Methionine

Details

• Internal ID: 427a3d99-f0d6-41f0-9178-f5c0929be59a
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Alpha amino acids and derivatives > Methionine and derivatives
• IUPAC Name: (2S)-2-amino-4-methylsulfanylbutanoic acid
• SMILES (Canonical): CSCCC(C(=O)O)N
• SMILES (Isomeric): CSCC[C@@H](C(=O)O)N
• InChI: InChI=1S/C5H11NO2S/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1
• InChI Key: FFEARJCKVFRZRR-BYPYZUCNSA-N
• Popularity: 34,787 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅H₁₁NO₂S
• Molecular Weight: 149.21 g/mol
• Exact Mass: 149.05104977 g/mol
• Topological Polar Surface Area (TPSA): 88.60 Ų
• XlogP: -1.90
• Atomic LogP (AlogP): 0.15
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• 63-68-3
• methionine
• h-Met-oh
• (S)-2-Amino-4-(methylthio)butanoic acid
• Cymethion
• Liquimeth
• L-(-)-Methionine
• S-Methionine
• Neo-methidin
• L-Methioninum
• Methilanin
• (L)-Methionine
• Acimethin
• (S)-methionine
• metionina
• Methionine (VAN)
• Methioninum
• (2S)-2-amino-4-(methylsulfanyl)butanoic acid
• Metionina [DCIT]
• L-Methionin
• L-alpha-Amino-gamma-methylmercaptobutyric acid
• h-Met-h
• Methioninum [INN-Latin]
• L-Homocysteine, S-methyl-
• met
• CCRIS 5528
• CCRIS 5536
• HSDB 4317
• L(-)-Amino-gamma-methylthiobutyric acid
• L-Met
• 2-Amino-4-methylthiobutanoic acid (S)-
• L-alpha-Amino-gamma-methylthiobutyric acid
• L-gamma-Methylthio-alpha-aminobutyric acid
• 2-Amino-4-(methylthio)butyric acid, (S)-
• METHIONINE, L-
• Butanoic acid, 2-amino-4-(methylthio)-, (S)-
• Methionine [USAN:INN]
• UNII-AE28F7PNPL
• (S)-2-amino-4-(methylthio)butyric acid
• AE28F7PNPL
• Toxin WAR (Bacillus thuringiensis strain PS205C)
• EINECS 200-562-9
• (2S)-2-amino-4-methylsulfanyl-butanoic acid
• C-11 Methionine
• NSC 22946
• gamma-Methylthio-alpha-aminobutyric acid
• CHEBI:16643
• L-a-Amino-g-methylthiobutyric acid
• carbon-11 methionine
• S-Methyl-L-homocysteine
• (S)-(+)-Methionine
• MFCD00063097
• NSC-22946
• (2S)-2-Amino-4-methylsulfanylbutanoic acid
• C-11 Met
• CHEMBL42336
• DTXSID5040548
• L-2-Amino-4methylthiobutyric acid
• Methionine [USAN:USP:INN:BAN]
• meritonin
• (35S)Methionine
• L-Methionine-34S
• METHIONINE (II)
• METHIONINE [II]
• METHIONINE (MART.)
• METHIONINE [MART.]
• Hmet
• 1006386-95-3
• METHIONINE (EP MONOGRAPH)
• METHIONINE [EP MONOGRAPH]
• METHIONINE (USP MONOGRAPH)
• METHIONINE [USP MONOGRAPH]
• LEUCINE IMPURITY B (EP IMPURITY)
• LEUCINE IMPURITY B [EP IMPURITY]
• 58576-49-1
• 2-amino-4-(methylthio)-butyric acid
• l-2-Amino-4-(methylthio)butyric acid
• (2S)-2-amino-4-(methylsulfanyl)butanoate
• L-2-Amino-4-(methylthio)butanoic acid
• L-metionina
• (C5-H11-N-O2-S)x-
• L-Lobamine
• 3h-l-methionine
• g-Methylthio-a-aminobutyric acid
• racemic methionine
• 1wkm
• NSC 118113
• D-2-Amino-4-(methylthio)butanoic acid
• Toxin WAR
• Butyric acid, 2-amino-4-(methylthio)-
• 2-Amino-4-(methylthio)butyrate
• Methionine (USP)
• L(-)-Methionin
• a-Amino-g-methylmercaptobutyric acid
• methioninum racemicum
• L-Methionine,(S)
• (R)-2-Amino-4-(methylmercapto)butyric acid
• 1pg2
• 1qq9
• L-Methionine Z (TN)
• METHIONINE [MI]
• L-Methionine (JP17)
• METHIONINE [INN]
• 128488-79-9
• METHIONINE [HSDB]
• METHIONINE [INCI]
• METHIONINE [USAN]
• (S)-2-Amino-4-(methylmercapto)butyric acid
• Methionine (L-Methionine)
• METHIONINE [VANDF]
• Methionine, L- (8CI)
• bmse000044
• bmse000915
• D0PO8E
• L-METHIONINE [FCC]
• L-METHIONINE [JAN]
• SCHEMBL4226
• G-methylthio-a-aminobutyrate
• L-Methionine (H-Met-OH)
• METHIONINE [WHO-DD]
• 2-Amino-4-methylthiobutanoate
• L-a-amino-g-methylthiobutyrate
• L-METHIONINE [USP-RS]
• GTPL4814
• A-amino-g-methylmercaptobutyrate
• IS_METHIONINE-METHYL-D3
• DTXCID3020548
• SCHEMBL15702352
• V03AB26
• Pharmakon1600-01301006
• alpha-amino-alpha-aminobutyric acid
• gamma-methylthio-alpha-aminobutyrate
• HY-N0326
• L-2-Amino-4-methylthiobutyric acid
• BDBM50142500
• MFCD00801344
• NSC760117
• s5633
• L-alpha-amino-gamma-methylthiobutyrate
• L-Methionine, Vetec(TM), 98.5%
• (S)-2-Amino-4-(methylthio)butanoate
• AKOS000281626
• AKOS015852512
• L-Methionine, labeled with carbon-11
• alpha-amino-gamma-methylmercaptobutyrate
• CCG-266196
• CS-W020566
• DB00134
• LS-2338
• NSC-760117
• (S)-2-amino-4-(methylthio)-Butanoate
• NCGC00160620-01
• NCGC00160620-02
• AS-10898
• BP-31235
• (S)-2-amino-4-(methylthio)-Butanoic acid
• L-Methionine, BioUltra, >=99.5% (NT)
• A5456
• AM20100552
• M0099
• EN300-52631
• L-Methionine, SAJ special grade, >=98.5%
• C00073
• D00019
• D70895
• L(-)-amino-alpha-amino-alpha-aminobutyric acid
• L-Methionine, reagent grade, >=98% (HPLC)
• M-3100
• M02939
• M02945
• L-Methionine, Vetec(TM) reagent grade, >=98%
• A934626
• L-Methionine, Cell Culture Reagent (H-L-Met-OH)
• C6CB5837-2B49-4B25-AAB0-D305DAFE26EB
• Q22124685
• F1905-8241
• Z756440050
• L-Methionine, certified reference material, TraceCERT(R)
• Methionine, European Pharmacopoeia (EP) Reference Standard
• N-(2CT Resin)-L-Met-OH (200-400 mesh, > 0.3 mmol/g)
• L-Methionine, United States Pharmacopeia (USP) Reference Standard
• L-Methionine, Pharmaceutical Secondary Standard; Certified Reference Material
• Soft tissue sarcoma-associated protein (human clone WO2004048938-SEQID-1139)
• L-Methionine, from non-animal source, meets EP, JP, USP testing specifications, suitable for cell culture, 99.0-101.0%

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9749	97.49%
Caco-2	-	0.8850	88.50%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Lysosomes	0.7116	71.16%
OATP2B1 inhibitior	-	0.8438	84.38%
OATP1B1 inhibitior	+	0.9593	95.93%
OATP1B3 inhibitior	+	0.9409	94.09%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.9485	94.85%
P-glycoprotein inhibitior	-	0.9890	98.90%
P-glycoprotein substrate	-	0.9567	95.67%
CYP3A4 substrate	-	0.7306	73.06%
CYP2C9 substrate	+	0.5929	59.29%
CYP2D6 substrate	-	0.7911	79.11%
CYP3A4 inhibition	-	0.9758	97.58%
CYP2C9 inhibition	-	0.9489	94.89%
CYP2C19 inhibition	-	0.9510	95.10%
CYP2D6 inhibition	-	0.9567	95.67%
CYP1A2 inhibition	-	0.8295	82.95%
CYP2C8 inhibition	-	0.9890	98.90%
CYP inhibitory promiscuity	-	0.9938	99.38%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7300	73.00%
Carcinogenicity (trinary)	Non-required	0.7474	74.74%
Eye corrosion	-	0.9319	93.19%
Eye irritation	-	0.9541	95.41%
Skin irritation	-	0.6371	63.71%
Skin corrosion	+	0.6647	66.47%
Ames mutagenesis	-	0.8878	88.78%
Human Ether-a-go-go-Related Gene inhibition	-	0.7596	75.96%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	-	0.9500	95.00%
skin sensitisation	-	0.8520	85.20%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	-	0.5618	56.18%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.6888	68.88%
Acute Oral Toxicity (c)	IV	0.6189	61.89%
Estrogen receptor binding	-	0.8987	89.87%
Androgen receptor binding	-	0.8838	88.38%
Thyroid receptor binding	-	0.8213	82.13%
Glucocorticoid receptor binding	-	0.8962	89.62%
Aromatase binding	-	0.9395	93.95%
PPAR gamma	-	0.8735	87.35%
Honey bee toxicity	-	0.9697	96.97%
Biodegradation	+	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	-	0.8281	82.81%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.20%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	95.72%	83.82%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	91.37%	92.29%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.07%	99.17%
CHEMBL2581	P07339	Cathepsin D	87.04%	98.95%
CHEMBL236	P41143	Delta opioid receptor	85.28%	99.35%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.57%	93.56%
CHEMBL221	P23219	Cyclooxygenase-1	83.38%	90.17%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.51%	96.95%
CHEMBL1795117	Q8TEK3	Histone-lysine N-methyltransferase, H3 lysine-79 specific	81.21%	93.56%

Plants that contains it

• Allium cepa
• Allium rotundum
• Allium sativum
• Arabidopsis thaliana
• Astragalus hamosus
• Brassica napus
• Brassica oleracea
• Cannabis sativa
• Castanea sativa
• Cnestis palala
• Glycine max
• Indigofera hirsuta
• Juniperus scopulorum
• Nicotiana tabacum
• Opuntia ficus-indica
• Panax ginseng
• Pentaclethra macrophylla
• Pinus densiflora
• Pinus ponderosa
• Prunus domestica
• Psophocarpus tetragonolobus
• Ripariosida hermaphrodita
• Rosa nisami
• Senna obtusifolia
• Stellaria media
• Tradescantia spathacea

Cross-Links

• PubChem: 6137
• NPASS: NPC152451
• LOTUS: LTS0196746
• wikiData: Q22124685