ContaminantDB: Bradykinin hydroxyproline

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-26 20:38:36 UTC

Update Date

2016-11-09 01:22:15 UTC

Accession Number

CHEM040447

Identification

Common Name

Bradykinin hydroxyproline

Class

Small Molecule

Description

An oligopeptide that is an analogue of bradykinin in which the third amino acid, proline, is replaced with hydroxyproline.

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical 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 Mass

1076.208 g/mol

Monoisotopic Mass

1075.556 g/mol

CAS Registry Number

Not Available

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

SMILES

N[C@@H](CCCN=C(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](CCCN=C(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

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

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	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a6s-9207000011-778bbb0a73405e35634f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004j-9747101012-b42bd37379fc0239fd49	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01vx-9634000000-898b1109990e39d720e4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03ei-9000000002-518cbf6703868bad51a5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0nmi-9100000002-705fbadd909ee3cd89a5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pi3-9101100211-d0a28afc2dea8e0ade64	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056r-9000010000-3768382c99716ff616a2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05r0-9000110040-80ee3c9f32cad674a089	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00du-9670230000-91b46fbe51940280f335	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-c21b1d88b052e58559e6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0r70-9000000022-0be97a67b8c9ae981318	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014l-9003760021-faaf717115ac5976cb44	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0011728

FooDB ID

FDB028409

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

148618

ChEBI ID

133051

PubChem Compound ID

169947

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=2156727

2. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762.

3. Palkhiwala SA, Frishman WH, Warshafsky S: Bradykinin for the treatment of cardiovascular disease. Heart Dis. 2001 Sep-Oct;3(5):333-9.

Bradykinin hydroxyproline (CHEM040447)

Structure for CHEM040447: Bradykinin hydroxyproline