NP-MRD: Showing NP-Card for Crotanecine (NP0051157)

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Record Information

Version

2.0

Created at

2022-04-27 22:34:02 UTC

Updated at

2022-04-27 22:34:03 UTC

NP-MRD ID

NP0051157

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Crotanecine

Description

Crotanecine 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. Crotanecine is found in Crotalaria spp. Crotanecine was first documented in 2006 (PMID: 16468814). Based on a literature review very few articles have been published on Crotanecine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       1.465  -2.016   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       1.465  -0.476   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.905  -1.246   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.000  -2.492   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.476  -3.956   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.982  -4.277   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.929   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.834  -1.246   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.929  -2.492   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.405  -3.956   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       5.374  -1.246   0.000  0.00  0.00           O+0
CONECT    1    2    5   10                                                  
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    1    6                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    2    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9    1   11                                                  
CONECT   11   10                                                            
CONECT   12    9                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₈H₁₃NO₃

Average Mass

171.1960 Da

Monoisotopic Mass

171.08954 Da

IUPAC Name

(1S,2R,7aR)-7-(hydroxymethyl)-2,3,5,7a-tetrahydro-1H-pyrrolizine-1,2-diol

Traditional Name

crotanecine

CAS Registry Number

Not Available

SMILES

OCC1=CCN2C[C@@H](O)[C@@H](O)[C@@H]12

InChI Identifier

InChI=1S/C8H13NO3/c10-4-5-1-2-9-3-6(11)8(12)7(5)9/h1,6-8,10-12H,2-4H2/t6-,7-,8-/m1/s1

InChI Key

VMWCRDCGNVMCGJ-BWZBUEFSSA-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
Crotalaria spp.	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
Pyrrolizine
N-alkylpyrrolidine
1,3-aminoalcohol
Pyrrolidine
Pyrroline
1,2-aminoalcohol
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Primary alcohol
Organooxygen compound
Organonitrogen compound
Amine
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

pyrrolizines (CHEBI:3925 )
Pyrrolizidine alkaloids (C10284 )

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	-1.3	ALOGPS
logP	-1.9	ChemAxon
logS	0.55	ALOGPS
pKa (Strongest Acidic)	13.31	ChemAxon
pKa (Strongest Basic)	7.43	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	63.93 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	44.02 m³·mol⁻¹	ChemAxon
Polarizability	17.31 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002083

Chemspider ID

349365

KEGG Compound ID

C10284

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

394146

PDB ID

Not Available

ChEBI ID

3925

Good Scents ID

Not Available

References

General References

Cicchi S, Marradi M, Vogel P, Goti A: One-pot synthesis of cyclic nitrones and their conversion to pyrrolizidines: 7a-epi-crotanecine inhibits alpha-mannosidases. J Org Chem. 2006 Feb 17;71(4):1614-9. doi: 10.1021/jo0523518. [PubMed:16468814 ]

Showing NP-Card for Crotanecine (NP0051157)

MOL for NP0051157 (Crotanecine)

3D MOL for NP0051157 (Crotanecine)

3D SDF for NP0051157 (Crotanecine)

3D-SDF for NP0051157 (Crotanecine)

PDB for NP0051157 (Crotanecine)

3D PDB for NP0051157 (Crotanecine)

SMILES for NP0051157 (Crotanecine)

INCHI for NP0051157 (Crotanecine)

Structure for NP0051157 (Crotanecine)

3D Structure for NP0051157 (Crotanecine)