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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:30:16 UTC

Update Date

2023-02-21 17:18:44 UTC

HMDB ID

HMDB0029412

Secondary Accession Numbers

HMDB29412

Metabolite Identification

Common Name

Betonicine

Description

Betonicine (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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(-)-Betonicine	ChEBI
(2S-trans)-2-Carboxylato-4-hydroxy-1,1-dimethylpyrrolidinium	ChEBI
4-Hydroxystachydrine	ChEBI
trans-4-Hydroxy-L-proline betaine	Kegg
4-Hydroxy-1,1-dimethylpyrrolidinium-2-carboxylate	HMDB
4-Hydroxy-stachydrine	HMDB
4-Hydroxyproline betaine	HMDB
Achillein	HMDB
4-Hydroxy-L-prolinebetaine	HMDB
Achilleine	HMDB
Betonicin	HMDB
trans-4-Hydroxyproline betaine	HMDB
Betonicine	ChEBI

Chemical Formula

C₇H₁₃NO₃

Average Molecular Weight

159.183

Monoisotopic Molecular Weight

159.089543287

IUPAC Name

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

Traditional Name

(-)-betonicine

CAS Registry Number

515-25-3

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 Key

MUNWAHDYFVYIKH-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.

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
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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

secondary alcohol (CHEBI:85533 )
amino-acid betaine (CHEBI:85533 )
pyrrolidine alkaloid (CHEBI:85533 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0029412)
Cytoplasm (HMDB: HMDB0029412)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0029412)
Feces (PMID: 27543620)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029412)

Source

Endogenous

Endogenous (HMDB: HMDB0029412)

Plant

Plant (HMDB: HMDB0029412)
Fabaceae (HMDB: HMDB0029412)

Exogenous

Food

Food (HMDB: HMDB0029412)

Fruit

Citrus

Citrus (HMDB: HMDB0029412)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Pulse

Pulses (FooDB: FOOD00867)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	252 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1000000 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	-4.240 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	12.2 g/L	ALOGPS
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	15.89 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	129.433	30932474
DeepCCS	[M-H]-	126.757	30932474
DeepCCS	[M-2H]-	162.97	30932474
DeepCCS	[M+Na]+	138.435	30932474
AllCCS	[M+H]+	131.6	32859911
AllCCS	[M+H-H2O]+	127.4	32859911
AllCCS	[M+NH4]+	135.5	32859911
AllCCS	[M+Na]+	136.6	32859911
AllCCS	[M-H]-	139.7	32859911
AllCCS	[M+Na-2H]-	140.9	32859911
AllCCS	[M+HCOO]-	142.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Betonicine	C[N+]1(C)C[C@H](O)C[C@H]1C([O-])=O	2126.5	Standard polar	33892256
Betonicine	C[N+]1(C)C[C@H](O)C[C@H]1C([O-])=O	1149.9	Standard non polar	33892256
Betonicine	C[N+]1(C)C[C@H](O)C[C@H]1C([O-])=O	1285.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Betonicine,1TMS,isomer #1	C[N+]1(C)C[C@H](O[Si](C)(C)C)C[C@H]1C(=O)[O-]	1385.8	Semi standard non polar	33892256
Betonicine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1C[C@@H](C(=O)[O-])[N+](C)(C)C1	1622.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Betonicine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-9100000000-50c5b1c24168d0a32658	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Betonicine GC-MS (1 TMS) - 70eV, Positive	splash10-0629-6900000000-39b7181df315007ea028	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Betonicine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Betonicine LC-ESI-QQ , positive-QTOF	splash10-0006-1900000000-eff9521990e036a811ba	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Betonicine LC-ESI-QQ , positive-QTOF	splash10-03dm-5900000000-0a8ce56fbb2260f1c94c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Betonicine LC-ESI-QQ , positive-QTOF	splash10-0bu9-9200000000-dd814eb7e302ebd54ac4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Betonicine LC-ESI-QQ , positive-QTOF	splash10-0a4i-9000000000-7a166858818cd35551e7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Betonicine LC-ESI-QQ , positive-QTOF	splash10-0a4i-9000000000-8bda725716df5ba24a82	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Betonicine 0V, Positive-QTOF	splash10-03di-0900000000-1858543faa980a7c11d8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Betonicine 30V, Positive-QTOF	splash10-052f-9000000000-1cb1487d66832440b034	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Betonicine 0V, Positive-QTOF	splash10-03di-0900000000-f4891c07d8ef91a2787e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Betonicine 10V, Positive-QTOF	splash10-03di-0900000000-9c97cd0b60404db6cff1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Betonicine 30V, Positive-QTOF	splash10-0a4r-9200000000-6314ab4658ce8c10a112	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Betonicine 10V, Positive-QTOF	splash10-03di-1900000000-9ae641ed4af38bb447b3	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Betonicine 10V, Positive-QTOF	splash10-03dl-0900000000-6a9f0e030e0567378c5f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Betonicine 20V, Positive-QTOF	splash10-03dl-4900000000-442e22b36ad486b30db5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Betonicine 40V, Positive-QTOF	splash10-05ai-9000000000-c8419ca7ef208db583d9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Betonicine 10V, Negative-QTOF	splash10-0a4i-0900000000-067ab41a06b72183a015	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Betonicine 20V, Negative-QTOF	splash10-0a4i-1900000000-ddc27ef204deb01df6bc	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Betonicine 40V, Negative-QTOF	splash10-0pi3-9000000000-8f4fc7a9a1b02c966f3d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Betonicine 10V, Positive-QTOF	splash10-03di-1900000000-cdf52381a0c2dde71659	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Betonicine 20V, Positive-QTOF	splash10-03dj-6900000000-c5fee471922a8688dc98	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Betonicine 40V, Positive-QTOF	splash10-0007-9000000000-44af82827b749a0aec27	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Betonicine 10V, Negative-QTOF	splash10-0a4i-0900000000-bae995f985c28e19f14c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Betonicine 20V, Negative-QTOF	splash10-0a4i-0900000000-bae995f985c28e19f14c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Betonicine 40V, Negative-QTOF	splash10-0a4l-8900000000-bef7213e00adbdebf43f	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	23425595	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal adenoma	27510537	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal adenoma	27510537	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

164642

PDB ID

Not Available

ChEBI ID

85533

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1701631

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Betonicine (HMDB0029412)

MOL for HMDB0029412 (Betonicine)

3D MOL for HMDB0029412 (Betonicine)

3D SDF for HMDB0029412 (Betonicine)

3D-SDF for HMDB0029412 (Betonicine)

PDB for HMDB0029412 (Betonicine)

3D PDB for HMDB0029412 (Betonicine)

SMILES for HMDB0029412 (Betonicine)

INCHI for HMDB0029412 (Betonicine)

Structure for HMDB0029412 (Betonicine)

3D Structure for HMDB0029412 (Betonicine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra