NP-MRD: Showing NP-Card for betonicine (NP0249936)

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Record Information

Version

2.0

Created at

2022-09-07 12:38:00 UTC

Updated at

2022-09-07 12:38:00 UTC

NP-MRD ID

NP0249936

Secondary Accession Numbers

None

Natural Product Identification

Common Name

betonicine

Description

4-Hydroxystachydrine belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. betonicine is found in Boscia angustifolia. 4-Hydroxystachydrine is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  N   UNK     0      -3.300  -2.760   0.000  0.00  0.00           N+1
HETATM    2  C   UNK     0      -4.546  -3.665   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.070  -5.130   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.530  -5.130   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.054  -3.665   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.211  -1.671   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.389  -1.671   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.033  -3.267   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -6.432  -1.779   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -7.122  -4.356   0.000  0.00  0.00           O-1
HETATM   11  O   UNK     0      -1.441  -6.219   0.000  0.00  0.00           O+0
HETATM   12  H   UNK     0      -1.043  -7.706   0.000  0.00  0.00           H+0
CONECT    1    2    5    6    7                                             
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    1    4                                                       
CONECT    6    1                                                            
CONECT    7    1                                                            
CONECT    8    2    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    4   12                                                       
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol

Synonyms

Value	Source
4-Hydroxy-stachydrine	HMDB
(2R)-4-Hydroxy-1,1-dimethylpyrrolidin-1-ium-2-carboxylic acid	Generator

Chemical Formula

C₇H₁₃NO₃

Average Mass

159.1830 Da

Monoisotopic Mass

159.08954 Da

IUPAC Name

(2R)-4-hydroxy-1,1-dimethylpyrrolidin-1-ium-2-carboxylate

Traditional Name

(2R)-4-hydroxy-1,1-dimethylpyrrolidin-1-ium-2-carboxylate

CAS Registry Number

Not Available

SMILES

[H]OC1C[C@H](C([O-])=O)[N+](C)(C)C1

InChI Identifier

InChI=1S/C7H13NO3/c1-8(2)4-5(9)3-6(8)7(10)11/h5-6,9H,3-4H2,1-2H3/t5?,6-/m1/s1

InChI Key

MUNWAHDYFVYIKH-PRJDIBJQSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Boscia angustifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Proline and derivatives

Alternative Parents

Substituents

Proline or derivatives
Alpha-amino acid
D-alpha-amino acid
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
N-alkylpyrrolidine
Tetraalkylammonium salt
Pyrrolidine
Quaternary ammonium salt
1,2-aminoalcohol
Carboxylic acid salt
Secondary alcohol
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Organic oxide
Organooxygen compound
Organonitrogen compound
Alcohol
Organic nitrogen compound
Organopnictogen compound
Carbonyl group
Amine
Hydrocarbon derivative
Organic oxygen compound
Organic salt
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

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	-1.5	ALOGPS
logP	-5	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	2.06	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	60.36 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	61.43 m³·mol⁻¹	ChemAxon
Polarizability	15.94 Å³	ChemAxon
Number of Rings	1	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

HMDB0029230

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

333078

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

375481

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for betonicine (NP0249936)

MOL for NP0249936 (betonicine)

3D MOL for NP0249936 (betonicine)

3D SDF for NP0249936 (betonicine)

3D-SDF for NP0249936 (betonicine)

PDB for NP0249936 (betonicine)

3D PDB for NP0249936 (betonicine)

SMILES for NP0249936 (betonicine)

INCHI for NP0249936 (betonicine)

Structure for NP0249936 (betonicine)

3D Structure for NP0249936 (betonicine)