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Showing NP-Card for (-)-Betonicine (NP0050673)

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Record Information
Version2.0
Created at2022-04-27 22:01:33 UTC
Updated at2022-04-27 22:01:34 UTC
NP-MRD IDNP0050673
Secondary Accession NumbersNone
Natural Product Identification
Common Name(-)-Betonicine
DescriptionBetonicine, also known as achillein, 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 an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Betonicine has been detected, but not quantified in, herbs and spices and pulses. This could make betonicine a potential biomarker for the consumption of these foods. (-)-Betonicine is found in Achillea millefolium , Betonica officinalis , Combretum micranthum , Marrubium vulgare and Stachys sylvatica. (-)-Betonicine was first documented in 2011 (PMID: 21838291). An amino-acid betaine that is trans-4-hydroxy-L-proline zwitterion in which both of the hydrogens attached to the nitrogen have been replaced by methyl groups (PMID: 25012968) (PMID: 24056934).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0050673 ((-)-Betonicine)


  Mrv1652302131922292D          

 11 11  0  0  0  0            999 V2000
10000.797610000.5336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.511810000.1207    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
10000.797610001.3593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4981 9998.6806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.743010000.1299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9979 9999.3453    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.8229 9999.3453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.077810000.1299    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.893410001.2608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.936010001.2508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.410410000.6149    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  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
  6  4  1  1  0  0  0
  8  1  1  6  0  0  0
 11 10  1  0  0  0  0
 11  9  1  0  0  0  0
 11  5  1  0  0  0  0
 11  8  1  0  0  0  0
M  CHG  2   2  -1  11   1
M  END
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3D MOL for NP0050673 ((-)-Betonicine)

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3D SDF for NP0050673 ((-)-Betonicine)

  Mrv1652302131922292D          

 11 11  0  0  0  0            999 V2000
10000.797610000.5336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.511810000.1207    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
10000.797610001.3593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4981 9998.6806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.743010000.1299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9979 9999.3453    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.8229 9999.3453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.077810000.1299    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.893410001.2608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.936010001.2508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.410410000.6149    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  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
  6  4  1  1  0  0  0
  8  1  1  6  0  0  0
 11 10  1  0  0  0  0
 11  9  1  0  0  0  0
 11  5  1  0  0  0  0
 11  8  1  0  0  0  0
M  CHG  2   2  -1  11   1
M  END
> <DATABASE_ID>
NP0050673

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[N+]1(C)C[C@H](O)C[C@H]1C([O-])=O

> <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-RITPCOANSA-N

> <FORMULA>
C7H13NO3

> <MOLECULAR_WEIGHT>
159.183

> <EXACT_MASS>
159.089543287

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
15.894499251759953

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,4R)-4-hydroxy-1,1-dimethylpyrrolidin-1-ium-2-carboxylate

> <ALOGPS_LOGP>
-1.54

> <JCHEM_LOGP>
-5.024127701138411

> <ALOGPS_LOGS>
-1.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.300851920687492

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.0584560741278652

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5570117202950957

> <JCHEM_POLAR_SURFACE_AREA>
60.36

> <JCHEM_REFRACTIVITY>
61.427600000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.22e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-betonicine

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0050673 ((-)-Betonicine)
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PDB for NP0050673 ((-)-Betonicine)
HEADER    PROTEIN                                 13-FEB-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-FEB-19         0                                  
HETATM    1  C   UNK     0    8668.1568667.663   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8669.4898666.892   0.000  0.00  0.00           O-1
HETATM    3  O   UNK     0    8668.1568669.204   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8663.8638664.204   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    8664.3208666.909   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8664.7968665.445   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8666.3368665.445   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8666.8128666.909   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8664.6018669.020   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8666.5478669.001   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0    8665.5668667.814   0.000  0.00  0.00           N+1
CONECT    1    2    3    8                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    6                                                            
CONECT    5    6   11                                                       
CONECT    6    5    7    4                                                  
CONECT    7    6    8                                                       
CONECT    8    7    1   11                                                  
CONECT    9   11                                                            
CONECT   10   11                                                            
CONECT   11   10    9    5    8                                             
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

Download
3D PDB for NP0050673 ((-)-Betonicine)
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SMILES for NP0050673 ((-)-Betonicine)
C[N+]1(C)C[C@H](O)C[C@H]1C([O-])=O
Download
INCHI for NP0050673 ((-)-Betonicine)
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
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View in JSmol
Synonyms
ValueSource
(-)-BetonicineChEBI
(2S-trans)-2-Carboxylato-4-hydroxy-1,1-dimethylpyrrolidiniumChEBI
4-HydroxystachydrineChEBI
trans-4-Hydroxy-L-proline betaineKegg
4-Hydroxy-1,1-dimethylpyrrolidinium-2-carboxylateHMDB
4-Hydroxy-stachydrineHMDB
4-Hydroxyproline betaineHMDB
AchilleinHMDB
4-Hydroxy-L-prolinebetaineHMDB
AchilleineHMDB
BetonicinHMDB
trans-4-Hydroxyproline betaineHMDB
BetonicineChEBI
Chemical FormulaC7H13NO3
Average Mass159.1830 Da
Monoisotopic Mass159.08954 Da
IUPAC Name(2S,4R)-4-hydroxy-1,1-dimethylpyrrolidin-1-ium-2-carboxylate
Traditional Name(-)-betonicine
CAS Registry NumberNot Available
SMILES
C[N+]1(C)C[C@H](O)C[C@H]1C([O-])=O
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 KeyMUNWAHDYFVYIKH-RITPCOANSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Achillea millefoliumPlant
Betonica officinalisPlant
Combretum micranthumPlant
Marrubium vulgarePlant
Stachys sylvaticaPlant
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.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentProline and derivatives  
Alternative Parents
Substituents
  • Proline or derivatives
    • 

  • Alpha-amino acid
    • 

  • L-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 FrameworkAliphatic heteromonocyclic compounds
External Descriptors
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
logP-1.5ALOGPS
logP-5ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)2.06ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area60.36 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity61.43 m³·mol⁻¹ChemAxon
Polarizability15.89 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0029412  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000502  
KNApSAcK IDC00001345  
Chemspider ID144333  
KEGG Compound IDC08269  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound164642  
PDB IDNot Available
ChEBI ID85533  
Good Scents IDNot Available
References
General References
  1. Bashir A, Hoffmann T, Kempf B, Xie X, Smits SHJ, Bremer E: Plant-derived compatible solutes proline betaine and betonicine confer enhanced osmotic and temperature stress tolerance to Bacillus subtilis. Microbiology (Reading). 2014 Oct;160(Pt 10):2283-2294. doi: 10.1099/mic.0.079665-0. Epub 2014 Jul 10. [PubMed:25012968  ] 
  2. Zhao S, Kumar R, Sakai A, Vetting MW, Wood BM, Brown S, Bonanno JB, Hillerich BS, Seidel RD, Babbitt PC, Almo SC, Sweedler JV, Gerlt JA, Cronan JE, Jacobson MP: Discovery of new enzymes and metabolic pathways by using structure and genome context. Nature. 2013 Oct 31;502(7473):698-702. doi: 10.1038/nature12576. Epub 2013 Sep 22. [PubMed:24056934  ] 
  3. Servillo L, Giovane A, Balestrieri ML, Bata-Csere A, Cautela D, Castaldo D: Betaines in fruits of Citrus genus plants. J Agric Food Chem. 2011 Sep 14;59(17):9410-6. doi: 10.1021/jf2014815. Epub 2011 Aug 12. [PubMed:21838291  ]