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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:15:28 UTC

HMDB ID

HMDB0001131

Secondary Accession Numbers

HMDB01131

Metabolite Identification

Common Name

Iminoaspartic acid

Description

Iminoaspartic acid, also known as iminosuccinate or iminoaspartate, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Iminoaspartic acid exists in all living species, ranging from bacteria to plants to humans. Iminoaspartic acid has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make iminoaspartic acid a potential biomarker for the consumption of these foods. Iminoaspartic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Iminoaspartic acid.

Structure

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
Iminoaspartate	ChEBI
Iminosuccinate	ChEBI
Iminosuccinic acid	ChEBI
alpha-Iminosuccinate	HMDB
imino-Butanedioate	HMDB
imino-Butanedioic acid	HMDB

Chemical Formula

C₄H₅NO₄

Average Molecular Weight

131.0868

Monoisotopic Molecular Weight

131.021857653

IUPAC Name

2-iminobutanedioic acid

Traditional Name

iminosuccinic acid

CAS Registry Number

79067-61-1

SMILES

OC(=O)CC(=N)C(O)=O

InChI Identifier

InChI=1S/C4H5NO4/c5-2(4(8)9)1-3(6)7/h5H,1H2,(H,6,7)(H,8,9)

InChI Key

NMUOATVLLQEYHI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Dicarboxylic acids and derivatives

Direct Parent

Dicarboxylic acids and derivatives

Alternative Parents

Substituents

Fatty acid
Dicarboxylic acid or derivatives
Ketimine
Carboxylic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Imine
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

C4-dicarboxylic acid (CHEBI:50616 )
aspartic acid derivative (CHEBI:50616 )
ketimine (CHEBI:50616 )
Dicarboxylic acids (LMFA01170110 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0001131)

Source

Endogenous

Endogenous (HMDB: HMDB0001131)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

NAD Biosynthesis (PathBank: SMP0121297)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	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	4.26 g/L	ALOGPS
logP	-0.83	ALOGPS
logP	-0.51	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	3.28	ChemAxon
pKa (Strongest Basic)	2.48	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	98.45 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	36.81 m³·mol⁻¹	ChemAxon
Polarizability	10.55 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]+	130.519	32859911
AllCCS	[M-H]-	122.366	32859911
DeepCCS	[M+H]+	125.482	30932474
DeepCCS	[M-H]-	122.291	30932474
DeepCCS	[M-2H]-	159.209	30932474
DeepCCS	[M+Na]+	134.161	30932474
AllCCS	[M+H]+	130.5	32859911
AllCCS	[M+H-H2O]+	126.4	32859911
AllCCS	[M+NH4]+	134.4	32859911
AllCCS	[M+Na]+	135.5	32859911
AllCCS	[M-H]-	122.4	32859911
AllCCS	[M+Na-2H]-	125.0	32859911
AllCCS	[M+HCOO]-	127.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.3 minutes	32390414
Predicted by Siyang on May 30, 2022	9.4753 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.22 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	332.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	561.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	367.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	50.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	243.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	90.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	285.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	236.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	704.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	607.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	38.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	731.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	229.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	331.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	725.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	384.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	435.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Iminoaspartic acid	OC(=O)CC(=N)C(O)=O	1990.0	Standard polar	33892256
Iminoaspartic acid	OC(=O)CC(=N)C(O)=O	1259.2	Standard non polar	33892256
Iminoaspartic acid	OC(=O)CC(=N)C(O)=O	1458.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Iminoaspartic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)CC(=N)C(=O)O	1456.3	Semi standard non polar	33892256
Iminoaspartic acid,1TMS,isomer #2	C[Si](C)(C)OC(=O)C(=N)CC(=O)O	1392.3	Semi standard non polar	33892256
Iminoaspartic acid,1TMS,isomer #3	C[Si](C)(C)N=C(CC(=O)O)C(=O)O	1425.3	Semi standard non polar	33892256
Iminoaspartic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CC(=N)C(=O)O[Si](C)(C)C	1476.0	Semi standard non polar	33892256
Iminoaspartic acid,2TMS,isomer #2	C[Si](C)(C)N=C(CC(=O)O[Si](C)(C)C)C(=O)O	1510.5	Semi standard non polar	33892256
Iminoaspartic acid,2TMS,isomer #3	C[Si](C)(C)N=C(CC(=O)O)C(=O)O[Si](C)(C)C	1457.2	Semi standard non polar	33892256
Iminoaspartic acid,3TMS,isomer #1	C[Si](C)(C)N=C(CC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1561.9	Semi standard non polar	33892256
Iminoaspartic acid,3TMS,isomer #1	C[Si](C)(C)N=C(CC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1500.2	Standard non polar	33892256
Iminoaspartic acid,3TMS,isomer #1	C[Si](C)(C)N=C(CC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1714.0	Standard polar	33892256
Iminoaspartic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC(=N)C(=O)O	1703.8	Semi standard non polar	33892256
Iminoaspartic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(=N)CC(=O)O	1658.7	Semi standard non polar	33892256
Iminoaspartic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N=C(CC(=O)O)C(=O)O	1669.7	Semi standard non polar	33892256
Iminoaspartic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC(=N)C(=O)O[Si](C)(C)C(C)(C)C	1919.7	Semi standard non polar	33892256
Iminoaspartic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	1943.5	Semi standard non polar	33892256
Iminoaspartic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N=C(CC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	1900.0	Semi standard non polar	33892256
Iminoaspartic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2132.8	Semi standard non polar	33892256
Iminoaspartic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2095.0	Standard non polar	33892256
Iminoaspartic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2108.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Iminoaspartic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-000l-9100000000-bf5c48c685bd4d8bc19c	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Iminoaspartic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00dl-9330000000-0a7a3a014d87506d9d5c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Iminoaspartic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Iminoaspartic 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iminoaspartic acid 10V, Positive-QTOF	splash10-03y0-7900000000-1e7dec8cec535849b8dd	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iminoaspartic acid 20V, Positive-QTOF	splash10-00y0-9000000000-ee01d5b059cd84acc52a	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iminoaspartic acid 40V, Positive-QTOF	splash10-00kf-9000000000-f7639f26eeb1737eca80	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iminoaspartic acid 10V, Negative-QTOF	splash10-001r-4900000000-48f2522721d80612277b	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iminoaspartic acid 20V, Negative-QTOF	splash10-01q0-9600000000-13c57e1870999d070c90	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iminoaspartic acid 40V, Negative-QTOF	splash10-066u-9000000000-142f158a200b457f476f	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iminoaspartic acid 10V, Positive-QTOF	splash10-022i-9200000000-e1da89bee87bd924e1ae	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iminoaspartic acid 20V, Positive-QTOF	splash10-0076-9000000000-70ef4189d44ac80a3dfc	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iminoaspartic acid 40V, Positive-QTOF	splash10-0006-9000000000-200c8786c16249cb72fb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iminoaspartic acid 10V, Negative-QTOF	splash10-0019-9300000000-f687c619ff4a390ee8bf	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iminoaspartic acid 20V, Negative-QTOF	splash10-00kr-9000000000-32d59cbcdf8623884b2e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iminoaspartic acid 40V, Negative-QTOF	splash10-014l-9000000000-3062f88f5ced7624b9bb	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, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-18	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 (predicted from logP)

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Iminosuccinic acid

METLIN ID

6025

PubChem Compound

796

PDB ID

Not Available

ChEBI ID

50616

Food Biomarker Ontology

Not Available

VMH ID

IASP

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Putative L-aspartate dehydrogenase

General function:: Involved in oxidoreductase activity
Specific function:: Specifically catalyzes the NAD or NADP-dependent dehydrogenation of L-aspartate to iminoaspartate (By similarity).
Gene Name:: ASPDH
Uniprot ID:: A6ND91
Molecular weight:: 18655.255

Showing metabocard for Iminoaspartic acid (HMDB0001131)

MOL for HMDB0001131 (Iminoaspartic acid)

3D MOL for HMDB0001131 (Iminoaspartic acid)

3D SDF for HMDB0001131 (Iminoaspartic acid)

3D-SDF for HMDB0001131 (Iminoaspartic acid)

PDB for HMDB0001131 (Iminoaspartic acid)

3D PDB for HMDB0001131 (Iminoaspartic acid)

SMILES for HMDB0001131 (Iminoaspartic acid)

INCHI for HMDB0001131 (Iminoaspartic acid)

Structure for HMDB0001131 (Iminoaspartic acid)

3D Structure for HMDB0001131 (Iminoaspartic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes