Basic information
- CAS
58-82-2- Standard SMILES
NC(N)=NCCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CO)NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CCCN1C(=O)[C@@H](N)CCCN=C(N)N)C(=O)O- InChIKey
QXZGBUJJYSLZLT-FDISYFBBSA-N- Molecular formula
- C50H73N15O11
- Average molar mass
- 1,060.2 g/mol
- Monoisotopic mass
- 1,059.5613982
Overview
Bradykinin is a linear nonapeptide messenger belonging to the kinin group of proteins, with amino acid sequence RPPGFSPFR. Enzymatically produced from kallidin in the blood, it is a powerful vasodilator that causes smooth muscle contraction, and may mediate inflammation. It has a role as a vasodilator agent and a human blood serum metabolite. It is a conjugate base of a bradykinin(2+).
Names & identifiers
- Preferred name
- Bradykinin
- IUPAC
- (2S)-2-[[(2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-2-[[2-[[(2S)-1-[(2S)-1-[(2S)-2-amino-5-(diaminomethylideneamino)pentanoyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-3-hydroxypropanoyl]pyrrolidine-2-carbonyl]amino]-3-phenylpropanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid
- English name
- BRADYKININ
- Molecular formula
- C50H73N15O11
- Molecular weight
- 1060.21
Names & synonyms
BRADYKININ58-82-2L-BradykininKallidin ICallidin IKallidin-9(2S)-2-[[(2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-2-[[2-[[(2S)-1-[(2S)-1-[(2S)-2-amino-5-(diaminomethylideneamino)pentanoyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-3-hydroxypropanoyl]pyrrolidine-2-carbonyl]amino]-3-phenylpropanoyl]amino]-5-(diaminomethylideneamino)pentanoic acidBRS-640S8TIM42R2WCHEBI:3165DTXSID50893681Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg
Show more names
bkbrs640prs640C00306RPPGFSPFRBRADYZIDECallideicKallidinⅠ
(2S)-2-(((2S)-2-(((2S)-1-((2S)-2-(((2S)-2-((2-(((2S)-1-((2S)-1-((2S)-2-amino-5-(diaminomethylideneamino)pentanoyl)pyrrolidine-2-carbonyl)pyrrolidine-2-carbonyl)amino)acetyl)amino)-3-phenylpropanoyl)amino)-3-hydroxypropanoyl)pyrrolidine-2-carbonyl)amino)-3-phenylpropanoyl)amino)-5-(diaminomethylideneamino)pentanoic acid(2S)-2-((2S)-2-(((2S)-1-((2S)-2-((2S)-2-(2-(((2S)-1-(((2S)-1-((2S)-2-amino-5-carbamimidamidopentanoyl)pyrrolidin-2-yl)carbonyl)pyrrolidin-2-yl)formamido)acetamido)-3-phenylpropanamido)-3-hydroxypropanoyl)pyrrolidin-2-yl)formamido)-3-phenylpropanamido)-5-carbamimidamidopentanoic acid(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-(2-{[(2S)-1-{[(2S)-1-[(2S)-2-amino-5-carbamimidamidopentanoyl]pyrrolidin-2-yl]carbonyl}pyrrolidin-2-yl]formamido}acetamido)-3-phenylpropanamido]-3-hydroxypropanoyl]pyrrolidin-2-yl]formamido}-3-phenylpropanamido]-5-carbamimidamidopentanoic acidRefChem:388840DTXCID501323800Arg Pro Pro Gly Phe Ser Pro Phe Arg200-398-8Synthetic bradykinin
Properties
Computed structural properties
- XLogP
- -4.8
- Topological polar surface area
- 419 Ų
- Hydrogen bond donors
- 12
- Hydrogen bond acceptors
- 14
- Rotatable bonds
- 27
- Heavy atoms
- 76
- Formal charge
- 0
- Complexity
- 2,080
Experimental & physicochemical properties
Physical DescriptionSolid
Collision Cross Section
343.33 Ų [M+2H]2+ [CCS Type: DT; Method: stepped-field]
314.6 Ų [M+H]+
Physicochemical properties
- Melting point
- 170 °C · 170°C (rough estimate)
- Boiling point
- 811.85 °C · 811.85°C (rough estimate)
- alpha
- 25 · D25 -76.5° (c = 1.37 in 1N acetic acid)
- Density
- 1.1171 · 1.1171 (rough estimate)
- refractive index
- 1.693 · 1.6930 (estimate)
- RTECS
- 1530000 · EE1530000
- storage temp.
- 20 °C · −20°C
- solubility
- 2 O: · H2O: >40 mg/mL
- form
- White to off-white lyophilized solid
- pka
- 3.34 · 3.34±0.10(Predicted)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- F
- 3-10-23
- wgk
- 3
- safety_code
- 22-24/25
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationDrugs used to cause dilation of the blood vessels.
Tissue LocationsProstate
Applications
UsesBradykinin is used to lower blood pressure, increase bradykinin (by inhibiting its degradation) further lowering blood pressure. Bradykinin dilates blood vessels via the release of prostacyclin, nitric oxide, and endothelium-derived hyperpolarizing factor.
UsesLeucine Enkephalin acetate salt hydrate has been used in the calibration of the Q-Tof Micro hybrid, triple quadrupole-orthogonal acceleration time of flight (TOF) instrument in single-stage TOF mode. It has also been used to perform the calibration of mass spectrometry. It has also been used in liquid chromatography-mass spectrometry (LCMS)/MS for calibration of the system and for relative correction of the spectra.
General DescriptionInduces the release of nitric oxide. Other physiological functions include stimulation of pain receptors, inhibition of cAMP accumulation, induction of smooth muscle contraction, and vasodilation. Also involved in edema resulting from trauma or injury. Improves post-ischemic recovery of heart via a nitric oxide-dependent mechanism.
Suppliers72 total
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]
上海钰博生物科技有限公司021-60514606 18321282235 · [email protected]
上海毕得医药科技股份有限公司400-1647117 13681763483 · [email protected]
Hangzhou Go Top Peptide Biotech0571-88211921 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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