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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-03-23 01:54:51 UTC

Update Date

2023-02-21 17:30:55 UTC

HMDB ID

HMDB0062472

Secondary Accession Numbers

HMDB62472

Metabolite Identification

Common Name

glycinamide

Description

glycinamide, also known as aminomethylamide, belongs to the class of organic compounds known as carboximidic acids. These are organic acids with the general formula RC(=N)-OH (R=H, organic group). glycinamide is a very strong basic compound (based on its pKa). Glycinamide is a chemical compound with the molecular formula C2H6N2O. In humans, glycinamide is involved in the metabolic disorder called the purine nucleoside phosphorylase deficiency pathway. Its ΔpKa/°C is -0.029 and it has a solubility in water at 0 °C of 6.4 M.Glycinamide is a reagent used in the synthesis of glycineamide ribonucleotide (an intermediate in de novo purine biosynthesis). The hydrochloride salt of glycinamide, glycinamide hydrochloride, is one of Good's buffers with a pH in the physiological range. Glycinamide hydrochloride has a pKa near the physiological pH (8.20 at 20°C), making it useful in cell culture work. It is the amide derivative of the amino acid glycine.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
AMINOMETHYLAMIDE	ChEBI
Glycinamid	ChEBI
Glycine amide	ChEBI
Glycine amide hydrochloride	HMDB
Glycine amide hydrobromide	HMDB

Chemical Formula

C₂H₆N₂O

Average Molecular Weight

74.0818

Monoisotopic Molecular Weight

74.048012824

IUPAC Name

2-aminoacetamide

Traditional Name

glycinamide

CAS Registry Number

598-41-4

SMILES

NCC(N)=O

InChI Identifier

InChI=1S/C2H6N2O/c3-1-2(4)5/h1,3H2,(H2,4,5)

InChI Key

BEBCJVAWIBVWNZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carboximidic acids. These are organic acids with the general formula RC(=N)-OH (R=H, organic group).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboximidic acids and derivatives

Sub Class

Carboximidic acids

Direct Parent

Carboximidic acids

Alternative Parents

Substituents

Carboximidic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

glycine derivative (CHEBI:42843 )
amino acid amide (CHEBI:42843 )

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	544 g/l	ALOGPS
LogP	-2.49	ALOGPS

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-2.5	ALOGPS
logP	-2	ChemAxon
logS	0.87	ALOGPS
pKa (Strongest Acidic)	16.37	ChemAxon
pKa (Strongest Basic)	8.15	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	69.11 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	17.83 m³·mol⁻¹	ChemAxon
Polarizability	7.05 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]+	112.538	31661259
DarkChem	[M-H]-	105.522	31661259
DeepCCS	[M+H]+	121.333	30932474
DeepCCS	[M-H]-	119.49	30932474
DeepCCS	[M-2H]-	154.842	30932474
DeepCCS	[M+Na]+	128.65	30932474
AllCCS	[M+H]+	122.3	32859911
AllCCS	[M+H-H2O]+	117.8	32859911
AllCCS	[M+NH4]+	126.5	32859911
AllCCS	[M+Na]+	127.7	32859911
AllCCS	[M-H]-	125.4	32859911
AllCCS	[M+Na-2H]-	131.0	32859911
AllCCS	[M+HCOO]-	137.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
glycinamide	NCC(N)=O	1723.9	Standard polar	33892256
glycinamide	NCC(N)=O	823.6	Standard non polar	33892256
glycinamide	NCC(N)=O	1030.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
glycinamide,1TMS,isomer #1	C[Si](C)(C)NCC(N)=O	1193.6	Semi standard non polar	33892256
glycinamide,1TMS,isomer #1	C[Si](C)(C)NCC(N)=O	1094.5	Standard non polar	33892256
glycinamide,1TMS,isomer #1	C[Si](C)(C)NCC(N)=O	1996.5	Standard polar	33892256
glycinamide,1TMS,isomer #2	C[Si](C)(C)NC(=O)CN	1103.0	Semi standard non polar	33892256
glycinamide,1TMS,isomer #2	C[Si](C)(C)NC(=O)CN	1105.9	Standard non polar	33892256
glycinamide,1TMS,isomer #2	C[Si](C)(C)NC(=O)CN	2138.5	Standard polar	33892256
glycinamide,2TMS,isomer #1	C[Si](C)(C)NCC(=O)N[Si](C)(C)C	1279.6	Semi standard non polar	33892256
glycinamide,2TMS,isomer #1	C[Si](C)(C)NCC(=O)N[Si](C)(C)C	1263.0	Standard non polar	33892256
glycinamide,2TMS,isomer #1	C[Si](C)(C)NCC(=O)N[Si](C)(C)C	1515.8	Standard polar	33892256
glycinamide,2TMS,isomer #2	C[Si](C)(C)N(CC(N)=O)[Si](C)(C)C	1369.8	Semi standard non polar	33892256
glycinamide,2TMS,isomer #2	C[Si](C)(C)N(CC(N)=O)[Si](C)(C)C	1348.4	Standard non polar	33892256
glycinamide,2TMS,isomer #2	C[Si](C)(C)N(CC(N)=O)[Si](C)(C)C	1783.5	Standard polar	33892256
glycinamide,2TMS,isomer #3	C[Si](C)(C)N(C(=O)CN)[Si](C)(C)C	1272.0	Semi standard non polar	33892256
glycinamide,2TMS,isomer #3	C[Si](C)(C)N(C(=O)CN)[Si](C)(C)C	1335.6	Standard non polar	33892256
glycinamide,2TMS,isomer #3	C[Si](C)(C)N(C(=O)CN)[Si](C)(C)C	1690.7	Standard polar	33892256
glycinamide,3TMS,isomer #1	C[Si](C)(C)NC(=O)CN([Si](C)(C)C)[Si](C)(C)C	1454.4	Semi standard non polar	33892256
glycinamide,3TMS,isomer #1	C[Si](C)(C)NC(=O)CN([Si](C)(C)C)[Si](C)(C)C	1407.4	Standard non polar	33892256
glycinamide,3TMS,isomer #1	C[Si](C)(C)NC(=O)CN([Si](C)(C)C)[Si](C)(C)C	1442.8	Standard polar	33892256
glycinamide,3TMS,isomer #2	C[Si](C)(C)NCC(=O)N([Si](C)(C)C)[Si](C)(C)C	1380.7	Semi standard non polar	33892256
glycinamide,3TMS,isomer #2	C[Si](C)(C)NCC(=O)N([Si](C)(C)C)[Si](C)(C)C	1383.9	Standard non polar	33892256
glycinamide,3TMS,isomer #2	C[Si](C)(C)NCC(=O)N([Si](C)(C)C)[Si](C)(C)C	1396.9	Standard polar	33892256
glycinamide,4TMS,isomer #1	C[Si](C)(C)N(CC(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	1581.2	Semi standard non polar	33892256
glycinamide,4TMS,isomer #1	C[Si](C)(C)N(CC(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	1523.5	Standard non polar	33892256
glycinamide,4TMS,isomer #1	C[Si](C)(C)N(CC(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	1401.0	Standard polar	33892256
glycinamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC(N)=O	1399.3	Semi standard non polar	33892256
glycinamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC(N)=O	1323.4	Standard non polar	33892256
glycinamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC(N)=O	2180.7	Standard polar	33892256
glycinamide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)CN	1336.9	Semi standard non polar	33892256
glycinamide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)CN	1310.4	Standard non polar	33892256
glycinamide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)CN	2243.6	Standard polar	33892256
glycinamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC(=O)N[Si](C)(C)C(C)(C)C	1723.4	Semi standard non polar	33892256
glycinamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC(=O)N[Si](C)(C)C(C)(C)C	1650.0	Standard non polar	33892256
glycinamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC(=O)N[Si](C)(C)C(C)(C)C	1678.1	Standard polar	33892256
glycinamide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CC(N)=O)[Si](C)(C)C(C)(C)C	1747.1	Semi standard non polar	33892256
glycinamide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CC(N)=O)[Si](C)(C)C(C)(C)C	1725.1	Standard non polar	33892256
glycinamide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CC(N)=O)[Si](C)(C)C(C)(C)C	1849.6	Standard polar	33892256
glycinamide,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C(=O)CN)[Si](C)(C)C(C)(C)C	1672.2	Semi standard non polar	33892256
glycinamide,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C(=O)CN)[Si](C)(C)C(C)(C)C	1686.7	Standard non polar	33892256
glycinamide,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C(=O)CN)[Si](C)(C)C(C)(C)C	1743.4	Standard polar	33892256
glycinamide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2056.9	Semi standard non polar	33892256
glycinamide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1998.9	Standard non polar	33892256
glycinamide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1793.3	Standard polar	33892256
glycinamide,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2016.3	Semi standard non polar	33892256
glycinamide,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1992.4	Standard non polar	33892256
glycinamide,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1767.9	Standard polar	33892256
glycinamide,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2338.1	Semi standard non polar	33892256
glycinamide,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2316.1	Standard non polar	33892256
glycinamide,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1873.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - glycinamide GC-MS (2 TMS)	splash10-0udi-3900000000-2539519bfe43c84c88eb	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - glycinamide GC-MS (2 TMS)	splash10-0fe0-3911000000-bc961d6504813cb6a235	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - glycinamide GC-MS (3 TMS)	splash10-00dr-3900000000-edffb19ec1b3e35737c7	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - glycinamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9000000000-51ca8832dcd98d57ce85	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - glycinamide 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 - glycinamide 10V, Positive-QTOF	splash10-004i-9000000000-e45353804e77c1f30e0b	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - glycinamide 20V, Positive-QTOF	splash10-053r-9000000000-a212521b9cdf392e7a95	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - glycinamide 40V, Positive-QTOF	splash10-0a59-9000000000-92d310499244b03b3e35	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - glycinamide 10V, Negative-QTOF	splash10-00di-9000000000-6bedd94d73112a31c093	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - glycinamide 20V, Negative-QTOF	splash10-00di-9000000000-d3372f9513a13600f30e	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - glycinamide 40V, Negative-QTOF	splash10-0006-9000000000-8393c24e9c324ce4452f	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - glycinamide 10V, Positive-QTOF	splash10-004i-9000000000-303c985782d1b02d8665	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - glycinamide 20V, Positive-QTOF	splash10-057i-9000000000-2e3de551c82bf3bce448	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - glycinamide 40V, Positive-QTOF	splash10-052f-9000000000-efc32a8d19218e8ce421	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - glycinamide 10V, Negative-QTOF	splash10-00di-9000000000-87753cf4baa848fb8803	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - glycinamide 20V, Negative-QTOF	splash10-00di-9000000000-b1cced23e1f0f410bf29	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - glycinamide 40V, Negative-QTOF	splash10-0006-9000000000-90726b17dc36e29c5299	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)	2021-09-25	Wishart Lab	View Spectrum
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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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, 900 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

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

DB03636

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

Glycinamide

METLIN ID

Not Available

PubChem Compound

69020

PDB ID

Not Available

ChEBI ID

42843

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 glycinamide (HMDB0062472)

MOL for HMDB0062472 (glycinamide)

3D MOL for HMDB0062472 (glycinamide)

3D SDF for HMDB0062472 (glycinamide)

3D-SDF for HMDB0062472 (glycinamide)

PDB for HMDB0062472 (glycinamide)

3D PDB for HMDB0062472 (glycinamide)

SMILES for HMDB0062472 (glycinamide)

INCHI for HMDB0062472 (glycinamide)

Structure for HMDB0062472 (glycinamide)

3D Structure for HMDB0062472 (glycinamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra