L-threonine (CHEBI:16857)

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CHEBI:16857 - L-threonine

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ChEBI Name	L-threonine

ChEBI ID	CHEBI:16857

ChEBI ASCII Name	L-threonine

Definition	An optically active form of threonine having L-configuration.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:45843, CHEBI:42083, CHEBI:45983, CHEBI:13175, CHEBI:6308, CHEBI:21403

Supplier Information	No supplier information found for this compound.

Download	Molfile XML SDF

more structures >>

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16 15 0 0 0 0 999 V2000

0.4303 1.5436 -0.7027 N 0 0 0 0 0 0 0 0 0 0 0 0

0.0566 0.1229 -0.7065 C 0 0 2 0 0 0 0 0 0 0 0 0

-1.3093 -0.0389 -0.0906 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.6832 0.7323 0.7610 O 0 0 0 0 0 0 0 0 0 0 0 0

1.0794 -0.6757 0.1040 C 0 0 2 0 0 0 0 0 0 0 0 0

1.1031 -0.1931 1.4488 O 0 0 0 0 0 0 0 0 0 0 0 0

2.4661 -0.5115 -0.5213 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.1105 -1.0398 -0.4881 O 0 0 0 0 0 0 0 0 0 0 0 0

0.4341 1.8397 0.2619 H 0 0 0 0 0 0 0 0 0 0 0 0

0.0385 -0.2453 -1.7323 H 0 0 0 0 0 0 0 0 0 0 0 0

0.8021 -1.7299 0.1011 H 0 0 0 0 0 0 0 0 0 0 0 0

1.3521 0.7403 1.4064 H 0 0 0 0 0 0 0 0 0 0 0 0

3.1947 -1.0804 0.0561 H 0 0 0 0 0 0 0 0 0 0 0 0

2.4480 -0.8796 -1.5471 H 0 0 0 0 0 0 0 0 0 0 0 0

2.7434 0.5427 -0.5185 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.9869 -1.1437 -0.0929 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 1 0 0 0 0

1 9 1 0 0 0 0

2 3 1 0 0 0 0

4 3 2 0 0 0 0

5 2 1 0 0 0 0

6 5 1 0 0 0 0

6 12 1 0 0 0 0

7 5 1 0 0 0 0

8 3 1 0 0 0 0

8 16 1 0 0 0 0

10 2 1 0 0 0 0

11 5 1 0 0 0 0

13 7 1 0 0 0 0

14 7 1 0 0 0 0

15 7 1 0 0 0 0

M END): 26 ms

reading 16 atoms

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Wikipedia	License
Threonine (symbol Thr or T) is an amino acid that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated −NH+3 form when dissolved in water), a carboxyl group (which is in the deprotonated −COO− form when dissolved in water), and a side chain containing a hydroxyl group, making it a polar, uncharged amino acid. It is essential in humans, meaning the body cannot synthesize it: it must be obtained from the diet. Threonine is synthesized from aspartate in bacteria such as E. coli. It is encoded by all the codons starting AC (ACU, ACC, ACA, and ACG). Threonine sidechains are often hydrogen bonded; the most common small motifs formed are based on interactions with serine: ST turns, ST motifs (often at the beginning of alpha helices) and ST staples (usually at the middle of alpha helices).
Read full article at Wikipedia

Formula

C4H9NO3

Net Charge

Average Mass

119.11920

Monoisotopic Mass

119.05824

InChI

InChI=1S/C4H9NO3/c1-2(6)3(5)4(7)8/h2-3,6H,5H2,1H3,(H,7,8)/t2-,3+/m1/s1

InChIKey

AYFVYJQAPQTCCC-GBXIJSLDSA-N

SMILES

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

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Saccharomyces cerevisiae (NCBI:txid4932)	See: PubMed
Saccharomyces cerevisiae (NCBI:txid4932)	Source: yeast.sf.net See: PubMed
Escherichia coli (NCBI:txid562)	See: PubMed
Escherichia coli (NCBI:txid562)	See: PubMed
Homo sapiens (NCBI:txid9606)	See: DOI

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound ) Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	micronutrient Any nutrient required in small quantities by organisms throughout their life in order to orchestrate a range of physiological functions. Saccharomyces cerevisiae metabolite Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ). plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. (via 2-amino-3-hydroxybutanoic acid ) Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli. mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). algal metabolite Any eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae. Daphnia magna metabolite A Daphnia metabolite produced by the species Daphnia magna. (via threonine )

Application(s):	nutraceutical A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	L-threonine (CHEBI:16857) has role Escherichia coli metabolite (CHEBI:76971) L-threonine (CHEBI:16857) has role Saccharomyces cerevisiae metabolite (CHEBI:75772) L-threonine (CHEBI:16857) has role algal metabolite (CHEBI:84735) L-threonine (CHEBI:16857) has role human metabolite (CHEBI:77746) L-threonine (CHEBI:16857) has role micronutrient (CHEBI:27027) L-threonine (CHEBI:16857) has role mouse metabolite (CHEBI:75771) L-threonine (CHEBI:16857) has role nutraceutical (CHEBI:50733) L-threonine (CHEBI:16857) has role plant metabolite (CHEBI:76924) L-threonine (CHEBI:16857) is a L-α-amino acid (CHEBI:15705) L-threonine (CHEBI:16857) is a aspartate family amino acid (CHEBI:22658) L-threonine (CHEBI:16857) is a proteinogenic amino acid (CHEBI:83813) L-threonine (CHEBI:16857) is a threonine (CHEBI:26986) L-threonine (CHEBI:16857) is conjugate acid of L-threoninate (CHEBI:32820) L-threonine (CHEBI:16857) is conjugate base of L-threoninium (CHEBI:32822) L-threonine (CHEBI:16857) is enantiomer of D-threonine (CHEBI:16398) L-threonine (CHEBI:16857) is tautomer of L-threonine zwitterion (CHEBI:57926)

Incoming	L-threonine derivative (CHEBI:84189) has functional parent L-threonine (CHEBI:16857) Ala-Leu-Leu-Thr (CHEBI:73368) has functional parent L-threonine (CHEBI:16857) Ala-Leu-Thr-Gln (CHEBI:73372) has functional parent L-threonine (CHEBI:16857) Ala-Leu-Thr-Pro (CHEBI:73292) has functional parent L-threonine (CHEBI:16857) Ala-Phe-Thr-Ser (CHEBI:73377) has functional parent L-threonine (CHEBI:16857) Ala-Thr-Ala-Pro (CHEBI:73381) has functional parent L-threonine (CHEBI:16857) Arg-Thr-Cys-Cys (CHEBI:73404) has functional parent L-threonine (CHEBI:16857) Arg-Thr-Thr-Asp (CHEBI:138503) has functional parent L-threonine (CHEBI:16857) Asn-Met-Thr-Thr (CHEBI:138506) has functional parent L-threonine (CHEBI:16857) Asp-Leu-Thr-Asp (CHEBI:73433) has functional parent L-threonine (CHEBI:16857) Asp-Leu-Thr-Ser (CHEBI:73434) has functional parent L-threonine (CHEBI:16857) Asp-Met-Thr-Pro (CHEBI:73436) has functional parent L-threonine (CHEBI:16857) Asp-Thr (CHEBI:141427) has functional parent L-threonine (CHEBI:16857) Cys-Met-Thr-Tyr (CHEBI:73459) has functional parent L-threonine (CHEBI:16857) delanzomib (CHEBI:141530) has functional parent L-threonine (CHEBI:16857) Glu-Arg-Gly-Met-Thr (CHEBI:191943) has functional parent L-threonine (CHEBI:16857) Glu-Thr (CHEBI:73510) has functional parent L-threonine (CHEBI:16857) Glu-Thr-Thr-Tyr (CHEBI:73489) has functional parent L-threonine (CHEBI:16857) Glu-Val-Thr-Leu-Tyr peptide residue (CHEBI:85622) has functional parent L-threonine (CHEBI:16857) Ile-Thr (CHEBI:141441) has functional parent L-threonine (CHEBI:16857) Leu-Thr (CHEBI:73589) has functional parent L-threonine (CHEBI:16857) Leu-Thr-Ala (CHEBI:73572) has functional parent L-threonine (CHEBI:16857) Leu-Thr-Asp (CHEBI:73573) has functional parent L-threonine (CHEBI:16857) Leu-Thr-Gln (CHEBI:73574) has functional parent L-threonine (CHEBI:16857) Leu-Thr-Ser (CHEBI:73575) has functional parent L-threonine (CHEBI:16857) Lys-Glu-Thr (CHEBI:144459) has functional parent L-threonine (CHEBI:16857) Lys-Thr (CHEBI:73606) has functional parent L-threonine (CHEBI:16857) Lys-Thr-Pro-Pro (CHEBI:73596) has functional parent L-threonine (CHEBI:16857) Lys-Thr-Trp-Tyr (CHEBI:73597) has functional parent L-threonine (CHEBI:16857) Met-Thr (CHEBI:73614) has functional parent L-threonine (CHEBI:16857) Phe-Arg-Thr (CHEBI:144556) has functional parent L-threonine (CHEBI:16857) Phe-Pro-Thr (CHEBI:138789) has functional parent L-threonine (CHEBI:16857) Phe-Thr (CHEBI:73636) has functional parent L-threonine (CHEBI:16857) Pro-Thr (CHEBI:141395) has functional parent L-threonine (CHEBI:16857) Ser-Thr (CHEBI:141393) has functional parent L-threonine (CHEBI:16857) Thr-Ala-Ala (CHEBI:73654) has functional parent L-threonine (CHEBI:16857) Thr-Ala-Asp (CHEBI:73655) has functional parent L-threonine (CHEBI:16857) Thr-Ala-His (CHEBI:73656) has functional parent L-threonine (CHEBI:16857) Thr-Ala-Ser (CHEBI:73657) has functional parent L-threonine (CHEBI:16857) Thr-Asn (CHEBI:157889) has functional parent L-threonine (CHEBI:16857) Thr-Asp-Gly (CHEBI:73658) has functional parent L-threonine (CHEBI:16857) Thr-His (CHEBI:73663) has functional parent L-threonine (CHEBI:16857) Thr-Ile (CHEBI:141446) has functional parent L-threonine (CHEBI:16857) Thr-Lys (CHEBI:157893) has functional parent L-threonine (CHEBI:16857) Thr-Pro (CHEBI:73662) has functional parent L-threonine (CHEBI:16857) Thr-Pro-Pro (CHEBI:164196) has functional parent L-threonine (CHEBI:16857) Thr-Pro-Tyr (CHEBI:73661) has functional parent L-threonine (CHEBI:16857) Thr-Ser (CHEBI:73664) has functional parent L-threonine (CHEBI:16857) Thr-Thr (CHEBI:73665) has functional parent L-threonine (CHEBI:16857) Thr-Thr-Asp (CHEBI:73659) has functional parent L-threonine (CHEBI:16857) Thr-Thr-Thr (CHEBI:144905) has functional parent L-threonine (CHEBI:16857) Thr-Trp (CHEBI:73666) has functional parent L-threonine (CHEBI:16857) Thr-Trp-Asp (CHEBI:73660) has functional parent L-threonine (CHEBI:16857) Thr-Tyr (CHEBI:73667) has functional parent L-threonine (CHEBI:16857) Trp-Thr (CHEBI:141450) has functional parent L-threonine (CHEBI:16857) Tyr-Thr (CHEBI:141458) has functional parent L-threonine (CHEBI:16857) L-threoninium (CHEBI:32822) is conjugate acid of L-threonine (CHEBI:16857) L-threoninate (CHEBI:32820) is conjugate base of L-threonine (CHEBI:16857) D-threonine (CHEBI:16398) is enantiomer of L-threonine (CHEBI:16857) L-threonin-O³-yl group (CHEBI:32825) is substituent group from L-threonine (CHEBI:16857) L-threonine residue (CHEBI:30013) is substituent group from L-threonine (CHEBI:16857) L-threonino group (CHEBI:32824) is substituent group from L-threonine (CHEBI:16857) L-threonyl group (CHEBI:32823) is substituent group from L-threonine (CHEBI:16857) L-threonine zwitterion (CHEBI:57926) is tautomer of L-threonine (CHEBI:16857)

IUPAC Name

L-threonine

Synonyms	Sources
(2S)-threonine	ChemIDplus
(2S,3R)-(-)-Threonine	HMDB
(2S,3R)-2-amino-3-hydroxybutanoic acid	IUPAC
2-Amino-3-hydroxybutyric acid	KEGG COMPOUND
L-(-)-Threonine	DrugBank
L-2-Amino-3-hydroxybutyric acid	HMDB
L-α-amino-β-hydroxybutyric acid	NIST Chemistry WebBook
L-Threonin	ChEBI
L-Threonine	KEGG COMPOUND
T	ChEBI
Thr	ChEBI
THREONINE	PDBeChem

Manual Xrefs	Databases
4254	DrugCentral
C00001394	KNApSAcK
C00188	KEGG COMPOUND
c0413	UM-BBD
D00041	KEGG DRUG
DB00156	DrugBank
ECMDB00167	ECMDB
HMDB0000167	HMDB
THR	PDBeChem
Threonine	Wikipedia
YMDB00214	YMDB
View more database links

Registry Numbers	Types	Sources
1721646	Reaxys Registry Number	Reaxys
72-19-5	CAS Registry Number	KEGG COMPOUND
72-19-5	CAS Registry Number	ChemIDplus
72-19-5	CAS Registry Number	NIST Chemistry WebBook
82510	Gmelin Registry Number	Gmelin

Citations	Types	Sources
11964235	PubMed citation	Europe PMC
12523390	PubMed citation	Europe PMC
16659349	PubMed citation	Europe PMC
17379183	PubMed citation	Europe PMC
22289691	PubMed citation	Europe PMC
22342587	PubMed citation	Europe PMC
22513921	PubMed citation	Europe PMC
22770225	PubMed citation	Europe PMC
24671569	PubMed citation	Europe PMC

Last Modified

13 January 2023

CHEBI:16857 - L-threonine

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