Basic information

CPKB ID	CP00340
IUPAC Name	(2S)-1-[(4R,7S,10S,13S,16S,19R)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-benzyl-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]-N-[(2S)-1-[(2-amino-2-oxoethyl)amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]pyrrolidine-2-carboxamide
Synonyms	(2S)-1-[(4R,7S,10S,13S,16S,19R)-19-Amino-7-(2-Amino-2-Oxoethyl)-10-(3-Amino-3-Oxopropyl)-13-Benzyl-16-[(4-Hydroxyphenyl)Methyl]-6,9,12,15,18-Pentaoxo-1,2-Dithia-5,8,11,14,17-Pentazacycloicosane-4-Carbonyl]-N-[(2S)-1-[(2-Amino-2-Oxoethyl)Amino]-5-(Diaminomethylideneamino)-1-Oxopentan-2-Yl]Pyrrolidine-2-Carboxamide (2S)-1-[(4R,7S,10S,13S,16S,19R)-19-Amino-7-(2-Amino-2-Oxoethyl)-10-(3-Amino-3-Oxopropyl)-16-[(4-Hydroxyphenyl)Methyl]-6,9,12,15,18-Pentaoxo-13-(Phenylmethyl)1,2-Dithia-5,8,11,14,17-Pentazacycloicosane-4-Carbonyl]-N-[(2S)-1-[(2-Amino-2-Oxoethyl)Amino]-5-(Diaminomethylideneamino)-1-Oxopentan-2-Yl]Pyrrolidine-2-Carboxamide (Arg8)-Vasopressin [3H]Argipressin-Tannate [3H]Vasopressin [8-Arginine]Vasopressin [Arg8]-Vasopressin [Cyclo-S-S]Cyfqncprg-Nh2 1,2-Dithia-5,8,11,14,17-Pentaazacycloeicosane-10-Propionamide,-19-Amino-13-Benzyl-7-(Carbamoylmethyl)-4-[2-[[1-[(Carbamoylmethyl)Carbamoyl]-4-Guanidinobutyl]Carbamoyl]-1-Pyrrolidinylcarbonyl]-16-P-Hyd 1-{[(4R,7S,10S,13S,16S,19R)-19-Amino-7-(2-Amino-2-Oxoethyl)-10-(3-Amino-3-Oxopropyl)-13-Benzyl-16-(4-Hydroxybenzyl)-6,9,12,15,18-Pentaoxo-1,2-Dithia-5,8,11,14,17-Pentaazacycloicosan-4-Yl]Carbonyl}-L-Prolyl-L-Arginylglycinamide 113-79-1 113A791 3-(Phenylalanine)-8-Arginineoxytocin 8-Arginine-Vasopressin 8-L-Arginine-Vasopressin Arg8-Vasopressin Arginine-Vasopressin-(Avp) Arginine-8-Vasopressin Arginine-Vasopressin Argipresina Argipresina-[Inn-Spanish] Argipressin Argipressin-[Inn:Ban] Argipressin-[Inn] Argipressin-Or-Lypressin Argipressin-Tannate Argipressin-Tannate-[Usan] Argipressina Argipressina-[Dcit] Argipressine Argipressine-[Inn-French] Argipressinum Argipressinum-[Inn-Latin] Arg-Vasopressin Avp Bdbm35667 Bdbm50044777 Beta-Hypophamine Cas-113-79-1 Chebi:34543 Chembl373742 Cys-Tyr-Phe-Gln-Asn-Cys-Pro-Arg-Gly-Nh2[Disulfide-Bridge:-1-6] Dtxsid0048349 Einecs-204-035-4 Glycinamide,-L-Cysteinyl-L-Tyrosyl-L-Phenylalanyl-L-Glutaminyl-L-Asparaginyl-L-Cysteinyl-L-Prolyl-L-Arginyl-,-Cyclic-(1>6)-Disulfide Gtpl2168 H-Cys-Tyr-Phe-Gln-Asn-Cys-Pro-Arg-Gly-Nh2 Mfcd00076738 Ncgc00166306-01 Ncgc00166306-02 Ncgc00188439-01 Oxytocin,-3-(L-Phenylalanine)-8-L-Arginine- Pitressin Q183011 Rindervasopressin Roxybenzyl-6,9,12,15,18-Pentaoxo--(6Ci) Schembl17874853 Schembl43139 Tox21_113037 Unii-Y4907O6Mfd Vasophysin Vasopressin-(Arginine-Form) Vasopressin,-8-L-Arginine- Vasopressin,-8-L-Arginine--(7Ci,8Ci,9Ci) Y4907O6Mfd
Source	Synthetic construct [Division : Synthetic] Wikipedia: Synthetic construct PubChem
Function	Anti-Diuretic PubChem
Information	Argipressin is a synthetic peptide identical to the endogenous nonapeptide hormone with antidiuretic property. Synthesized in the hypothalamus and stored/released from the posterior lobe of the pituitary, argipressin's primary function is regulating extracellular fluid volume. This agent can also act as a vasoconstrictor, increasing blood pressure and systemic vascular resistance. Ascidiacyclamide is a cyclic peptide. Bacitracin A is a homodetic cyclic peptide consisting of (4R)-2-[(1S,2S)-1-amino-2-methylbutyl]-4,5-dihydro-1,3-thiazole-4-carboxylic acid attached head-to-tail to L-leucyl,D-glutamyl, L-lysyl, D-ornityl, L-isoleucyl, D-phenylalanyl, L-histidyl. D-aspartyl and L-asparaginyl residues coupled in sequence and cyclised by condensation of the side-chain amino group of the L-lysyl residue with the C-terminal carboxylic acid group. It is the major component of bacitracin. It has a role as an antibacterial agent and an antimicrobial agent. It is a homodetic cyclic peptide and a polypeptide. PubChem\|644077

Legend

Structure

Molecular Formula	C46H65N15O12S2
Molecular Weight	1083.437855 g/mol
SMILES RUN SEA Predictions	N=C(N)NCCC[C@H](NC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](Cc2ccc(O)cc2)C(=O)N[C@@H](Cc2ccccc2)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N1)C(=O)NCC(N)=O PubChem\|644077
InChI	InChI=1S/C46H65N15O12S2/c47-27-22-74-75-23-33(45(73)61-17-5-9-34(61)44(72)56-28(8-4-16-53-46(51)52)39(67)54-21-37(50)65)60-43(71)32(20-36(49)64)59-40(68)29(14-15-35(48)63)55-41(69)31(18-24-6-2-1-3-7-24)58-42(70)30(57-38(27)66)19-25-10-12-26(62)13-11-25/h1-3,6-7,10-13,27-34,62H,4-5,8-9,14-23,47H2,(H2,48,63)(H2,49,64)(H2,50,65)(H,54,67)(H,55,69)(H,56,72)(H,57,66)(H,58,70)(H,59,68)(H,60,71)(H4,51,52,53)/t27-,28-,29-,30-,31-,32-,33-,34-/m0/s1
InChIKey	KBZOIRJILGZLEJ-XNGUIWTONA-N

2D Structure PubChem\|644077

Sequence

IUPAC Condensed	H-Cys(1)-Tyr-Phe-Gln-Asn-Cys(1)-Pro-Arg-Gly-NH2 PubChem\|644077
Amino acid chain	H-Cys(1)--Tyr--Phe--Gln--Asn--Cys(1)--Pro--Arg--Gly-NH2 CyclicPepedia\|PP
Graph representation	H-Cys,Tyr,Phe,Gln,Asn,Cys,Pro,Arg,Gly-NH2 @0,5 CyclicPepedia\|PP
One letter code from Structure	CYFQNCPRG CyclicPepedia\|Struct2seq
Amino acid chain from Structure	Cys(1)--Tyr--Phe--Gln--Asn--Cys(1)--Pro--Orn--CO CyclicPepedia\|Struct2seq
Description of the conversion sequence	The one letter code and Amino acid chain derived from the structural transformation may be inconsistent, with the Amino acid chain containing Essential Amino acid and the one letter code not.
svg Image PubChem\|644077

Chemical and Physical Properties

CyclicPepedia|Struc2Seq + PP

Structure Properties

Property Name	Property Value
Exact Mass	1083.437855
Number of Rings	4.0
Complexity	0.706666667
XlogP3 AA	-5.19483
Heavy Atom Count	75.0
Hydrogen Bond Donor Count	15.0
Hydrogen Bond Acceptor Count	16.0
Rotatable Bond Count	19.0

Property Name	Property Value
Formal Charge	0.0
Refractivity	274.7621
Rule_of_Five	0.0
Number of Atoms	75.0
Topological Polar Surface Area	461.43
Refractivity	274.7621
Veber Rule	0.0
Ghose Filter	0.0

Property Name	Property Value
RDKit Fingerprint	01100010100000101100100011011000110001100111110000101010100000000110101111101111101110010110110010010101000001001010011000110010000001001000110000101111000100000101001010100011100110001111100110100100101001001000000100000101010100000101001110011110011100101111000110001000000010001001100000000010011010010011001001010101010100000011111011110110101000000010011000001001100010000010000000100010010100000100100100001100000011100100101000110011110011100000100100010110111000010000000100000010001010010100100000101110110000010110100111011101100110001100101010011110101000100100010110000000000010111100101000111001111010011000100000001101100000111100001110110111011001000110001010000000010101001100011100011000101101000000010111110011001001011000101010110010001110101011101110011000000001100001001010011000001001001001110000001101111010110000011011111001010000110011011100010001010100000100111000010011001101100010111000010100011100111010010000011111001000001011110101010000011000010110001000110011010100000011000000111101001101110011110110001010100000001011000101001010101001100111100011001001110110000001001101011010000000101011100110001001110111001000111010011000100110100110100111001000010011101110111011000001100001001101110111100100011100110111000010010000111111000010001000000000000001111000110001001001011010100001000001110110101001010011101110010001011110110001010000010000000101001000001010000101110000001100100011000101101011001000000011111010001101001011101101111110110001100001010000111011011011010000100100100111010011100000001000110100110010101100100011101000101110100111001001010111100010000001000010000011000000100010110000010100000000100000010000010001001011010100101010000101000010010001011110000100110101000011010110101001100000100111011001010100100110010110100000001000100001010010000011010011111001101100100010110000011111100111110011000000100000000000100011100000010100001101101110010100101101000011010000010101001010010111110110100001111001011011001000000011001101100111000001001100110010011000001001101110000100000000111100000011
Morgan Fingerprint	0100100000100000000000000100000000000000001000000000000000000000100000000000000010000000001000000000000000000000000101000000000010000000000010010001000000000000000000000000010100000000000000000100010000000000000000000000000000000000000000000010000000000100000000000000000000000000000000000100000000000100000000100010000000000000000000000000000000000000001110000010000001000000000000000000010010000000001000000000000010000000000100001001000000000010000000001010000000000000100000100000001000000000000000010000000100000000000000000001000000001000010000010000000100000000000001000010000000010000001001000000000000000000100000011010000000000000000000000010000000000000010100000001000000000000010000000000000000001000000000000000001000100000100100000100000000100000000000010000000000000000000000000000001000001001100000000000000000001000100001000000001001001000000000000000000000100000000000010000011000010000000000000000000000000010000000010000000000000000000001000000000000000000000000010000000000000000000010000000000000010000
MACCS Keys	00000000000000100000000001000000000010000001000000000110000000000001000000010111101111001011100111001000101000110100011111101101110111001111101101111011111111110111110

Sequence Properties

Property Name	Property Value
Boman Index	2.30666666666666
Instability	9.27777777777778
Charge	0.873181142023468

Binding Target

Other evidence

Property Name	Property ID
TTD	D0N4OW
DrugMAP	DMQ2FPC

Manufacturers

Manufacturers Name	Value
CreativePeptides	Argipressin
Bayer healthcare pharmaceuticals	Argipressin
Upsher smith laboratories	Argipressin
Merck	Argipressin

Manufacturers Name	Value
Apotex	Argipressin
Baxter Healthcare Corp	Argipressin
Pharmasources	Argipressin
Novartis	Argipressin
AstraZeneca	Argipressin

Forecasting tools

Forecasting tools	Value
Structure to Sequence	N=C(N)NCCC[C@H](NC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](Cc2ccc(O)cc2)C(=O)N[C@@H](Cc2ccccc2)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N1)C(=O)NCC(N)=O
Structure Properties	N=C(N)NCCC[C@H](NC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](Cc2ccc(O)cc2)C(=O)N[C@@H](Cc2ccccc2)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N1)C(=O)NCC(N)=O
Sequence to Structure	CYFQNCPRG
Sequence Properties	CYFQNCPRG
Expasy ProtParam Tool	CYFQNCPRG
SEA	RUN SEA Predictions

Information Source

Property Name	Property ID
Patents	KBZOIRJILGZLEJ-XNGUIWTONA-N
pubchem	644077
Drugbank	Argipressin
DRAMP3	Argipressin
Uniprot	Argipressin
Cybase	Argipressin
CONOSERVER	Argipressin
BindingDB	BDBM50044777
CHEMBL	CHEMBL373742
CTD	D001127
Wikipedia	Vasopressin_(medication)
KEGG Compound/Drug	Argipressin
CHEBI	CHEBI:34543
EPA DSSTox	DTXSID0048349
FDA Global Substance Registration System (GSRS)	Y4907O6MFD
DTP/NCI	Argipressin
Chemspider	KBZOIRJILGZLEJ-XNGUIWTONA-N
VARIDT	DR00247

Reference

Pubmed_ID	Title	DOI	Journal
1628422	Comparison of the properties of the CsA analogs monoacetyl CyC (o-acetyl-threonine2 cyclosporin) and methyl-alanyl CsA (N-methyl-L-alanyl6 cyclosporin); monoacetyl cyclosporin is immunosuppressive without binding to cyclophilin	10.1111/j.1365-2249.1992.tb06892.x.	Clin Exp Immunol
Comparison of the properties of the CsA analogs monoacetyl CyC (o-acetyl-threonine2 cyclosporin) and methyl-alanyl CsA (N-methyl-L-alanyl6 cyclosporin); monoacetyl cyclosporin is immunosuppressive without binding to cyclophilin Abstract Cyclosporin (CsA) is an immunosuppressant which binds to cyclophilin (Cyp). The relationship between Cyp binding and immunosuppression has been questioned since one of the analogs of CsA, N-methyl-L-alanyl6 cyclosporin (methyl-alanyl CsA) binds to Cyp but is not immunosuppressive. We compared the immunosuppressive properties of CsA, methyl-alanyl CsA and o-acetyl-threonine2 cyclosporin (monoacetyl CyC), since monoacetyl CyC does not bind to Cyp when tested in cell-free assays and its immunosuppressive properties had not been tested. Cyp is a peptidyl-prolyl isomerase which is abundant in all human tissues, yet the activities of CsA are mostly confined to inhibition of T cell and thymocyte activation, and to neuro- and nephro-toxicity and are independent of inhibition of the isomerase. Activation of thymocytes and of T cells is regulated by the binding of a nuclear factor(s) (NFs) to the NF-AT region (-285 to -255) of the IL-2 promoter. We studied inhibition of binding to the NF-AT region of NFs derived from primary cultures of thymocytes treated with CsA or its analogs. In addition, we compared the effect of CsA and its analogs on the expression of the IL-2 gene in a stably transfected Jurkat-cell line (Fgl 5) which contains three copies of NF-AT and the reporter enzyme beta-galactosidase; and on inhibition of proliferation induced by concanavalin A (Con A) or IL-2. We found that monoacetyl CyC which does not bind to Cyp is immunosuppressive by our criteria when tested in cultured cells due to either a different mechanism of action or to metabolic activation.
2053827	Effect of the quality of fat substrate on the dynamics of fatty acid utilization during biosynthesis of cephalosporin C	None	Antibiot Khimioter
Effect of the quality of fat substrate on the dynamics of fatty acid utilization during biosynthesis of cephalosporin C Abstract Influence of the quality of the fats used on their utilization in the process of cephalosporin C fermentation and accumulation was studied. A decrease in the level of all the fractions of the fatty acids was observed during the fermentation process. The antibiotic yield with the use of oxidized fats was lower. Treatment of the fats with gaseous nitrogen prevented their oxidation. It was supposed that the decreased yields of the antibiotic were associated with the influence of the oxidized fats on the biosynthetic processes.
2339848	Experimental pulmonary eosinophilia in mice by Ascaris suum extract	10.1164/ajrccm/141.5_Pt_1.1289.	Am Rev Respir Dis
Experimental pulmonary eosinophilia in mice by Ascaris suum extract Abstract The transnasal administration of an extract of the parasite Ascaris suum (Asc) to C57BL/6 mice for 3 wk produced marked eosinophilia in the bronchoalveolar lavage (BAL) fluid. This pulmonary eosinophilia was not accompanied by blood eosinophilia. The oral administration of cyclosporin, 50 mg/kg body weight, every other day significantly suppressed the pulmonary eosinophilia. Athymic C57BL/6-nu/nu mice failed to develop pulmonary eosinophilia. These data indicate that pulmonary eosinophilia caused by this parasite extract is T-cell-dependent. Genetically mast-cell-deficient (WB X C57BL/6)F1-W/WV (W/WV) mice developed marked eosinophilia in the BAL, which shows that mast cells are not necessary in the formation of eosinophilia in BAL in this model. C57BL/6, W/WV, and Balb-C mice that developed eosinophilia in the BAL also showed elevated total IgE levels and IgE titers against Asc in the sera. On the other hand, C57BL/6-nu/nu mice and IgE low-responder SJL mice, which developed little eosinophilia, did not show elevated total IgE levels and IgE titers against Asc in the sera. However, oral administration of cyclosporin, 50 mg/kg, which inhibited eosinophilia in the BAL in C57BL/6 mice, did not significantly inhibit the elevation of total IgE or IgE against Asc in the sera. This indicates that serum IgE production is not required for the formation of eosinophilia.
3435104	Dosage, timing, and route of administration of cyclosporin A and nonimmunosuppressive derivatives of dihydrocyclosporin A and cyclosporin C against Schistosoma mansoni in vivo and in vitro	10.1128/AAC.31.10.1567.	Antimicrob Agents Chemother
Dosage, timing, and route of administration of cyclosporin A and nonimmunosuppressive derivatives of dihydrocyclosporin A and cyclosporin C against Schistosoma mansoni in vivo and in vitro Abstract The prophylactic and therapeutic effects of cyclosporin A (CsA) against percutaneous Schistosoma mansoni infection in MF1 mice were dose related and dependent on the temporal relationship between drug administration and infection. Antischistosomal activity, assessed by worm recovery from the host 6 weeks after infection, was most effective (complete worm elimination) when CsA was administered at the time of infection. Oral administration of CsA was less effective than subcutaneous injection, and no prophylactic activity was demonstrated by the former route. Derivatives of dihydrocyclosporin A and cyclosporin C, which have been reported to exert only poor immunosuppressive activity, exhibited efficacy against S. mansoni similar to that of CsA and were also less effective when given orally. Subcutaneous, but not oral CsA reduced cercarial skin penetration and transformation success; the derivative of dihydrocyclosporin A, however, was without effect. Moreover, CsA, but not the derivative of dihydrocyclosporin A, reduced the number of worms established after intraperitoneal injection of cercariae. These data provide further insight into the antischistosomal activity of cyclosporins, which appears to be distinct from their immunomodulatory properties, since parasite killing was retained both in immunologically disparate mice and with poorly immunosuppressive cyclosporin derivatives.