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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2012-09-11 17:55:04 UTC

Update Date

2023-02-21 17:23:14 UTC

HMDB ID

HMDB0033206

Secondary Accession Numbers

HMDB33206

Metabolite Identification

Common Name

Arsenobetaine

Description

Arsenobetaine is found in crustaceans. Arsenobetaine is found in algae, lobsters, sharks, etc. Arsenobetaine is an organoarsenic compound that is the main source of arsenic found in fish. It is the arsenic analogue of trimethylglycine, commonly known as betaine. The biochemistry and its biosynthesis are similar to the biosynthesis of choline and betaine. The; Besides several other arsenic compounds, such as dimethylarsine and trimethylarsine, arsenobetaine is a common substance in the marine biological systems for arsenic detoxification.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(Carboxymethyl)trimethylarsonium hydroxide inner salt	HMDB
(Carboxymethyl)trimethylarsonium hydroxide inner salt, 9ci	HMDB
2-(trimethylarsonio)Acetate	HMDB
Arsenobetaine monohydrate	HMDB
Arsonium, (carboxymethyl)trimethyl-, hydroxide, inner salt	HMDB

Chemical Formula

C₅H₁₁AsO₂

Average Molecular Weight

178.0612

Monoisotopic Molecular Weight

177.997501013

IUPAC Name

2-(trimethylarsaniumyl)acetate

Traditional Name

arsenobetaine

CAS Registry Number

64436-13-1

SMILES

C[As+](C)(C)CC([O-])=O

InChI Identifier

InChI=1S/C5H11AsO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3

InChI Key

SPTHHTGLGVZZRH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetraorganoarsonium salts. These are organoarsenic compounds, where the arsenic atom is tetrasubstituted by organic groups. They have the general structure R4[As+]X-, X=any atom but H.

Kingdom

Organic compounds

Super Class

Organometallic compounds

Class

Organometalloid compounds

Sub Class

Organoarsenic compounds

Direct Parent

Tetraorganoarsonium salts

Alternative Parents

Substituents

Tetraorganoarsonium salt
Carboxylic acid salt
Oxygen-containing organoarsenic compound
Organic metalloid salt
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic salt
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

organic salt (CHEBI:82392 )

Ontology

Physiological effect

Health effect

Digestive system disorder

Gastrointestinal disorder

Nausea (HMDB: HMDB0033206)
Vomiting (HMDB: HMDB0033206)

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033206)
Cytoplasm (HMDB: HMDB0033206)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0033206)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Route of exposure

Parenteral

Dermal (HMDB: HMDB0033206)
Inhalation (HMDB: HMDB0033206)

Enteral

Ingestion (HMDB: HMDB0033206)

Source

Exogenous

Food

Food (HMDB: HMDB0033206)
Seafood (HMDB: HMDB0033206)

Aquatic origin

Crustacean

Crustaceans (FooDB: FOOD00862)

Endogenous

Animal

Animal (HMDB: HMDB0033206)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033206)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	204 - 210 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6 g/L	ALOGPS
logP	1.84	ALOGPS
logP	0.94	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	2.9	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	2	ChemAxon
Refractivity	39.27 m³·mol⁻¹	ChemAxon
Polarizability	13.9 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	115.7	32859911
AllCCS	[M+H-H2O]+	112.9	32859911
AllCCS	[M+NH4]+	118.3	32859911
AllCCS	[M+Na]+	119.0	32859911
AllCCS	[M-H]-	146.2	32859911
AllCCS	[M+Na-2H]-	149.1	32859911
AllCCS	[M+HCOO]-	152.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Arsenobetaine	C[As+](C)(C)CC([O-])=O	1181.0	Standard polar	33892256
Arsenobetaine	C[As+](C)(C)CC([O-])=O	896.7	Standard non polar	33892256
Arsenobetaine	C[As+](C)(C)CC([O-])=O	1019.8	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 - Arsenobetaine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0400-2900000000-87ae859df28e772e20de	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arsenobetaine 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arsenobetaine 10V, Positive-QTOF	splash10-004i-0900000000-db2b71a9b1e552a5dd68	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arsenobetaine 20V, Positive-QTOF	splash10-004i-2900000000-7451c19f2ce0c2ad26fe	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arsenobetaine 40V, Positive-QTOF	splash10-0550-3900000000-13badada4bf33596b142	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arsenobetaine 10V, Negative-QTOF	splash10-004i-2900000000-04587c1087dd728fb563	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arsenobetaine 20V, Negative-QTOF	splash10-004i-3900000000-49065dd3149cd41b348f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arsenobetaine 40V, Negative-QTOF	splash10-004i-5900000000-d2fc0322a2d3012fa8de	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arsenobetaine 10V, Negative-QTOF	splash10-004i-0900000000-4b7657b48ada1743bb00	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arsenobetaine 20V, Negative-QTOF	splash10-004i-0900000000-4b7657b48ada1743bb00	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arsenobetaine 40V, Negative-QTOF	splash10-004i-0900000000-4b7657b48ada1743bb00	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arsenobetaine 10V, Positive-QTOF	splash10-004i-0900000000-af29e072762dfc4849f7	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arsenobetaine 20V, Positive-QTOF	splash10-0gb9-0900000000-b8c4f424419f918c487e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arsenobetaine 40V, Positive-QTOF	splash10-0udi-0900000000-0e1ff95f34f41b01777d	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
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
Urine	Detected and Quantified	0.00129 (0.00108-0.00154) umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	National Health a...	details
Urine	Detected and Quantified	0.00107 (0.000921-0.00125) umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	National Health a...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Not Available

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

Arsenobetaine

METLIN ID

Not Available

PubChem Compound

47364

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

ARSENB

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for Arsenobetaine (HMDB0033206)

MOL for HMDB0033206 (Arsenobetaine)

3D MOL for HMDB0033206 (Arsenobetaine)

3D SDF for HMDB0033206 (Arsenobetaine)

3D-SDF for HMDB0033206 (Arsenobetaine)

PDB for HMDB0033206 (Arsenobetaine)

3D PDB for HMDB0033206 (Arsenobetaine)

SMILES for HMDB0033206 (Arsenobetaine)

INCHI for HMDB0033206 (Arsenobetaine)

Structure for HMDB0033206 (Arsenobetaine)

3D Structure for HMDB0033206 (Arsenobetaine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra