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Showing metabocard for Betonicine (HMDB0029412)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:30:16 UTC
Update Date2023-02-21 17:18:44 UTC
HMDB IDHMDB0029412
Secondary Accession Numbers
  • HMDB29412
Metabolite Identification
Common NameBetonicine
DescriptionBetonicine (4-hydroxy-L-prolinebetaine) and its cis isomer, turicine, are naturally occurring substituted pyrrolidines. It is not naturally produced by humans and can only be obtained through consumption of certain plant products. Betonicine was used as an analgesic 1000 years ago and is still available commercially from herbalists today. Betonicine has been isolated from Achillea millefolium L. (common yarrow) and probably from A. atrata L. (black yarrow); it is an alkaloid. Betonicine has been identified as a metabolically inert cell protectant that protects plants against extremes in osmolarity and growth temperatures. Betonicine is found in the fruit juices of yellow orange, blood orange, lemon, mandarin and bitter orange (PMID: 21838291 )
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0029412 (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 HMDB0029412 (Betonicine)

HMDB0029412
     RDKit          3D
Betonicine
 24 24  0  0  0  0  0  0  0  0999 V2000
   -1.1294   -0.2728    1.6467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4961   -0.3278    0.3630 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.2538   -1.0557   -0.6114 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7962   -1.0135    0.5091 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6622   -0.4809   -0.6089 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9532   -0.2368   -0.1597 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0104    0.7982   -1.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0915    0.9763   -0.0391 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1400    1.8032   -0.6360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2689    1.4045   -1.0220 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8783    3.1589   -0.7981 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.2843   -1.3215    2.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4499    0.2420    2.3566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1145    0.2309    1.5648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3075   -1.1242   -0.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2547   -0.6156   -1.6176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8878   -2.1208   -0.6918 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2442   -0.7239    1.4800 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6939   -2.1005    0.4196 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7289   -1.1670   -1.4626 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9226    0.0804    0.7654 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6849    1.6519   -0.9710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5381    0.7120   -2.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3223    1.5028    0.8395 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  8  2  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  3 16  1  0
  3 17  1  0
  4 18  1  0
  4 19  1  0
  5 20  1  6
  6 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  1
M  CHG  2   2   1  11  -1
M  END
Download

3D SDF for HMDB0029412 (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>
HMDB0029412

> <DATABASE_NAME>
hmdb

> <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

$$$$
Download

3D-SDF for HMDB0029412 (Betonicine)

HMDB0029412
     RDKit          3D
Betonicine
 24 24  0  0  0  0  0  0  0  0999 V2000
   -1.1294   -0.2728    1.6467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4961   -0.3278    0.3630 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.2538   -1.0557   -0.6114 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7962   -1.0135    0.5091 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6622   -0.4809   -0.6089 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9532   -0.2368   -0.1597 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0104    0.7982   -1.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0915    0.9763   -0.0391 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1400    1.8032   -0.6360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2689    1.4045   -1.0220 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8783    3.1589   -0.7981 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.2843   -1.3215    2.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4499    0.2420    2.3566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1145    0.2309    1.5648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3075   -1.1242   -0.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2547   -0.6156   -1.6176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8878   -2.1208   -0.6918 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2442   -0.7239    1.4800 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6939   -2.1005    0.4196 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7289   -1.1670   -1.4626 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9226    0.0804    0.7654 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6849    1.6519   -0.9710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5381    0.7120   -2.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3223    1.5028    0.8395 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  8  2  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  3 16  1  0
  3 17  1  0
  4 18  1  0
  4 19  1  0
  5 20  1  6
  6 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  1
M  CHG  2   2   1  11  -1
M  END
Download

PDB for HMDB0029412 (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
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3D PDB for HMDB0029412 (Betonicine)

COMPND    HMDB0029412
HETATM    1  C1  UNL     1      -1.129  -0.273   1.647  1.00  0.00           C  
HETATM    2  N1  UNL     1      -0.496  -0.328   0.363  1.00  0.00           N1+
HETATM    3  C2  UNL     1      -1.254  -1.056  -0.611  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.796  -1.014   0.509  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.662  -0.481  -0.609  1.00  0.00           C  
HETATM    6  O1  UNL     1       2.953  -0.237  -0.160  1.00  0.00           O  
HETATM    7  C5  UNL     1       1.010   0.798  -1.071  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.091   0.976  -0.039  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.140   1.803  -0.636  1.00  0.00           C  
HETATM   10  O2  UNL     1      -2.269   1.404  -1.022  1.00  0.00           O  
HETATM   11  O3  UNL     1      -0.878   3.159  -0.798  1.00  0.00           O1-
HETATM   12  H1  UNL     1      -1.284  -1.322   2.022  1.00  0.00           H  
HETATM   13  H2  UNL     1      -0.450   0.242   2.357  1.00  0.00           H  
HETATM   14  H3  UNL     1      -2.114   0.231   1.565  1.00  0.00           H  
HETATM   15  H4  UNL     1      -2.308  -1.124  -0.214  1.00  0.00           H  
HETATM   16  H5  UNL     1      -1.255  -0.616  -1.618  1.00  0.00           H  
HETATM   17  H6  UNL     1      -0.888  -2.121  -0.692  1.00  0.00           H  
HETATM   18  H7  UNL     1       1.244  -0.724   1.480  1.00  0.00           H  
HETATM   19  H8  UNL     1       0.694  -2.101   0.420  1.00  0.00           H  
HETATM   20  H9  UNL     1       1.729  -1.167  -1.463  1.00  0.00           H  
HETATM   21  H10 UNL     1       2.923   0.080   0.765  1.00  0.00           H  
HETATM   22  H11 UNL     1       1.685   1.652  -0.971  1.00  0.00           H  
HETATM   23  H12 UNL     1       0.538   0.712  -2.063  1.00  0.00           H  
HETATM   24  H13 UNL     1       0.322   1.503   0.839  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    4    8
CONECT    3   15   16   17
CONECT    4    5   18   19
CONECT    5    6    7   20
CONECT    6   21
CONECT    7    8   22   23
CONECT    8    9   24
CONECT    9   10   10   11
END
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SMILES for HMDB0029412 (Betonicine)

C[N+]1(C)C[C@H](O)C[C@H]1C([O-])=O
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INCHI for HMDB0029412 (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 JSmolView NMR AssignmentsView Stereo Labels
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 Molecular Weight159.183
Monoisotopic Molecular Weight159.089543287
IUPAC Name(2S,4R)-4-hydroxy-1,1-dimethylpyrrolidin-1-ium-2-carboxylate
Traditional Name(-)-betonicine
CAS Registry Number515-25-3
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
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
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point252 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000000 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-4.240 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal adenoma 		details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal adenoma 		details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1701631
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .