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Details

Stereochemistry ABSOLUTE
Molecular Formula C32H37N5O5
Molecular Weight 571.6667
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TETRAPEPTIDE-15

SMILES

N[C@@H](CC1=CC=C(O)C=C1)C(=O)N2CCC[C@H]2C(=O)N[C@@H](CC3=CC=CC=C3)C(=O)N[C@@H](CC4=CC=CC=C4)C(N)=O

InChI

InChIKey=XIJHWXXXIMEHKW-LJWNLINESA-N
InChI=1S/C32H37N5O5/c33-25(18-23-13-15-24(38)16-14-23)32(42)37-17-7-12-28(37)31(41)36-27(20-22-10-5-2-6-11-22)30(40)35-26(29(34)39)19-21-8-3-1-4-9-21/h1-6,8-11,13-16,25-28,38H,7,12,17-20,33H2,(H2,34,39)(H,35,40)(H,36,41)/t25-,26-,27-,28-/m0/s1

HIDE SMILES / InChI

Molecular Formula C32H37N5O5
Molecular Weight 571.6667
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Tetrapeptide-15 (Endomorphin-2) is an endogenous agonist at μ-opioid receptors (μORs) in the spinal cord; it exhibits antinociceptive/analgesic, immunosuppressive, and pro-angiogenic activities. Endomorphin-2 increases pain thresholds in animal models of thermal pain and inhibits the formation of antibodies in other cellular models. In HUVECs, this peptide stimulates proliferation, migration, adhesion, and tube formation.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.69 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Endomorphin-2, at doses of 3, 10 and 30 ug, i.c.v., dose-dependently inhibited the number of capsaicin-induced coughs.
Route of Administration: Other
In Vitro Use Guide
Endomorphin-2 (100 uM) produced a significant inhibition, of both the frequency (-22.8%) and the amplitude (-30.5%) of the spontaneous IPSCs in rat cardiac vagal neurons.
Substance Class Chemical
Record UNII
3PH5M0466G
Record Status Validated (UNII)
Record Version