MET-enkephalin

Details

• Internal ID: b2735339-b1ce-4182-b3c7-38a415e1219a
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Peptides > Oligopeptides
• IUPAC Name: (2S)-2-[[(2S)-2-[[2-[[2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylsulfanylbutanoic acid
• SMILES (Canonical): CSCCC(C(=O)O)NC(=O)C(CC1=CC=CC=C1)NC(=O)CNC(=O)CNC(=O)C(CC2=CC=C(C=C2)O)N
• SMILES (Isomeric): CSCC[C@@H](C(=O)O)NC(=O)[C@H](CC1=CC=CC=C1)NC(=O)CNC(=O)CNC(=O)[C@H](CC2=CC=C(C=C2)O)N
• InChI: InChI=1S/C27H35N5O7S/c1-40-12-11-21(27(38)39)32-26(37)22(14-17-5-3-2-4-6-17)31-24(35)16-29-23(34)15-30-25(36)20(28)13-18-7-9-19(33)10-8-18/h2-10,20-22,33H,11-16,28H2,1H3,(H,29,34)(H,30,36)(H,31,35)(H,32,37)(H,38,39)/t20-,21-,22-/m0/s1
• InChI Key: YFGBQHOOROIVKG-FKBYEOEOSA-N
• Popularity: 4,487 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₅N₅O₇S
• Molecular Weight: 573.70 g/mol
• Exact Mass: 573.22571965 g/mol
• Topological Polar Surface Area (TPSA): 225.00 Ų
• XlogP: -2.10
• Atomic LogP (AlogP): -0.46
• H-Bond Acceptor: 8
• H-Bond Donor: 7
• Rotatable Bonds: 16

Synonyms

• H-Tyr-Gly-Gly-Phe-Met-OH
• Methionine enkephalin
• 58569-55-4
• Tyr-Gly-Gly-Phe-Met-OH
• METENKEFALIN
• TYR-GLY-GLY-PHE-MET
• [Met]enkephalin
• [5-Methionine]Enkephalin
• (Met5)-enkephalin
• Opioid growth factor
• Metenkefalin [INN]
• 9JEZ9OD3AS
• CHEMBL13786
• ENKEPHALIN, METHIONINE
• (2S)-2-[[(2S)-2-[[2-[[2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylsulfanylbutanoic acid
• [Met5]-ENKEPHALIN
• [Met5]Enkephalin acetate salt hydrate
• Metenkephalin
• (2S)-2-[[(2S)-2-[[2-[[2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenyl-propanoyl]amino]-4-methylsulfanyl-butanoic acid
• opioid growth factor (OGF)
• 82362-17-2
• UNII-9JEZ9OD3AS
• CHEBI:6618
• Porcine beta-endorphin 1-5
• met-enkefalin
• CCRIS 4225
• Met5-Enkephalin
• NP2 Enkephalin
• NSC-374896
• [Met]-enkephalin
• Met-Enk
• 1-5 Adrenorphin
• (2S,5S,14S)-14-Amino-5-benzyl-15-(4-hydroxyphenyl)-2-(2-(methylthio)ethyl)-4,7,10,13-tetraoxo-3,6,9,12-tetraazapentadecan-1-oic acid
• EINECS 261-335-8
• Sh-pentapeptide-19
• NSC 374896
• Inno-105
• L-Methionine, L-tyrosylglycylglycyl-L-phenylalanyl-
• 1-5-Adrenorphin (human)
• Enkephalin-(5-l-methionine)
• METENKEFALIN [WHO-DD]
• SCHEMBL632433
• GTPL1614
• DTXSID80332078
• IRT-101
• YFGBQHOOROIVKG-FKBYEOEOSA-N
• HY-P0073
• SH-PENTAPEPTIDE-19 [INCI]
• BDBM50019056
• MFCD00076415
• AKOS030525639
• CS-5426
• DB12668
• NCGC00163683-01
• 2-[[2-[[2-[[2-[[2-amino-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylsulfanylbutanoic acid
• AS-58159
• C75740
• A915141
• Met-Enkephalin (H-L-Tyr-Gly-Gly-L-Phe-L-Met-OH)
• N-(N-(N-(N-L-Tyrosylglycyl)glycyl)-L-phenylalanyl)-L-methionine
• Adrenorphin (human), 6-de-L-arginine-7-de-L-arginine-8-de-L-valinamide-
• ([Met]-enkephalin)2-[2-(2-{2-[2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-acetylamino}-acetylamino)-3-phenyl-propionylamino]-4-methylsulfanyl-butyric acid([Met]-enkephalin
• (S)-2-[(S)-2-(2-{2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-acetylamino}-acetylamino)-3-phenyl-propionylamino]-4-methylsulfanyl-butyric acid
• 2-[(S)-2-(2-{2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-acetylamino}-acetylamino)-1-oxo-3-phenyl-propylamino]-4-methylsulfanyl-butyric acid
• 2-[1-[1-amino-2-(4-hydroxyphenyl)-(1S)-ethylcarboxamidomethylcarboxamidomethylcarboxamido]-2-phenyl-(1S)-ethylcarboxamido]-4-methylsulfanyl-(2S)-butanoic acid
• 2-[2-(2-{2-[2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-acetylamino}-acetylamino)-3-phenyl-propionylamino]-4-methylsulfanyl-butyric acid
• L-TYROSYLGLYCYLGLYCYL-L-PHENYLALANYL-L-METHIONINE .BETA.-ENDORPHIN HUMAN-(1-5)-PEPTIDE

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8447	84.47%
Caco-2	-	0.9209	92.09%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6760	67.60%
OATP2B1 inhibitior	-	0.8568	85.68%
OATP1B1 inhibitior	+	0.8212	82.12%
OATP1B3 inhibitior	+	0.9437	94.37%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.8253	82.53%
P-glycoprotein inhibitior	+	0.6428	64.28%
P-glycoprotein substrate	-	0.5372	53.72%
CYP3A4 substrate	+	0.5979	59.79%
CYP2C9 substrate	-	0.6189	61.89%
CYP2D6 substrate	-	0.7944	79.44%
CYP3A4 inhibition	-	0.8880	88.80%
CYP2C9 inhibition	-	0.8501	85.01%
CYP2C19 inhibition	-	0.7569	75.69%
CYP2D6 inhibition	-	0.6373	63.73%
CYP1A2 inhibition	-	0.9385	93.85%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	-	0.9771	97.71%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8200	82.00%
Carcinogenicity (trinary)	Non-required	0.6751	67.51%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.9541	95.41%
Skin irritation	-	0.7892	78.92%
Skin corrosion	-	0.9414	94.14%
Ames mutagenesis	-	0.8300	83.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4723	47.23%
Micronuclear	+	0.6500	65.00%
Hepatotoxicity	-	0.6986	69.86%
skin sensitisation	-	0.9070	90.70%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.7398	73.98%
Acute Oral Toxicity (c)	III	0.7609	76.09%
Estrogen receptor binding	+	0.6305	63.05%
Androgen receptor binding	+	0.7289	72.89%
Thyroid receptor binding	+	0.5663	56.63%
Glucocorticoid receptor binding	+	0.5630	56.30%
Aromatase binding	-	0.5212	52.12%
PPAR gamma	+	0.6875	68.75%
Honey bee toxicity	-	0.8405	84.05%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.8737	87.37%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL236	P41143	Delta opioid receptor	1.03 nM	EC50	via Super-PRED
CHEMBL233	P35372	Mu opioid receptor	13 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.83%	98.95%
CHEMBL1255126	O15151	Protein Mdm4	97.82%	90.20%
CHEMBL3060	Q9Y345	Glycine transporter 2	96.79%	99.17%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	96.00%	92.29%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.81%	91.11%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	95.18%	95.50%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	94.57%	97.21%
CHEMBL221	P23219	Cyclooxygenase-1	93.41%	90.17%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	93.12%	93.10%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.91%	96.09%
CHEMBL5701	Q9H2K8	Serine/threonine-protein kinase TAO3	92.86%	96.67%
CHEMBL4040	P28482	MAP kinase ERK2	92.46%	83.82%
CHEMBL5261	Q7L7X3	Serine/threonine-protein kinase TAO1	90.66%	89.33%
CHEMBL1907594	P30926	Neuronal acetylcholine receptor; alpha3/beta4	90.45%	97.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.57%	95.56%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	88.69%	96.95%
CHEMBL3359	P21462	Formyl peptide receptor 1	87.88%	93.56%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	87.72%	100.00%
CHEMBL2514	O95665	Neurotensin receptor 2	87.42%	100.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	85.36%	93.00%
CHEMBL2535	P11166	Glucose transporter	84.57%	98.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.43%	94.45%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	83.02%	94.62%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.78%	95.89%
CHEMBL2095164	P49354	Geranylgeranyl transferase type I	82.47%	92.80%
CHEMBL3401	O75469	Pregnane X receptor	81.59%	94.73%
CHEMBL4101	P17612	cAMP-dependent protein kinase alpha-catalytic subunit	81.00%	82.86%
CHEMBL5939	Q9NZ08	Endoplasmic reticulum aminopeptidase 1	80.99%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	80.04%	91.19%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 443363
• LOTUS: LTS0113875
• wikiData: Q1960495