MiMeDB: Showing metabocard for L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid (MMDBc0008060)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-15 01:02:04 UTC

Update Date

2025-10-07 16:05:24 UTC

Metabolite ID

MMDBc0008060

Metabolite Identification

Common Name

L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid

Description

L-threo-α-amino-β,γ-dihydroxybutyric acid is a dihydroxy amino acid. There is limited literature available on this metabolite, indicating that further research may be needed to fully understand its biological significance and potential applications.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Hydroxythreonine	ChEBI
alpha-Amino-beta,gamma-dihydroxybutyric acid	MeSH

Molecular Formula

C₄H₉NO₄

Average Mass

135.1186

Monoisotopic Mass

135.053157781

IUPAC Name

(2S,3S)-2-amino-3,4-dihydroxybutanoic acid

Traditional Name

hydroxythreonine

CAS Registry Number

Not Available

SMILES

N[C@@H]([C@H](O)CO)C(O)=O

InChI Identifier

InChI=1S/C4H9NO4/c5-3(4(8)9)2(7)1-6/h2-3,6-7H,1,5H2,(H,8,9)/t2-,3+/m1/s1

InChI Key

JBNUARFQOCGDRK-GBXIJSLDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

L-alpha-amino acid
Beta-hydroxy acid
Short-chain hydroxy acid
Hydroxy acid
Fatty acid
1,3-aminoalcohol
1,2-diol
Amino acid
Secondary alcohol
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Primary alcohol
Organooxygen compound
Organonitrogen compound
Primary amine
Primary aliphatic amine
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Amine
Alcohol
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid (CHEBI:28330 )
L-threonine derivative (CHEBI:28330 )
hydroxy-amino acid (CHEBI:28330 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	357 g/L	ALOGPS
logP	-3.4	ALOGPS
logP	-4.5	ChemAxon
logS	0.42	ALOGPS
pKa (Strongest Acidic)	1.92	ChemAxon
pKa (Strongest Basic)	8.62	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	103.78 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	28 m³·mol⁻¹	ChemAxon
Polarizability	12.04 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00ec-9000000000-ed89b9334f5be14dc8c5	2016-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014r-4900000000-dbd9d3d88c247a29f9c9	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9100000000-2070d819d44de1960ae0	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9100000000-283552f8bd87ff9d06d5	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-8900000000-75b8c2945f1960264b7f	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pw9-9400000000-43e8a71f87678ae42e12	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05fr-9000000000-437c14b312f426383b44	2015-09-15	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-23	558.9
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	443.6
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (void)	2025-10-23	44.6
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	221.5
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (void)	2025-10-23	302.4
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-23	362.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-23	490.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	940.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	938.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	218.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	548.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-23	232.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-23	28.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	439.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	772.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-23	124.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-23	370.8
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	713.1
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	607.9

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid_TMS_1	C[Si](C)(C)O[C@H](CO)[C@H](N)C(=O)O	standard non polar	2025-10-23	1893.55
Gas Chromatography	L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid_TMS_2	C[Si](C)(C)OC[C@@H](O)[C@H](N)C(=O)O	standard non polar	2025-10-23	2008.27
Gas Chromatography	L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid_TMS_3	C[Si](C)(C)OC(=O)[C@@H](N)[C@H](O)CO	standard non polar	2025-10-23	1737.87
Gas Chromatography	L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid_TMS_4	C[Si](C)(C)N[C@H](C(=O)O)[C@H](O)CO	standard non polar	2025-10-23	1776.54
Gas Chromatography	L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid_TMS_5	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](N)C(=O)O	standard non polar	2025-10-23	1790.39
Gas Chromatography	L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid_TMS_6	C[Si](C)(C)OC(=O)[C@@H](N)[C@@H](CO)O[Si](C)(C)C	standard non polar	2025-10-23	1771.8
Gas Chromatography	L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid_TMS_7	C[Si](C)(C)N[C@H](C(=O)O)[C@@H](CO)O[Si](C)(C)C	standard non polar	2025-10-23	2090.32
Gas Chromatography	L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid_TMS_8	C[Si](C)(C)OC[C@@H](O)[C@H](N)C(=O)O[Si](C)(C)C	standard non polar	2025-10-23	1784.29
Gas Chromatography	L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid_TMS_9	C[Si](C)(C)N[C@H](C(=O)O)[C@H](O)CO[Si](C)(C)C	standard non polar	2025-10-23	2072.8
Gas Chromatography	L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid_TMS_10	C[Si](C)(C)N[C@H](C(=O)O[Si](C)(C)C)[C@H](O)CO	standard non polar	2025-10-23	1817.96
Gas Chromatography	L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid_TMS_11	C[Si](C)(C)N([C@H](C(=O)O)[C@H](O)CO)[Si](C)(C)C	standard non polar	2025-10-23	1927.19
Gas Chromatography	L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid_TMS_12	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](N)C(=O)O[Si](C)(C)C	standard non polar	2025-10-23	2484.36
Gas Chromatography	L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid_TMS_13	C[Si](C)(C)N[C@H](C(=O)O)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C	standard non polar	2025-10-23	1680.88
Gas Chromatography	L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid_TMS_14	C[Si](C)(C)N[C@H](C(=O)O[Si](C)(C)C)[C@@H](CO)O[Si](C)(C)C	standard non polar	2025-10-23	1620.8
Gas Chromatography	L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid_TMS_15	C[Si](C)(C)O[C@H](CO)[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-23	1439.07
Gas Chromatography	L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid_TMS_16	C[Si](C)(C)N[C@H](C(=O)O[Si](C)(C)C)[C@H](O)CO[Si](C)(C)C	standard non polar	2025-10-23	2132.72
Gas Chromatography	L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid_TMS_17	C[Si](C)(C)OC[C@@H](O)[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-23	2209.93
Gas Chromatography	L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid_TMS_18	C[Si](C)(C)OC(=O)[C@H]([C@H](O)CO)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-23	1279.54
Gas Chromatography	L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid_TMS_19	C[Si](C)(C)N[C@H](C(=O)O[Si](C)(C)C)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C	standard non polar	2025-10-23	2519.61
Gas Chromatography	L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid_TMS_20	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-23	2421.65
Gas Chromatography	L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid_TMS_21	C[Si](C)(C)OC(=O)[C@H]([C@@H](CO)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-23	1765.4
Gas Chromatography	L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid_TMS_22	C[Si](C)(C)OC[C@@H](O)[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-23	2062.55
Gas Chromatography	L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid_TMS_23	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-23	2525.23
Gas Chromatography	L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid_TMS_1	C[Si](C)(C)O[C@H](CO)[C@H](N)C(=O)O	standard polar	2025-10-23	1340.73
Gas Chromatography	L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid_TMS_2	C[Si](C)(C)OC[C@@H](O)[C@H](N)C(=O)O	standard polar	2025-10-23	2111.98
Gas Chromatography	L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid_TMS_3	C[Si](C)(C)OC(=O)[C@@H](N)[C@H](O)CO	standard polar	2025-10-23	1795.26
Gas Chromatography	L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid_TMS_4	C[Si](C)(C)N[C@H](C(=O)O)[C@H](O)CO	standard polar	2025-10-23	2066.62
Gas Chromatography	L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid_TMS_5	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](N)C(=O)O	standard polar	2025-10-23	2022.48
Gas Chromatography	L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid_TMS_6	C[Si](C)(C)OC(=O)[C@@H](N)[C@@H](CO)O[Si](C)(C)C	standard polar	2025-10-23	2451.73
Gas Chromatography	L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid_TMS_7	C[Si](C)(C)N[C@H](C(=O)O)[C@@H](CO)O[Si](C)(C)C	standard polar	2025-10-23	1830.75
Gas Chromatography	L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid_TMS_8	C[Si](C)(C)OC[C@@H](O)[C@H](N)C(=O)O[Si](C)(C)C	standard polar	2025-10-23	2105.12
Gas Chromatography	L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid_TMS_9	C[Si](C)(C)N[C@H](C(=O)O)[C@H](O)CO[Si](C)(C)C	standard polar	2025-10-23	1897.04
Gas Chromatography	L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid_TMS_10	C[Si](C)(C)N[C@H](C(=O)O[Si](C)(C)C)[C@H](O)CO	standard polar	2025-10-23	2096.48
Gas Chromatography	L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid_TMS_11	C[Si](C)(C)N([C@H](C(=O)O)[C@H](O)CO)[Si](C)(C)C	standard polar	2025-10-23	1799.74
Gas Chromatography	L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid_TMS_12	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](N)C(=O)O[Si](C)(C)C	standard polar	2025-10-23	1748.89
Gas Chromatography	L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid_TMS_13	C[Si](C)(C)N[C@H](C(=O)O)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C	standard polar	2025-10-23	2178.16
Gas Chromatography	L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid_TMS_14	C[Si](C)(C)N[C@H](C(=O)O[Si](C)(C)C)[C@@H](CO)O[Si](C)(C)C	standard polar	2025-10-23	2252.23
Gas Chromatography	L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid_TMS_15	C[Si](C)(C)O[C@H](CO)[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-23	1838.68
Gas Chromatography	L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid_TMS_16	C[Si](C)(C)N[C@H](C(=O)O[Si](C)(C)C)[C@H](O)CO[Si](C)(C)C	standard polar	2025-10-23	2061.64
Gas Chromatography	L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid_TMS_17	C[Si](C)(C)OC[C@@H](O)[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-23	2689.71
Gas Chromatography	L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid_TMS_18	C[Si](C)(C)OC(=O)[C@H]([C@H](O)CO)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-23	2496.36
Gas Chromatography	L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid_TMS_19	C[Si](C)(C)N[C@H](C(=O)O[Si](C)(C)C)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C	standard polar	2025-10-23	2665.73
Gas Chromatography	L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid_TMS_20	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-23	1671.2
Gas Chromatography	L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid_TMS_21	C[Si](C)(C)OC(=O)[C@H]([C@@H](CO)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-23	2036.6
Gas Chromatography	L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid_TMS_22	C[Si](C)(C)OC[C@@H](O)[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-23	2614.23
Gas Chromatography	L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid_TMS_23	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-23	2540.36

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Actinobacteria	1	Human	Metabolic reconstruction
Bacteria	Actinobacteria	1	Human	Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C06056

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

193577

PDB ID

Not Available

ChEBI ID

28330

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for L-threo-Î±-amino-Î², Î³-dihydroxybutyric acid (MMDBc0008060)

MOL for #<Metabolite:0x00007f9a90907b58>

3D MOL for #<Metabolite:0x00007f9a90907b58>

3D SDF for #<Metabolite:0x00007f9a90907b58>

3D-SDF for #<Metabolite:0x00007f9a90907b58>

PDB for #<Metabolite:0x00007f9a90907b58>

3D PDB for #<Metabolite:0x00007f9a90907b58>

SMILES for #<Metabolite:0x00007f9a90907b58>

INCHI for #<Metabolite:0x00007f9a90907b58>

Structure for #<Metabolite:0x00007f9a90907b58>

3D Structure for #<Metabolite:0x00007f9a90907b58>