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Record Information
Version1.0
Created at2021-06-21 00:59:15 UTC
Updated at2021-06-30 00:19:26 UTC
NP-MRD IDNP0043637
Secondary Accession NumbersNone
Natural Product Identification
Common Nameklymollin J
Provided ByJEOL DatabaseJEOL Logo
Description(1R,2R,3R,4S,5S,6R,7S,8R,10S,11S,14R)-5,14-bis(acetyloxy)-6-(chloromethyl)-6,10,11-trihydroxy-10,14-dimethyl-3-(propan-2-yl)-15-oxatricyclo[6.6.1.0²,⁷]Pentadecan-4-yl acetate belongs to the class of organic compounds known as eunicellane and asbestinane diterpenoids. These are diterpenoids with a structure based on either the eunicellane (5,14-cyclocembrane) or the asbestinane skeleton. klymollin J is found in Klyxum molle. It was first documented in 2013 (Lin, M. -C., et al.). Based on a literature review very few articles have been published on (1R,2R,3R,4S,5S,6R,7S,8R,10S,11S,14R)-5,14-bis(acetyloxy)-6-(chloromethyl)-6,10,11-trihydroxy-10,14-dimethyl-3-(propan-2-yl)-15-oxatricyclo[6.6.1.0²,⁷]Pentadecan-4-yl acetate.
Structure
Thumb
Synonyms
ValueSource
(1R,2R,3R,4S,5S,6R,7S,8R,10S,11S,14R)-5,14-Bis(acetyloxy)-6-(chloromethyl)-6,10,11-trihydroxy-10,14-dimethyl-3-(propan-2-yl)-15-oxatricyclo[6.6.1.0,]pentadecan-4-yl acetic acidGenerator
Chemical FormulaC26H41ClO10
Average Mass549.0500 Da
Monoisotopic Mass548.23883 Da
IUPAC Name(1R,2S,3R,4S,5S,6R,7R,8R,9R,12S,13S)-5,9-bis(acetyloxy)-3-(chloromethyl)-3,12,13-trihydroxy-9,13-dimethyl-6-(propan-2-yl)-15-oxatricyclo[6.6.1.0^{2,7}]pentadecan-4-yl acetate
Traditional Name(1R,2S,3R,4S,5S,6R,7R,8R,9R,12S,13S)-5,9-bis(acetyloxy)-3-(chloromethyl)-3,12,13-trihydroxy-6-isopropyl-9,13-dimethyl-15-oxatricyclo[6.6.1.0^{2,7}]pentadecan-4-yl acetate
CAS Registry NumberNot Available
SMILES
[H]O[C@@]1([H])C([H])([H])C([H])([H])[C@](OC(=O)C([H])([H])[H])(C([H])([H])[H])[C@]2([H])O[C@]([H])(C([H])([H])[C@@]1(O[H])C([H])([H])[H])[C@]1([H])[C@@]2([H])[C@@]([H])(C([H])(C([H])([H])[H])C([H])([H])[H])[C@]([H])(OC(=O)C([H])([H])[H])[C@]([H])(OC(=O)C([H])([H])[H])[C@@]1(O[H])C([H])([H])Cl
InChI Identifier
InChI=1S/C26H41ClO10/c1-12(2)18-19-20(26(33,11-27)23(35-14(4)29)21(18)34-13(3)28)16-10-24(6,32)17(31)8-9-25(7,22(19)36-16)37-15(5)30/h12,16-23,31-33H,8-11H2,1-7H3/t16-,17+,18-,19-,20-,21+,22-,23+,24+,25-,26-/m1/s1
InChI KeyNXDBLMKPWYADDE-XVDRNVAYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Klyxum molleJEOL database
    • Lin, M. -C., et al, J. Nat. Prod. 76, 1661 (2013)
Chemical Taxonomy
Description Belongs to the class of organic compounds known as eunicellane and asbestinane diterpenoids. These are diterpenoids with a structure based on either the eunicellane (5,14-cyclocembrane) or the asbestinane skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentEunicellane and asbestinane diterpenoids
Alternative Parents
Substituents
  • Cladiellane diterpenoid
  • Eunicellane-type diterpenoid
  • Tricarboxylic acid or derivatives
  • Cyclitol or derivatives
  • Cyclic alcohol
  • Tertiary alcohol
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Chlorohydrin
  • Halohydrin
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Alkyl chloride
  • Carbonyl group
  • Organic oxygen compound
  • Organohalogen compound
  • Alkyl halide
  • Organochloride
  • 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
logP1.95ALOGPS
logP0.45ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)12.68ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area148.82 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity130.41 m³·mol⁻¹ChemAxon
Polarizability55.6 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
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 IDNot Available
Chemspider ID30771247
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Lin, M. -C., et al. (2013). Lin, M. -C., et al, J. Nat. Prod. 76, 1661 (2013). J. Nat. Prod..