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Record Information
Version2.0
Created at2022-09-05 20:35:59 UTC
Updated at2022-09-05 20:35:59 UTC
NP-MRD IDNP0219563
Secondary Accession NumbersNone
Natural Product Identification
Common Namemethyl (1r,4s,5r,9s,10r,12s,13r)-13-(hydroxymethyl)-5,9-dimethyltetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate
Description(5Beta,8alpha,9beta,10alpha,12alpha)-17-Hydroxyatisane-18-oic acid methyl ester, also known as (5β,8α,9β,10α,12α)-17-hydroxyatisane-18-Oate methyl ester, 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. methyl (1r,4s,5r,9s,10r,12s,13r)-13-(hydroxymethyl)-5,9-dimethyltetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate is found in Mallotus nudiflorus. It was first documented in 2022 (PMID: 36075691). Based on a literature review a significant number of articles have been published on (5beta,8alpha,9beta,10alpha,12alpha)-17-Hydroxyatisane-18-oic acid methyl ester (PMID: 36075690) (PMID: 36075689) (PMID: 36075688) (PMID: 36075687).
Structure
Thumb
Synonyms
ValueSource
(5b,8a,9b,10a,12a)-17-Hydroxyatisane-18-Oate methyl esterGenerator
(5b,8a,9b,10a,12a)-17-Hydroxyatisane-18-Oic acid methyl esterGenerator
(5beta,8alpha,9beta,10alpha,12alpha)-17-Hydroxyatisane-18-Oate methyl esterGenerator
(5Β,8α,9β,10α,12α)-17-hydroxyatisane-18-Oate methyl esterGenerator
(5Β,8α,9β,10α,12α)-17-hydroxyatisane-18-Oic acid methyl esterGenerator
Chemical FormulaC21H34O3
Average Mass334.5000 Da
Monoisotopic Mass334.25079 Da
IUPAC Namemethyl (1R,4S,5R,9S,10R,12S,13R)-13-(hydroxymethyl)-5,9-dimethyltetracyclo[10.2.2.0^{1,10}.0^{4,9}]hexadecane-5-carboxylate
Traditional Namemethyl (1R,4S,5R,9S,10R,12S,13R)-13-(hydroxymethyl)-5,9-dimethyltetracyclo[10.2.2.0^{1,10}.0^{4,9}]hexadecane-5-carboxylate
CAS Registry NumberNot Available
SMILES
COC(=O)[C@]1(C)CCC[C@]2(C)[C@@H]1CC[C@@]13CC[C@@H](C[C@@H]21)[C@H](CO)C3
InChI Identifier
InChI=1S/C21H34O3/c1-19-7-4-8-20(2,18(23)24-3)16(19)6-10-21-9-5-14(11-17(19)21)15(12-21)13-22/h14-17,22H,4-13H2,1-3H3/t14-,15-,16-,17-,19+,20+,21+/m0/s1
InChI KeyYSYQTDVOZWSRET-OOPZRWPMSA-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
Trewia nudifloraLOTUS 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
  • Alkaloid or derivatives
  • Methyl ester
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • 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
logP3.94ChemAxon
pKa (Strongest Acidic)17.91ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity94.21 m³·mol⁻¹ChemAxon
Polarizability39.02 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 Compound101773026
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]