the trichothecene nucleus and the structure and position of the side-chain. trichoverritone is found in Paramyrothecium roridum. trichoverritone was first documented in 2015 (PMID: 26320597). Based on a literature review very few articles have been published on trichoverritone (PMID: 31026874).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC35H46O11
Average Mass642.7420 Da
Monoisotopic Mass642.30401 Da
IUPAC Name(1'S,2S,2'R,7'R,9'R,11'R)-2'-({[(2E)-5-hydroxy-3-methylpent-2-enoyl]oxy}methyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-11'-yl (2Z,4E)-7-hydroxy-6-[2-(5-oxo-2,5-dihydrofuran-3-yl)ethoxy]octa-2,4-dienoate
Traditional Name(1'S,2S,2'R,7'R,9'R,11'R)-2'-({[(2E)-5-hydroxy-3-methylpent-2-enoyl]oxy}methyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^{2,7}]dodecan]-5'-en-11'-yl (2Z,4E)-7-hydroxy-6-[2-(5-oxo-2H-furan-3-yl)ethoxy]octa-2,4-dienoate
CAS Registry NumberNot Available
SMILES
CC(O)C(OCCC1=CC(=O)OC1)\C=C\C=C/C(=O)O[C@@H]1C[C@H]2O[C@@H]3C=C(C)CC[C@]3(COC(=O)\C=C(/C)CCO)[C@]1(C)[C@]21CO1
InChI Identifier
InChI=1S/C35H46O11/c1-22-9-12-34(20-43-31(39)16-23(2)10-13-36)28(15-22)45-29-18-27(33(34,4)35(29)21-44-35)46-30(38)8-6-5-7-26(24(3)37)41-14-11-25-17-32(40)42-19-25/h5-8,15-17,24,26-29,36-37H,9-14,18-21H2,1-4H3/b7-5+,8-6-,23-16+/t24?,26?,27-,28-,29-,33-,34-,35+/m1/s1
InChI KeySBZMQFWYHDOLHG-MZKSFLEOSA-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
Myrothecium roridumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as trichothecenes. These are sesquiterpene mycotoxins structurally characterized by the presence of an epoxide ring and a benzopyran derivative with a variant number of hydroxyl, acetyl, or other substituents. The most important structural features causing the biological activities of trichothecenes are the 12,13-epoxy ring, the presence of hydroxyl or acetyl groups at appropriate positions on the trichothecene nucleus and the structure and position of the side-chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentTrichothecenes
Alternative Parents
Substituents
  • Trichothecene skeleton
  • Tricarboxylic acid or derivatives
  • Fatty alcohol
  • Oxepane
  • Fatty acid ester
  • Fatty acyl
  • Oxane
  • 2-furanone
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Dihydrofuran
  • Secondary alcohol
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Oxirane
  • Dialkyl ether
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic 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
logP3.05ChemAxon
pKa (Strongest Acidic)7.16ChemAxon
pKa (Strongest Basic)-1.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area150.35 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity170.48 m³·mol⁻¹ChemAxon
Polarizability68.27 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00012660
Chemspider ID52085223
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound102595325
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Mondol MA, Surovy MZ, Islam MT, Schuffler A, Laatsch H: Macrocyclic Trichothecenes from Myrothecium roridum Strain M10 with Motility Inhibitory and Zoosporicidal Activities against Phytophthora nicotianae. J Agric Food Chem. 2015 Oct 14;63(40):8777-86. doi: 10.1021/acs.jafc.5b02366. Epub 2015 Sep 29. [PubMed:26320597 ]
  2. Lakornwong W, Kanokmedhakul K, Soytong K, Unartngam A, Tontapha S, Amornkitbamrung V, Kanokmedhakul S: Types A and D Trichothecene Mycotoxins from the Fungus Myrothecium roridum. Planta Med. 2019 Jul;85(9-10):774-780. doi: 10.1055/a-0895-5753. Epub 2019 Apr 26. [PubMed:31026874 ]
  3. LOTUS database [Link]