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Record Information
Version2.0
Created at2022-04-28 11:03:24 UTC
Updated at2022-04-28 11:03:24 UTC
NP-MRD IDNP0066822
Secondary Accession NumbersNone
Natural Product Identification
Common Name(+)-Lapidilectine B
DescriptionLapidilectine B belongs to the class of organic compounds known as indolecarboxylic acids. Indolecarboxylic acids are compounds containing a carboxylic acid group linked to an indole. (+)-Lapidilectine B is found in Kopsia grandifolia and Kopsia lapidilecta. (+)-Lapidilectine B was first documented in 2012 (PMID: 22214219). Based on a literature review a small amount of articles have been published on Lapidilectine B (PMID: 28838428) (PMID: 26834054) (PMID: 35011332) (PMID: 29572984).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC21H22N2O4
Average Mass366.4170 Da
Monoisotopic Mass366.15796 Da
IUPAC Namemethyl (1R,9R,10R,12R)-20-oxo-19-oxa-8,16-diazahexacyclo[8.8.2.2^{9,12}.0^{1,9}.0^{2,7}.0^{12,16}]docosa-2,4,6,13-tetraene-8-carboxylate
Traditional Namemethyl (1R,9R,10R,12R)-20-oxo-19-oxa-8,16-diazahexacyclo[8.8.2.2^{9,12}.0^{1,9}.0^{2,7}.0^{12,16}]docosa-2,4,6,13-tetraene-8-carboxylate
CAS Registry NumberNot Available
SMILES
COC(=O)N1C2=CC=CC=C2[C@]23CCN4CC=C[C@]44CC[C@]12[C@@H](C4)C(=O)O3
InChI Identifier
InChI=1S/C21H22N2O4/c1-26-18(25)23-16-6-3-2-5-14(16)21-10-12-22-11-4-7-19(22)8-9-20(21,23)15(13-19)17(24)27-21/h2-7,15H,8-13H2,1H3/t15-,19+,20+,21+/m0/s1
InChI KeyGLOIILVAVSJIEX-LWILDLIXSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Kopsia grandifoliaLOTUS Database
Kopsia lapidilectaPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indolecarboxylic acids. Indolecarboxylic acids are compounds containing a carboxylic acid group linked to an indole.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndolecarboxylic acids and derivatives
Direct ParentIndolecarboxylic acids
Alternative Parents
Substituents
  • Indolecarboxylic acid
  • Aralkylamine
  • Gamma butyrolactone
  • Benzenoid
  • Pyrroline
  • Tetrahydrofuran
  • Carbamic acid ester
  • Carboxylic acid ester
  • Lactone
  • Carbonic acid derivative
  • Tertiary amine
  • Tertiary aliphatic amine
  • Amino acid or derivatives
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Carboxylic acid derivative
  • Azacycle
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Amine
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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
logP2.03ALOGPS
logP2ChemAxon
logS-2.6ALOGPS
pKa (Strongest Basic)9.82ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area59.08 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity98.1 m³·mol⁻¹ChemAxon
Polarizability38.11 ųChemAxon
Number of Rings6ChemAxon
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 IDC00024469
Chemspider ID26630927
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12138542
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Arai S, Nakajima M, Nishida A: Total Synthesis of Lundurine and Related Alkaloids: Synthetic Approaches and Strategies. Alkaloids Chem Biol. 2017;78:167-204. doi: 10.1016/bs.alkal.2017.01.001. Epub 2017 Feb 28. [PubMed:28838428 ]
  2. Nakajima M, Arai S, Nishida A: Total Syntheses of (+)-Grandilodine C and (+)-Lapidilectine B and Determination of their Absolute Stereochemistry. Angew Chem Int Ed Engl. 2016 Mar 1;55(10):3473-6. doi: 10.1002/anie.201510561. Epub 2016 Feb 2. [PubMed:26834054 ]
  3. Schultz EE, Pujanauski BG, Sarpong R: Synthetic studies toward lapidilectine-type Kopsia alkaloids. Org Lett. 2012 Jan 20;14(2):648-51. doi: 10.1021/ol203302f. Epub 2012 Jan 3. [PubMed:22214219 ]
  4. Higuchi K, Matsumura K, Arai T, Ito M, Sugiyama S: Intramolecular Aminolactonization for Synthesis of Furoindolin-2-One. Molecules. 2021 Dec 24;27(1). pii: molecules27010102. doi: 10.3390/molecules27010102. [PubMed:35011332 ]
  5. Gao Y, Fan M, Geng Q, Ma D: Total Synthesis of Lapidilectine B Enabled by Manganese(III)-Mediated Oxidative Cyclization of Indoles. Chemistry. 2018 May 2;24(25):6547-6550. doi: 10.1002/chem.201801312. Epub 2018 Apr 17. [PubMed:29572984 ]