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Record Information
Version2.0
Created at2022-09-05 18:03:19 UTC
Updated at2022-09-05 18:03:19 UTC
NP-MRD IDNP0217640
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1'r,2s,3s,3'r,5r,7'r,9's,10'e)-9'-hydroxy-10'-(hydroxymethyl)-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)spiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecane]-10',13'-dien-12'-one
DescriptionOphiobolin J belongs to the class of organic compounds known as ophiobolane sesterterpenoids. These are sesterterpnoids with a structure based on the ophiobolane backbone. Ophiobolane is a tricyclic compound consisting of two cyclopentane rings joined by a cyclooctane ring, and carries a methyl group at the 1-, 4-, and 8-position, as well as a 6-methylheptane group at the 12-position. (1'r,2s,3s,3'r,5r,7'r,9's,10'e)-9'-hydroxy-10'-(hydroxymethyl)-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)spiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecane]-10',13'-dien-12'-one is found in Drechslera gigantea. (1'r,2s,3s,3'r,5r,7'r,9's,10'e)-9'-hydroxy-10'-(hydroxymethyl)-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)spiro[oxolane-2,6'-tricyclo[9.3.0.0³,⁷]tetradecane]-10',13'-dien-12'-one was first documented in 2006 (PMID: 16962149). Based on a literature review very few articles have been published on Ophiobolin J.
Structure
Thumb
Synonyms
ValueSource
8-Epi-ophiobolin JMeSH
Chemical FormulaC25H36O4
Average Mass400.5590 Da
Monoisotopic Mass400.26136 Da
IUPAC Name(1'R,2S,3S,3'R,5R,7'R,9'S)-9'-hydroxy-10'-(hydroxymethyl)-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)spiro[oxolane-2,6'-tricyclo[9.3.0.0^{3,7}]tetradecane]-10',13'-dien-12'-one
Traditional Name(1'R,2S,3S,3'R,5R,7'R,9'S)-9'-hydroxy-10'-(hydroxymethyl)-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)spiro[oxolane-2,6'-tricyclo[9.3.0.0^{3,7}]tetradecane]-10',13'-dien-12'-one
CAS Registry NumberNot Available
SMILES
C[C@H]1C[C@@H](O[C@@]11CC[C@]2(C)C[C@@H]3C(C)=CC(=O)\C3=C(CO)\[C@@H](O)C[C@@H]12)C=C(C)C
InChI Identifier
InChI=1S/C25H36O4/c1-14(2)8-17-10-16(4)25(29-17)7-6-24(5)12-18-15(3)9-21(28)23(18)19(13-26)20(27)11-22(24)25/h8-9,16-18,20,22,26-27H,6-7,10-13H2,1-5H3/b23-19+/t16-,17-,18+,20-,22+,24+,25-/m0/s1
InChI KeyLFYREHKMIHWZQF-NULHPQIKSA-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
Drechslera giganteaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ophiobolane sesterterpenoids. These are sesterterpnoids with a structure based on the ophiobolane backbone. Ophiobolane is a tricyclic compound consisting of two cyclopentane rings joined by a cyclooctane ring, and carries a methyl group at the 1-, 4-, and 8-position, as well as a 6-methylheptane group at the 12-position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesterterpenoids
Direct ParentOphiobolane sesterterpenoids
Alternative Parents
Substituents
  • Ophiobolane sesterterpenoid
  • Oxolane
  • Ketone
  • Secondary alcohol
  • Dialkyl ether
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • 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
logP3.32ChemAxon
pKa (Strongest Acidic)14.36ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity116.6 m³·mol⁻¹ChemAxon
Polarizability46.18 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 ID78442551
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14035919
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Evidente A, Andolfi A, Cimmino A, Vurro M, Fracchiolla M, Charudattan R, Motta A: Ophiobolin E and 8-epi-ophiobolin J produced by Drechslera gigantea, a potential mycoherbicide of weedy grasses. Phytochemistry. 2006 Oct;67(20):2281-7. doi: 10.1016/j.phytochem.2006.07.016. Epub 2006 Sep 7. [PubMed:16962149 ]
  2. LOTUS database [Link]