Details of the Drug

General Information of Drug (ID: DM4R6UV)

Drug Name
BRADYKININ
Synonyms
BRADYKININ; Kallidin I; 58-82-2; L-Bradykinin; Synthetic bradykinin; Bradykinin (synthetic); Callidin I; UNII-S8TIM42R2W; Kallidin 9; BRS 640; PRS 640; S8TIM42R2W; CHEBI:3165; CHEMBL406291; Bradykinin, Lysyl; BK; Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg; EINECS 200-398-8; L-arginyl-L-prolyl-L-prolylglycyl-L-phenylalanyl-L-seryl-L-prolyl-L-phenylalanyl-L-arginine
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 5 Molecular Weight (mw) 1060.2
Logarithm of the Partition Coefficient (xlogp) -4.8
Rotatable Bond Count (rotbonds) 27
Hydrogen Bond Donor Count (hbonddonor) 12
Hydrogen Bond Acceptor Count (hbondacc) 14
Chemical Identifiers
Formula
C50H73N15O11
IUPAC Name
(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
Canonical SMILES
C1C[C@H](N(C1)C(=O)[C@@H]2CCCN2C(=O)[C@H](CCCN=C(N)N)N)C(=O)NCC(=O)N[C@@H](CC3=CC=CC=C3)C(=O)N[C@@H](CO)C(=O)N4CCC[C@H]4C(=O)N[C@@H](CC5=CC=CC=C5)C(=O)N[C@@H](CCCN=C(N)N)C(=O)O
InChI
InChI=1S/C50H73N15O11/c51-32(16-7-21-56-49(52)53)45(72)65-25-11-20-39(65)47(74)64-24-9-18-37(64)43(70)58-28-40(67)59-34(26-30-12-3-1-4-13-30)41(68)62-36(29-66)46(73)63-23-10-19-38(63)44(71)61-35(27-31-14-5-2-6-15-31)42(69)60-33(48(75)76)17-8-22-57-50(54)55/h1-6,12-15,32-39,66H,7-11,16-29,51H2,(H,58,70)(H,59,67)(H,60,69)(H,61,71)(H,62,68)(H,75,76)(H4,52,53,56)(H4,54,55,57)/t32-,33-,34-,35-,36-,37-,38-,39-/m0/s1
InChIKey
QXZGBUJJYSLZLT-FDISYFBBSA-N
Cross-matching ID
PubChem CID
439201
ChEBI ID
CHEMBL406291
CAS Number
58-82-2
UNII
S8TIM42R2W
DrugBank ID
DB12126
TTD ID
D0X0BI
INTEDE ID
DR1812
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
B2 bradykinin receptor (BDKRB2) TTGY8IW BKRB2_HUMAN Inhibitor [1]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cathepsin K (CTSK) DEG3S8C CATK_HUMAN Substrate [2]
Angiotensin-converting enzyme 2 (ACE2) DEGPI81 ACE2_HUMAN Substrate [3]
Arginine carboxypeptidase (CPN1) DEPWYLT CBPN_HUMAN Substrate [4]
Soluble aminopeptidase P (sAmp) DE8E6X9 XPP1_HUMAN Substrate [5]
Carboxypeptidase M (CPM) DE1TNRG CBPM_HUMAN Substrate [6]
Cathepsin H (CTSH) DEHEZPI CATH_HUMAN Substrate [7]
Dipeptidyl peptidase II (DPP7) DEIORCK DPP2_HUMAN Substrate [8]
PABA peptide hydrolase (MEP1B) DEKBXUC MEP1B_HUMAN Substrate [9]
Prolyl endopeptidase (PREP) DEVSCNZ PPCE_HUMAN Substrate [10]
Thimet oligopeptidase (THOP1) DE95LJC THOP1_HUMAN Substrate [11]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
B2 bradykinin receptor (BDKRB2) DTT BDKRB2 6.64E-04 -0.24 -0.54
Prolyl endopeptidase (PREP) DME PREP 2.85E-01 -8.06E-02 -1.15E-01
Arginine carboxypeptidase (CPN1) DME CPN1 6.02E-16 -1.48E-01 -4.63E-01
PABA peptide hydrolase (MEP1B) DME MEP1B 5.94E-07 -1.76E-01 -4.20E-01
Dipeptidyl peptidase II (DPP7) DME DPP7 2.50E-59 4.02E-01 1.17E+00
Cathepsin H (CTSH) DME CTSH 5.92E-01 -8.46E-02 -1.10E-01
Angiotensin-converting enzyme 2 (ACE2) DME ACE2 6.32E-01 6.30E-03 2.97E-02
Cathepsin K (CTSK) DME CTSK 3.42E-104 1.01E+00 1.64E+00
Thimet oligopeptidase (THOP1) DME THOP1 2.83E-06 -1.78E-01 -4.15E-01
Soluble aminopeptidase P (sAmp) DME XPNPEP1 6.11E-02 -8.81E-02 -1.40E-01
Carboxypeptidase M (CPM) DME CPM 6.33E-05 1.36E-01 2.10E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Synthesis and biological evaluation of bradykinin B(1)/B(2) and selective B(1) receptor antagonists. J Med Chem. 2000 Jun 15;43(12):2382-6.
2 A cysteine-type carboxypeptidase, cathepsin X, generates peptide receptor agonists. Int Immunopharmacol. 2010 Jan;10(1):134-9.
3 Nunn's Applied Respiratory Physiology (Eighth Edition). Chapter 11 - Nonrespiratory Functions of the Lung.2017, Pages 203-214.e2
4 Regulation of chemerin bioactivity by plasma carboxypeptidase N, carboxypeptidase B (activated thrombin-activable fibrinolysis inhibitor), and platelets. J Biol Chem. 2009 Jan 9;284(2):751-8.
5 Cloning, expression, and characterization of human cytosolic aminopeptidase P: a single manganese(II)-dependent enzyme. Biochemistry. 2000 Dec 12;39(49):15121-8.
6 Interactions between carboxypeptidase M and kinin B1 receptor in endothelial cells. Inflamm Res. 2019 Oct;68(10):845-855.
7 Human brain cathepsin H as a neuropeptide and bradykinin metabolizing enzyme. Peptides. 2003 Dec;24(12):1977-84.
8 Purification of two dipeptidyl aminopeptidases II from rat brain and their action on proline-containing neuropeptides. J Neurochem. 1989 Apr;52(4):1284-93.
9 Human and mouse homo-oligomeric meprin A metalloendopeptidase: substrate and inhibitor specificities. Biol Chem. 2007 Nov;388(11):1163-72.
10 Bradykinin release and inactivation in brain of rats submitted to an experimental model of Alzheimer's disease. Peptides. 2006 Dec;27(12):3363-9.
11 Expression and activity of thimet oligopeptidase (TOP) are modified in the hippocampus of subjects with temporal lobe epilepsy (TLE). Epilepsia. 2014 May;55(5):754-62.