NP-MRD: Showing NP-Card for l-(+)-Isoleucine betaine (NP0044939)

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Record Information

Version

2.0

Created at

2022-03-10 18:51:28 UTC

Updated at

2022-03-10 22:21:30 UTC

NP-MRD ID

NP0044939

Secondary Accession Numbers

None

Natural Product Identification

Common Name

l-(+)-Isoleucine betaine

Description

L-(+)-isoleucine betaine, also known as Isoleucine betaine, belongs to the class of compounds known as betaines. A betaine is any neutral chemical compound with a positively charged cationic functional group such as a quaternary ammonium cation that bears no hydrogen atom and with a negatively charged functional group such as a carboxylate group that may not be adjacent to the cationic site. Isoleucine betaine can also be classified as a quaternary ammonium salt with three methyl groups and one carboxyl group attached to the nitrogen atom via C-2. Isoleucine betaine is a naturally occurring organic compound first isolated from Cannabis seeds in 1973. The structure of isoleucine betaine was determined by spectroscopic methods and confirmed by synthesis (https://Doi.Org/10.1016/0031-9422(73)80454-6). Isoleucine betaine was first isolated and identified as a cannabis constituent in 1973 (PMID:6991645 ).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 30  0  0  0  0  0  0  0  0999 V2000
    2.9259    1.2063   -0.0751 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5644    0.7470   -0.6278 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9986   -0.2064    0.3483 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9584   -1.3784    0.4863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3502   -0.7365    0.1006 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4599   -1.5590   -1.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4170   -2.3823   -1.3040 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4576   -1.4939   -2.1714 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.4381    0.1962    0.1485 N   0  0  2  0  0  4  0  0  0  0  0  0
   -1.6296    0.9560   -1.0396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3778    1.0119    1.3486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6360   -0.6324    0.3148 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7413    0.5799   -0.4854 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9099    1.1479    1.0342 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1466    2.2436   -0.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7724    0.3556   -1.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9785    1.7132   -0.6674 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0117    0.2957    1.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5452   -1.3559    1.4008 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6621   -1.4223   -0.3795 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4124   -2.3580    0.4624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5580   -1.4561    0.9527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6861    0.9423   -1.3812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3828    2.0401   -0.9261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0380    0.4882   -1.8585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7484    1.8926    1.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0584    0.3588    2.1806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4094    1.3741    1.6014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4151   -1.6083    0.7528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3757   -0.1355    0.9720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1046   -0.8244   -0.6873 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
  3  2  1  0
  2  1  1  0
  3  5  1  0
  5  6  1  0
  6  8  1  0
  6  7  2  0
  5  9  1  0
  9 10  1  6
  9 11  1  0
  9 12  1  0
  3 18  1  1
  4 19  1  0
  4 20  1  0
  4 21  1  0
  2 16  1  0
  2 17  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  5 22  1  1
 10 23  1  0
 10 24  1  0
 10 25  1  0
 11 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 12 31  1  0
M  CHG  2   8  -1   9   1
M  END


  Mrv1652307312018372D          

 14 13  0  0  1  0            999 V2000
   -0.1914   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9520   -1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9520   -1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.7145    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    2.6664   -2.3645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -2.3645    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.5230   -0.3020    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -1.5395    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  7  2  1  6  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  8  9  1  1  0  0  0
 10  3  1  0  0  0  0
 10  4  1  0  0  0  0
 10  5  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  2  0  0  0  0
 12  9  1  0  0  0  0
  7 13  1  1  0  0  0
  8 14  1  6  0  0  0
M  CHG  2  10   1  12  -1
M  END
> <DATABASE_ID>
NP0044939

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@](C)(CC)[C@]([H])(C([O-])=O)[N+](C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C9H19NO2/c1-6-7(2)8(9(11)12)10(3,4)5/h7-8H,6H2,1-5H3/t7-,8+/m0/s1

> <INCHI_KEY>
WEFWRGFGKPRQQC-JGVFFNPUSA-N

> <FORMULA>
C9H19NO2

> <MOLECULAR_WEIGHT>
173.256

> <EXACT_MASS>
173.141578856

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
19.557910632492558

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S)-3-methyl-2-(trimethylazaniumyl)pentanoate

> <ALOGPS_LOGP>
-2.05

> <JCHEM_LOGP>
-2.593355713805079

> <ALOGPS_LOGS>
-3.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.6850082994733757

> <JCHEM_POLAR_SURFACE_AREA>
40.129999999999995

> <JCHEM_REFRACTIVITY>
70.91390000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.35e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S)-3-methyl-2-(trimethylammonio)pentanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 31-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-JUL-20         0                                  
HETATM    1  C   UNK     0      -0.357  -1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.310   0.206   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.311  -0.564   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.747  -2.667   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.207   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.976  -2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.644  -2.104   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.644  -3.644   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       4.977  -1.334   0.000  0.00  0.00           N+1
HETATM   11  O   UNK     0       4.977  -4.414   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.310  -4.414   0.000  0.00  0.00           O-1
HETATM   13  H   UNK     0       0.976  -0.564   0.000  0.00  0.00           H+0
HETATM   14  H   UNK     0       2.310  -2.874   0.000  0.00  0.00           H+0
CONECT    1    6                                                            
CONECT    2    7                                                            
CONECT    3   10                                                            
CONECT    4   10                                                            
CONECT    5   10                                                            
CONECT    6    1    7                                                       
CONECT    7    2    6    8   13                                             
CONECT    8    7    9   10   14                                             
CONECT    9    8   11   12                                                  
CONECT   10    3    4    5    8                                             
CONECT   11    9                                                            
CONECT   12    9                                                            
CONECT   13    7                                                            
CONECT   14    8                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

View in JSmol

Synonyms

Value	Source
(2R,3S)-3-Methyl-2-(trimethylazaniumyl)pentanoic acid	Generator

Chemical Formula

C₉H₁₉NO₂

Average Mass

173.2560 Da

Monoisotopic Mass

173.14158 Da

IUPAC Name

(2R,3S)-3-methyl-2-(trimethylazaniumyl)pentanoate

Traditional Name

(2R,3S)-3-methyl-2-(trimethylammonio)pentanoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C9H19NO2/c1-6-7(2)8(9(11)12)10(3,4)5/h7-8H,6H2,1-5H3/t7-,8+/m0/s1

InChI Key

WEFWRGFGKPRQQC-JGVFFNPUSA-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
Cannabis sativa	NULL	Not Available

Chemical Taxonomy

Classification

Not classified

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	-2	ALOGPS
logP	-2.6	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	2.69	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.13 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	70.91 m³·mol⁻¹	ChemAxon
Polarizability	19.56 Å³	ChemAxon
Number of Rings	0	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for l-(+)-Isoleucine betaine (NP0044939)

MOL for NP0044939 (l-(+)-Isoleucine betaine)

3D MOL for NP0044939 (l-(+)-Isoleucine betaine)

3D SDF for NP0044939 (l-(+)-Isoleucine betaine)

3D-SDF for NP0044939 (l-(+)-Isoleucine betaine)

PDB for NP0044939 (l-(+)-Isoleucine betaine)

3D PDB for NP0044939 (l-(+)-Isoleucine betaine)

SMILES for NP0044939 (l-(+)-Isoleucine betaine)

INCHI for NP0044939 (l-(+)-Isoleucine betaine)

Structure for NP0044939 (l-(+)-Isoleucine betaine)

3D Structure for NP0044939 (l-(+)-Isoleucine betaine)