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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:30:26 UTC

Update Date

2022-03-07 02:53:50 UTC

HMDB ID

HMDB0033747

Secondary Accession Numbers

HMDB33747

Metabolite Identification

Common Name

(±)-2,2'-Iminobispropanoic acid

Description

(±)-2,2'-Iminobispropanoic acid, also known as 2,2'-iminodipropanoate or alanopine, belongs to the class of organic compounds known as alanine and derivatives. Alanine and derivatives are compounds containing alanine or a derivative thereof resulting from reaction of alanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom (±)-2,2'-Iminobispropanoic acid has been detected, but not quantified in, mollusks. This could make (±)-2,2'-iminobispropanoic acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on (±)-2,2'-Iminobispropanoic acid.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2,2'-Iminodipropanoate	ChEBI
Alanopine	ChEBI
Meso-N-(1-carboxyethyl)-alanine	Kegg
2,2'-Iminodipropanoic acid	Generator
(±)-2,2'-iminobispropanoate	Generator
(+/-)-form	HMDB
2,2'-Iminobispropanoic acid	HMDB
2,2'-Iminodipropionic acid	HMDB, MeSH
N-(1-Carboxyethyl)-L-alanine	HMDB
Alanopine, (L)-isomer	MeSH, HMDB
Meso-2,2'-iminobispropanoate	Generator

Chemical Formula

C₆H₁₁NO₄

Average Molecular Weight

161.1558

Monoisotopic Molecular Weight

161.068807845

IUPAC Name

2-[(1-carboxyethyl)amino]propanoic acid

Traditional Name

alanopine

CAS Registry Number

19149-54-3

SMILES

CC(NC(C)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C6H11NO4/c1-3(5(8)9)7-4(2)6(10)11/h3-4,7H,1-2H3,(H,8,9)(H,10,11)

InChI Key

FIOHTMQGSFVHEZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alanine and derivatives. Alanine and derivatives are compounds containing alanine or a derivative thereof resulting from reaction of alanine 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

Alanine and derivatives

Alternative Parents

Substituents

Alanine or derivatives
Alpha-amino acid
Dicarboxylic acid or derivatives
Amino acid
Carboxylic acid
Secondary aliphatic amine
Secondary amine
Amine
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organopnictogen compound
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

amino dicarboxylic acid (CHEBI:857 )
amino acid opine (CHEBI:857 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB33747)
Extracellular (HMDB: HMDB33747)

Route of exposure

Enteral

Ingestion (HMDB: HMDB33747)

Source

Exogenous

Food

Food (HMDB: HMDB33747)

Aquatic origin

Mollusk

Mollusks (FooDB: FOOD00868)

Endogenous

Animal

Animal (HMDB: HMDB33747)

Not Available

Nutrient (HMDB: HMDB33747)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	234 - 235 °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	35.2 g/L	ALOGPS
logP	-2	ALOGPS
logP	-2.8	ChemAxon
logS	-0.66	ALOGPS
pKa (Strongest Acidic)	2.48	ChemAxon
pKa (Strongest Basic)	8.79	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.63 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	35.85 m³·mol⁻¹	ChemAxon
Polarizability	15.12 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
DarkChem	[M+H]+	135.832	31661259
DarkChem	[M-H]-	131.003	31661259
DeepCCS	[M+H]+	129.43	30932474
DeepCCS	[M-H]-	125.859	30932474
DeepCCS	[M-2H]-	163.114	30932474
DeepCCS	[M+Na]+	138.207	30932474
AllCCS	[M+H]+	137.7	32859911
AllCCS	[M+H-H2O]+	133.9	32859911
AllCCS	[M+NH4]+	141.3	32859911
AllCCS	[M+Na]+	142.3	32859911
AllCCS	[M-H]-	132.1	32859911
AllCCS	[M+Na-2H]-	134.1	32859911
AllCCS	[M+HCOO]-	136.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(??)-2,2'-Iminobispropanoic acid	CC(NC(C)C(O)=O)C(O)=O	2473.3	Standard polar	33892256
(??)-2,2'-Iminobispropanoic acid	CC(NC(C)C(O)=O)C(O)=O	1208.2	Standard non polar	33892256
(??)-2,2'-Iminobispropanoic acid	CC(NC(C)C(O)=O)C(O)=O	1421.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(??)-2,2'-Iminobispropanoic acid,1TMS,isomer #1	CC(NC(C)C(=O)O[Si](C)(C)C)C(=O)O	1408.7	Semi standard non polar	33892256
(??)-2,2'-Iminobispropanoic acid,1TMS,isomer #2	CC(C(=O)O)N(C(C)C(=O)O)[Si](C)(C)C	1556.4	Semi standard non polar	33892256
(??)-2,2'-Iminobispropanoic acid,2TMS,isomer #1	CC(NC(C)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1468.1	Semi standard non polar	33892256
(??)-2,2'-Iminobispropanoic acid,2TMS,isomer #2	CC(C(=O)O)N(C(C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1556.6	Semi standard non polar	33892256
(±)-2,2'-Iminobispropanoic acid,3TMS,isomer #1	CC(C(=O)O[Si](C)(C)C)N(C(C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1606.1	Semi standard non polar	33892256
(±)-2,2'-Iminobispropanoic acid,3TMS,isomer #1	CC(C(=O)O[Si](C)(C)C)N(C(C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1547.6	Standard non polar	33892256
(??)-2,2'-Iminobispropanoic acid,1TBDMS,isomer #1	CC(NC(C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	1661.0	Semi standard non polar	33892256
(??)-2,2'-Iminobispropanoic acid,1TBDMS,isomer #2	CC(C(=O)O)N(C(C)C(=O)O)[Si](C)(C)C(C)(C)C	1808.3	Semi standard non polar	33892256
(??)-2,2'-Iminobispropanoic acid,2TBDMS,isomer #1	CC(NC(C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1905.3	Semi standard non polar	33892256
(??)-2,2'-Iminobispropanoic acid,2TBDMS,isomer #2	CC(C(=O)O)N(C(C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2034.7	Semi standard non polar	33892256
(±)-2,2'-Iminobispropanoic acid,3TBDMS,isomer #1	CC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2244.1	Semi standard non polar	33892256
(±)-2,2'-Iminobispropanoic acid,3TBDMS,isomer #1	CC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2195.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-2,2'-Iminobispropanoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-00tf-9300000000-96d8515a641318edc19b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-2,2'-Iminobispropanoic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00du-9310000000-a98c36c5cf8d9eff6e4b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-2,2'-Iminobispropanoic acid 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 - (±)-2,2'-Iminobispropanoic acid , positive-QTOF	splash10-02t9-0900000000-e9c486395babd0c27831	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (±)-2,2'-Iminobispropanoic acid , positive-QTOF	splash10-02t9-0900000000-44390e9653caacbf83a6	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-2,2'-Iminobispropanoic acid 10V, Positive-QTOF	splash10-03xr-1900000000-59ab22c2ca6dbaca1145	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-2,2'-Iminobispropanoic acid 20V, Positive-QTOF	splash10-01b9-9800000000-7bf391205f1d37e7b478	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-2,2'-Iminobispropanoic acid 40V, Positive-QTOF	splash10-00di-9100000000-0951cbeed0499a825222	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-2,2'-Iminobispropanoic acid 10V, Negative-QTOF	splash10-03di-0900000000-b7795e67867e2588ab6f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-2,2'-Iminobispropanoic acid 20V, Negative-QTOF	splash10-03di-2900000000-1d7acfe03b875fee54be	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-2,2'-Iminobispropanoic acid 40V, Negative-QTOF	splash10-00di-9100000000-d34f16d278d629e44af8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-2,2'-Iminobispropanoic acid 10V, Positive-QTOF	splash10-01bc-9800000000-285bc026287cc593c328	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-2,2'-Iminobispropanoic acid 20V, Positive-QTOF	splash10-00di-9100000000-e96f1d4f2877267f1db5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-2,2'-Iminobispropanoic acid 40V, Positive-QTOF	splash10-00dl-9000000000-585051d720ef8ccba673	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-2,2'-Iminobispropanoic acid 10V, Negative-QTOF	splash10-000i-9100000000-4d7750f83af8f8aa330e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-2,2'-Iminobispropanoic acid 20V, Negative-QTOF	splash10-000i-9200000000-27d015ab0872cbaff7df	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-2,2'-Iminobispropanoic acid 40V, Negative-QTOF	splash10-007c-9000000000-5dbcc70df7c96b1149db	2021-09-22	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

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB012195

KNApSAcK ID

Not Available

Chemspider ID

388972

KEGG Compound ID

C03210

BioCyc ID

CPD-310

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

439943

PDB ID

Not Available

ChEBI ID

857

Food Biomarker Ontology

Not Available

VMH ID

Not Available

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 (±)-2,2'-Iminobispropanoic acid (HMDB0033747)

MOL for HMDB0033747 ((±)-2,2'-Iminobispropanoic acid)

3D MOL for HMDB0033747 ((±)-2,2'-Iminobispropanoic acid)

3D SDF for HMDB0033747 ((±)-2,2'-Iminobispropanoic acid)

3D-SDF for HMDB0033747 ((±)-2,2'-Iminobispropanoic acid)

PDB for HMDB0033747 ((±)-2,2'-Iminobispropanoic acid)

3D PDB for HMDB0033747 ((±)-2,2'-Iminobispropanoic acid)

SMILES for HMDB0033747 ((±)-2,2'-Iminobispropanoic acid)

INCHI for HMDB0033747 ((±)-2,2'-Iminobispropanoic acid)

Structure for HMDB0033747 ((±)-2,2'-Iminobispropanoic acid)

3D Structure for HMDB0033747 ((±)-2,2'-Iminobispropanoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra