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Record Information
Version2.0
Created at2022-09-12 00:57:06 UTC
Updated at2022-09-12 00:57:06 UTC
NP-MRD IDNP0322269
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2r,4as,5s,7r,8r,8as)-4,4a-diformyl-5-hydroxy-7,8-dimethyl-8-[(2z)-3-methylpenta-2,4-dien-1-yl]-1,2,5,6,7,8a-hexahydronaphthalen-2-yl butanoate
Description(2R,4aS,5S,7R,8R,8aS)-4,4a-diformyl-5-hydroxy-7,8-dimethyl-8-[(2Z)-3-methylpenta-2,4-dien-1-yl]-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-yl butanoate belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations. (2r,4as,5s,7r,8r,8as)-4,4a-diformyl-5-hydroxy-7,8-dimethyl-8-[(2z)-3-methylpenta-2,4-dien-1-yl]-1,2,5,6,7,8a-hexahydronaphthalen-2-yl butanoate is found in Casearia sylvestris. Based on a literature review very few articles have been published on (2R,4aS,5S,7R,8R,8aS)-4,4a-diformyl-5-hydroxy-7,8-dimethyl-8-[(2Z)-3-methylpenta-2,4-dien-1-yl]-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-yl butanoate.
Structure
Thumb
Synonyms
ValueSource
(2R,4AS,5S,7R,8R,8as)-4,4a-diformyl-5-hydroxy-7,8-dimethyl-8-[(2Z)-3-methylpenta-2,4-dien-1-yl]-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-yl butanoic acidGenerator
Chemical FormulaC24H34O5
Average Mass402.5310 Da
Monoisotopic Mass402.24062 Da
IUPAC Name(2R,4aS,5S,7R,8R,8aS)-4,4a-diformyl-5-hydroxy-7,8-dimethyl-8-[(2Z)-3-methylpenta-2,4-dien-1-yl]-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-yl butanoate
Traditional Name(2R,4aS,5S,7R,8R,8aS)-4,4a-diformyl-5-hydroxy-7,8-dimethyl-8-[(2Z)-3-methylpenta-2,4-dien-1-yl]-1,2,5,6,7,8a-hexahydronaphthalen-2-yl butanoate
CAS Registry NumberNot Available
SMILES
CCCC(=O)O[C@@H]1C[C@H]2[C@](C)(C\C=C(\C)C=C)[C@H](C)C[C@H](O)[C@@]2(C=O)C(C=O)=C1
InChI Identifier
InChI=1S/C24H34O5/c1-6-8-22(28)29-19-12-18(14-25)24(15-26)20(13-19)23(5,10-9-16(3)7-2)17(4)11-21(24)27/h7,9,12,14-15,17,19-21,27H,2,6,8,10-11,13H2,1,3-5H3/b16-9-/t17-,19+,20+,21+,23-,24+/m1/s1
InChI KeyJNCWBVCCDFJVEI-ISYBQSFZSA-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
Casearia sylvestrisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentColensane and clerodane diterpenoids
Alternative Parents
Substituents
  • Clerodane diterpenoid
  • Fatty acid ester
  • Fatty acyl
  • Cyclic alcohol
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Aldehyde
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic 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
logP3.27ChemAxon
pKa (Strongest Acidic)14.45ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area80.67 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity114.39 m³·mol⁻¹ChemAxon
Polarizability44.68 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 ID28944882
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound162820271
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]