Np mrd loader

Record Information
Version2.0
Created at2022-09-07 23:40:50 UTC
Updated at2022-09-07 23:40:50 UTC
NP-MRD IDNP0258293
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3e)-3-ethylidene-1h,2h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizine
DescriptionDeplancheine belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety. (3e)-3-ethylidene-1h,2h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizine is found in Aspidosperma excelsum. (3e)-3-ethylidene-1h,2h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizine was first documented in 2009 (PMID: 19572756). Based on a literature review a small amount of articles have been published on Deplancheine (PMID: 33769684) (PMID: 29080246) (PMID: 28466512) (PMID: 23758537).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC17H20N2
Average Mass252.3610 Da
Monoisotopic Mass252.16265 Da
IUPAC Name(3E)-3-ethylidene-1H,2H,3H,4H,6H,7H,12H,12bH-indolo[2,3-a]quinolizine
Traditional Name(3E)-3-ethylidene-1H,2H,4H,6H,7H,12H,12bH-indolo[2,3-a]quinolizine
CAS Registry NumberNot Available
SMILES
C\C=C1/CCC2N(CCC3=C2NC2=CC=CC=C32)C1
InChI Identifier
InChI=1S/C17H20N2/c1-2-12-7-8-16-17-14(9-10-19(16)11-12)13-5-3-4-6-15(13)18-17/h2-6,16,18H,7-11H2,1H3/b12-2+
InChI KeyGVGJKCCVRKFWAF-SWGQDTFXSA-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
Aspidosperma excelsumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassPyridoindoles
Direct ParentBeta carbolines
Alternative Parents
Substituents
  • Beta-carboline
  • 3-alkylindole
  • Quinolizine
  • Indole
  • Aralkylamine
  • Piperidine
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic 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
logP3.37ChemAxon
pKa (Strongest Acidic)16.37ChemAxon
pKa (Strongest Basic)6.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area19.03 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity80.53 m³·mol⁻¹ChemAxon
Polarizability30.53 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4533618
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5386990
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. He G, List B, Christmann M: Unified Synthesis of Polycyclic Alkaloids by Complementary Carbonyl Activation*. Angew Chem Int Ed Engl. 2021 Jun 7;60(24):13591-13596. doi: 10.1002/anie.202102518. Epub 2021 May 1. [PubMed:33769684 ]
  2. Wang Y, Zhang P, Di X, Dai Q, Zhang ZM, Zhang J: Gold-Catalyzed Asymmetric Intramolecular Cyclization of N-Allenamides for the Synthesis of Chiral Tetrahydrocarbolines. Angew Chem Int Ed Engl. 2017 Dec 11;56(50):15905-15909. doi: 10.1002/anie.201709595. Epub 2017 Nov 20. [PubMed:29080246 ]
  3. Wang SG, Xia ZL, Xu RQ, Liu XJ, Zheng C, You SL: Construction of Chiral Tetrahydro-beta-Carbolines: Asymmetric Pictet-Spengler Reaction of Indolyl Dihydropyridines. Angew Chem Int Ed Engl. 2017 Jun 19;56(26):7440-7443. doi: 10.1002/anie.201703178. Epub 2017 May 23. [PubMed:28466512 ]
  4. Mondal P, Argade NP: Enantioselective total synthesis of desbromoarborescidines A-C and the formal synthesis of (S)-deplancheine. J Org Chem. 2013 Jul 5;78(13):6802-8. doi: 10.1021/jo401079v. Epub 2013 Jun 25. [PubMed:23758537 ]
  5. da Silva WA, Rodrigues MT Jr, Shankaraiah N, Ferreira RB, Andrade CK, Pilli RA, Santos LS: Novel supramolecular palladium catalyst for the asymmetric reduction of imines in aqueous media. Org Lett. 2009 Aug 6;11(15):3238-41. doi: 10.1021/ol9011772. [PubMed:19572756 ]
  6. LOTUS database [Link]