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Record Information
Version2.0
Created at2022-09-11 20:04:50 UTC
Updated at2022-09-11 20:04:50 UTC
NP-MRD IDNP0319176
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1r,2r,3r,6r,7r,10r)-2-ethyl-1-hydroxy-6-methyl-10-[(2r,4r)-4-methyl-5-oxooxolan-2-yl]-4-oxa-11-azatricyclo[9.4.1.0³,⁷]hexadecane-5,8,16-trione
Description(1R,2R,3R,6R,7R,10R)-2-ethyl-1-hydroxy-6-methyl-10-[(2R,4R)-4-methyl-5-oxooxolan-2-yl]-4-oxa-11-azatricyclo[9.4.1.0³,⁷]Hexadecane-5,8,16-trione belongs to the class of organic compounds known as caprolactams. These are cyclic amides of caproic acid. Caproic acid is the carboxylic acid derived from hexane with the general formula C5H11COOH. (1r,2r,3r,6r,7r,10r)-2-ethyl-1-hydroxy-6-methyl-10-[(2r,4r)-4-methyl-5-oxooxolan-2-yl]-4-oxa-11-azatricyclo[9.4.1.0³,⁷]hexadecane-5,8,16-trione is found in Stemona tuberosa. Based on a literature review very few articles have been published on (1R,2R,3R,6R,7R,10R)-2-ethyl-1-hydroxy-6-methyl-10-[(2R,4R)-4-methyl-5-oxooxolan-2-yl]-4-oxa-11-azatricyclo[9.4.1.0³,⁷]Hexadecane-5,8,16-trione.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC22H31NO7
Average Mass421.4900 Da
Monoisotopic Mass421.21005 Da
IUPAC Name(1R,2R,3R,6R,7R,10R)-2-ethyl-1-hydroxy-6-methyl-10-[(2R,4R)-4-methyl-5-oxooxolan-2-yl]-4-oxa-11-azatricyclo[9.4.1.0^{3,7}]hexadecane-5,8,16-trione
Traditional Name(1R,2R,3R,6R,7R,10R)-2-ethyl-1-hydroxy-6-methyl-10-[(2R,4R)-4-methyl-5-oxooxolan-2-yl]-4-oxa-11-azatricyclo[9.4.1.0^{3,7}]hexadecane-5,8,16-trione
CAS Registry NumberNot Available
SMILES
CC[C@@H]1[C@H]2OC(=O)[C@H](C)[C@H]2C(=O)C[C@H]([C@H]2C[C@@H](C)C(=O)O2)N2CCCC[C@]1(O)C2=O
InChI Identifier
InChI=1S/C22H31NO7/c1-4-13-18-17(12(3)20(26)30-18)15(24)10-14(16-9-11(2)19(25)29-16)23-8-6-5-7-22(13,28)21(23)27/h11-14,16-18,28H,4-10H2,1-3H3/t11-,12-,13-,14-,16-,17+,18-,22-/m1/s1
InChI KeyIOWYJOAVWWYTFW-UWCKOGLMSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Stemona tuberosaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as caprolactams. These are cyclic amides of caproic acid. Caproic acid is the carboxylic acid derived from hexane with the general formula C5H11COOH.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassCaprolactams
Direct ParentCaprolactams
Alternative Parents
Substituents
  • Caprolactam
  • Azepane
  • Dicarboxylic acid or derivatives
  • Gamma butyrolactone
  • Tetrahydrofuran
  • Tertiary carboxylic acid amide
  • Tertiary alcohol
  • Carboxamide group
  • Carboxylic acid ester
  • Ketone
  • Lactone
  • Carboxylic acid derivative
  • Oxacycle
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • 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
logP1.59ChemAxon
pKa (Strongest Acidic)12.53ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area110.21 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity104.31 m³·mol⁻¹ChemAxon
Polarizability43.72 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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound163072404
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]