Np mrd loader

Record Information
Version2.0
Created at2022-09-06 08:13:39 UTC
Updated at2022-09-06 08:13:39 UTC
NP-MRD IDNP0228530
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2s,3r,6s)-6-[(1e,3e,5e)-deca-1,3,5-trien-1-yl]-2-methylpiperidin-3-ol
DescriptionMicrocosamine A belongs to the class of organic compounds known as piperidines. Piperidines are compounds containing a piperidine ring, which is a saturated aliphatic six-member ring with one nitrogen atom and five carbon atoms. (2s,3r,6s)-6-[(1e,3e,5e)-deca-1,3,5-trien-1-yl]-2-methylpiperidin-3-ol is found in Microcos paniculata. (2s,3r,6s)-6-[(1e,3e,5e)-deca-1,3,5-trien-1-yl]-2-methylpiperidin-3-ol was first documented in 2013 (PMID: 23327794). Based on a literature review a small amount of articles have been published on Microcosamine A (PMID: 30406652) (PMID: 34918520) (PMID: 27553201) (PMID: 26565783).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC16H27NO
Average Mass249.3980 Da
Monoisotopic Mass249.20926 Da
IUPAC Name(2S,3R,6S)-6-[(1E,3E,5E)-deca-1,3,5-trien-1-yl]-2-methylpiperidin-3-ol
Traditional Name(2S,3R,6S)-6-[(1E,3E,5E)-deca-1,3,5-trien-1-yl]-2-methylpiperidin-3-ol
CAS Registry NumberNot Available
SMILES
CCCC\C=C\C=C\C=C\[C@@H]1CC[C@@H](O)[C@H](C)N1
InChI Identifier
InChI=1S/C16H27NO/c1-3-4-5-6-7-8-9-10-11-15-12-13-16(18)14(2)17-15/h6-11,14-18H,3-5,12-13H2,1-2H3/b7-6+,9-8+,11-10+/t14-,15+,16+/m0/s1
InChI KeyLSCWHIBYDGDOLC-CCORAGHZSA-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
Microcos paniculataLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as piperidines. Piperidines are compounds containing a piperidine ring, which is a saturated aliphatic six-member ring with one nitrogen atom and five carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPiperidines
Sub ClassNot Available
Direct ParentPiperidines
Alternative Parents
Substituents
  • Piperidine
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Azacycle
  • Secondary amine
  • Secondary aliphatic amine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic 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
logP3.56ChemAxon
pKa (Strongest Acidic)14.61ChemAxon
pKa (Strongest Basic)9.28ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area32.26 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity81.56 m³·mol⁻¹ChemAxon
Polarizability32.64 ųChemAxon
Number of Rings1ChemAxon
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 ID29417574
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound25140000
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Macha L, Ha HJ: Total Synthesis and Absolute Stereochemical Assignment of Microgrewiapine A and Its Stereoisomers. J Org Chem. 2019 Jan 4;84(1):94-103. doi: 10.1021/acs.joc.8b02342. Epub 2018 Nov 16. [PubMed:30406652 ]
  2. Still PC, Yi B, Gonzalez-Cestari TF, Pan L, Pavlovicz RE, Chai HB, Ninh TN, Li C, Soejarto DD, McKay DB, Kinghorn AD: Alkaloids from Microcos paniculata with cytotoxic and nicotinic receptor antagonistic activities. J Nat Prod. 2013 Feb 22;76(2):243-9. doi: 10.1021/np3007414. Epub 2013 Jan 17. [PubMed:23327794 ]
  3. Davies SG, Fletcher AM, Roberts PM, Taylor CE, Thomson JE: Synthesis and Configuration of O-Acetyl Microgrewiapine A: Phantomization of O-Acetyl 6-epi-Microgrewiapine A. J Nat Prod. 2022 Jan 28;85(1):306-312. doi: 10.1021/acs.jnatprod.1c00847. Epub 2021 Dec 17. [PubMed:34918520 ]
  4. Zhang G, Zhang N, Xu L, Wu HT, Chen D, Lin QH, Luo LZ: A new piperidine alkaloid from the leaves of Microcos paniculata L. Nat Prod Res. 2017 Jan;31(2):169-174. doi: 10.1080/14786419.2016.1224868. Epub 2016 Aug 24. [PubMed:27553201 ]
  5. Raji Reddy C, Latha B, Warudikar K, Singarapu KK: Total synthesis of a piperidine alkaloid, microcosamine A. Org Biomol Chem. 2016 Jan 7;14(1):251-8. doi: 10.1039/c5ob02085a. Epub 2015 Nov 13. [PubMed:26565783 ]
  6. LOTUS database [Link]