Basic information

CPKB ID	CP00063
IUPAC Name	(3S,6S,9R,12S)-6-(4-aminobutyl)-12-benzyl-9-(1H-indol-3-ylmethyl)-3-[(1R)-1-phenylmethoxyethyl]-1,4,7,10,13-pentazacycloicosane-2,5,8,11,14-pentone
Synonyms	(3S,6S,9R,12S)-6-(4-Aminobutyl)-12-Benzyl-9-(1H-Indol-3-Ylmethyl)-3-[(1R)-1-Phenylmethoxyethyl]-1,4,7,10,13-Pentazacycloicosane-2,5,8,11,14-Pentone (3S,6S,9R,12S)-9-((1H-Indol-3-Yl)Methyl)-6-(4-Aminobutyl)-12-Benzyl-3-((R)-1-(Benzyloxy)Ethyl)-1,4,7,10,13-Pentaazacycloicosane-2,5,8,11,14-Pentaone 6-(4-Aminobutyl)-12-Benzyl-3-[1-(Benzyloxy)Ethyl]-9-[(1H-Indol-3-Yl)Methyl]-1,4,7,10,13-Pentaazacycloicosa-1,4,7,10,13-Pentaene-2,5,8,11,14-Pentol 7-Cpp 84211-54-1 Akos024457638 Antagonist-Srif-A Cpp1 Cs-0028990 Cycam Cyclo-(7-Ahep-Phe-Trp-Lys-Bzl-Thr)-Somatostatin Cyclo(7-Ahep-Phe-Trp-Lys-Thr(Bzl)) Cyclo-(7-Aminoheptanoyl-Phe-D-Trp-Lys-Thr(Bzl)) Cyclo-(7-Aminoheptanoyl-Phe-D-Trp-Lys-Thr[Bzl]) Cyclo(7-Aminoheptanoyl-Phe-D-Trp-Lys-Thr[Bzl]),->=95%-(Hplc),-Powder Cyclo(7-Aminoheptanoylphenylalanyl-Tryptophyl-Lysyl-Benzylthreonyl) Cyclo-(7-Aminoheptanoyl-Phenylalanyl-Tryptophyl-Lysyl-Benzylthreonyl)-Somatostatin Cyclosomatostatin Cyclo-Somatostatin Dtxsid901004468 Hy-P1201 L-Threonine,-N-(7-Amino-1-Oxoheptyl)-L-Phenylalanyl-D-Tryptophyl-L-Lysyl-O-(Phenylmethyl)-,-(2S-(1(R(R)),2Alpha,3Abeta,7Abeta))- Somatostatin,-Cyclo-(7-Ahep-Phe-Trp-Lys-Bzl-Thr)- Somatostatin,-Cyclo-(7-Aminoheptanoyl-Phenylalanyl-Tryptophyl-Lysyl-Benzylthreonyl)- Zinc95670552

Legend

Structure

Molecular Formula	C44H57N7O6
Molecular Weight	779.4370325 g/mol
SMILES RUN SEA Predictions	C[C@@H](OCc1ccccc1)[C@@H]1NC(=O)[C@H](CCCCN)NC(=O)[C@@H](Cc2c[nH]c3ccccc23)NC(=O)[C@H](Cc2ccccc2)NC(=O)CCCCCCNC1=O PubChem\|122080
InChI	InChI=1S/C44H57N7O6/c1-30(57-29-32-18-8-5-9-19-32)40-44(56)46-25-15-3-2-10-23-39(52)48-37(26-31-16-6-4-7-17-31)42(54)50-38(27-33-28-47-35-21-12-11-20-34(33)35)43(55)49-36(41(53)51-40)22-13-14-24-45/h4-9,11-12,16-21,28,30,36-38,40,47H,2-3,10,13-15,22-27,29,45H2,1H3,(H,46,56)(H,48,52)(H,49,55)(H,50,54)(H,51,53)/t30-,36+,37+,38-,40+/m1/s1
InChIKey	YHVHQZYJGWGAKN-CMVFKNNYNA-N

2D Structure PubChem\|122080

Sequence

IUPAC Condensed	cyclo[Lys-Thr(Bn)-Unk-Phe-D-Trp] PubChem\|122080
Amino acid chain	Lys(1)--Thr(Bn)--Unk--Phe--D-Trp(1) CyclicPepedia\|PP
Graph representation	Lys,Thr(Bn),Unk,Phe,D-Trp @0,4 CyclicPepedia\|PP
One letter code from Structure	FWKT CyclicPepedia\|Struct2seq
Amino acid chain from Structure	Ac-Phe(1)--Trp--Lys--C7:0(1) 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.

Chemical and Physical Properties

CyclicPepedia|Struc2Seq + PP

Structure Properties

Property Name	Property Value
Exact Mass	779.4370325
Number of Rings	5.0
Complexity	0.666666667
XlogP3 AA	3.7069
Heavy Atom Count	57.0
Hydrogen Bond Donor Count	7.0
Hydrogen Bond Acceptor Count	7.0
Rotatable Bond Count	12.0

Property Name	Property Value
Formal Charge	0.0
Refractivity	219.5646
Rule_of_Five	0.0
Number of Atoms	57.0
Topological Polar Surface Area	196.54
Refractivity	219.5646
Veber Rule	0.0
Ghose Filter	0.0

Property Name	Property Value
RDKit Fingerprint	11000111110100100111010111110000111000101111000000011111101011101110101111101100111111010011110011110101110101101010011001110111000001011100111100001111000010000100001000011001010111001111000101110000101101101000000110010000010011000101000100001100011101101111000110001110000111111111010000100010000001011111100101010011110100000011111110011110011100000000111100000011000001000010101001101111010100000111000100001111000010110001001000111111110010101000010000010010111000011100000000000110001101000111100100101101011101101110110110001101101010101101100001010110101001100111010010001001010110111100100110010001000010011110100000111011110000101111100111100111011001000110111110111111010111011001011100110000100101000000010100001011101101001111101010001010001110100110110110011001000111001001011010001011001100011010100100001001111011110000001011101011101101110101011100100011000110001101001001000011001101000110111100110110011100110010110000011110001010011001110010010010111101010111001001111001110101001100100000111101111111110111110110111111110001001111010001001100111001100011100001010011110110100101001001001010000001101000000011101101010000010100101000011000000010110000101111001001011011011111000000001000000100001101010011100100011101010111000011011001100101000110101110011010000000011001110100111001111010111101100111000000100001001111111111100010010110110011110010110001011101001111001000000011010101011100000011100101100011001010001001111100110001111011101111101111010100110001110000101011101010000000100100100011101011110111011100010100011111110100000100100000100100000101001011010101100010000011100110101011010010100000011110101000000000000110010010001111000011000110001011100100010001100101111110101100101101000101000110001000100000100011011001011101011010010111101010000010100001111110100000100011111111101100100101111010111110100111111010100001100001010110011011101010010000001101101001010100101101000101011011010111101110000111110111000011011001011111011001011001101001101110000101111110110110000000000011101100010000100100111001110011
Morgan Fingerprint	0110100000100000000000000000000001000000001000000000000000100000100000000000000010000000001000000000000000000000000100010000000000000000000000000001000000000000100000000000000100000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000100000010000100000000000000000100010000100010100000000101100001100000000000000000000110000000100000000000000000000000010100000000000000000000000000000000000000001001000000000000000000000010000000000000001000000010000000001100000000000000000000000000000000000000000000000000000001010000000000000000000000000000000100000000000000000000000000000000000000000100000000000000000000000010000000000000010000000000000000001000000000010000000000000000001000000000001000100000000000000100000000000001000000000000000000000000000000000000000000000010000000001000000000000000100000000110000001000001000000000000000000000000000100010000000000000000000000000100000000000010000100000000000000000000000001000000000000000000000001000000000000001010000000100000000000110000
MACCS Keys	00000000000000000000000000000000000000000000000000000010000000000100000000000001001110000111100111001100110001110000111011000111110110001110101101110011111111111111110

Sequence Properties

Property Name	Property Value
Boman Index	0.702499999999999
Instability	7.5
Charge	0.997689265540743

Manufacturers

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

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

Forecasting tools

Forecasting tools	Value
Structure to Sequence	C[C@@H](OCc1ccccc1)[C@@H]1NC(=O)[C@H](CCCCN)NC(=O)[C@@H](Cc2c[nH]c3ccccc23)NC(=O)[C@H](Cc2ccccc2)NC(=O)CCCCCCNC1=O
Structure Properties	C[C@@H](OCc1ccccc1)[C@@H]1NC(=O)[C@H](CCCCN)NC(=O)[C@@H](Cc2c[nH]c3ccccc23)NC(=O)[C@H](Cc2ccccc2)NC(=O)CCCCCCNC1=O
Sequence to Structure	FWKT
Sequence Properties	FWKT
Expasy ProtParam Tool	FWKT
SEA	RUN SEA Predictions

Information Source

Property Name	Property ID
Patents	YHVHQZYJGWGAKN-CMVFKNNYNA-N
pubchem	122080
Drugbank	Cyclosomatostatin
DRAMP3	Cyclosomatostatin
Uniprot	Cyclosomatostatin
Cybase	Cyclosomatostatin
CONOSERVER	Cyclosomatostatin
BindingDB	C[C@@H](OCc1ccccc1)[C@@H]1NC(=O)[C@H](CCCCN)NC(=O)[C@@H](Cc2c[nH]c3ccccc23)NC(=O)[C@H](Cc2ccccc2)NC(=O)CCCCCCNC1=O
CHEMBL	Cyclosomatostatin
CTD	Cyclosomatostatin
Wikipedia	Cyclosomatostatin
KEGG Compound/Drug	Cyclosomatostatin
CHEBI	YHVHQZYJGWGAKN-CMVFKNNYNA-N
EPA DSSTox	DTXSID901004468
FDA Global Substance Registration System (GSRS)	Cyclosomatostatin
DTP/NCI	Cyclosomatostatin
Chemspider	YHVHQZYJGWGAKN-CMVFKNNYNA-N

Reference

Pubmed_ID	Title	DOI	Journal
3806605	Analogues of the cytostatic and antimitogenic agents chlamydocin and HC-toxin: synthesis and biological activity of chloromethyl ketone and diazomethyl ketone functionalized cyclic tetrapeptides	10.1021/jm00384a013.	J Med Chem
Analogues of the cytostatic and antimitogenic agents chlamydocin and HC-toxin: synthesis and biological activity of chloromethyl ketone and diazomethyl ketone functionalized cyclic tetrapeptides Abstract The synthesis and biological activity of four novel analogues of the cytostatic and antimitogenic agents chlamydocin and HC-toxin are reported in which the natural products' reactive epoxy ketone side-chain moiety is replaced by a chloromethyl or a diazomethyl ketone functionality, but the respective 12-membered cyclic tetrapeptide ring systems are retained. Syntheses of the linear tetrapeptide sequences were, in each case, achieved by conventional methodology and designed such that cyclization would be onto proline. The use of suitably protected L-2-aminosuberic acid (Asu) enabled the ready assimilation of the desired chloromethyl and diazomethyl ketone functionalities after cyclization. Cyclization was accomplished by using bis(2-oxo-3-oxazolidinyl)phosphinic chloride (BOP-Cl). Yields of cyclic product were comparable to or, in the case of the HC-toxin ring system, better than those previously reported. Liberation of the Asu-side-chain acid and manipulation to the required functionalities via mixed anhydride to the diazomethyl ketone and quenching with HCl to yield the chloromethyl ketone was achieved in excellent yield for the HC-toxin analogues but in only moderate yield for the chlamydocin analogue. The antimitogenic activities of HC-toxin chloromethyl ketone (IC50 = 30-40 ng/mL) and chlamydocin chloromethyl ketone (IC50 = 3-10 ng/mL) were found to be 3-4-fold lower than those of the natural products themselves. The diazomethyl ketone analogue of HC-toxin was found to be inactive (IC50 greater than 2000 ng/mL). A modification of the HC-toxin peptide ring system, L-Phe3-HC-toxin chloromethyl ketone was found not to be a more active analogue (IC50 = 40-100 ng/mL). The nature of the putative target molecule, the binding interactions of the various analogues and the contribution of rate of inhibition toward activity are briefly discussed. The chloromethyl ketones herein reported constitute the most potent synthetic antimitogenic cyclic tetrapeptide analogues yet designed."
3918884	Reciprocal biological activities of the cyclic tetrapeptides chlamydocin and HC-toxin	10.1007/BF02004498.	Experientia
Reciprocal biological activities of the cyclic tetrapeptides chlamydocin and HC-toxin Abstract Chlamydocin, a potent cytostatic agent against cultured mammalian cells, and HC-toxin, a host-specific phytotoxin, are cyclic tetrapeptides containing the same epoxide alpha-amino acid. We show here that these compounds have reciprocal biological activity; HC-toxin is cytostatic against cultured mastocytoma cells, and chlamydocin has host-specific toxin activity against maize. Chlamydocin and another related cyclic peptide, Cyl-2, are less host-specific than HC-toxin because maize tolerant to HC-toxin is more sensitive to chlamydocin and Cyl-2.
4857466	Isolation and structural clarification of chlamydocin	10.1002/hlca.19740570306.	Helv Chim Acta
Isolation and structural clarification of chlamydocin Abstract No profile to view