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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 20:51:20 UTC

Update Date

2021-09-26 22:50:44 UTC

HMDB ID

HMDB0243603

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(3R,4R)-3-Amino-1-hydroxy-4-methylpyrrolidin-2-one

Description

(3R,4R)-3-Amino-1-hydroxy-4-methylpyrrolidin-2-one, also known as cis-4-methyl-ha-966, belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. Based on a literature review very few articles have been published on (3R,4R)-3-Amino-1-hydroxy-4-methylpyrrolidin-2-one. This compound has been identified in human blood as reported by (PMID: 31557052 ). (3r,4r)-3-amino-1-hydroxy-4-methylpyrrolidin-2-one is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (3R,4R)-3-Amino-1-hydroxy-4-methylpyrrolidin-2-one is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
L 687414, (3R-cis)-Isomer	HMDB
cis-4-Methyl-ha-966	HMDB

Chemical Formula

C₅H₁₀N₂O₂

Average Molecular Weight

130.147

Monoisotopic Molecular Weight

130.07422757

IUPAC Name

3-amino-1-hydroxy-4-methylpyrrolidin-2-one

Traditional Name

3-amino-1-hydroxy-4-methylpyrrolidin-2-one

CAS Registry Number

Not Available

SMILES

CC1CN(O)C(=O)C1N

InChI Identifier

InChI=1S/C5H10N2O2/c1-3-2-7(9)5(8)4(3)6/h3-4,9H,2,6H2,1H3

InChI Key

SKYSFPFYQBZGDC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

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 and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Pyrrolidone
2-pyrrolidone
Pyrrolidine
Hydroxamic acid
Lactam
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organic oxide
Organic oxygen compound
Carbonyl group
Amine
Organic nitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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

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
logP	-1.6	ALOGPS
logP	-1.7	ChemAxon
logS	0.71	ALOGPS
pKa (Strongest Acidic)	7.72	ChemAxon
pKa (Strongest Basic)	8.61	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.56 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	31.54 m³·mol⁻¹	ChemAxon
Polarizability	12.73 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
DeepCCS	[M+H]+	129.536	30932474
DeepCCS	[M-H]-	127.02	30932474
DeepCCS	[M-2H]-	163.753	30932474
DeepCCS	[M+Na]+	138.614	30932474
AllCCS	[M+H]+	127.6	32859911
AllCCS	[M+H-H2O]+	123.0	32859911
AllCCS	[M+NH4]+	131.9	32859911
AllCCS	[M+Na]+	133.2	32859911
AllCCS	[M-H]-	122.3	32859911
AllCCS	[M+Na-2H]-	124.4	32859911
AllCCS	[M+HCOO]-	126.8	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.	0.9 minutes	32390414
Predicted by Siyang on May 30, 2022	8.8944 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.97 minutes	32390414

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(3R,4R)-3-Amino-1-hydroxy-4-methylpyrrolidin-2-one	CC1CN(O)C(=O)C1N	1387.8	Semi standard non polar	33892256
(3R,4R)-3-Amino-1-hydroxy-4-methylpyrrolidin-2-one	CC1CN(O)C(=O)C1N	1387.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(3R,4R)-3-Amino-1-hydroxy-4-methylpyrrolidin-2-one,1TMS,isomer #1	CC1CN(O)C(=O)C1N[Si](C)(C)C	1495.3	Semi standard non polar	33892256
(3R,4R)-3-Amino-1-hydroxy-4-methylpyrrolidin-2-one,1TMS,isomer #1	CC1CN(O)C(=O)C1N[Si](C)(C)C	1372.5	Standard non polar	33892256
(3R,4R)-3-Amino-1-hydroxy-4-methylpyrrolidin-2-one,1TMS,isomer #1	CC1CN(O)C(=O)C1N[Si](C)(C)C	2285.6	Standard polar	33892256
(3R,4R)-3-Amino-1-hydroxy-4-methylpyrrolidin-2-one,2TMS,isomer #1	CC1CN(O)C(=O)C1N([Si](C)(C)C)[Si](C)(C)C	1625.2	Semi standard non polar	33892256
(3R,4R)-3-Amino-1-hydroxy-4-methylpyrrolidin-2-one,2TMS,isomer #1	CC1CN(O)C(=O)C1N([Si](C)(C)C)[Si](C)(C)C	1601.3	Standard non polar	33892256
(3R,4R)-3-Amino-1-hydroxy-4-methylpyrrolidin-2-one,2TMS,isomer #1	CC1CN(O)C(=O)C1N([Si](C)(C)C)[Si](C)(C)C	2102.0	Standard polar	33892256
(3R,4R)-3-Amino-1-hydroxy-4-methylpyrrolidin-2-one,1TBDMS,isomer #1	CC1CN(O)C(=O)C1N[Si](C)(C)C(C)(C)C	1710.5	Semi standard non polar	33892256
(3R,4R)-3-Amino-1-hydroxy-4-methylpyrrolidin-2-one,1TBDMS,isomer #1	CC1CN(O)C(=O)C1N[Si](C)(C)C(C)(C)C	1634.1	Standard non polar	33892256
(3R,4R)-3-Amino-1-hydroxy-4-methylpyrrolidin-2-one,1TBDMS,isomer #1	CC1CN(O)C(=O)C1N[Si](C)(C)C(C)(C)C	2343.0	Standard polar	33892256
(3R,4R)-3-Amino-1-hydroxy-4-methylpyrrolidin-2-one,2TBDMS,isomer #1	CC1CN(O)C(=O)C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1998.8	Semi standard non polar	33892256
(3R,4R)-3-Amino-1-hydroxy-4-methylpyrrolidin-2-one,2TBDMS,isomer #1	CC1CN(O)C(=O)C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2075.2	Standard non polar	33892256
(3R,4R)-3-Amino-1-hydroxy-4-methylpyrrolidin-2-one,2TBDMS,isomer #1	CC1CN(O)C(=O)C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2175.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (3R,4R)-3-Amino-1-hydroxy-4-methylpyrrolidin-2-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-05dl-9000000000-558df0c88198f19352b1	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (3R,4R)-3-Amino-1-hydroxy-4-methylpyrrolidin-2-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (3R,4R)-3-Amino-1-hydroxy-4-methylpyrrolidin-2-one 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 - (3R,4R)-3-Amino-1-hydroxy-4-methylpyrrolidin-2-one 10V, Positive-QTOF	splash10-001i-0900000000-0db39df32375421a2e8b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3R,4R)-3-Amino-1-hydroxy-4-methylpyrrolidin-2-one 20V, Positive-QTOF	splash10-08n9-8900000000-95f22d996ba04a17ef61	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3R,4R)-3-Amino-1-hydroxy-4-methylpyrrolidin-2-one 40V, Positive-QTOF	splash10-052f-9000000000-7c830765a44377db9478	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3R,4R)-3-Amino-1-hydroxy-4-methylpyrrolidin-2-one 10V, Negative-QTOF	splash10-004i-1900000000-4de88ef0eb198e855d90	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3R,4R)-3-Amino-1-hydroxy-4-methylpyrrolidin-2-one 20V, Negative-QTOF	splash10-03mm-9300000000-43b3426f302354b0f12a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3R,4R)-3-Amino-1-hydroxy-4-methylpyrrolidin-2-one 40V, Negative-QTOF	splash10-0006-9000000000-10e923f0fd8b5531bcd4	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	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

14073439

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14804746

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for (3R,4R)-3-Amino-1-hydroxy-4-methylpyrrolidin-2-one (HMDB0243603)

MOL for HMDB0243603 ((3R,4R)-3-Amino-1-hydroxy-4-methylpyrrolidin-2-one)

3D MOL for HMDB0243603 ((3R,4R)-3-Amino-1-hydroxy-4-methylpyrrolidin-2-one)

3D SDF for HMDB0243603 ((3R,4R)-3-Amino-1-hydroxy-4-methylpyrrolidin-2-one)

3D-SDF for HMDB0243603 ((3R,4R)-3-Amino-1-hydroxy-4-methylpyrrolidin-2-one)

PDB for HMDB0243603 ((3R,4R)-3-Amino-1-hydroxy-4-methylpyrrolidin-2-one)

3D PDB for HMDB0243603 ((3R,4R)-3-Amino-1-hydroxy-4-methylpyrrolidin-2-one)

SMILES for HMDB0243603 ((3R,4R)-3-Amino-1-hydroxy-4-methylpyrrolidin-2-one)

INCHI for HMDB0243603 ((3R,4R)-3-Amino-1-hydroxy-4-methylpyrrolidin-2-one)

Structure for HMDB0243603 ((3R,4R)-3-Amino-1-hydroxy-4-methylpyrrolidin-2-one)

3D Structure for HMDB0243603 ((3R,4R)-3-Amino-1-hydroxy-4-methylpyrrolidin-2-one)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra