Leucine enkephalin

Details

• Internal ID: 26ce1f97-81be-4da7-b94d-2a33cb5751d1
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Peptides
• IUPAC Name: (2S)-2-[[(2S)-2-[[2-[[2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoic acid
• SMILES (Canonical): CC(C)CC(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): CC(C)C[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/C28H37N5O7/c1-17(2)12-23(28(39)40)33-27(38)22(14-18-6-4-3-5-7-18)32-25(36)16-30-24(35)15-31-26(37)21(29)13-19-8-10-20(34)11-9-19/h3-11,17,21-23,34H,12-16,29H2,1-2H3,(H,30,35)(H,31,37)(H,32,36)(H,33,38)(H,39,40)/t21-,22-,23-/m0/s1
• InChI Key: URLZCHNOLZSCCA-VABKMULXSA-N
• Popularity: 5,431 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₇N₅O₇
• Molecular Weight: 555.60 g/mol
• Exact Mass: 555.26929854 g/mol
• Topological Polar Surface Area (TPSA): 200.00 Ų
• XlogP: -2.30
• Atomic LogP (AlogP): -0.16
• H-Bond Acceptor: 7
• H-Bond Donor: 7
• Rotatable Bonds: 15

Synonyms

• [Leu5]-Enkephalin
• 58822-25-6
• leucine enkephalin
• Enkephalin
• Tyr-Gly-Gly-Phe-Leu
• Enkephalins
• Enkephalin L
• Leucyl-enkephalin
• [Leu]enkephalin
• Leucine-enkephalin
• ENKEPHALIN, LEUCINE
• H-Tyr-Gly-Gly-Phe-Leu-OH
• [5-Leucine]Enkephalin
• Leu5-Enkephalin
• Tyr-Gly-Gly-Phe-Leu-OH
• Leucine- enkephalin
• [Leu 5]enkephalin
• Dynorphin-(1-5)
• (2S)-2-[[(2S)-2-[[2-[[2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoic acid
• CHEMBL8234
• L-Tyr-Gly-Gly-L-Phe-L-Leu
• CHEBI:89656
• L-Tyrosylglycylglycyl-L-phenylalanyl-L-leucine
• RI01R707R6
• ICI 114740
• N-(N-(N-(N-L-Tyrosylglycyl)glycyl)-L-phenylalanyl)-L-leucine
• 59141-40-1
• Leu-enkephalin;Leucine enkephalin;Leucyl-enkephalin
• L-Leucine, N-(N-(N-(N-L-tyrosylglycyl)glycyl)-L-phenylalanyl)-
• (2S)-2-[(2S)-2-(2-{2-[(2S)-2-AMINO-3-(4-HYDROXYPHENYL)PROPANAMIDO]ACETAMIDO}ACETAMIDO)-3-PHENYLPROPANAMIDO]-4-METHYLPENTANOIC ACID
• UNII-RI01R707R6
• TyrGlyGlyPheLeu
• CCRIS 6338
• NSC350588
• 14-18-6
• NSC-350588
• LeuENK
• EINECS 261-457-1
• Leu-ENK
• [Leu(5)]enkephalin
• NSC 350588
• [Leu(5)]-enkephalin
• PENTAPEPTIDE-5
• L-ENK
• SM-PEPTIDE-1
• SH-PENTAPEPTIDE-5
• Y-G-G-F-L
• SCHEMBL631959
• PENTAPEPTIDE-5 [INCI]
• CHEMBL218452
• DTXSID00905127
• SH-PENTAPEPTIDE-5 [INCI]
• URLZCHNOLZSCCA-VABKMULXSA-N
• 2-[2-(2-{2-[2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-acetylamino}-acetylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid
• HY-P0288
• BDBM50001465
• BDBM50128075
• MFCD00076406
• AKOS024456832
• ICI-114740
• NCGC00167126-01
• MS-30127
• Leu-Enkephalin (H-L-Tyr-Gly-Gly-L-Phe-L-Leu-OH)
• Q6533903
• Tyr-Gly-Pro-Phe-Leu-Arg-Arg-Ile-Arg-Arg-Lys-NH2
• Leu-enkephalin; Leucine enkephalin; Leucyl-enkephalin
• L-LEUCINE, L-TYROSYLGLYCYLGLYCYL-L-PHENYLALANYL-
• ([Leu]-enkephalin)2-[2-(2-{2-[2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-acetylamino}-acetylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid
• (2S)-2-[[(2S)-2-[[2-[[2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]acetyl]amino]
• (2S,5S,14S)-14-amino-5-benzyl-15-(4-hydroxyphenyl)-2-isobutyl-4,7,10,13-tetraoxo-3,6,9,12-tetraazapentadecan-1-oic acid
• (enkephalin)2-[2-(2-{2-[2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-acetylamino}-acetylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid
• (S)-2-[(S)-2-(2-{2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-acetylamino}-acetylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid
• 2-[(S)-2-(2-{2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-acetylamino}-acetylamino)-1-oxo-3-phenyl-propylamino]-4-methyl-pentanoic acid
• 2-[(S)-2-(2-{2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-acetylamino}-acetylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid
• 2-[1-[1-amino-2-(4-hydroxyphenyl)-(1S)-ethylcarboxamidomethylcarboxamidomethylcarboxamido]-2-phenyl-(1S)-ethylcarboxamido]-4-methyl-(2S)-pentanoic acid
• 2-[2-(2-{2-[2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-acetylamino}-acetylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid(Enkephalin)
• 2-{1-[1-amino-2-(4-hydroxyphenyl)ethylcarboxamidomethylcarboxamidomethylcarboxamido]-2-phenylethylcarboxamido}-4-methylpentanoic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9197	91.97%
Caco-2	-	0.9057	90.57%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7147	71.47%
OATP2B1 inhibitior	-	0.8578	85.78%
OATP1B1 inhibitior	+	0.9044	90.44%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.7194	71.94%
P-glycoprotein inhibitior	+	0.6106	61.06%
P-glycoprotein substrate	+	0.5123	51.23%
CYP3A4 substrate	+	0.5622	56.22%
CYP2C9 substrate	-	0.5951	59.51%
CYP2D6 substrate	-	0.7951	79.51%
CYP3A4 inhibition	-	0.8733	87.33%
CYP2C9 inhibition	-	0.8964	89.64%
CYP2C19 inhibition	-	0.7214	72.14%
CYP2D6 inhibition	-	0.8363	83.63%
CYP1A2 inhibition	-	0.9278	92.78%
CYP2C8 inhibition	-	0.5919	59.19%
CYP inhibitory promiscuity	-	0.9434	94.34%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.7700	77.00%
Carcinogenicity (trinary)	Non-required	0.6493	64.93%
Eye corrosion	-	0.9934	99.34%
Eye irritation	-	0.9580	95.80%
Skin irritation	-	0.8226	82.26%
Skin corrosion	-	0.9504	95.04%
Ames mutagenesis	-	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3609	36.09%
Micronuclear	+	0.6700	67.00%
Hepatotoxicity	+	0.5160	51.60%
skin sensitisation	-	0.9105	91.05%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.7595	75.95%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.8642	86.42%
Acute Oral Toxicity (c)	III	0.7162	71.62%
Estrogen receptor binding	+	0.5890	58.90%
Androgen receptor binding	+	0.7804	78.04%
Thyroid receptor binding	+	0.5764	57.64%
Glucocorticoid receptor binding	+	0.5901	59.01%
Aromatase binding	-	0.5635	56.35%
PPAR gamma	+	0.7014	70.14%
Honey bee toxicity	-	0.8933	89.33%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.9425	94.25%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL236	P41143	Delta opioid receptor	0.08 nM	EC50	via Super-PRED
CHEMBL237	P41145	Kappa opioid receptor	80 nM	EC50	via Super-PRED
CHEMBL233	P35372	Mu opioid receptor	1.3 nM	EC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.91%	98.95%
CHEMBL3837	P07711	Cathepsin L	98.57%	96.61%
CHEMBL1255126	O15151	Protein Mdm4	98.04%	90.20%
CHEMBL221	P23219	Cyclooxygenase-1	96.94%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.48%	91.11%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	95.09%	92.29%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.07%	99.17%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	94.73%	97.21%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	94.20%	95.50%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	94.02%	93.10%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.99%	96.09%
CHEMBL5701	Q9H2K8	Serine/threonine-protein kinase TAO3	92.99%	96.67%
CHEMBL5261	Q7L7X3	Serine/threonine-protein kinase TAO1	92.79%	89.33%
CHEMBL1907594	P30926	Neuronal acetylcholine receptor; alpha3/beta4	92.21%	97.23%
CHEMBL3359	P21462	Formyl peptide receptor 1	91.16%	93.56%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	90.84%	96.95%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	90.65%	100.00%
CHEMBL2095164	P49354	Geranylgeranyl transferase type I	89.78%	92.80%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.44%	95.56%
CHEMBL4040	P28482	MAP kinase ERK2	88.70%	83.82%
CHEMBL2514	O95665	Neurotensin receptor 2	88.66%	100.00%
CHEMBL2535	P11166	Glucose transporter	84.97%	98.75%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.49%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.73%	97.14%
CHEMBL3891	P07384	Calpain 1	83.05%	93.04%
CHEMBL3401	O75469	Pregnane X receptor	82.77%	94.73%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.91%	93.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.45%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.84%	94.45%

Plants that contains it

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Cross-Links

• PubChem: 461776
• LOTUS: LTS0273127
• wikiData: Q6533903