Structure via PubChem · Public domain (PubChem)
vasoactive intestinal peptide
Sign in to saveAlso known as VIP, VIP(125-152), vasoactive intestinal polypeptide
hormone that affects blood pressure / heart rate
Chemical data
- Formula
- C147H237N43O43S
- Molecular weight
- 3326.8 g/mol
- IUPAC name
- (2S)-4-amino-2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-3-(1H-imidazol-5-yl)propanoyl]amino]-3-hydroxypropanoyl]amino]-3-carboxypropanoyl]amino]propanoyl]amino]-3-methylbutanoyl]amino]-3-phenylpropanoyl]amino]-3-hydroxybutanoyl]amino]-3-carboxypropanoyl]amino]-4-oxobutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-hydroxybutanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylpentanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]hexanoyl]amino]-5-oxopentanoyl]amino]-4-methylsulfanylbutanoyl]amino]propanoyl]amino]-3-methylbutanoyl]amino]hexanoyl]amino]hexanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-methylpentanoyl]amino]-4-oxobutanoyl]amino]-3-hydroxypropanoyl]amino]-3-methylpentanoyl]amino]-4-methylpentanoyl]amino]-4-oxobutanoic acid
- SMILES
- CC[C@H](C)[C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(=O)N)C(=O)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC1=CC=C(C=C1)O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC2=CC=C(C=C2)O)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC3=CC=CC=C3)NC(=O)[C@H](C(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC4=CN=CN4)N
- InChIKey
- VBUWHHLIZKOSMS-RIWXPGAOSA-N
- XLogP
- -16.6
- Polar surface area
- 1480 Ų
- H-bond donors
- 49
- H-bond acceptors
- 51
- Formal charge
- 0
via PubChem
Research
15,099 papers- Vasoactive intestinal peptide.Journal of endocrinological investigation · 1986
- Therapeutic potential of vasoactive intestinal peptide and its receptor VPAC2 in type 2 diabetes.Frontiers in endocrinology · 2022
- Vasoactive intestinal peptide in the heart.Annals of the New York Academy of Sciences · 1988
- Recent advances in vasoactive intestinal peptide physiology and pathophysiology: focus on the gastrointestinal system.F1000Research · 2019
- Vasoactive intestinal peptide as a coronary vasodilator.Annals of the New York Academy of Sciences · 1988
via PubMed
Clinical Trials
12 registered- NACOMPLETEDThe Effects of a Long-lasting Infusion of Vasoactive Intestinal Peptide (VIP) on Headache, Cranial Hemodynamic and Autonomic Symptoms in Healthy VolunteersDanish Headache Center · NCT03989817
- PHASE1COMPLETEDPhase I Study of Vasoactive Intestinal Peptide in Patients With Acute Respiratory Distress Syndrome and SepsisStony Brook University · NCT00004494
- COMPLETEDVasoactive Intestinal Peptide in COPDMedical University of Vienna · NCT00464932
- PHASE2TERMINATEDPhase 2 Study to Assess Safety, Tolerability and Efficacy of Once Weekly SC Pemziviptadil (PB1046) in Subjects With Symptomatic PAHPhaseBio Pharmaceuticals Inc. · NCT03556020
- NACOMPLETEDThe Effects of a Long-lasting Infusion of Vasoactive Intestinal Peptide (VIP) in Episodic Migraine PatientsDanish Headache Center · NCT04260035
- PHASE2/PHASE3TERMINATEDInhaled ZYESAMI™ (Aviptadil Acetate) for the Treatment of Severe COVID-19APR Applied Pharma Research s.a. · NCT04360096
Wikidata facts
- Subclass of
- gastrointestinal hormone
- Mass
- 3326.8
Show 4 more facts
- chemical formula
- C₁₄₇H₂₃₇N₄₃O₄₃S
- cell component
- perikaryon
- found in taxon
- Homo sapiens
via Wikidata · CC0