NP-MRD: Showing NP-Card for Cuscohygrine (NP0045876)

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Record Information

Version

2.0

Created at

2022-03-17 19:44:42 UTC

Updated at

2022-03-17 19:44:42 UTC

NP-MRD ID

NP0045876

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cuscohygrine

Description

Cuscohygrine, also known as bellaradine, 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. Cuscohygrine usually comes with other, more potent alkaloids like atropine or cocaine. Cuscohygrine is a very strong basic compound (based on its pKa). Cuscohygrine is a pyrrolidine alkaloid found in coca. Outside of the human body, Cuscohygrine has been detected, but not quantified in, fruits and potato. This could make cuscohygrine a potential biomarker for the consumption of these foods. It is easily soluble in water and forms an optically inactive crystalline hydrate C13H24N2O·3H2O, which melts at 40-41 °C. ; Cuscohygrine is an oil, which can be distilled without decomposition only in vacuum. Cuscohygrine is found in Anisodus tanguticus, Apis cerana, Argyreia mollis, Atropa baetica, Atropa belladonna , Brugmansia suaveolens, Brugmansia candida, Calystegia sepium , Convolvulus arvensis, Convolvulus erinaceus, Cyphomandra betacea , Cyphomandra betaceae, Datura ceratocaula , Datura inoxia, Datura spp., Datura stramonium , Duboisia myoporoides, Erythroxylon coca , Erythroxylon novogranatense, Erythroxylum argentinum, Erythroxylum cataractarum, Erythroxylum coca , Erythroxylum monogynum, Erythroxylum novogranatense, Hyoscyamus albus , Hyoscyamus boveanus, Hyoscyamus desertorum, Hyoscyamus muticus , Hyoscyamus niger , Mandragora autumnale, Mandragora autumnalis , Mandragora autunnale, Mandragora officinarum L. , Mandragora vernalis, Physalis alkekengi , Physalis minima, Physalis peruviana , Physalis solanacea, Salpichora origanifolia, Scopolia carniolica, Scopolia spp., Solandra grandiflora and Withania somnifera . It can be extracted from plants of the family Solanaceae as well, including Atropa belladonna (deadly nightshade), Datura inoxia and Datura stramonium (jimson weed).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061305082D          

 16 17  0  0  0  0            999 V2000
    2.6434   -1.1524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1934    2.9251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -2.1920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3608    1.8301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7629   -1.4073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9128    1.2170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -2.1920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7733    2.5446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954   -0.0974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3810    1.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954   -0.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6665    1.5526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3810    0.3151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4280   -1.4073    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5803    2.3731    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6665   -0.0974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
 11  5  1  0  0  0  0
 11  9  1  0  0  0  0
 12  6  1  0  0  0  0
 12 10  1  0  0  0  0
 13  9  1  0  0  0  0
 13 10  1  0  0  0  0
 14  1  1  0  0  0  0
 14  7  1  0  0  0  0
 14 11  1  0  0  0  0
 15  2  1  0  0  0  0
 15  8  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0045876

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1CCCC1CC(=O)CC1CCCN1C

> <INCHI_IDENTIFIER>
InChI=1S/C13H24N2O/c1-14-7-3-5-11(14)9-13(16)10-12-6-4-8-15(12)2/h11-12H,3-10H2,1-2H3

> <INCHI_KEY>
ZEBIACKKLGVLFZ-UHFFFAOYSA-N

> <FORMULA>
C13H24N2O

> <MOLECULAR_WEIGHT>
224.3425

> <EXACT_MASS>
224.1888634

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
26.199997698697345

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,3-bis(1-methylpyrrolidin-2-yl)propan-2-one

> <ALOGPS_LOGP>
1.53

> <JCHEM_LOGP>
1.2944313309999997

> <ALOGPS_LOGS>
-1.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.665844592918024

> <JCHEM_PKA_STRONGEST_BASIC>
9.130722930961912

> <JCHEM_POLAR_SURFACE_AREA>
23.55

> <JCHEM_REFRACTIVITY>
66.874

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.92e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cuscohygrine

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       4.934  -2.151   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.961   5.460   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.415  -4.092   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.540   3.416   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.891  -2.627   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.571   2.272   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.875  -4.092   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.310   4.750   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.645  -0.182   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.311   2.128   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.645  -1.722   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.977   2.898   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.311   0.588   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       6.399  -2.627   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0       4.817   4.430   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0       4.977  -0.182   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2   15                                                            
CONECT    3    5    7                                                       
CONECT    4    6    8                                                       
CONECT    5    3   11                                                       
CONECT    6    4   12                                                       
CONECT    7    3   14                                                       
CONECT    8    4   15                                                       
CONECT    9   11   13                                                       
CONECT   10   12   13                                                       
CONECT   11    5    9   14                                                  
CONECT   12    6   10   15                                                  
CONECT   13    9   10   16                                                  
CONECT   14    1    7   11                                                  
CONECT   15    2    8   12                                                  
CONECT   16   13                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Value	Source
Cuskhygrine	Kegg
1,3-Bis(1-methyl-2-pyrrolidinyl)-2-propanone, 9ci	HMDB
Bellaradine	HMDB
Hellaradine	HMDB
Meso-cuscohygrine	HMDB

Chemical Formula

C₁₃H₂₄N₂O

Average Mass

224.3425 Da

Monoisotopic Mass

224.18886 Da

IUPAC Name

1,3-bis(1-methylpyrrolidin-2-yl)propan-2-one

Traditional Name

cuscohygrine

CAS Registry Number

454-14-8

SMILES

CN1CCCC1CC(=O)CC1CCCN1C

InChI Identifier

InChI=1S/C13H24N2O/c1-14-7-3-5-11(14)9-13(16)10-12-6-4-8-15(12)2/h11-12H,3-10H2,1-2H3

InChI Key

ZEBIACKKLGVLFZ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anisodus tanguticus	LOTUS Database	35616633
Apis cerana	LOTUS Database	35616633
Argyreia mollis	Plant	KNApSAcK
Atropa baetica	Plant	KNApSAcK
Atropa belladonna	Plant	KNApSAcK
Brugmansia suaveolens	LOTUS Database	35616633
Brugmansia x candida	LOTUS Database	35616633
Calystegia sepium	Plant	KNApSAcK
Convolvulus arvensis	LOTUS Database	35616633
Convolvulus erinaceus	Plant	KNApSAcK
Cyphomandra betacea	Plant	KNApSAcK
Cyphomandra betaceae	Plant	KNApSAcK
Datura ceratocaula	Plant	KNApSAcK
Datura inoxia	LOTUS Database	35616633
Datura spp.	Plant	KNApSAcK
Datura stramonium	Plant	KNApSAcK
Duboisia myoporoides	LOTUS Database	35616633
Erythroxylon coca	-	KNApSAcK
Erythroxylon novogranatense	-	KNApSAcK
Erythroxylum argentinum	LOTUS Database	35616633
Erythroxylum cataractarum	Plant	KNApSAcK
Erythroxylum coca	Plant	KNApSAcK
Erythroxylum monogynum	LOTUS Database	35616633
Erythroxylum novogranatense	Plant	KNApSAcK
Hyoscyamus albus	Plant	KNApSAcK
Hyoscyamus boveanus	Plant	KNApSAcK
Hyoscyamus desertorum	Plant	KNApSAcK
Hyoscyamus muticus	Plant	KNApSAcK
Hyoscyamus niger	Plant	KNApSAcK
Mandragora autumnale	Plant	KNApSAcK
Mandragora autumnalis	Plant	KNApSAcK
Mandragora autunnale	Plant	KNApSAcK
Mandragora officinarum L.	Plant	KNApSAcK
Mandragora vernalis	Plant	KNApSAcK
Physalis alkekengi	Plant	KNApSAcK
Physalis minima	LOTUS Database	35616633
Physalis peruviana	Plant	KNApSAcK
Physalis solanacea	LOTUS Database	35616633
Salpichora origanifolia	-	KNApSAcK
Scopolia carniolica	LOTUS Database	35616633
Scopolia spp.	Plant	KNApSAcK
Solandra grandiflora	LOTUS Database	35616633
Solanum tuberosum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Withania somnifera	Plant	KNApSAcK

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.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Not Available

Sub Class

Not Available

Direct Parent

Alkaloids and derivatives

Alternative Parents

Substituents

Alkaloid or derivatives
Beta-aminoketone
N-alkylpyrrolidine
Pyrrolidine
Ketone
Tertiary amine
Tertiary aliphatic amine
Organoheterocyclic compound
Azacycle
Organopnictogen compound
Organic nitrogen compound
Amine
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Pyrrolidine alkaloids (C06521 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.53	ALOGPS
logP	1.29	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	17.67	ChemAxon
pKa (Strongest Basic)	9.13	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	23.55 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	66.87 m³·mol⁻¹	ChemAxon
Polarizability	26.2 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon