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Showing NP-Card for (-)-coniine (NP0242915)

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Record Information
Version2.0
Created at2022-09-07 03:20:51 UTC
Updated at2022-09-07 03:20:51 UTC
NP-MRD IDNP0242915
Secondary Accession NumbersNone
Natural Product Identification
Common Name(-)-coniine
Description(-)-Coniine, also known as coniine or cicutine, belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus. (-)-coniine is found in Aloe globuligemma, Aloidendron sabaeum, Aloe viguieri and Conium maculatum. (-)-coniine was first documented in 2020 (PMID: 32281758). Based on a literature review a small amount of articles have been published on (-)-Coniine (PMID: 32039338) (PMID: 31909622) (PMID: 34431644).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0242915 ((-)-coniine)


  Mrv1652309072205202D          

  9  9  0  0  1  0            999 V2000
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
M  END
Download

3D MOL for NP0242915 ((-)-coniine)

     RDKit          3D

 26 26  0  0  0  0  0  0  0  0999 V2000
    3.4347   -0.3439   -0.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.4702   -0.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3502    0.8861    0.0693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1610    0.8769    0.1003 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6937   -0.0611    1.1585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2071    0.1849    1.2025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7570   -0.3531   -0.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7108   -0.4693   -1.1535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7499    0.5863   -1.1630 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7609    0.6947   -0.4872 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8277   -0.5415    0.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8965   -1.0621   -0.9435 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6108   -1.1754    0.5778 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5984   -0.7943   -1.2213 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7017    1.6350   -0.6677 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7438    1.2106    1.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4830    1.9070    0.3985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2709    0.1330    2.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5239   -1.1269    0.8448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3636    1.2967    1.1689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6748   -0.2467    2.0856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6595    0.2060   -0.4332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1345   -1.3908    0.1391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2243   -1.4766   -1.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2427   -0.4354   -2.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0087    0.3303   -1.8330 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  4  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  2 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  1
  5 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
M  END
Download

3D SDF for NP0242915 ((-)-coniine)


  Mrv1652309072205202D          

  9  9  0  0  1  0            999 V2000
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0242915

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC[C@@H]1CCCCN1

> <INCHI_IDENTIFIER>
InChI=1S/C8H17N/c1-2-5-8-6-3-4-7-9-8/h8-9H,2-7H2,1H3/t8-/m1/s1

> <INCHI_KEY>
NDNUANOUGZGEPO-MRVPVSSYSA-N

> <FORMULA>
C8H17N

> <MOLECULAR_WEIGHT>
127.231

> <EXACT_MASS>
127.136099551

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
16.475391197309

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-propylpiperidine

> <JCHEM_LOGP>
2.0411537446666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.580740541813658

> <JCHEM_POLAR_SURFACE_AREA>
12.03

> <JCHEM_REFRACTIVITY>
40.3792

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-propylpiperidine

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0242915 ((-)-coniine)

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PDB for NP0242915 ((-)-coniine)
HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       0.000   1.540   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END

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3D PDB for NP0242915 ((-)-coniine)
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SMILES for NP0242915 ((-)-coniine)
CCC[C@@H]1CCCCN1
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INCHI for NP0242915 ((-)-coniine)
InChI=1S/C8H17N/c1-2-5-8-6-3-4-7-9-8/h8-9H,2-7H2,1H3/t8-/m1/s1
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View in JSmol
Synonyms
ValueSource
Coniine, (S)-isomerMeSH
ConiineMeSH
KoniinMeSH
CicutineMeSH
ConicineMeSH
Coniine hydrochloride, (+-)-isomerMeSH
Coniine hydrochloride, (S)-isomerMeSH
Coniine, (+-)-isomerMeSH
Coniine hydrobromide, (S)-isomerMeSH
Chemical FormulaC8H17N
Average Mass127.2310 Da
Monoisotopic Mass127.13610 Da
IUPAC Name(2R)-2-propylpiperidine
Traditional Name(2R)-2-propylpiperidine
CAS Registry NumberNot Available
SMILES
CCC[C@@H]1CCCCN1
InChI Identifier
InChI=1S/C8H17N/c1-2-5-8-6-3-4-7-9-8/h8-9H,2-7H2,1H3/t8-/m1/s1
InChI KeyNDNUANOUGZGEPO-MRVPVSSYSA-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
Aloe globuligemmaLOTUS Database
Aloe sabaeaLOTUS Database
Aloe viguieriLOTUS Database
Conium maculatumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.
KingdomOrganic compounds  
Super ClassAlkaloids and derivatives  
ClassNot Available
Sub ClassNot Available
Direct ParentAlkaloids and derivatives  
Alternative Parents
Substituents
  • Alkaloid or derivatives
    • 

  • Piperidine
    • 

  • Azacycle
    • 

  • Organoheterocyclic compound
    • 

  • Secondary amine
    • 

  • Secondary aliphatic amine
    • 

  • Organic nitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organonitrogen compound
    • 

  • Amine
    • 

  • 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
logP2.04ChemAxon
pKa (Strongest Basic)10.58ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.03 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity40.38 m³·mol⁻¹ChemAxon
Polarizability16.48 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID553587  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound638021  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Basile C: [Rhabdomyolysis: have you considered food poisoning from quails?]. G Ital Nefrol. 2020 Apr 9;37(2):2020-vol2. [PubMed:32281758  ] 
  2. Deardorff DR, Niman SW, Paulsen MI, Sookezian A, Whalen ME, Finlayson CJ, Frivold C, Brown HC, Cannon JS: Combined Enzyme- and Transition Metal-Catalyzed Strategy for the Enantioselective Syntheses of Nitrogen Heterocycles: (-)-Coniine, DAB-1, and Nectrisine. ACS Omega. 2020 Jan 23;5(4):2005-2014. doi: 10.1021/acsomega.9b03990. eCollection  2020 Feb 4. [PubMed:32039338  ] 
  3. Koo SM, Vendola AJ, Momm SN, Morken JP: Alkyl Group Migration in Ni-Catalyzed Conjunctive Coupling with C(sp(3)) Electrophiles: Reaction Development and Application to Targets of Interest. Org Lett. 2020 Jan 17;22(2):666-669. doi: 10.1021/acs.orglett.9b04453. Epub 2020  Jan 7. [PubMed:31909622  ] 
  4. Konopka T: What kind of poison was used in "The Name of the Rose"? Arch Med Sadowej Kryminol. 2020;70(4):191-201. doi: 10.5114/amsik.2020.104944. [PubMed:34431644  ] 
  5. LOTUS database [Link]