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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 22:06:01 UTC

Update Date

2021-09-26 22:53:07 UTC

HMDB ID

HMDB0244983

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3-Hydroxynorvaline

Description

3-Hydroxynorvaline 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). Based on a literature review very few articles have been published on 3-Hydroxynorvaline. This compound has been identified in human blood as reported by (PMID: 31557052 ). 3-hydroxynorvaline is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 3-Hydroxynorvaline 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
DL-beta-Hydroxynorvaline	ChEBI
DL-b-Hydroxynorvaline	Generator
DL-Β-hydroxynorvaline	Generator
2-Amino-3-hydroxypentanoate	HMDB
3-Hydroxynorvaline, threo-(DL)-isomer	HMDB
alpha-Amino beta-hydroxyvaleric acid	HMDB
beta-Hydroxynorvaline	HMDB
3-Hydroxynorvaline	MeSH

Chemical Formula

C₅H₁₁NO₃

Average Molecular Weight

133.147

Monoisotopic Molecular Weight

133.073893218

IUPAC Name

2-amino-3-hydroxypentanoic acid

Traditional Name

2-amino-3-hydroxypentanoic acid

CAS Registry Number

Not Available

SMILES

CCC(O)C(N)C(O)=O

InChI Identifier

InChI=1S/C5H11NO3/c1-2-3(7)4(6)5(8)9/h3-4,7H,2,6H2,1H3,(H,8,9)

InChI Key

LGVJIYCMHMKTPB-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
Beta-hydroxy acid
Branched fatty acid
Methyl-branched fatty acid
Short-chain hydroxy acid
Hydroxy fatty acid
Hydroxy acid
Fatty acyl
Fatty acid
Amino acid
Secondary alcohol
Carboxylic acid
Monocarboxylic acid or derivatives
Alcohol
Organonitrogen compound
Organooxygen compound
Primary aliphatic amine
Primary amine
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Amine
Organic nitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

non-proteinogenic amino acid derivative (CHEBI:74112 )
non-proteinogenic alpha-amino acid (CHEBI:74112 )

Ontology

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	-2.7	ALOGPS
logP	-2.9	ChemAxon
logS	0.39	ALOGPS
pKa (Strongest Acidic)	2.34	ChemAxon
pKa (Strongest Basic)	8.99	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	83.55 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	30.98 m³·mol⁻¹	ChemAxon
Polarizability	13.25 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
DeepCCS	[M+H]+	127.424	30932474
DeepCCS	[M-H]-	124.576	30932474
DeepCCS	[M-2H]-	161.222	30932474
DeepCCS	[M+Na]+	136.053	30932474
AllCCS	[M+H]+	133.1	32859911
AllCCS	[M+H-H2O]+	129.0	32859911
AllCCS	[M+NH4]+	136.9	32859911
AllCCS	[M+Na]+	138.1	32859911
AllCCS	[M-H]-	125.2	32859911
AllCCS	[M+Na-2H]-	127.9	32859911
AllCCS	[M+HCOO]-	130.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxynorvaline	CCC(O)C(N)C(O)=O	2291.5	Standard polar	33892256
3-Hydroxynorvaline	CCC(O)C(N)C(O)=O	1238.3	Standard non polar	33892256
3-Hydroxynorvaline	CCC(O)C(N)C(O)=O	1678.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxynorvaline,3TMS,isomer #1	CCC(O[Si](C)(C)C)C(N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1478.5	Semi standard non polar	33892256
3-Hydroxynorvaline,3TMS,isomer #1	CCC(O[Si](C)(C)C)C(N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1467.0	Standard non polar	33892256
3-Hydroxynorvaline,3TMS,isomer #1	CCC(O[Si](C)(C)C)C(N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1505.9	Standard polar	33892256
3-Hydroxynorvaline,3TMS,isomer #2	CCC(O[Si](C)(C)C)C(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1607.0	Semi standard non polar	33892256
3-Hydroxynorvaline,3TMS,isomer #2	CCC(O[Si](C)(C)C)C(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1506.6	Standard non polar	33892256
3-Hydroxynorvaline,3TMS,isomer #2	CCC(O[Si](C)(C)C)C(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1667.5	Standard polar	33892256
3-Hydroxynorvaline,3TMS,isomer #3	CCC(O)C(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1586.4	Semi standard non polar	33892256
3-Hydroxynorvaline,3TMS,isomer #3	CCC(O)C(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1476.8	Standard non polar	33892256
3-Hydroxynorvaline,3TMS,isomer #3	CCC(O)C(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1693.3	Standard polar	33892256
3-Hydroxynorvaline,4TMS,isomer #1	CCC(O[Si](C)(C)C)C(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1672.1	Semi standard non polar	33892256
3-Hydroxynorvaline,4TMS,isomer #1	CCC(O[Si](C)(C)C)C(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1582.6	Standard non polar	33892256
3-Hydroxynorvaline,4TMS,isomer #1	CCC(O[Si](C)(C)C)C(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1516.2	Standard polar	33892256
3-Hydroxynorvaline,3TBDMS,isomer #1	CCC(O[Si](C)(C)C(C)(C)C)C(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2080.9	Semi standard non polar	33892256
3-Hydroxynorvaline,3TBDMS,isomer #1	CCC(O[Si](C)(C)C(C)(C)C)C(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2056.3	Standard non polar	33892256
3-Hydroxynorvaline,3TBDMS,isomer #1	CCC(O[Si](C)(C)C(C)(C)C)C(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1954.0	Standard polar	33892256
3-Hydroxynorvaline,3TBDMS,isomer #2	CCC(O[Si](C)(C)C(C)(C)C)C(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2219.2	Semi standard non polar	33892256
3-Hydroxynorvaline,3TBDMS,isomer #2	CCC(O[Si](C)(C)C(C)(C)C)C(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2113.6	Standard non polar	33892256
3-Hydroxynorvaline,3TBDMS,isomer #2	CCC(O[Si](C)(C)C(C)(C)C)C(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2017.5	Standard polar	33892256
3-Hydroxynorvaline,3TBDMS,isomer #3	CCC(O)C(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	2209.4	Semi standard non polar	33892256
3-Hydroxynorvaline,3TBDMS,isomer #3	CCC(O)C(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	2108.6	Standard non polar	33892256
3-Hydroxynorvaline,3TBDMS,isomer #3	CCC(O)C(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	2046.8	Standard polar	33892256
3-Hydroxynorvaline,4TBDMS,isomer #1	CCC(O[Si](C)(C)C(C)(C)C)C(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	2470.7	Semi standard non polar	33892256
3-Hydroxynorvaline,4TBDMS,isomer #1	CCC(O[Si](C)(C)C(C)(C)C)C(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	2354.1	Standard non polar	33892256
3-Hydroxynorvaline,4TBDMS,isomer #1	CCC(O[Si](C)(C)C(C)(C)C)C(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	2035.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxynorvaline GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ab9-9000000000-31fecbf72ef77b003452	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxynorvaline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxynorvaline GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxynorvaline GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxynorvaline GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxynorvaline GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxynorvaline GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxynorvaline GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxynorvaline GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxynorvaline GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxynorvaline GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxynorvaline GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxynorvaline GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxynorvaline GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxynorvaline GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxynorvaline GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-11-03	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 - 3-Hydroxynorvaline 10V, Positive-QTOF	splash10-00dr-9200000000-e78fd35e7a10b8d2021b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxynorvaline 20V, Positive-QTOF	splash10-00dr-9000000000-a671466413e2cfe5db76	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxynorvaline 40V, Positive-QTOF	splash10-0006-9000000000-96de0bbf41b78e111ee6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxynorvaline 10V, Negative-QTOF	splash10-001i-1900000000-76912b4a7834d7cee82f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxynorvaline 20V, Negative-QTOF	splash10-05fr-9000000000-3f67374ee1ff6eba956c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxynorvaline 40V, Negative-QTOF	splash10-0a4l-9000000000-7f7a349d45a987d1cd4a	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

C00052682

Chemspider ID

58607

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

65097

PDB ID

Not Available

ChEBI ID

74112

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 3-Hydroxynorvaline (HMDB0244983)

MOL for HMDB0244983 (3-Hydroxynorvaline)

3D MOL for HMDB0244983 (3-Hydroxynorvaline)

3D SDF for HMDB0244983 (3-Hydroxynorvaline)

3D-SDF for HMDB0244983 (3-Hydroxynorvaline)

PDB for HMDB0244983 (3-Hydroxynorvaline)

3D PDB for HMDB0244983 (3-Hydroxynorvaline)

SMILES for HMDB0244983 (3-Hydroxynorvaline)

INCHI for HMDB0244983 (3-Hydroxynorvaline)

Structure for HMDB0244983 (3-Hydroxynorvaline)

3D Structure for HMDB0244983 (3-Hydroxynorvaline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra