tyrosyl-1,2,3,4-tetrahydro-3-isoquinolinecarbonyl-phenylalanyl-phenylalanine profile

tyrosyl-1,2,3,4-tetrahydro-3-isoquinolinecarbonyl-phenylalanyl-phenylalanine: a delta opioid antagonist [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	644210
CHEMBL ID	191751
MeSH ID	M0219250

Synonym
tyr-tic-phe-phe-oh
l-phenylalanine, l-tyrosyl-(3s)-1,2,3,4-tetrahydro-3-isoquinolinecarbonyl-l-phenylalanyl- (9ci)
tipp (opioid antagonist)
h-tyr-tic-phe-phe-oh
l-tyrosyl-l-1,2,3,4-tetrahydro-3-isoquinolinecarbonyl-l- phenylalanyl-l-phenylalanine
l-phenylalanine, l-tyrosyl-l-1,2,3,4-tetrahydro-3-isoquinolinecarbonyl-l-phenylalanyl-
l-alanine, n-[[(3s)-2-[(2s)-2-amino-3-(4-hydroxyphenyl)-1-oxopropyl]-1,2,3,4-tetrahydro-3-isoquinolinyl]carbonyl]-3-phenyl-l-alanyl-3-phenyl-
146369-65-5
tyrosyl-1,2,3,4-tetrahydro-3-isoquinolinecarbonyl- phenylalanyl-phenylalanine
tipp
tyrosyl-1,2,3,4-tetrahydro-3-isoquinolinecarbonyl-phenylalanyl-phenylalanine
l-tyrosyl-l-1,2,3,4-tetrahydro-3-isoquinolinecarbonyl-l-phenylalanyl-l-phenylalanine
(2s)-2-[[(2s)-2-[[(3s)-2-[(2s)-2-amino-3-(4-hydroxyphenyl)propanoyl]-3,4-dihydro-1h-isoquinoline-3-carbonyl]amino]-3-phenylpropanoyl]amino]-3-phenylpropanoic acid
CHEMBL191751 ,
bdbm50068664
2-[2-({(s)-2-[2-amino-3-(4-hydroxy-phenyl)-propionyl]-4-methyl-1,2,3,4-tetrahydro-isoquinoline-3-carbonyl}-amino)-3-phenyl-propionylamino]-3-phenyl-propionic acid
qh25ys93hx ,
unii-qh25ys93hx
DTXSID60163362
tyr-tic-phe-pheoh
tyr-tic-phe-phe
l-tyrosyl-(3s)-1,2,3,4-tetrahydro-3-isoquinolinecarbonyl-l-phenylalanyl-l-phenylalanine
l-phenylalanine, l-tyrosyl-(3s)-1,2,3,4-tetrahydro-3-isoquinolinecarbonyl-l-phenylalanyl-
AKOS040744605

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Delta-type opioid receptor	Mus musculus (house mouse)	IC50 (µMol)	0.0100	0.0001	0.7298	10.0000	AID148643; AID148790
Delta-type opioid receptor	Mus musculus (house mouse)	Ki	0.0012	0.0000	0.5393	9.4000	AID149082
Mu-type opioid receptor	Rattus norvegicus (Norway rat)	IC50 (µMol)	17.6200	0.0001	0.8874	10.0000	AID151446; AID151459
Mu-type opioid receptor	Homo sapiens (human)	Ki	4.5000	0.0000	0.4197	10.0000	AID151594
Delta-type opioid receptor	Homo sapiens (human)	Ki	0.0036	0.0000	0.5978	9.9300	AID149650; AID149663
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Delta-type opioid receptor	Rattus norvegicus (Norway rat)	Ke	0.0035	0.0006	0.0711	0.7540	AID149638; AID149639; AID149640
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messenger	Mu-type opioid receptor	Homo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled acetylcholine receptor signaling pathway	Mu-type opioid receptor	Homo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathway	Mu-type opioid receptor	Homo sapiens (human)
sensory perception	Mu-type opioid receptor	Homo sapiens (human)
negative regulation of cell population proliferation	Mu-type opioid receptor	Homo sapiens (human)
sensory perception of pain	Mu-type opioid receptor	Homo sapiens (human)
G protein-coupled opioid receptor signaling pathway	Mu-type opioid receptor	Homo sapiens (human)
behavioral response to ethanol	Mu-type opioid receptor	Homo sapiens (human)
positive regulation of neurogenesis	Mu-type opioid receptor	Homo sapiens (human)
negative regulation of Wnt protein secretion	Mu-type opioid receptor	Homo sapiens (human)
positive regulation of ERK1 and ERK2 cascade	Mu-type opioid receptor	Homo sapiens (human)
calcium ion transmembrane transport	Mu-type opioid receptor	Homo sapiens (human)
cellular response to morphine	Mu-type opioid receptor	Homo sapiens (human)
regulation of cellular response to stress	Mu-type opioid receptor	Homo sapiens (human)
regulation of NMDA receptor activity	Mu-type opioid receptor	Homo sapiens (human)
neuropeptide signaling pathway	Mu-type opioid receptor	Homo sapiens (human)
immune response	Delta-type opioid receptor	Homo sapiens (human)
G protein-coupled receptor signaling pathway	Delta-type opioid receptor	Homo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messenger	Delta-type opioid receptor	Homo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled receptor signaling pathway	Delta-type opioid receptor	Homo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathway	Delta-type opioid receptor	Homo sapiens (human)
adult locomotory behavior	Delta-type opioid receptor	Homo sapiens (human)
negative regulation of gene expression	Delta-type opioid receptor	Homo sapiens (human)
negative regulation of protein-containing complex assembly	Delta-type opioid receptor	Homo sapiens (human)
positive regulation of CREB transcription factor activity	Delta-type opioid receptor	Homo sapiens (human)
positive regulation of peptidyl-serine phosphorylation	Delta-type opioid receptor	Homo sapiens (human)
response to nicotine	Delta-type opioid receptor	Homo sapiens (human)
G protein-coupled opioid receptor signaling pathway	Delta-type opioid receptor	Homo sapiens (human)
eating behavior	Delta-type opioid receptor	Homo sapiens (human)
regulation of mitochondrial membrane potential	Delta-type opioid receptor	Homo sapiens (human)
regulation of calcium ion transport	Delta-type opioid receptor	Homo sapiens (human)
cellular response to growth factor stimulus	Delta-type opioid receptor	Homo sapiens (human)
cellular response to hypoxia	Delta-type opioid receptor	Homo sapiens (human)
cellular response to toxic substance	Delta-type opioid receptor	Homo sapiens (human)
neuropeptide signaling pathway	Delta-type opioid receptor	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
G-protein alpha-subunit binding	Mu-type opioid receptor	Homo sapiens (human)
G protein-coupled receptor activity	Mu-type opioid receptor	Homo sapiens (human)
beta-endorphin receptor activity	Mu-type opioid receptor	Homo sapiens (human)
voltage-gated calcium channel activity	Mu-type opioid receptor	Homo sapiens (human)
protein binding	Mu-type opioid receptor	Homo sapiens (human)
morphine receptor activity	Mu-type opioid receptor	Homo sapiens (human)
G-protein beta-subunit binding	Mu-type opioid receptor	Homo sapiens (human)
neuropeptide binding	Mu-type opioid receptor	Homo sapiens (human)
G protein-coupled opioid receptor activity	Delta-type opioid receptor	Homo sapiens (human)
protein binding	Delta-type opioid receptor	Homo sapiens (human)
receptor serine/threonine kinase binding	Delta-type opioid receptor	Homo sapiens (human)
G protein-coupled enkephalin receptor activity	Delta-type opioid receptor	Homo sapiens (human)
neuropeptide binding	Delta-type opioid receptor	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
endosome	Mu-type opioid receptor	Homo sapiens (human)
endoplasmic reticulum	Mu-type opioid receptor	Homo sapiens (human)
Golgi apparatus	Mu-type opioid receptor	Homo sapiens (human)
plasma membrane	Mu-type opioid receptor	Homo sapiens (human)
axon	Mu-type opioid receptor	Homo sapiens (human)
dendrite	Mu-type opioid receptor	Homo sapiens (human)
perikaryon	Mu-type opioid receptor	Homo sapiens (human)
synapse	Mu-type opioid receptor	Homo sapiens (human)
plasma membrane	Mu-type opioid receptor	Homo sapiens (human)
neuron projection	Mu-type opioid receptor	Homo sapiens (human)
plasma membrane	Delta-type opioid receptor	Homo sapiens (human)
synaptic vesicle membrane	Delta-type opioid receptor	Homo sapiens (human)
dendrite membrane	Delta-type opioid receptor	Homo sapiens (human)
presynaptic membrane	Delta-type opioid receptor	Homo sapiens (human)
axon terminus	Delta-type opioid receptor	Homo sapiens (human)
spine apparatus	Delta-type opioid receptor	Homo sapiens (human)
postsynaptic density membrane	Delta-type opioid receptor	Homo sapiens (human)
neuronal dense core vesicle	Delta-type opioid receptor	Homo sapiens (human)
plasma membrane	Delta-type opioid receptor	Homo sapiens (human)
neuron projection	Delta-type opioid receptor	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (52)

Assay ID	Title	Year	Journal	Article
AID151604	Binding affinity towards Opioid receptor mu 1 on rat forebrain membranes by [3H]sufentanil displacement.	1998	Journal of medicinal chemistry, Dec-17, Volume: 41, Issue:26	Side chain methyl substitution in the delta-opioid receptor antagonist TIPP has an important effect on the activity profile.
AID149225	Inhibition of cyclic adenosine 3',5'-monophosphate (cAMP) formation by recombinant Opioid receptor delta 1 in adenylyl cyclase assay	2002	Journal of medicinal chemistry, Aug-29, Volume: 45, Issue:18	Solid phase synthesis and evaluation of Tyr-Tic-Phe-Phe(p-NHCOCH(2)Br) ([Phe(p-bromoacetamide)(4)]TIPP), a potent affinity label for delta opioid receptors.
AID151446	Inhibitory activity against Opioid receptor mu 1 using [3H]DAMGO	2002	Journal of medicinal chemistry, Aug-29, Volume: 45, Issue:18	Solid phase synthesis and evaluation of Tyr-Tic-Phe-Phe(p-NHCOCH(2)Br) ([Phe(p-bromoacetamide)(4)]TIPP), a potent affinity label for delta opioid receptors.
AID767390	Antagonist activity at mu/kappa opioid receptor in guinea pig ileum assessed as inhibition of electrically-stimulated muscle contraction	2013	Bioorganic & medicinal chemistry letters, Sep-15, Volume: 23, Issue:18	N-terminal guanidinylation of TIPP (Tyr-Tic-Phe-Phe) peptides results in major changes of the opioid activity profile.
AID714434	Displacement of [3H]DSLET from delta opioid receptor in rat brain membrane after 2 hrs	2012	Bioorganic & medicinal chemistry letters, Mar-01, Volume: 22, Issue:5	Novel TIPP (H-Tyr-Tic-Phe-Phe-OH) analogues displaying a wide range of efficacies at the δ opioid receptor. Discovery of two highly potent and selective δ opioid agonists.
AID767394	Selectivity ratio of Ki for mu opioid receptor in rat brain membranes to Ki for delta opioid receptor in rat brain membranes	2013	Bioorganic & medicinal chemistry letters, Sep-15, Volume: 23, Issue:18	N-terminal guanidinylation of TIPP (Tyr-Tic-Phe-Phe) peptides results in major changes of the opioid activity profile.
AID79025	In vitro agonist activity in electrically stimulated guinea pig ileum.	1998	Journal of medicinal chemistry, Dec-17, Volume: 41, Issue:26	Side chain methyl substitution in the delta-opioid receptor antagonist TIPP has an important effect on the activity profile.
AID440690	Agonist activity at mu opioid receptor in guinea pig ileum assessed as effect on muscle contraction	2009	Journal of medicinal chemistry, Nov-12, Volume: 52, Issue:21	Agonist vs antagonist behavior of delta opioid peptides containing novel phenylalanine analogues in place of Tyr(1).
AID275691	Displacement of [3H]DAMGO from mu opioid receptor in Wistar rat brain membrane	2007	Journal of medicinal chemistry, Jan-25, Volume: 50, Issue:2	Beta-methyl substitution of cyclohexylalanine in Dmt-Tic-Cha-Phe peptides results in highly potent delta opioid antagonists.
AID149939	Tested for binding affinity against delta opioid receptor by displacing [3H]- DSLET radioligand from rat brain membrane preparations	1993	Journal of medicinal chemistry, Oct-15, Volume: 36, Issue:21	TIPP[psi]: a highly potent and stable pseudopeptide delta opioid receptor antagonist with extraordinary delta selectivity.
AID275695	Antagonism at delta opioid receptor determined against DPDPE in electrically induced mouse vas deferens	2007	Journal of medicinal chemistry, Jan-25, Volume: 50, Issue:2	Beta-methyl substitution of cyclohexylalanine in Dmt-Tic-Cha-Phe peptides results in highly potent delta opioid antagonists.
AID224591	Tested for binding affinity against mu opioid receptor fby displacing [3H]- DAMGO radioligand from rat brain membrane preparations	1993	Journal of medicinal chemistry, Oct-15, Volume: 36, Issue:21	TIPP[psi]: a highly potent and stable pseudopeptide delta opioid receptor antagonist with extraordinary delta selectivity.
AID149950	Relative potency to that of [Leu5]- enkephalin	1993	Journal of medicinal chemistry, Oct-15, Volume: 36, Issue:21	TIPP[psi]: a highly potent and stable pseudopeptide delta opioid receptor antagonist with extraordinary delta selectivity.
AID767393	Antagonist activity at delta opioid receptor in mouse vas deferens assessed as inhibition of electrically-stimulated muscle contraction	2013	Bioorganic & medicinal chemistry letters, Sep-15, Volume: 23, Issue:18	N-terminal guanidinylation of TIPP (Tyr-Tic-Phe-Phe) peptides results in major changes of the opioid activity profile.
AID714433	Displacement of [3H]DAMGO from mu opioid receptor in rat brain membrane after 2 hrs	2012	Bioorganic & medicinal chemistry letters, Mar-01, Volume: 22, Issue:5	Novel TIPP (H-Tyr-Tic-Phe-Phe-OH) analogues displaying a wide range of efficacies at the δ opioid receptor. Discovery of two highly potent and selective δ opioid agonists.
AID275692	Displacement of [3H]Ile5,6-deltorphin from delta opioid receptor in Wistar rat brain membrane	2007	Journal of medicinal chemistry, Jan-25, Volume: 50, Issue:2	Beta-methyl substitution of cyclohexylalanine in Dmt-Tic-Cha-Phe peptides results in highly potent delta opioid antagonists.
AID440689	Antagonist activity at delta opioid receptor in mouse vas deferens assessed as inhibition of DPDPE-stimulated muscle contraction	2009	Journal of medicinal chemistry, Nov-12, Volume: 52, Issue:21	Agonist vs antagonist behavior of delta opioid peptides containing novel phenylalanine analogues in place of Tyr(1).
AID244571	Atagonist activity of compound against DPDPE-induced electrically evoked contractions of mouse vas deferens	2005	Journal of medicinal chemistry, May-19, Volume: 48, Issue:10	A new structural motif for mu-opioid antagonists.
AID767396	Displacement of [3H]DSLET from delta opioid receptor in rat brain membranes	2013	Bioorganic & medicinal chemistry letters, Sep-15, Volume: 23, Issue:18	N-terminal guanidinylation of TIPP (Tyr-Tic-Phe-Phe) peptides results in major changes of the opioid activity profile.
AID149132	Binding affinity towards Opioid receptor kappa 1 on guinea pig cerebellum membranes by [3H]U-69593 displacement.	1998	Journal of medicinal chemistry, Dec-17, Volume: 41, Issue:26	Side chain methyl substitution in the delta-opioid receptor antagonist TIPP has an important effect on the activity profile.
AID440687	Selectivity ratio of Ki for rat delta opioid receptor to guinea pig kappa opioid receptor	2009	Journal of medicinal chemistry, Nov-12, Volume: 52, Issue:21	Agonist vs antagonist behavior of delta opioid peptides containing novel phenylalanine analogues in place of Tyr(1).
AID149638	Tested for antagonistic activity against delta opioid receptor from mouse vas deferens, using DPDPE as agonist	1993	Journal of medicinal chemistry, Oct-15, Volume: 36, Issue:21	TIPP[psi]: a highly potent and stable pseudopeptide delta opioid receptor antagonist with extraordinary delta selectivity.
AID714438	Antagonist activity at delta opioid receptor in mouse vas deferens assessed as inhibition of DPDPE-induced effect	2012	Bioorganic & medicinal chemistry letters, Mar-01, Volume: 22, Issue:5	Novel TIPP (H-Tyr-Tic-Phe-Phe-OH) analogues displaying a wide range of efficacies at the δ opioid receptor. Discovery of two highly potent and selective δ opioid agonists.
AID275694	Agonist activity at mu opioid receptor in electrically stimulated guinea pig ileum	2007	Journal of medicinal chemistry, Jan-25, Volume: 50, Issue:2	Beta-methyl substitution of cyclohexylalanine in Dmt-Tic-Cha-Phe peptides results in highly potent delta opioid antagonists.
AID224710	Relative potency to that of [Leu5]- enkephalin	1993	Journal of medicinal chemistry, Oct-15, Volume: 36, Issue:21	TIPP[psi]: a highly potent and stable pseudopeptide delta opioid receptor antagonist with extraordinary delta selectivity.
AID151594	Affinity towards human Opioid receptor mu 1 on CHO cell membranes using [3H]DAMGO displacement.	2000	Journal of medicinal chemistry, Dec-28, Volume: 43, Issue:26	Extended TIP(P) analogues as precursors for labeled delta-opioid receptor ligands.
AID767397	Displacement of [3H]DAMGO from mu opioid receptor in rat brain membranes	2013	Bioorganic & medicinal chemistry letters, Sep-15, Volume: 23, Issue:18	N-terminal guanidinylation of TIPP (Tyr-Tic-Phe-Phe) peptides results in major changes of the opioid activity profile.
AID151459	Binding assay evaluated using DAMGO radioligand in CHO cells transfected with rat Opioid receptor mu 1	2000	Journal of medicinal chemistry, Dec-28, Volume: 43, Issue:26	Synthesis and evaluation of isothiocyanate-containing derivatives of the delta-opioid receptor antagonist Tyr-Tic-Phe-Phe (TIPP) as potential affinity labels for delta-opioid receptors.
AID440686	Selectivity ratio of Ki for rat delta opioid receptor to rat mu opioid receptor	2009	Journal of medicinal chemistry, Nov-12, Volume: 52, Issue:21	Agonist vs antagonist behavior of delta opioid peptides containing novel phenylalanine analogues in place of Tyr(1).
AID440685	Displacement of [3H]U69-593 from kappa opioid receptor in guinea pig brain membrane	2009	Journal of medicinal chemistry, Nov-12, Volume: 52, Issue:21	Agonist vs antagonist behavior of delta opioid peptides containing novel phenylalanine analogues in place of Tyr(1).
AID714436	Selectivity ratio of Ki for rat mu opioid receptor to Ki for rat delta opioid receptor	2012	Bioorganic & medicinal chemistry letters, Mar-01, Volume: 22, Issue:5	Novel TIPP (H-Tyr-Tic-Phe-Phe-OH) analogues displaying a wide range of efficacies at the δ opioid receptor. Discovery of two highly potent and selective δ opioid agonists.
AID767395	Displacement of [3H]U69,593 from kappa opioid receptor in guinea pig brain membranes	2013	Bioorganic & medicinal chemistry letters, Sep-15, Volume: 23, Issue:18	N-terminal guanidinylation of TIPP (Tyr-Tic-Phe-Phe) peptides results in major changes of the opioid activity profile.
AID149639	Tested for antagonistic activity against delta opioid receptor from mouse vas deferens, using [D-Ala2] Deltorphin 1 as agonist	1993	Journal of medicinal chemistry, Oct-15, Volume: 36, Issue:21	TIPP[psi]: a highly potent and stable pseudopeptide delta opioid receptor antagonist with extraordinary delta selectivity.
AID233133	Selectivity for binding to mu and delta opioid receptors	2002	Journal of medicinal chemistry, Aug-29, Volume: 45, Issue:18	Solid phase synthesis and evaluation of Tyr-Tic-Phe-Phe(p-NHCOCH(2)Br) ([Phe(p-bromoacetamide)(4)]TIPP), a potent affinity label for delta opioid receptors.
AID149650	Affinity towards human Opioid receptor delta 1 on CHO cell membranes using [3H]DPDPE displacement.	2000	Journal of medicinal chemistry, Dec-28, Volume: 43, Issue:26	Extended TIP(P) analogues as precursors for labeled delta-opioid receptor ligands.
AID149663	Binding affinity towards human Opioid receptor delta 1 on NxG108CC15 (human neuroglioblastoma) cell membranes by [3H]DPDPE displacement.	1998	Journal of medicinal chemistry, Dec-17, Volume: 41, Issue:26	Side chain methyl substitution in the delta-opioid receptor antagonist TIPP has an important effect on the activity profile.
AID714446	Antagonist activity at human delta opioid receptor expressed in HEK293 cells by [35S]GTP binding assay	2012	Bioorganic & medicinal chemistry letters, Mar-01, Volume: 22, Issue:5	Novel TIPP (H-Tyr-Tic-Phe-Phe-OH) analogues displaying a wide range of efficacies at the δ opioid receptor. Discovery of two highly potent and selective δ opioid agonists.
AID431615	Antagonist activity against delta opioid receptor in mouse vas deferens assessed as effect on deltorphin 2-induced contraction	2009	Journal of medicinal chemistry, Sep-10, Volume: 52, Issue:17	Influence of the side chain next to C-terminal benzimidazole in opioid pseudopeptides containing the Dmt-Tic pharmacophore.
AID714441	Agonist activity at delta opioid receptor in guinea pig ileum	2012	Bioorganic & medicinal chemistry letters, Mar-01, Volume: 22, Issue:5	Novel TIPP (H-Tyr-Tic-Phe-Phe-OH) analogues displaying a wide range of efficacies at the δ opioid receptor. Discovery of two highly potent and selective δ opioid agonists.
AID138520	Inhibition of electrically evoked contractions of MVD. In MVD assay, the opioid effect was primarily mediated by delta-receptor	1998	Journal of medicinal chemistry, Dec-17, Volume: 41, Issue:26	Side chain methyl substitution in the delta-opioid receptor antagonist TIPP has an important effect on the activity profile.
AID275693	Selectivity for wistar rat delta opioid receptor over mu opioid receptor	2007	Journal of medicinal chemistry, Jan-25, Volume: 50, Issue:2	Beta-methyl substitution of cyclohexylalanine in Dmt-Tic-Cha-Phe peptides results in highly potent delta opioid antagonists.
AID148643	Inhibitory activity against Opioid receptor delta 1 using [3H]DPDPE	2002	Journal of medicinal chemistry, Aug-29, Volume: 45, Issue:18	Solid phase synthesis and evaluation of Tyr-Tic-Phe-Phe(p-NHCOCH(2)Br) ([Phe(p-bromoacetamide)(4)]TIPP), a potent affinity label for delta opioid receptors.
AID767392	Selectivity ratio of Ki for kappa opioid receptor in guinea pig brain membranes to Ki for delta opioid receptor in rat brain membranes	2013	Bioorganic & medicinal chemistry letters, Sep-15, Volume: 23, Issue:18	N-terminal guanidinylation of TIPP (Tyr-Tic-Phe-Phe) peptides results in major changes of the opioid activity profile.
AID148790	Binding assay evaluated using DPPE radioligand in CHO cells transfected with mouse Opioid receptor delta 1	2000	Journal of medicinal chemistry, Dec-28, Volume: 43, Issue:26	Synthesis and evaluation of isothiocyanate-containing derivatives of the delta-opioid receptor antagonist Tyr-Tic-Phe-Phe (TIPP) as potential affinity labels for delta-opioid receptors.
AID149640	Tested for antagonistic activity against delta opioid receptor from mouse vas deferens, using [Leu5]- enkephalin as agonist	1993	Journal of medicinal chemistry, Oct-15, Volume: 36, Issue:21	TIPP[psi]: a highly potent and stable pseudopeptide delta opioid receptor antagonist with extraordinary delta selectivity.
AID714435	Displacement of [3H]U69,593 from kappa opioid receptor in guinea pig brain membrane after 2 hrs	2012	Bioorganic & medicinal chemistry letters, Mar-01, Volume: 22, Issue:5	Novel TIPP (H-Tyr-Tic-Phe-Phe-OH) analogues displaying a wide range of efficacies at the δ opioid receptor. Discovery of two highly potent and selective δ opioid agonists.
AID187140	Antagonistic potency against delta-agonist in the mouse vas deferens (MVD) assay	2000	Journal of medicinal chemistry, Dec-28, Volume: 43, Issue:26	Extended TIP(P) analogues as precursors for labeled delta-opioid receptor ligands.
AID440683	Displacement of [3H]DSLET from delta opioid receptor in rat brain membrane	2009	Journal of medicinal chemistry, Nov-12, Volume: 52, Issue:21	Agonist vs antagonist behavior of delta opioid peptides containing novel phenylalanine analogues in place of Tyr(1).
AID138521	Inhibition of electrically evoked contractions of MVD. In MVD assay, the opioid effects are primarily mediated by delta-receptors; partial agonist (max 45%)	1998	Journal of medicinal chemistry, Dec-17, Volume: 41, Issue:26	Side chain methyl substitution in the delta-opioid receptor antagonist TIPP has an important effect on the activity profile.
AID714445	Agonist activity at human delta opioid receptor expressed in HEK293 cells by [35S]GTP binding assay relative to DPDPE	2012	Bioorganic & medicinal chemistry letters, Mar-01, Volume: 22, Issue:5	Novel TIPP (H-Tyr-Tic-Phe-Phe-OH) analogues displaying a wide range of efficacies at the δ opioid receptor. Discovery of two highly potent and selective δ opioid agonists.
AID149082	Binding affinity towards Opioid receptor delta 1	2002	Journal of medicinal chemistry, Aug-29, Volume: 45, Issue:18	Solid phase synthesis and evaluation of Tyr-Tic-Phe-Phe(p-NHCOCH(2)Br) ([Phe(p-bromoacetamide)(4)]TIPP), a potent affinity label for delta opioid receptors.
AID440684	Displacement of [3H]DAMGO from mu opioid receptor in rat brain membrane	2009	Journal of medicinal chemistry, Nov-12, Volume: 52, Issue:21	Agonist vs antagonist behavior of delta opioid peptides containing novel phenylalanine analogues in place of Tyr(1).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	17 (35.42)	18.2507
2000's	17 (35.42)	29.6817
2010's	8 (16.67)	24.3611
2020's	6 (12.50)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	2 (4.00%)	5.53%
Reviews	4 (8.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	44 (88.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
histamine [no description available]	2.11	1	aralkylamino compound; imidazoles	human metabolite; mouse metabolite; neurotransmitter
iodine Iodine: A nonmetallic element of the halogen group that is represented by the atomic symbol I, atomic number 53, and atomic weight of 126.90. It is a nutritionally essential element, especially important in thyroid hormone synthesis. In solution, it has anti-infective properties and is used topically.. diiodine : Molecule comprising two covalently bonded iodine atoms with overall zero charge..	1.98	1	diatomic iodine	nutrient
thiorphan Thiorphan: A potent inhibitor of membrane metalloendopeptidase (ENKEPHALINASE). Thiorphan potentiates morphine-induced ANALGESIA and attenuates naloxone-precipitated withdrawal symptoms.	2	1	N-acyl-amino acid
alanine Alanine: A non-essential amino acid that occurs in high levels in its free state in plasma. It is produced from pyruvate by transamination. It is involved in sugar and acid metabolism, increases IMMUNITY, and provides energy for muscle tissue, BRAIN, and the CENTRAL NERVOUS SYSTEM.. alanine : An alpha-amino acid that consists of propionic acid bearing an amino substituent at position 2.	2.02	1	alanine zwitterion; alanine; L-alpha-amino acid; proteinogenic amino acid; pyruvate family amino acid	EC 4.3.1.15 (diaminopropionate ammonia-lyase) inhibitor; fundamental metabolite
serine Serine: A non-essential amino acid occurring in natural form as the L-isomer. It is synthesized from GLYCINE or THREONINE. It is involved in the biosynthesis of PURINES; PYRIMIDINES; and other amino acids.. serine : An alpha-amino acid that is alanine substituted at position 3 by a hydroxy group.	2.46	2	L-alpha-amino acid; proteinogenic amino acid; serine family amino acid; serine zwitterion; serine	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
tyrosine Tyrosine: A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin.. tyrosine : An alpha-amino acid that is phenylalanine bearing a hydroxy substituent at position 4 on the phenyl ring.	2.69	3	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; proteinogenic amino acid; tyrosine	EC 1.3.1.43 (arogenate dehydrogenase) inhibitor; fundamental metabolite; micronutrient; nutraceutical
2-naphthylamine 2-Naphthylamine: A naphthalene derivative with carcinogenic action.. 2-naphthylamine : A naphthylamine carrying the amino group at position 2.	2.02	1	naphthylamine	carcinogenic agent
2-amino-3-phenylbutanoic acid [no description available]	1.99	1
enkephalin, d-penicillamine (2,5)- Enkephalin, D-Penicillamine (2,5)-: A disulfide opioid pentapeptide that selectively binds to the DELTA OPIOID RECEPTOR. It possesses antinociceptive activity.. DPDPE : A heterodetic cyclic peptide that is a cyclic enkephalin analogue, having D-penicillaminyl residues located at positions 2 and 5, which form the heterocycle via a disulfide bond.	3.51	8	heterodetic cyclic peptide	delta-opioid receptor agonist
n,n-diallyl-tyrosyl-alpha-aminoisobutyric acid-phenylalanyl-leucine [no description available]	2.4	2
racecadotril racecadotril: parenterally active enkephalinase inhibitor	2	1	N-acyl-amino acid
enkephalin, ser(2), leu(5), thr(6)- enkephalin, Ser(2), Leu(5), Thr(6)-: specific probe for the delta-opiate receptor subtype in brain membranes	2	1	oligopeptide
phenylalanyl-leucyl-phenylalanyl-glutaminyl-prolyl-glutaminyl-arginyl-phenylalaninamide phenylalanyl-leucyl-phenylalanyl-glutaminyl-prolyl-glutaminyl-arginyl-phenylalaninamide: endogenous opioid antagonist octapeptide from bovine brain	2	1
biotin vitamin B7 : Any member of a group of vitamers that belong to the chemical structural class called biotins that exhibit biological activity against vitamin B7 deficiency. Vitamin B7 deficiency is very rare in individuals who take a normal balanced diet. Foods rich in biotin are egg yolk, liver, cereals, vegetables (spinach, mushrooms) and rice. Symptoms associated with vitamin B7 deficiency include thinning hair, scaly skin rashes around eyes, nose and mouth, and brittle nails. The vitamers include biotin and its ionized and salt forms.	2.05	1	biotins; vitamin B7	coenzyme; cofactor; Escherichia coli metabolite; fundamental metabolite; human metabolite; mouse metabolite; nutraceutical; prosthetic group; Saccharomyces cerevisiae metabolite
diprenorphine Diprenorphine: A narcotic antagonist similar in action to NALOXONE. It is used to remobilize animals after ETORPHINE neuroleptanalgesia and is considered a specific antagonist to etorphine.	2	1	morphinane alkaloid
enkephalin, leucine Enkephalin, Leucine: One of the endogenous pentapeptides with morphine-like activity. It differs from MET-ENKEPHALIN in the LEUCINE at position 5. Its first four amino acid sequence is identical to the tetrapeptide sequence at the N-terminal of BETA-ENDORPHIN.. Leu-enkephalin : A pentapeptide comprising L-tyrosine, glycine, glycine, L-phenylalanine and L-leucine residues joined in sequence by peptide linkages. It is an endogenous opioid peptide produced in vertebrate species, including rodents, primates and humans that results from decomposition of proenkephalin or dynorphin and exhibits antinociceptive properties.	3.38	7	pentapeptide; peptide zwitterion	analgesic; delta-opioid receptor agonist; human metabolite; mu-opioid receptor agonist; neurotransmitter; rat metabolite
deltorphin deltorphin: isolated from skin of Phyllomedusa sauvagei; has affinity to opioid receptor; note deltorphin I and deltorphin II are available, they have Ala in position 2	2.4	2	peptide
naloxone Naloxone: A specific opiate antagonist that has no agonist activity. It is a competitive antagonist at mu, delta, and kappa opioid receptors.. naloxone : A synthetic morphinane alkaloid that is morphinone in which the enone double bond has been reduced to a single bond, the hydrogen at position 14 has been replaced by a hydroxy group, and the methyl group attached to the nitrogen has been replaced by an allyl group. A specific opioid antagonist, it is used (commonly as its hydrochloride salt) to reverse the effects of opioids, both following their use of opioids during surgery and in cases of known or suspected opioid overdose.	3.12	5	morphinane alkaloid; organic heteropentacyclic compound; tertiary alcohol	antidote to opioid poisoning; central nervous system depressant; mu-opioid receptor antagonist
morphine Meconium: The thick green-to-black mucilaginous material found in the intestines of a full-term fetus. It consists of secretions of the INTESTINAL GLANDS; BILE PIGMENTS; FATTY ACIDS; AMNIOTIC FLUID; and intrauterine debris. It constitutes the first stools passed by a newborn.	2.72	3	morphinane alkaloid; organic heteropentacyclic compound; tertiary amino compound	anaesthetic; drug allergen; environmental contaminant; geroprotector; mu-opioid receptor agonist; opioid analgesic; plant metabolite; vasodilator agent; xenobiotic
7-benzylidenenaltrexone 7-benzylidenenaltrexone: structure given in first source; a highly selective delta1-opioid receptor antagonist	2.25	1	phenanthrenes
naltrexone Naltrexone: Derivative of noroxymorphone that is the N-cyclopropylmethyl congener of NALOXONE. It is a narcotic antagonist that is effective orally, longer lasting and more potent than naloxone, and has been proposed for the treatment of heroin addiction. The FDA has approved naltrexone for the treatment of alcohol dependence.. naltrexone : An organic heteropentacyclic compound that is naloxone substituted in which the allyl group attached to the nitrogen is replaced by a cyclopropylmethyl group. A mu-opioid receptor antagonist, it is used to treat alcohol dependence.	3.11	5	cyclopropanes; morphinane-like compound; organic heteropentacyclic compound	antidote to opioid poisoning; central nervous system depressant; environmental contaminant; mu-opioid receptor antagonist; xenobiotic
norbinaltorphimine norbinaltorphimine: kappa opiate receptor antagonist; structure given in first source	2.25	1	isoquinolines
dermorphin dermorphin: opiate-like peptide present in amphibian skin	1.98	1	oligopeptide
enkephalin, ala(2)-mephe(4)-gly(5)- Enkephalin, Ala(2)-MePhe(4)-Gly(5)-: An enkephalin analog that selectively binds to the MU OPIOID RECEPTOR. It is used as a model for drug permeability experiments.	3.1	5
naltrindole benzofuran naltrindole benzofuran: structure given in first source	2.46	2	morphinane alkaloid
naltrindole naltrindole: delta opioid receptor antagonist	2.9	4	isoquinolines
tetrodotoxin Tetrodotoxin: An aminoperhydroquinazoline poison found mainly in the liver and ovaries of fishes in the order TETRAODONTIFORMES, which are eaten. The toxin causes paresthesia and paralysis through interference with neuromuscular conduction.. tetrodotoxin : A quinazoline alkaloid that is a marine toxin isolated from fish such as puffer fish. It has been shown to exhibit potential neutotoxicity due to its ability to block voltage-gated sodium channels.	2	1	azatetracycloalkane; oxatetracycloalkane; quinazoline alkaloid	animal metabolite; bacterial metabolite; marine metabolite; neurotoxin; voltage-gated sodium channel blocker
deltorphin i, ala(2)- deltorphin I, Ala(2)-: isolated from skin extracts of frogs belonging to the genus Phyllomedusa; has affinity to opioid receptors	1.98	1	peptide
picrotoxin Picrotoxin: A noncompetitive antagonist at GABA-A receptors and thus a convulsant. Picrotoxin blocks the GAMMA-AMINOBUTYRIC ACID-activated chloride ionophore. Although it is most often used as a research tool, it has been used as a CNS stimulant and an antidote in poisoning by CNS depressants, especially the barbiturates.. picrotoxin : A mixture consisting of equimolar amounts of picrotoxinin and picrotin found in the climbing plant Anamirta cocculus.	2	1
guanosine 5'-o-(3-thiotriphosphate) Guanosine 5'-O-(3-Thiotriphosphate): Guanosine 5'-(trihydrogen diphosphate), monoanhydride with phosphorothioic acid. A stable GTP analog which enjoys a variety of physiological actions such as stimulation of guanine nucleotide-binding proteins, phosphoinositide hydrolysis, cyclic AMP accumulation, and activation of specific proto-oncogenes.	2.94	4	nucleoside triphosphate analogue

Condition	Relationship Strength	Studies	Trials
Muscle Contraction A process leading to shortening and/or development of tension in muscle tissue. Muscle contraction occurs by a sliding filament mechanism whereby actin filaments slide inward among the myosin filaments.	2.71	3	0
Chronic Illness [description not available]	2.41	1	0
Recrudescence [description not available]	5.41	3	1
Inguinal Hernia [description not available]	6.47	6	2
Acute Post-operative Pain [description not available]	6.47	6	2
Chronic Disease Diseases which have one or more of the following characteristics: they are permanent, leave residual disability, are caused by nonreversible pathological alteration, require special training of the patient for rehabilitation, or may be expected to require a long period of supervision, observation, or care (Dictionary of Health Services Management, 2d ed). For epidemiological studies chronic disease often includes HEART DISEASES; STROKE; CANCER; and diabetes (DIABETES MELLITUS, TYPE 2).	2.41	1	0
Hernia, Inguinal An abdominal hernia with an external bulge in the GROIN region. It can be classified by the location of herniation. Indirect inguinal hernias occur through the internal inguinal ring. Direct inguinal hernias occur through defects in the ABDOMINAL WALL (transversalis fascia) in Hesselbach's triangle. The former type is commonly seen in children and young adults; the latter in adults.	6.47	6	2
Pain, Postoperative Pain during the period after surgery.	6.47	6	2
Pain, Chronic [description not available]	5.31	3	1
Chronic Pain Aching sensation that persists for more than a few months. It may or may not be associated with trauma or disease, and may persist after the initial injury has healed. Its localization, character, and timing are more vague than with acute pain.	5.31	3	1
Dysesthesia [description not available]	3.52	1	0
Anoxemia [description not available]	2.25	1	0
Injury, Myocardial Reperfusion [description not available]	2.46	2	0
Hypoxia Sub-optimal OXYGEN levels in the ambient air of living organisms.	2.25	1	0
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.07	1	0
Anxiety Feelings or emotions of dread, apprehension, and impending disaster but not disabling as with ANXIETY DISORDERS.	2.07	1	0
Benign Neoplasms, Brain [description not available]	1.98	1	0
Brain Neoplasms Neoplasms of the intracranial components of the central nervous system, including the cerebral hemispheres, basal ganglia, hypothalamus, thalamus, brain stem, and cerebellum. Brain neoplasms are subdivided into primary (originating from brain tissue) and secondary (i.e., metastatic) forms. Primary neoplasms are subdivided into benign and malignant forms. In general, brain tumors may also be classified by age of onset, histologic type, or presenting location in the brain.	1.98	1	0
Neuroblastoma A common neoplasm of early childhood arising from neural crest cells in the sympathetic nervous system, and characterized by diverse clinical behavior, ranging from spontaneous remission to rapid metastatic progression and death. This tumor is the most common intraabdominal malignancy of childhood, but it may also arise from thorax, neck, or rarely occur in the central nervous system. Histologic features include uniform round cells with hyperchromatic nuclei arranged in nests and separated by fibrovascular septa. Neuroblastomas may be associated with the opsoclonus-myoclonus syndrome. (From DeVita et al., Cancer: Principles and Practice of Oncology, 5th ed, pp2099-2101; Curr Opin Oncol 1998 Jan;10(1):43-51)	1.98	1	0
Morphine Abuse [description not available]	1.98	1	0
Drug Withdrawal Symptoms [description not available]	1.98	1	0
Morphine Dependence Strong dependence, both physiological and emotional, upon morphine.	1.98	1	0
Substance Withdrawal Syndrome Physiological and psychological symptoms associated with withdrawal from the use of a drug after prolonged administration or habituation. The concept includes withdrawal from smoking or drinking, as well as withdrawal from an administered drug.	1.98	1	0
Addiction, Opioid [description not available]	2.91	1	0
Opioid-Related Disorders Disorders related to or resulting from abuse or misuse of OPIOIDS.	2.91	1	0
Arrhythmia [description not available]	2	1	0
Arrhythmias, Cardiac Any disturbances of the normal rhythmic beating of the heart or MYOCARDIAL CONTRACTION. Cardiac arrhythmias can be classified by the abnormalities in HEART RATE, disorders of electrical impulse generation, or impulse conduction.	2	1	0

tyrosyl-1,2,3,4-tetrahydro-3-isoquinolinecarbonyl-phenylalanyl-phenylalanine

Description

Cross-References

Synonyms (24)

Protein Targets (5)

Inhibition Measurements

Other Measurements

Biological Processes (31)

Molecular Functions (11)

Ceullar Components (16)

Bioassays (52)

Research

Studies (48)

Market Indicators

Research Demand Index: 10.59

Study Types

tyrosyl-1,2,3,4-tetrahydro-3-isoquinolinecarbonyl-phenylalanyl-phenylalanine

Description

Cross-References

Synonyms (24)

Protein Targets (5)

Inhibition Measurements

Other Measurements

Biological Processes (31)

Molecular Functions (11)

Ceullar Components (16)

Bioassays (52)

Research

Studies (48)

Market Indicators

Research Demand Index: 10.59

Study Types

Related Drugs (30)

Related Conditions (27)