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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:44:41 UTC

Update Date

2023-02-21 17:21:08 UTC

HMDB ID

HMDB0031658

Secondary Accession Numbers

HMDB31658

Metabolite Identification

Common Name

L-2-Amino-5-hydroxypentanoic acid

Description

L-2-Amino-5-hydroxypentanoic acid, also known as 5-hydroxy-2-aminovalerate or 5-OH-2-NH2-valerate, 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 L-2-Amino-5-hydroxypentanoic acid.

Structure

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
L-2-Amino-5-hydroxypentanoate	Generator
2-Amino-5-hydroxypentanoate	HMDB
2-Amino-5-hydroxyvaleric acid	HMDB
2-Amino-5-hydroxyvaleric acid, (L)-isomer	HMDB
5-Hydroxy-2-aminovalerate	HMDB
5-OH-2-NH2-Valerate	HMDB
5-Hydroxy-2-aminovaleric acid	HMDB
5-Hydroxynorvaline	HMDB
alpha-Amino-delta-hydroxyvaleric acid	HMDB
2-Amino-5-hydroxyvaleric acid, (DL)-isomer	HMDB
HAVA-5 CPD	HMDB

Chemical Formula

C₅H₁₁NO₃

Average Molecular Weight

133.1457

Monoisotopic Molecular Weight

133.073893223

IUPAC Name

2-amino-5-hydroxypentanoic acid

Traditional Name

5-hydroxy norvaline

CAS Registry Number

Not Available

SMILES

NC(CCCO)C(O)=O

InChI Identifier

InChI=1S/C5H11NO3/c6-4(5(8)9)2-1-3-7/h4,7H,1-3,6H2,(H,8,9)

InChI Key

CZWARROQQFCFJB-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
Fatty acid
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organic oxide
Primary amine
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Primary aliphatic amine
Organic oxygen compound
Carbonyl group
Amine
Organic nitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0031658)
Cytoplasm (HMDB: HMDB0031658)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031658)

Source

Endogenous

Endogenous (HMDB: HMDB0031658)

Plant

Fabaceae (HMDB: HMDB0031658)

Exogenous

Food

Food (HMDB: HMDB0031658)

Pulse

Pulses (FooDB: FOOD00867)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	231.5 °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	268 g/L	ALOGPS
logP	-3.2	ALOGPS
logP	-3.3	ChemAxon
logS	0.3	ALOGPS
pKa (Strongest Acidic)	2.36	ChemAxon
pKa (Strongest Basic)	9.22	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	4	ChemAxon
Refractivity	31.55 m³·mol⁻¹	ChemAxon
Polarizability	13.47 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]+	127.369	31661259
DarkChem	[M-H]-	123.71	31661259
DeepCCS	[M+H]+	129.81	30932474
DeepCCS	[M-H]-	127.038	30932474
DeepCCS	[M-2H]-	163.383	30932474
DeepCCS	[M+Na]+	138.072	30932474
AllCCS	[M+H]+	131.1	32859911
AllCCS	[M+H-H2O]+	127.0	32859911
AllCCS	[M+NH4]+	134.9	32859911
AllCCS	[M+Na]+	136.0	32859911
AllCCS	[M-H]-	125.3	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
L-2-Amino-5-hydroxypentanoic acid	NC(CCCO)C(O)=O	2280.6	Standard polar	33892256
L-2-Amino-5-hydroxypentanoic acid	NC(CCCO)C(O)=O	1315.6	Standard non polar	33892256
L-2-Amino-5-hydroxypentanoic acid	NC(CCCO)C(O)=O	1689.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
L-2-Amino-5-hydroxypentanoic acid,1TMS,isomer #1	C[Si](C)(C)OCCCC(N)C(=O)O	1408.9	Semi standard non polar	33892256
L-2-Amino-5-hydroxypentanoic acid,1TMS,isomer #2	C[Si](C)(C)OC(=O)C(N)CCCO	1363.0	Semi standard non polar	33892256
L-2-Amino-5-hydroxypentanoic acid,1TMS,isomer #3	C[Si](C)(C)NC(CCCO)C(=O)O	1459.5	Semi standard non polar	33892256
L-2-Amino-5-hydroxypentanoic acid,2TMS,isomer #1	C[Si](C)(C)OCCCC(N)C(=O)O[Si](C)(C)C	1443.9	Semi standard non polar	33892256
L-2-Amino-5-hydroxypentanoic acid,2TMS,isomer #2	C[Si](C)(C)NC(CCCO[Si](C)(C)C)C(=O)O	1537.6	Semi standard non polar	33892256
L-2-Amino-5-hydroxypentanoic acid,2TMS,isomer #3	C[Si](C)(C)NC(CCCO)C(=O)O[Si](C)(C)C	1478.7	Semi standard non polar	33892256
L-2-Amino-5-hydroxypentanoic acid,2TMS,isomer #4	C[Si](C)(C)N(C(CCCO)C(=O)O)[Si](C)(C)C	1662.6	Semi standard non polar	33892256
L-2-Amino-5-hydroxypentanoic acid,3TMS,isomer #1	C[Si](C)(C)NC(CCCO[Si](C)(C)C)C(=O)O[Si](C)(C)C	1553.0	Semi standard non polar	33892256
L-2-Amino-5-hydroxypentanoic acid,3TMS,isomer #1	C[Si](C)(C)NC(CCCO[Si](C)(C)C)C(=O)O[Si](C)(C)C	1611.9	Standard non polar	33892256
L-2-Amino-5-hydroxypentanoic acid,3TMS,isomer #2	C[Si](C)(C)OCCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1728.7	Semi standard non polar	33892256
L-2-Amino-5-hydroxypentanoic acid,3TMS,isomer #2	C[Si](C)(C)OCCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1660.2	Standard non polar	33892256
L-2-Amino-5-hydroxypentanoic acid,3TMS,isomer #3	C[Si](C)(C)OC(=O)C(CCCO)N([Si](C)(C)C)[Si](C)(C)C	1669.8	Semi standard non polar	33892256
L-2-Amino-5-hydroxypentanoic acid,3TMS,isomer #3	C[Si](C)(C)OC(=O)C(CCCO)N([Si](C)(C)C)[Si](C)(C)C	1607.0	Standard non polar	33892256
L-2-Amino-5-hydroxypentanoic acid,4TMS,isomer #1	C[Si](C)(C)OCCCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1772.2	Semi standard non polar	33892256
L-2-Amino-5-hydroxypentanoic acid,4TMS,isomer #1	C[Si](C)(C)OCCCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1726.1	Standard non polar	33892256
L-2-Amino-5-hydroxypentanoic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCCC(N)C(=O)O	1662.6	Semi standard non polar	33892256
L-2-Amino-5-hydroxypentanoic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(N)CCCO	1586.2	Semi standard non polar	33892256
L-2-Amino-5-hydroxypentanoic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(CCCO)C(=O)O	1696.9	Semi standard non polar	33892256
L-2-Amino-5-hydroxypentanoic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCCC(N)C(=O)O[Si](C)(C)C(C)(C)C	1886.0	Semi standard non polar	33892256
L-2-Amino-5-hydroxypentanoic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(CCCO[Si](C)(C)C(C)(C)C)C(=O)O	1993.4	Semi standard non polar	33892256
L-2-Amino-5-hydroxypentanoic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(CCCO)C(=O)O[Si](C)(C)C(C)(C)C	1917.0	Semi standard non polar	33892256
L-2-Amino-5-hydroxypentanoic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C(CCCO)C(=O)O)[Si](C)(C)C(C)(C)C	2073.6	Semi standard non polar	33892256
L-2-Amino-5-hydroxypentanoic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CCCO[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2172.3	Semi standard non polar	33892256
L-2-Amino-5-hydroxypentanoic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CCCO[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2202.3	Standard non polar	33892256
L-2-Amino-5-hydroxypentanoic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2354.7	Semi standard non polar	33892256
L-2-Amino-5-hydroxypentanoic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2253.4	Standard non polar	33892256
L-2-Amino-5-hydroxypentanoic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(CCCO)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2321.6	Semi standard non polar	33892256
L-2-Amino-5-hydroxypentanoic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(CCCO)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2215.4	Standard non polar	33892256
L-2-Amino-5-hydroxypentanoic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCCC(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	2597.3	Semi standard non polar	33892256
L-2-Amino-5-hydroxypentanoic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCCC(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	2465.0	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-2-Amino-5-hydroxypentanoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-05a6-9100000000-63670356f1f15e7bbc76	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-2-Amino-5-hydroxypentanoic acid GC-MS (2 TMS) - 70eV, Positive	splash10-022j-9710000000-4fd2b94ea4fc27065882	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-2-Amino-5-hydroxypentanoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-2-Amino-5-hydroxypentanoic acid 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 - L-2-Amino-5-hydroxypentanoic acid 10V, Positive-QTOF	splash10-01c9-9700000000-c24b5453866bc6f6592f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-2-Amino-5-hydroxypentanoic acid 20V, Positive-QTOF	splash10-00dr-9100000000-55450bfbe46e34bffe96	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-2-Amino-5-hydroxypentanoic acid 40V, Positive-QTOF	splash10-05fu-9000000000-27da1e54806fb2b82100	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-2-Amino-5-hydroxypentanoic acid 10V, Negative-QTOF	splash10-001i-2900000000-dce94fad816b54ac4daa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-2-Amino-5-hydroxypentanoic acid 20V, Negative-QTOF	splash10-001i-6900000000-7618a92619cf1ec99033	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-2-Amino-5-hydroxypentanoic acid 40V, Negative-QTOF	splash10-00di-9000000000-9ff90ef53329bf3e770c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-2-Amino-5-hydroxypentanoic acid 10V, Positive-QTOF	splash10-000i-9100000000-4df1098451484fb33e8e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-2-Amino-5-hydroxypentanoic acid 20V, Positive-QTOF	splash10-00di-9000000000-8bdebf0e8c284c78dd3c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-2-Amino-5-hydroxypentanoic acid 40V, Positive-QTOF	splash10-00di-9000000000-04153b111ef6c554f474	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-2-Amino-5-hydroxypentanoic acid 10V, Negative-QTOF	splash10-001i-0900000000-14afaaf9851e0545a5fa	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-2-Amino-5-hydroxypentanoic acid 20V, Negative-QTOF	splash10-001i-5900000000-9701ae6156ae87958a81	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-2-Amino-5-hydroxypentanoic acid 40V, Negative-QTOF	splash10-0006-9000000000-b142416ce7a091942de7	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	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

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

FDB008318

KNApSAcK ID

Not Available

Chemspider ID

86255

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

95562

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for L-2-Amino-5-hydroxypentanoic acid (HMDB0031658)

MOL for HMDB0031658 (L-2-Amino-5-hydroxypentanoic acid)

3D MOL for HMDB0031658 (L-2-Amino-5-hydroxypentanoic acid)

3D SDF for HMDB0031658 (L-2-Amino-5-hydroxypentanoic acid)

3D-SDF for HMDB0031658 (L-2-Amino-5-hydroxypentanoic acid)

PDB for HMDB0031658 (L-2-Amino-5-hydroxypentanoic acid)

3D PDB for HMDB0031658 (L-2-Amino-5-hydroxypentanoic acid)

SMILES for HMDB0031658 (L-2-Amino-5-hydroxypentanoic acid)

INCHI for HMDB0031658 (L-2-Amino-5-hydroxypentanoic acid)

Structure for HMDB0031658 (L-2-Amino-5-hydroxypentanoic acid)

3D Structure for HMDB0031658 (L-2-Amino-5-hydroxypentanoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra