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Record Information
Version2.0
Created at2022-09-12 14:06:53 UTC
Updated at2022-09-12 14:06:53 UTC
NP-MRD IDNP0329588
Secondary Accession NumbersNone
Natural Product Identification
Common Name4,18-bis(acetyloxy)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl 2-methylbutanoate
Description4,18-Bis(acetyloxy)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]Nonadecan-3-yl 2-methylbutanoate belongs to the class of organic compounds known as atisane diterpenoids. These are diterpenoids with a structure based on the atisane skeleton, which is a tetracyclic compound containing the [2,2,2]bicyc1ic ring system with the C15-C16 bridge attached at C12. 4,18-bis(acetyloxy)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl 2-methylbutanoate is found in Consolida glandulosa. 4,18-Bis(acetyloxy)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]Nonadecan-3-yl 2-methylbutanoate is a very strong basic compound (based on its pKa).
Structure
Thumb
Synonyms
ValueSource
4,18-Bis(acetyloxy)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0,.0,.0,.0,.0,]nonadecan-3-yl 2-methylbutanoic acidGenerator
4,18-Bis(acetyloxy)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl 2-methylbutanoic acidGenerator
Chemical FormulaC29H39NO9
Average Mass545.6290 Da
Monoisotopic Mass545.26248 Da
IUPAC Name4,18-bis(acetyloxy)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl 2-methylbutanoate
Traditional Name4,18-bis(acetyloxy)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl 2-methylbutanoate
CAS Registry NumberNot Available
SMILES
CCC(C)C(=O)OC1CC23C4C5CC67CC(=C)C(C(O)C6(O)C2N5CC4(C)C1OC(C)=O)C(O)C37OC(C)=O
InChI Identifier
InChI=1S/C29H39NO9/c1-7-12(2)23(35)38-17-10-27-19-16-9-26-8-13(3)18(21(34)29(26,27)39-15(5)32)20(33)28(26,36)24(27)30(16)11-25(19,6)22(17)37-14(4)31/h12,16-22,24,33-34,36H,3,7-11H2,1-2,4-6H3
InChI KeyNGOALRAWGUHGGI-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Consolida glandulosaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as atisane diterpenoids. These are diterpenoids with a structure based on the atisane skeleton, which is a tetracyclic compound containing the [2,2,2]bicyc1ic ring system with the C15-C16 bridge attached at C12.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentAtisane diterpenoids
Alternative Parents
Substituents
  • Atisane diterpenoid
  • Azaspirodecane
  • Quinolizidine
  • Indole or derivatives
  • Indolizidine
  • Alkaloid or derivatives
  • Isoindoline
  • Isoindole or derivatives
  • Tricarboxylic acid or derivatives
  • Azepane
  • Fatty acid ester
  • Fatty acyl
  • Piperidine
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Amino acid or derivatives
  • 1,2-aminoalcohol
  • Carboxylic acid ester
  • Polyol
  • Organoheterocyclic compound
  • Azacycle
  • Carboxylic acid derivative
  • Alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Amine
  • Organooxygen 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
logP0.85ALOGPS
logP-0.26ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)12.69ChemAxon
pKa (Strongest Basic)8.45ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area142.83 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity133.15 m³·mol⁻¹ChemAxon
Polarizability56.53 ųChemAxon
Number of Rings7ChemAxon
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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound73657588
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]