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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:47:31 UTC

Update Date

2023-02-21 17:29:02 UTC

HMDB ID

HMDB0041912

Secondary Accession Numbers

HMDB41912

Metabolite Identification

Common Name

Isonicotinylglycine

Description

Isonicotinylglycine, also known as isonicotinuric acid or isonicotinate, belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. Isonicotinylglycine 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 very few articles have been published on Isonicotinylglycine.

Structure

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

HEADER    PROTEIN                                 13-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-12         0                                  
HETATM    1  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001   5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       4.001   6.930   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      -1.334   5.390   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0      -5.335   4.620   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -4.001   6.930   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       0.000   3.080   0.000  0.00  0.00           O+0
CONECT    1    3    6                                                       
CONECT    2    4    6                                                       
CONECT    3    1    9                                                       
CONECT    4    2    9                                                       
CONECT    5    7   10                                                       
CONECT    6    1    2    8                                                  
CONECT    7    5   11   12                                                  
CONECT    8    6   10   13                                                  
CONECT    9    3    4                                                       
CONECT   10    5    8                                                       
CONECT   11    7                                                            
CONECT   12    7                                                            
CONECT   13    8                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Isonicotinuric acid	Kegg
Isonicotinate	Generator
Isonicotinic acid	Generator
2-[(Pyridin-4-yl)formamido]acetate	HMDB

Chemical Formula

C₈H₈N₂O₃

Average Molecular Weight

180.1607

Monoisotopic Molecular Weight

180.053492132

IUPAC Name

2-(pyridin-4-ylformamido)acetic acid

Traditional Name

isonicotinylglycine

CAS Registry Number

2015-20-5

SMILES

OC(=O)CNC(=O)C1=CC=NC=C1

InChI Identifier

InChI=1S/C8H8N2O3/c11-7(12)5-10-8(13)6-1-3-9-4-2-6/h1-4H,5H2,(H,10,13)(H,11,12)

InChI Key

HKCLSDCBERVTCT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids

Alternative Parents

Substituents

N-acyl-alpha-amino acid
Pyridine carboxylic acid or derivatives
Pyridine
Heteroaromatic compound
Secondary carboxylic acid amide
Carboxamide group
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Carbonyl group
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

N-acyl-amino acid (CHEBI:80617 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0041912)

Organ

Liver (HMDB: HMDB0041912)
Kidney (HMDB: HMDB0041912)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0041912)

Source

Endogenous

Endogenous (HMDB: HMDB0041912)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

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	4.42 g/L	ALOGPS
logP	-0.24	ALOGPS
logP	-1.4	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	2.87	ChemAxon
pKa (Strongest Basic)	3.57	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	79.29 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	43.96 m³·mol⁻¹	ChemAxon
Polarizability	16.82 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
DarkChem	[M+H]+	139.506	31661259
DarkChem	[M-H]-	137.202	31661259
DeepCCS	[M+H]+	136.778	30932474
DeepCCS	[M-H]-	134.357	30932474
DeepCCS	[M-2H]-	169.996	30932474
DeepCCS	[M+Na]+	144.501	30932474
AllCCS	[M+H]+	138.2	32859911
AllCCS	[M+H-H2O]+	134.0	32859911
AllCCS	[M+NH4]+	142.1	32859911
AllCCS	[M+Na]+	143.2	32859911
AllCCS	[M-H]-	137.0	32859911
AllCCS	[M+Na-2H]-	137.8	32859911
AllCCS	[M+HCOO]-	138.7	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.	2.01 minutes	32390414
Predicted by Siyang on May 30, 2022	9.289 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.66 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	201.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	734.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	291.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	61.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	163.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	43.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	259.5 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	306.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	467.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	580.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	42.8 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	913.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	173.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	202.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	625.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	304.3 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	247.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isonicotinylglycine	OC(=O)CNC(=O)C1=CC=NC=C1	2648.3	Standard polar	33892256
Isonicotinylglycine	OC(=O)CNC(=O)C1=CC=NC=C1	1663.2	Standard non polar	33892256
Isonicotinylglycine	OC(=O)CNC(=O)C1=CC=NC=C1	1837.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isonicotinylglycine,1TMS,isomer #1	C[Si](C)(C)OC(=O)CNC(=O)C1=CC=NC=C1	1881.8	Semi standard non polar	33892256
Isonicotinylglycine,1TMS,isomer #2	C[Si](C)(C)N(CC(=O)O)C(=O)C1=CC=NC=C1	1812.6	Semi standard non polar	33892256
Isonicotinylglycine,2TMS,isomer #1	C[Si](C)(C)OC(=O)CN(C(=O)C1=CC=NC=C1)[Si](C)(C)C	1806.7	Semi standard non polar	33892256
Isonicotinylglycine,2TMS,isomer #1	C[Si](C)(C)OC(=O)CN(C(=O)C1=CC=NC=C1)[Si](C)(C)C	1851.8	Standard non polar	33892256
Isonicotinylglycine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)C1=CC=NC=C1	2139.6	Semi standard non polar	33892256
Isonicotinylglycine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CC(=O)O)C(=O)C1=CC=NC=C1	2054.9	Semi standard non polar	33892256
Isonicotinylglycine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)C1=CC=NC=C1)[Si](C)(C)C(C)(C)C	2282.1	Semi standard non polar	33892256
Isonicotinylglycine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)C1=CC=NC=C1)[Si](C)(C)C(C)(C)C	2241.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Isonicotinylglycine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-2900000000-64d8518f4d46df311757	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isonicotinylglycine GC-MS (1 TMS) - 70eV, Positive	splash10-052r-5900000000-861d00394fbbeb83aae2	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isonicotinylglycine 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 - Isonicotinylglycine 10V, Positive-QTOF	splash10-001i-0900000000-c745b15beb9fda265ee0	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isonicotinylglycine 20V, Positive-QTOF	splash10-000i-0900000000-a1b14c44f44c0112dfe4	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isonicotinylglycine 40V, Positive-QTOF	splash10-0pc9-9600000000-ffc7ba18074ac8c45091	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isonicotinylglycine 10V, Negative-QTOF	splash10-004i-0900000000-42369262482cdc2a2fac	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isonicotinylglycine 20V, Negative-QTOF	splash10-004i-2900000000-31d4ae9e9f72c4c6fd3b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isonicotinylglycine 40V, Negative-QTOF	splash10-004i-9300000000-32d29e3800ad8dd34478	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isonicotinylglycine 10V, Negative-QTOF	splash10-004i-8900000000-135a9150e9f139a1c6b0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isonicotinylglycine 20V, Negative-QTOF	splash10-004i-9000000000-157cff7c1ac2d371964f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isonicotinylglycine 40V, Negative-QTOF	splash10-004i-9000000000-c2850ce6846335b0374d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isonicotinylglycine 10V, Positive-QTOF	splash10-0a4i-0900000000-f909c07fad8501140c92	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isonicotinylglycine 20V, Positive-QTOF	splash10-0a4i-2900000000-7409b41683e01ad305e6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isonicotinylglycine 40V, Positive-QTOF	splash10-004i-9200000000-bc5577ef0056c5bce1b4	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	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+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

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

141130

KEGG Compound ID

C16623

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

160607

PDB ID

Not Available

ChEBI ID

80617

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

Not Available

Showing metabocard for Isonicotinylglycine (HMDB0041912)

MOL for HMDB0041912 (Isonicotinylglycine)

3D MOL for HMDB0041912 (Isonicotinylglycine)

3D SDF for HMDB0041912 (Isonicotinylglycine)

3D-SDF for HMDB0041912 (Isonicotinylglycine)

PDB for HMDB0041912 (Isonicotinylglycine)

3D PDB for HMDB0041912 (Isonicotinylglycine)

SMILES for HMDB0041912 (Isonicotinylglycine)

INCHI for HMDB0041912 (Isonicotinylglycine)

Structure for HMDB0041912 (Isonicotinylglycine)

3D Structure for HMDB0041912 (Isonicotinylglycine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra