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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:30:21 UTC

Update Date

2022-03-07 02:52:09 UTC

HMDB ID

HMDB0029427

Secondary Accession Numbers

HMDB29427

Metabolite Identification

Common Name

L-Hypoglycin A

Description

L-Hypoglycin A belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). L-Hypoglycin A has been detected, but not quantified in, several different foods, such as european plums (Prunus domestica), opium poppies (Papaver somniferum), black crowberries (Empetrum nigrum), sorrels (Rumex acetosa), and alaska wild rhubarbs (Polygonum alpinum). This could make L-hypoglycin a a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on L-Hypoglycin A.

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-Amino-3-(2-methylenecyclopropyl)propionic acid	ChEBI
2-Amino-3-(2-methylenecyclopropyl)propionate	Generator
Hypoglycin	MeSH
Hypoglycin a	MeSH
Hypoglycin, (S)-isomer	MeSH
Hypoglycin, carboxy-(14)C-labeled	MeSH
2-amino-4,5-Methylenehex-5-enoic acid	HMDB
2-Methylenecyclopropanealanine	HMDB
2-Methylenecyclopropanylalanine	HMDB
2-MethyleneL-cyclopropanealanine	HMDB
alpha-amino-2-Methylenecyclopropanepropanoic acid	HMDB
alpha-amino-2-Methylenecyclopropanepropionic acid	HMDB
alpha-amino-beta-(2-Methylenecyclopropyl)propionic acid	HMDB
alpha-Aminomethylenecyclopropanepropionic acid	HMDB
beta-(Methylenecyclopropyl)alanine	HMDB
Hypoglycine a	HMDB
L-alpha-amino-beta-Methylenecyclopropanepropionic acid	HMDB
L-Hypoglycin	HMDB
2-Amino-3-(2-methylenecyclopropyl)propanoate	Generator

Chemical Formula

C₇H₁₁NO₂

Average Molecular Weight

141.1677

Monoisotopic Molecular Weight

141.078978601

IUPAC Name

2-amino-3-(2-methylidenecyclopropyl)propanoic acid

Traditional Name

hypoglycine A

CAS Registry Number

156-56-9

SMILES

NC(CC1CC1=C)C(O)=O

InChI Identifier

InChI=1S/C7H11NO2/c1-4-2-5(4)3-6(8)7(9)10/h5-6H,1-3,8H2,(H,9,10)

InChI Key

OOJZCXFXPZGUBJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids

Alternative Parents

Substituents

Alpha-amino acid
Carbocyclic fatty acid
Fatty acyl
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Organic oxide
Primary aliphatic amine
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Amine
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	280 - 284 °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	101 g/L	ALOGPS
logP	-2.2	ALOGPS
logP	-2.1	ChemAxon
logS	-0.15	ALOGPS
pKa (Strongest Acidic)	2.52	ChemAxon
pKa (Strongest Basic)	9.51	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	36.69 m³·mol⁻¹	ChemAxon
Polarizability	14.82 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]+	131.014	31661259
DarkChem	[M-H]-	125.887	31661259
DeepCCS	[M+H]+	125.302	30932474
DeepCCS	[M-H]-	122.179	30932474
DeepCCS	[M-2H]-	159.056	30932474
DeepCCS	[M+Na]+	133.963	30932474
AllCCS	[M+H]+	132.2	32859911
AllCCS	[M+H-H2O]+	127.9	32859911
AllCCS	[M+NH4]+	136.2	32859911
AllCCS	[M+Na]+	137.3	32859911
AllCCS	[M-H]-	129.6	32859911
AllCCS	[M+Na-2H]-	131.3	32859911
AllCCS	[M+HCOO]-	133.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
L-Hypoglycin A	NC(CC1CC1=C)C(O)=O	2101.0	Standard polar	33892256
L-Hypoglycin A	NC(CC1CC1=C)C(O)=O	1251.8	Standard non polar	33892256
L-Hypoglycin A	NC(CC1CC1=C)C(O)=O	1502.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
L-Hypoglycin A,1TMS,isomer #1	C=C1CC1CC(N)C(=O)O[Si](C)(C)C	1278.9	Semi standard non polar	33892256
L-Hypoglycin A,1TMS,isomer #2	C=C1CC1CC(N[Si](C)(C)C)C(=O)O	1377.1	Semi standard non polar	33892256
L-Hypoglycin A,2TMS,isomer #1	C=C1CC1CC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1406.9	Semi standard non polar	33892256
L-Hypoglycin A,2TMS,isomer #1	C=C1CC1CC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1458.7	Standard non polar	33892256
L-Hypoglycin A,2TMS,isomer #2	C=C1CC1CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1588.4	Semi standard non polar	33892256
L-Hypoglycin A,2TMS,isomer #2	C=C1CC1CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1520.2	Standard non polar	33892256
L-Hypoglycin A,3TMS,isomer #1	C=C1CC1CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1612.7	Semi standard non polar	33892256
L-Hypoglycin A,3TMS,isomer #1	C=C1CC1CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1594.3	Standard non polar	33892256
L-Hypoglycin A,1TBDMS,isomer #1	C=C1CC1CC(N)C(=O)O[Si](C)(C)C(C)(C)C	1505.6	Semi standard non polar	33892256
L-Hypoglycin A,1TBDMS,isomer #2	C=C1CC1CC(N[Si](C)(C)C(C)(C)C)C(=O)O	1637.1	Semi standard non polar	33892256
L-Hypoglycin A,2TBDMS,isomer #1	C=C1CC1CC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1842.5	Semi standard non polar	33892256
L-Hypoglycin A,2TBDMS,isomer #1	C=C1CC1CC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1898.4	Standard non polar	33892256
L-Hypoglycin A,2TBDMS,isomer #2	C=C1CC1CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2022.9	Semi standard non polar	33892256
L-Hypoglycin A,2TBDMS,isomer #2	C=C1CC1CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1967.5	Standard non polar	33892256
L-Hypoglycin A,3TBDMS,isomer #1	C=C1CC1CC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2252.6	Semi standard non polar	33892256
L-Hypoglycin A,3TBDMS,isomer #1	C=C1CC1CC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2240.8	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - L-Hypoglycin A GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-9000000000-1860e52823f730f63355	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Hypoglycin A GC-MS (1 TMS) - 70eV, Positive	splash10-0ukj-9100000000-bb541e9f44219160c2c0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Hypoglycin A GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Hypoglycin A GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Hypoglycin A GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Hypoglycin A GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Hypoglycin A GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	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 - L-Hypoglycin A 10V, Positive-QTOF	splash10-0005-9800000000-a5171a1c4df83880eaf3	2015-05-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Hypoglycin A 20V, Positive-QTOF	splash10-0002-9100000000-e69156f7fafd560dd124	2015-05-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Hypoglycin A 40V, Positive-QTOF	splash10-0gb9-9000000000-d466aa46e7a29ca5ad5c	2015-05-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Hypoglycin A 10V, Positive-QTOF	splash10-0005-9800000000-a5171a1c4df83880eaf3	2015-05-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Hypoglycin A 20V, Positive-QTOF	splash10-0002-9100000000-e69156f7fafd560dd124	2015-05-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Hypoglycin A 40V, Positive-QTOF	splash10-0gb9-9000000000-d466aa46e7a29ca5ad5c	2015-05-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Hypoglycin A 10V, Positive-QTOF	splash10-0005-9800000000-a5171a1c4df83880eaf3	2015-05-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Hypoglycin A 20V, Positive-QTOF	splash10-0002-9100000000-e69156f7fafd560dd124	2015-05-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Hypoglycin A 40V, Positive-QTOF	splash10-0gb9-9000000000-d466aa46e7a29ca5ad5c	2015-05-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Hypoglycin A 10V, Positive-QTOF	splash10-0005-9800000000-a5171a1c4df83880eaf3	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Hypoglycin A 20V, Positive-QTOF	splash10-0002-9100000000-e69156f7fafd560dd124	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Hypoglycin A 40V, Positive-QTOF	splash10-0gb9-9000000000-d466aa46e7a29ca5ad5c	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Hypoglycin A 10V, Negative-QTOF	splash10-0006-1900000000-d9b471c4d83e3c6242d6	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Hypoglycin A 20V, Negative-QTOF	splash10-00dl-7900000000-ea855029d5dfccb789a2	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Hypoglycin A 40V, Negative-QTOF	splash10-00di-9000000000-30d74facc5bc53038ca7	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Hypoglycin A 10V, Negative-QTOF	splash10-0006-1900000000-d9b471c4d83e3c6242d6	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Hypoglycin A 20V, Negative-QTOF	splash10-00dl-7900000000-ea855029d5dfccb789a2	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Hypoglycin A 40V, Negative-QTOF	splash10-00di-9000000000-30d74facc5bc53038ca7	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Hypoglycin A 10V, Negative-QTOF	splash10-0006-1900000000-d9b471c4d83e3c6242d6	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Hypoglycin A 20V, Negative-QTOF	splash10-00dl-7900000000-ea855029d5dfccb789a2	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Hypoglycin A 40V, Negative-QTOF	splash10-00di-9000000000-30d74facc5bc53038ca7	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Hypoglycin A 10V, Negative-QTOF	splash10-0006-1900000000-d9b471c4d83e3c6242d6	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Hypoglycin A 20V, Negative-QTOF	splash10-00dl-7900000000-ea855029d5dfccb789a2	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Hypoglycin A 40V, Negative-QTOF	splash10-00di-9000000000-30d74facc5bc53038ca7	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Hypoglycin A 10V, Negative-QTOF	splash10-0006-1900000000-23e6e4ddc37e52d21598	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Hypoglycin A

METLIN ID

Not Available

PubChem Compound

9081

PDB ID

Not Available

ChEBI ID

136270

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 L-Hypoglycin A (HMDB0029427)

MOL for HMDB0029427 (L-Hypoglycin A)

3D MOL for HMDB0029427 (L-Hypoglycin A)

3D SDF for HMDB0029427 (L-Hypoglycin A)

3D-SDF for HMDB0029427 (L-Hypoglycin A)

PDB for HMDB0029427 (L-Hypoglycin A)

3D PDB for HMDB0029427 (L-Hypoglycin A)

SMILES for HMDB0029427 (L-Hypoglycin A)

INCHI for HMDB0029427 (L-Hypoglycin A)

Structure for HMDB0029427 (L-Hypoglycin A)

3D Structure for HMDB0029427 (L-Hypoglycin A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra