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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-02-26 19:03:45 UTC

Update Date

2023-02-21 17:29:23 UTC

HMDB ID

HMDB0059778

Secondary Accession Numbers

HMDB59778

Metabolite Identification

Common Name

2-Pyrroloylglycine

Description

2-Pyrroloylglycine 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. 2-Pyrroloylglycine is an extremely weak basic (essentially neutral) compound (based on its pKa). These are organic compounds containing a glycine residue with the N-atom attached to another moiety through an N-ester bond.

Structure

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

HEADER    PROTEIN                                 26-FEB-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-FEB-13         0                                  
HETATM    1  C   UNK     0       2.589  -4.495   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.255  -3.725   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.923  -3.725   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       5.256  -4.495   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       6.590  -3.725   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.590  -2.185   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       7.924  -4.495   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       9.331  -3.869   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      10.361  -5.013   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.591  -6.347   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.085  -6.027   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.589  -6.035   0.000  0.00  0.00           O+0
CONECT    1    2    3   12                                                  
CONECT    2    1                                                            
CONECT    3    1    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    7                                                       
CONECT   12    1                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-[(1H-Pyrrol-2-yl)formamido]acetate	Generator

Chemical Formula

C₇H₈N₂O₃

Average Molecular Weight

168.15

Monoisotopic Molecular Weight

168.053492132

IUPAC Name

2-(1H-pyrrol-2-ylformamido)acetic acid

Traditional Name

(1H-pyrrol-2-ylformamido)acetic acid

CAS Registry Number

98276-81-4

SMILES

OC(=O)CNC(=O)C1=CC=CN1

InChI Identifier

InChI=1S/C7H8N2O3/c10-6(11)4-9-7(12)5-2-1-3-8-5/h1-3,8H,4H2,(H,9,12)(H,10,11)

InChI Key

GCBXCOXVQXMSOS-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
2-heteroaryl carboxamide
Pyrrole-2-carboxamide
Pyrrole-2-carboxylic acid or derivatives
Substituted pyrrole
Pyrrole
Heteroaromatic compound
Carboxamide group
Secondary carboxylic acid amide
Monocarboxylic acid or derivatives
Carboxylic acid
Organoheterocyclic compound
Azacycle
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Not Available

Not Available

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	8.92 g/L	ALOGPS
logP	0.12	ALOGPS
logP	-0.47	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	3.64	ChemAxon
pKa (Strongest Basic)	-2.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	82.19 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	40.75 m³·mol⁻¹	ChemAxon
Polarizability	15.8 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]+	137.962	31661259
DarkChem	[M-H]-	135.179	31661259
DeepCCS	[M+H]+	132.941	30932474
DeepCCS	[M-H]-	130.277	30932474
DeepCCS	[M-2H]-	166.632	30932474
DeepCCS	[M+Na]+	141.907	30932474
AllCCS	[M+H]+	135.9	32859911
AllCCS	[M+H-H2O]+	131.6	32859911
AllCCS	[M+NH4]+	139.9	32859911
AllCCS	[M+Na]+	141.0	32859911
AllCCS	[M-H]-	133.1	32859911
AllCCS	[M+Na-2H]-	134.2	32859911
AllCCS	[M+HCOO]-	135.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Pyrroloylglycine	OC(=O)CNC(=O)C1=CC=CN1	2625.7	Standard polar	33892256
2-Pyrroloylglycine	OC(=O)CNC(=O)C1=CC=CN1	1706.9	Standard non polar	33892256
2-Pyrroloylglycine	OC(=O)CNC(=O)C1=CC=CN1	1750.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Pyrroloylglycine,1TMS,isomer #1	C[Si](C)(C)OC(=O)CNC(=O)C1=CC=C[NH]1	1815.0	Semi standard non polar	33892256
2-Pyrroloylglycine,1TMS,isomer #2	C[Si](C)(C)N(CC(=O)O)C(=O)C1=CC=C[NH]1	1804.5	Semi standard non polar	33892256
2-Pyrroloylglycine,1TMS,isomer #3	C[Si](C)(C)N1C=CC=C1C(=O)NCC(=O)O	1846.1	Semi standard non polar	33892256
2-Pyrroloylglycine,2TMS,isomer #1	C[Si](C)(C)OC(=O)CN(C(=O)C1=CC=C[NH]1)[Si](C)(C)C	1734.5	Semi standard non polar	33892256
2-Pyrroloylglycine,2TMS,isomer #1	C[Si](C)(C)OC(=O)CN(C(=O)C1=CC=C[NH]1)[Si](C)(C)C	1821.1	Standard non polar	33892256
2-Pyrroloylglycine,2TMS,isomer #1	C[Si](C)(C)OC(=O)CN(C(=O)C1=CC=C[NH]1)[Si](C)(C)C	2321.5	Standard polar	33892256
2-Pyrroloylglycine,2TMS,isomer #2	C[Si](C)(C)OC(=O)CNC(=O)C1=CC=CN1[Si](C)(C)C	1887.3	Semi standard non polar	33892256
2-Pyrroloylglycine,2TMS,isomer #2	C[Si](C)(C)OC(=O)CNC(=O)C1=CC=CN1[Si](C)(C)C	1843.7	Standard non polar	33892256
2-Pyrroloylglycine,2TMS,isomer #2	C[Si](C)(C)OC(=O)CNC(=O)C1=CC=CN1[Si](C)(C)C	2327.4	Standard polar	33892256
2-Pyrroloylglycine,2TMS,isomer #3	C[Si](C)(C)N(CC(=O)O)C(=O)C1=CC=CN1[Si](C)(C)C	1887.2	Semi standard non polar	33892256
2-Pyrroloylglycine,2TMS,isomer #3	C[Si](C)(C)N(CC(=O)O)C(=O)C1=CC=CN1[Si](C)(C)C	1911.0	Standard non polar	33892256
2-Pyrroloylglycine,2TMS,isomer #3	C[Si](C)(C)N(CC(=O)O)C(=O)C1=CC=CN1[Si](C)(C)C	2286.3	Standard polar	33892256
2-Pyrroloylglycine,3TMS,isomer #1	C[Si](C)(C)OC(=O)CN(C(=O)C1=CC=CN1[Si](C)(C)C)[Si](C)(C)C	1900.9	Semi standard non polar	33892256
2-Pyrroloylglycine,3TMS,isomer #1	C[Si](C)(C)OC(=O)CN(C(=O)C1=CC=CN1[Si](C)(C)C)[Si](C)(C)C	1898.9	Standard non polar	33892256
2-Pyrroloylglycine,3TMS,isomer #1	C[Si](C)(C)OC(=O)CN(C(=O)C1=CC=CN1[Si](C)(C)C)[Si](C)(C)C	2079.8	Standard polar	33892256
2-Pyrroloylglycine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)C1=CC=C[NH]1	2062.8	Semi standard non polar	33892256
2-Pyrroloylglycine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CC(=O)O)C(=O)C1=CC=C[NH]1	2017.6	Semi standard non polar	33892256
2-Pyrroloylglycine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C=CC=C1C(=O)NCC(=O)O	2092.0	Semi standard non polar	33892256
2-Pyrroloylglycine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)C1=CC=C[NH]1)[Si](C)(C)C(C)(C)C	2190.2	Semi standard non polar	33892256
2-Pyrroloylglycine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)C1=CC=C[NH]1)[Si](C)(C)C(C)(C)C	2219.4	Standard non polar	33892256
2-Pyrroloylglycine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)C1=CC=C[NH]1)[Si](C)(C)C(C)(C)C	2468.0	Standard polar	33892256
2-Pyrroloylglycine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)C1=CC=CN1[Si](C)(C)C(C)(C)C	2360.1	Semi standard non polar	33892256
2-Pyrroloylglycine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)C1=CC=CN1[Si](C)(C)C(C)(C)C	2247.7	Standard non polar	33892256
2-Pyrroloylglycine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)C1=CC=CN1[Si](C)(C)C(C)(C)C	2446.6	Standard polar	33892256
2-Pyrroloylglycine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CC(=O)O)C(=O)C1=CC=CN1[Si](C)(C)C(C)(C)C	2370.2	Semi standard non polar	33892256
2-Pyrroloylglycine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CC(=O)O)C(=O)C1=CC=CN1[Si](C)(C)C(C)(C)C	2265.2	Standard non polar	33892256
2-Pyrroloylglycine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CC(=O)O)C(=O)C1=CC=CN1[Si](C)(C)C(C)(C)C	2437.0	Standard polar	33892256
2-Pyrroloylglycine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)C1=CC=CN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2567.6	Semi standard non polar	33892256
2-Pyrroloylglycine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)C1=CC=CN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2485.9	Standard non polar	33892256
2-Pyrroloylglycine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)C1=CC=CN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2400.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Pyrroloylglycine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9300000000-419daeabb7e7c6ec406e	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Pyrroloylglycine GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-9000000000-e7dc2fabada78760e62f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Pyrroloylglycine 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 - 2-Pyrroloylglycine 10V, Positive-QTOF	splash10-014i-4900000000-436b7fc7f90e42f03013	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Pyrroloylglycine 20V, Positive-QTOF	splash10-054o-9400000000-f07cb88f97c85f698001	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Pyrroloylglycine 40V, Positive-QTOF	splash10-0pdu-9000000000-2907f3578c76b8579bf2	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Pyrroloylglycine 10V, Negative-QTOF	splash10-014i-1900000000-c0bdf71248c13fd9e6df	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Pyrroloylglycine 20V, Negative-QTOF	splash10-00xr-9800000000-abd34b0f973020d13e3f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Pyrroloylglycine 40V, Negative-QTOF	splash10-06di-9000000000-0e2b4fee176811a491e8	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Pyrroloylglycine 10V, Negative-QTOF	splash10-014i-9800000000-a2a9c19868586d603194	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Pyrroloylglycine 20V, Negative-QTOF	splash10-014i-9000000000-3f070060c5785123e18c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Pyrroloylglycine 40V, Negative-QTOF	splash10-014i-9000000000-934959b3968566c9b35f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Pyrroloylglycine 10V, Positive-QTOF	splash10-0006-9000000000-f8a487365391532ca105	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Pyrroloylglycine 20V, Positive-QTOF	splash10-00kf-9100000000-5d30996e07acf8197706	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Pyrroloylglycine 40V, Positive-QTOF	splash10-0006-9000000000-b6eb5e169d01ba7a81bb	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

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21126202

PDB ID

Not Available

ChEBI ID

Not Available

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 2-Pyrroloylglycine (HMDB0059778)

MOL for HMDB0059778 (2-Pyrroloylglycine)

3D MOL for HMDB0059778 (2-Pyrroloylglycine)

3D SDF for HMDB0059778 (2-Pyrroloylglycine)

3D-SDF for HMDB0059778 (2-Pyrroloylglycine)

PDB for HMDB0059778 (2-Pyrroloylglycine)

3D PDB for HMDB0059778 (2-Pyrroloylglycine)

SMILES for HMDB0059778 (2-Pyrroloylglycine)

INCHI for HMDB0059778 (2-Pyrroloylglycine)

Structure for HMDB0059778 (2-Pyrroloylglycine)

3D Structure for HMDB0059778 (2-Pyrroloylglycine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra