Molecule

58-82-2

AlkaPlorer ID: AK093236

Synonym: None

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

Structure

SMILES: N=C(N)NCCC[C@H](N=C(O)[C@H](CC1=CC=CC=C1)N=C(O)[C@@H]1CCCN1C(=O)[C@H](CO)N=C(O)[C@H](CC1=CC=CC=C1)N=C(O)CN=C(O)[C@@H]1CCCN1C(=O)[C@@H]1CCCN1C(=O)[C@@H](N)CCCNC(=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

Reference

Multiple Bradykinin-Related Peptides From the Skin of the Frog, Rana temporaria

PubChem CID: 439201

CAS: 58-82-2

LOTUS: LTS0150409

NPASS: NPC324850

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Pelophylax lessonae	Pelophylax	Ranidae	Anura	Amphibia	Chordata	Metazoa	Eukaryota

Properties Information

Molecule Weight: 1060.2279999999994

TPSA？: 431.23

MolLogP？: 0.6324400000000088

Number of H-Donors: 14

Number of H-Acceptors: 13

RingCount: 5

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Canis lupus familiaris	Canis familiaris	ED15	2.8	ug kg-1	10.1021/jm00369a017
Cavia porcellus	Cavia porcellus	Activity	100.0	%	10.1021/jm9301954
Cavia porcellus	Cavia porcellus	pD2	7.4	None	10.1021/jm9301954
Cavia porcellus	Cavia porcellus	Potency	1.0	None	10.1021/jm00181a012
Homo sapiens	Angiotensin-converting enzyme	Km	180.0	nM	10.1021/acs.jmedchem.0c00441
Homo sapiens	Bradykinin B1 receptor	Alpha E	1.0	None	10.1021/jm00144a008
Homo sapiens	Bradykinin B1 receptor	Ki	10.0	nM	10.1021/jm990961s
Homo sapiens	Bradykinin B2 receptor	EC50	0.04898	nM	10.1021/jm900604g
Homo sapiens	Bradykinin B2 receptor	ED50	1.65	nM	10.1021/jm00144a008
Homo sapiens	Bradykinin B2 receptor	Emax	125.0	%	10.1021/jm900604g
Homo sapiens	Bradykinin B2 receptor	IC50	1.8	nM	10.1016/j.bmcl.2013.01.025
Homo sapiens	Bradykinin B2 receptor	Inhibition	4.0	%	10.1016/j.bmcl.2013.01.025
Homo sapiens	Bradykinin B2 receptor	Ki	0.065	nM	10.1021/jm9901531
Homo sapiens	Bradykinin B2 receptor	Ki	0.11	nM	10.1021/jm990961s
Homo sapiens	Bradykinin B2 receptor	Ki	0.65	nM	10.1021/jm9901529
Homo sapiens	Bradykinin B2 receptor	Ki	0.6761	nM	10.1021/jm950716i
Homo sapiens	Bradykinin B2 receptor	Ki	1.1	nM	10.1016/j.bmcl.2013.01.025
Homo sapiens	Bradykinin B2 receptor	pD	8.78	M	10.1021/jm00144a008
Homo sapiens	Bradykinin B2 receptor	Relative affinity	100.0	%	10.1021/jm00144a008
Homo sapiens	Histone acetyltransferase GCN5	Potency	35481.3	nM	None
Homo sapiens	Homo sapiens	Inhibition	nan	%	10.1021/jm990961s
Homo sapiens	Homo sapiens	pD2	7.4	None	10.1021/jm9901529
Homo sapiens	Homo sapiens	pD2	7.4	None	10.1021/jm9901531
Homo sapiens	Homo sapiens	pD2	7.9	None	10.1021/jm9901529
Homo sapiens	Homo sapiens	pD2	7.9	None	10.1021/jm9901531
Homo sapiens	Homo sapiens	pD2	7.9	None	10.1021/jm990961s
Homo sapiens	Homo sapiens	T1/2	0.45	hr	10.1021/jm950716i
Homo sapiens	Olfactory receptor 51E2	EC50	1.3	nM	None
Homo sapiens	Olfactory receptor 51E2	Ratio	0.762	None	None
Oryctolagus cuniculus	Oryctolagus cuniculus	Response	92.0	%	10.1021/jm00144a008
Plasmodium falciparum	Plasmodium falciparum	Activity	nan	None	10.1016/j.bmcl.2015.05.071
Plasmodium gallinaceum	Plasmodium gallinaceum	Activity	98.0	%	10.1016/j.bmcl.2015.05.071
Rattus norvegicus	Bradykinin B2 receptor	Ki	0.46	nM	10.1021/jm9901529
Rattus norvegicus	Rattus norvegicus	Activity	100.0	%	10.1021/jm9301954
Rattus norvegicus	Rattus norvegicus	Change	-37.0	%	10.1021/jm00183a002
Rattus norvegicus	Rattus norvegicus	Change	-19.0	%	10.1021/jm00183a002
Rattus norvegicus	Rattus norvegicus	pD2	7.33	None	10.1021/jm9901529
Rattus norvegicus	Rattus norvegicus	pD2	7.9	None	10.1021/jm9301954
Rattus norvegicus	Rattus norvegicus	pD2	8.3	None	10.1021/jm9901529
Rattus norvegicus	Rattus norvegicus	T1/2	0.13	hr	10.1021/jm950716i
Sus scrofa	Sus scrofa	T1/2	0.05	hr	10.1021/jm950716i
None	ADMET	Decrease	67.0	%	10.1021/jm00369a017
None	Unchecked	IC50	0.01	nM	10.1021/jm9301954
None	Unchecked	IC50	1.0	nM	10.1021/jm9301954
None	Unchecked	IC50	1.75	nM	10.1021/jm9301954
None	Unchecked	Ki	0.263	nM	10.1021/jm950716i
None	Unchecked	Ratio	1.0	None	10.1021/jm9301954
None	Unchecked	Ratio	7.0	None	10.1021/jm00369a017
None	Unchecked	Ratio	8.0	None	10.1021/jm00369a017
None	Unchecked	Ratio	25.0	None	10.1021/jm00369a017

Metabolism Information

AKRT ID	Reaction	Reaction Link ID
AKRT006404	CC(C)[C@H](NC(=O)[C@H](CO)NC(=O)[C@H](CCCNC(=N)N)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)CCCNC(=N)N)C(=O)N[C@@H](CCC(N)=O)C(=O)O>>N=C(N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CO)C(=O)N1CCC[C@H]1C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)O	enzymemap_69626
AKRT012293	CSCC[C@H](N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CO)C(=O)N1CCC[C@H]1C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)O>>N=C(N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CO)C(=O)N1CCC[C@H]1C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)O	enzymemap_65030
AKRT015880	N=C(N)NCCCC(N=C(O)C(Cc1ccccc1)N=C(O)C1CCCN1C(=O)C(CO)N=C(O)C(Cc1ccccc1)N=C(O)CN=C(O)C1CCCN1C(=O)C1CCCN1)C(=O)O.N=C(N)NCCC[C@H](N)C(=O)O>>N=C(N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CO)C(=O)N1CCC[C@H]1C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)O	MNXR195125
AKRT015946	N=C(N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CO)C(=O)N1CCC[C@H]1C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)O>>N=C(N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CO)C(=O)N1CCC[C@H]1C(=O)N[C@@H](Cc1ccccc1)C(=O)O	enzymemap_67581
AKRT015947	N=C(N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CO)C(=O)N1CCC[C@H]1C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)O>>N=C(N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CO)C(=O)N1CCC[C@H]1C(=O)O	71451
AKRT015948	N=C(N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CO)C(=O)N1CCC[C@H]1C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)O>>N=C(N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](Cc1ccccc1)C(=O)O	enzymemap_74594
AKRT015949	N=C(N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CO)C(=O)N1CCC[C@H]1C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)O>>N=C(N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)NCC(=O)O	enzymemap_74971
AKRT015950	N=C(N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CO)C(=O)N1CCC[C@H]1C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)O>>N=C(N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)O	enzymemap_66767
AKRT015951	N=C(N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CO)C(=O)N1CCC[C@H]1C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)O>>N=C(N)NCCC[C@H](N)C(=O)O	enzymemap_66024
AKRT015952	N=C(N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CO)C(=O)N1CCC[C@H]1C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)O>>N=C(N)NCCC[C@H](NC(=O)[C@@H](N)Cc1ccccc1)C(=O)O	71451
AKRT015953	N=C(N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CO)C(=O)N1CCC[C@H]1C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)O>>N=C(N)NCCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H]1CCCN1C(=O)[C@@H](N)CO)C(=O)O	enzymemap_74594
AKRT015954	N=C(N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CO)C(=O)N1CCC[C@H]1C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)O>>N=C(N)NCCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CO)NC(=O)[C@@H](N)Cc1ccccc1)C(=O)O	enzymemap_74971
AKRT015955	N=C(N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CO)C(=O)N1CCC[C@H]1C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)O>>N=C(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)CN)C(=O)O	enzymemap_66767
AKRT015956	N=C(N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CO)C(=O)N1CCC[C@H]1C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)O>>N=C(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)C1CCCN1)C(=O)O	enzymemap_66024
AKRT015957	N=C(N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CO)C(=O)N1CCC[C@H]1C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)O>>N=C(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]1CCCN1)C(=O)O	enzymemap_66207
AKRT015958	N=C(N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CO)C(=O)N1CCC[C@H]1C(=O)N[C@@H](Cc1ccccc1)C(=O)O.N=C(N)NCCC[C@H](N)C(=O)O>>N=C(N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CO)C(=O)N1CCC[C@H]1C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)O	MNXR131239
AKRT016193	N=C(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](CCCNC(=N)N)NC(=O)[C@@H](N)CCCCN)C(=O)O>>N=C(N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CO)C(=O)N1CCC[C@H]1C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)O	enzymemap_65030