ChemFOnt: Showing chemical card for Bradykinin hydroxyproline (CFc000007300)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:53:33 UTC

Chemfont ID

CFc000007300

Molecule Identification

Common Name

Bradykinin hydroxyproline

Definition

Bradykinin hydroxyproline is a bradykinin analog where the third amino acid, proline, is replaced with hydroxyproline. Bradykinin is a vasoactive kinin that is liberated from its substrate kininogen by the action of kallikrein, and is known to be involved in a wide range of biologic processes. It may play an important role in blood pressure regulation and the maintenance of normal blood flow. Moreover, in various pathologic states of the cardiovascular system, it appears to provide protective actions against ischemic injury, ventricular hypertrophy, congestive heart failure, and thrombosis. Bradykinin is a potent vasodilator that acts through endothelial B2 kinin receptors to stimulate the release of nitric oxide and endothelium-derived hyperpolarizing factor. Bradykinin deficiency states may play a role in some forms of hypertension, and a relative deficiency in bradykinin may be a contributing factor to worsening heart failure. Experimental studies revealed that mice lacking the B2 receptor gene were more likely to develop hypertension, cardiac hypertrophy, and myocardial damage. Kinins exert several biologic actions. They are involved in nociception, inflammation, capillary permeability, reactive hyperemia, and stimulation of cellular glucose uptake. Bradykinin is a polypeptide that circulates in the plasma in very low concentrations in comparison with the amount of bradykinin found in various body tissues. Kininogens (alpha-2 globulins) are synthesized in the liver and circulate at high concentrations in the plasma. There are two kininogenases that convert kininogens into bradykinin: plasma kallikrein, also known as Fletcher factor, and glandular kallikrein, also known as tissue kallikrein (PMID: 11975815 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-(L-4-Hydroxyproline)bradykinin	ChEBI
3-Hydroxy-pro-bradykinin	ChEBI
Arg-3-hyp-bradykinin	ChEBI
Arg-pro-hyp-gly-phe-ser-pro-phe-arg	ChEBI
Bradykinin hydroxy-pro(3)	ChEBI
Bradykinin, hydroxy-pro(3)	ChEBI
Hydroxy-pro(3)-bradykinin	ChEBI
Hydroxyproline(3)-bradykinin	ChEBI
L-Arg-L-pro-L-hyp-gly-L-phe-L-ser-L-pro-L-phe-L-arg	ChEBI
Arg-hyp(3)-bradykinin	HMDB
Bradykinin hydroxyproline	ChEBI
3-Hydroxyproline-bradykinin	HMDB
3-L-(trans-4-Hydroxyproline)-bradykinin	HMDB
L-Arginyl-L-prolyl-(4R)-4-hydroxy-L-prolylglycyl-L-phenylalanyl-L-seryl-L-prolyl-L-phenylalanyl-L-arginine	HMDB

Chemical Formula

C₅₀H₇₃N₁₅O₁₂

Average Molecular Weight

1076.2079

Monoisotopic Molecular Weight

1075.556312875

IUPAC Name

(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-(2-{[(2S,4R)-1-[(2S)-1-[(2S)-2-amino-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]-4-hydroxypyrrolidin-2-yl]formamido}acetamido)-3-phenylpropanamido]-3-hydroxypropanoyl]pyrrolidin-2-yl]formamido}-3-phenylpropanamido]-5-carbamimidamidopentanoic acid

Traditional Name

CAS Registry Number

37642-65-2

SMILES

N[C@@H](CCCNC(N)=N)C(=O)N1CCC[C@H]1C(=O)N1C[C@H](O)C[C@H]1C(=O)NCC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CO)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O

InChI Identifier

InChI=1S/C50H73N15O12/c51-32(15-7-19-56-49(52)53)45(73)64-22-10-18-38(64)47(75)65-27-31(67)25-39(65)43(71)58-26-40(68)59-34(23-29-11-3-1-4-12-29)41(69)62-36(28-66)46(74)63-21-9-17-37(63)44(72)61-35(24-30-13-5-2-6-14-30)42(70)60-33(48(76)77)16-8-20-57-50(54)55/h1-6,11-14,31-39,66-67H,7-10,15-28,51H2,(H,58,71)(H,59,68)(H,60,70)(H,61,72)(H,62,69)(H,76,77)(H4,52,53,56)(H4,54,55,57)/t31-,32+,33+,34+,35+,36+,37+,38+,39+/m1/s1

InChI Key

JXRLHZCEMXTCBN-DIBGMJQNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Substituents

Alpha-oligopeptide
Phenylalanine or derivatives
Proline or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
Alpha-amino acid amide
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
Amphetamine or derivatives
N-acylpyrrolidine
Pyrrolidine carboxylic acid or derivatives
Pyrrolidine-2-carboxamide
Monocyclic benzene moiety
Fatty amide
Fatty acyl
Benzenoid
Tertiary carboxylic acid amide
Pyrrolidine
Secondary carboxylic acid amide
Secondary alcohol
Amino acid or derivatives
Carboxamide group
Amino acid
Guanidine
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Azacycle
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxygen compound
Primary aliphatic amine
Organic nitrogen compound
Hydrocarbon derivative
Organonitrogen compound
Carbonyl group
Alcohol
Organic oxide
Organooxygen compound
Amine
Primary alcohol
Organopnictogen compound
Primary amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Prostate (HMDB: HMDB0011728)

Source

Endogenous

Endogenous (HMDB: HMDB0011728)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.087 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-7.9	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	-1	ChemAxon
pKa (Strongest Basic)	12.34	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	15	ChemAxon
Polar Surface Area	434.01 Å²	ChemAxon
Rotatable Bond Count	27	ChemAxon
Refractivity	296.4 m³·mol⁻¹	ChemAxon
Polarizability	111.32 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0011728

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028409

KNApSAcK ID

Not Available

Chemspider ID

148618

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

169947

PDB ID

Not Available

ChEBI ID

133051

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Bradykinin hydroxyproline (CFc000007300)

MOL for CFc000007300 (Bradykinin hydroxyproline)

3D MOL for CFc000007300 (Bradykinin hydroxyproline)

3D SDF for CFc000007300 (Bradykinin hydroxyproline)

3D-SDF for CFc000007300 (Bradykinin hydroxyproline)

PDB for CFc000007300 (Bradykinin hydroxyproline)

3D PDB for CFc000007300 (Bradykinin hydroxyproline)

SMILES for CFc000007300 (Bradykinin hydroxyproline)

INCHI for CFc000007300 (Bradykinin hydroxyproline)

Structure for CFc000007300 (Bradykinin hydroxyproline)

3D Structure for CFc000007300 (Bradykinin hydroxyproline)