Peptide

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Octreotide Acetate

Basic information

CPKB ID CP00575
IUPAC Name
acetic acid;(4R,7S,10S,13R,16S,19R)-10-(4-aminobutyl)-19-[[(2R)-2-amino-3-phenylpropanoyl]amino]-16-benzyl-N-[(2R,3R)-1,3-dihydroxybutan-2-yl]-7-[(1R)-1-hydroxyethyl]-13-(1H-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carboxamide
Synonyms
(4R,7S,10S,13R,16S,19R)-13-((1H-Indol-3-Yl)Methyl)-19-((R)-2-Amino-3-Phenylpropanamido)-10-(4-Aminobutyl)-16-Benzyl-N-((2R,3R)-1,3-Dihydroxybutan-2-Yl)-7-((R)-1-Hydroxyethyl)-6,9,12,15,18-Pentaoxo-1,2-Dithia-5,8,11,14,17-Pentaazacycloicosane-4-Carboxamide-Acetate
517O014
75R0U2568I
760176-26-9
79517-01-4
Acetic-Acid,10-(4-Aminobutyl)-19-[(2-Amino-3-Phenylpropanoyl)Amino]-16-Benzyl-N-(1,3-Dihydroxybutan-2-Yl)-7-(1-Hydroxyethyl)-13-(1H-Indol-3-Ylmethyl)-6,9,12,15,18-Pentaoxo-1,2-Dithia-5,8,11,14,17-Pentazacycloicosane-4-Carboxamide
Akos030485976
C2L
Ccris-8708
Chembl1200480
Cs-0944
D-Phenylalanyl-L-Cysteinyl-L-Phenylalanyl-D-Tryptophyl-L-Lysyl-L-Threonyl-N-((1R,2R)-2-Hydroxy-1-(Hydroxymethyl)Propyl)-L-Cysteinamide-Cyclic-(2->7)-Disulfide-Acetate-(Salt)
D-Phenylalanyl-L-Cysteinyl-L-Phenylalanyl-D-Tryptophyl-L-Lysyl-L-Threonyl-N-((1R,2R)-2-Hydroxy-1-(Hydroxymethyl)Propyl)-L-Cysteinamide-Cyclic-(2-7)-Disulfide-Acetate-(Salt)
D-Phenylalanyl-L-Hemicystyl-L-Phenylalanyl-D-Tryptophyl-L-Lysyl-L-Threonyl-L-Hemicystyl-L-Threoninol-Cyclic-(2->7)-Disulfide-Acetate-(Salt)
D-Phenylalanyl-L-Hemicystyl-L-Phenylalanyl-D-Tryptophyl-L-Lysyl-L-Threonyl-L-Hemicystyl-L-Threoninol-Cyclic-(2-7)-Disulfide-Acetate-(Salt)
Dtxsid601027489
Hy-17365
L-Cysteinamide,-D-Phenylalanyl-L-Cysteinyl-L-Phenylalanyl-D-Tryptophyl-L-Lysyl-L-Threonyl-N-(2-Hydroxy-1-(Hydroxymethyl)Propyl)-,-Cyclic-(2-7)-Disulfide,-(R-(R*,R*))-,-Acetate-(Salt)
L-Cysteinamide,-D-Phenylalanyl-L-Cysteinyl-L-Phenylalanyl-D-Tryptophyl-L-Lysyl-L-Threonyl-N-(2-Hydroxy-1-(Hydroxymethyl)Propyl)-,-Cyclic(2-7)-Disulfide,-(R-(R*,R*))-,-Acetate-(Salt)
L-Cysteinamide,-D-Phenylalanyl-L-Cysteinyl-L-Phenylalanyl-D-Tryptophyl-L-Lysyl-L-Threonyl-N-[(1R,2R)-2-Hydroxy-1-(Hydroxymethyl)Propyl]-,-Cyclic-(2-->7)-Disulfide,-Acetate-(1:1)
Longastatin
Longastatina
Longastatina-Lar
Mfcd08277638
Nsc-685403
Octeotride-Sdi
Octreoide-Acetate
Octreolin
Octreotide-(Acetate)
Octreotide-(As-Acetate)
Octreotide-Acetate
Octreotide-Acetate-(Preservative-Free)
Octreotide-Acetate-[Usan:Jan]
Octreotide-Acetate-Depot
Octreotide-Lar
Q27266405
Sandostatin
Sandostatin-Lar
Sandostatine
Sms-201-995-(Acetate)
Sms-201995
Sms-201995-Ac
Sms-201-995-Ac
Unii-75R0U2568I
Vap-003
Vp-003
Source

Synthetic construct [Division : Synthetic]

Wikipedia: Synthetic construct

PubChem  

Function

Growth Hormone, Glucagon And Insulin Inhibitor   PubChem  

Information

Octreotide Acetate is the acetate salt of a synthetic long-acting cyclic octapeptide with pharmacologic properties mimicking those of the natural hormone somatostatin. Octreotide is a more potent inhibitor of growth hormone, glucagon, and insulin than somatostatin. Similar to somatostatin, this agent also suppresses the luteinizing hormone response to gonadotropin-releasing hormone, decreases splanchnic blood flow, and inhibits the release of serotonin, gastrin, vasoactive intestinal peptide (VIP), secretin, motilin, pancreatic polypeptide, and thyroid stimulating hormone.

PubChem|6917964  

Legend

Structure

Download structure
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similarity structure
Molecular Formula

C51H70N10O12S2
Molecular Weight 1078.46161 g/mol
SMILES

RUN SEA Predictions

 CC(=O)O.C[C@@H](O)[C@@H]1NC(=O)[C@H](CCCCN)NC(=O)[C@@H](Cc2c[nH]c3ccccc23)NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@@H](NC(=O)[C@H](N)Cc2ccccc2)CSSC[C@@H](C(=O)N[C@H](CO)[C@@H](C)O)NC1=O  

PubChem|6917964
InChI
InChI=1S/C49H66N10O10S2.C2H4O2/c1-28(61)39(25-60)56-48(68)41-27-71-70-26-40(57-43(63)34(51)21-30-13-5-3-6-14-30)47(67)54-37(22-31-15-7-4-8-16-31)45(65)55-38(23-32-24-52-35-18-10-9-17-33(32)35)46(66)53-36(19-11-12-20-50)44(64)59-42(29(2)62)49(69)58-41;1-2(3)4/h3-10,13-18,24,28-29,34,36-42,52,60-62H,11-12,19-23,25-27,50-51H2,1-2H3,(H,53,66)(H,54,67)(H,55,65)(H,56,68)(H,57,63)(H,58,69)(H,59,64);1H3,(H,3,4)/t28-,29-,34-,36+,37+,38-,39-,40+,41+,42+;/m1./s1  
InChIKey
XQEJFZYLWPSJOV-BKCXUWJMNA-N
2D Structure
PubChem|6917964

Sequence

Graph alignment
Local alignment
IUPAC Condensed
H-D-Phe-Cys(1)-Phe-D-Trp-Lys-Thr-Cys(1)-Thr-ol.CH3CO2H  

PubChem|6917964
Amino acid chain
H-D-Phe--Cys(1)--Phe--D-Trp--Lys--Thr--Cys(1)--Thr--ol  

CyclicPepedia|PP
Graph representation
H-D-Phe,Cys,Phe,D-Trp,Lys,Thr,Cys,Thr,ol @1,6  

CyclicPepedia|PP
One letter code from Structure
FCFWKTC  

CyclicPepedia|Struct2seq
Amino acid chain from Structure
Phe--Cys(1)--Phe--Trp--Lys--Thr--Serol(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.
svg Image

PubChem|6917964

Chemical and Physical Properties

CyclicPepedia|Struc2Seq + PP

Structure Properties

Property Name Property Value
Exact Mass 1078.46161
Number of Rings 5.0
Complexity 0.72
XlogP3 AA -0.7145
Heavy Atom Count 75.0
Hydrogen Bond Donor Count 14.0
Hydrogen Bond Acceptor Count 15.0
Rotatable Bond Count 17.0
Property Name Property Value
Formal Charge 0.0
Refractivity 285.3636
Rule_of_Five 0.0
Number of Atoms 75.0
Topological Polar Surface Area 369.52
Refractivity 285.3636
Veber Rule 0.0
Ghose Filter 0.0
Property Name Property Value
RDKit Fingerprint
11000111110100100111110011110000111000100111100000011011101001101110101111101110111111010100100011110101110101001010011001110111000001011000111100001111000000000100001000011011000111001111000101110000101001001000000110000001010001000101000110001110011101101111000110001110000110101111110000000010000001011111000101011001110100000011111110111110011100000000111100001001000001000010101001101010010100000110000100001111000010110001101000111111110010100000110000010010111000011100000100000110001101000111100100101111111101111110110110001101101010101101100001010110101001101110010010001001000110111100101110010001001010011010100000111111110000111100100111110111011001000110111110111111010111001001011100110000101101000000000111001010101101001111101010110010001110101011101110011000000111001001011010011011001100011011100100011101111011110000011111111001101001110111111100110011000110000101001000000011001101101110111100110100011100110110110000011101001010011001110100010000011001010110001001110001110101000101000000111101111111110111110110111111110001001011010101001100101001100001100001000001110110000101001001001010000001101001100011101101110010010100101001011000100010110100101111001001010011111110011011001000000101001101110011100100011101010111001010011001101111000110101110001010000001111000110100011001011010111101101111010100101001001011111111010000011110110011110010110001011101001111001000000011000101101100000011100101101011001000001001111100100001001011101110101110010101110001110000101111001010010000110100101011111011110101011000010100011111110100100101100000100100100101001011010111100010000011100110101011010010100000010110100000000000100010010010001011001011000110001011100100000000110001111110100100100101000101010110101000100000100011011001011101111010010110100010001000100001111110100011110011111111101100100101111010111110100111111010000001100001010000011011101010010100001101101010010100101101000011011011010111001110010111110110100011011001011101011001001001101101100111000101111100110110001000000011101100010000100100111001010011
Morgan Fingerprint
0100000000100000000000000000000001000000001000000000000000100000100000000000000110000000001000000000000000000000000101010000000010000000000000000001000000000000100000000000000100000000000000000000000000000000000000000000101000010000000000000000000000000000000000000000000000000000001100000000000000000100000000000010001000000100100001100000000000000000000110000010100000000001000000000001010000000000001000000000000000000000000000001001000000000000000000000110000000000000001000100010000000001100000000000000110000000001000000000000000000000000000001000000000000000000000001000000000100000000000000000000000010000000000000000000000000010000000000000010000000000000010001000001000000000001010000000000000000000000000100000000001000100000000000000000000000000001000000000000000000000000001000000000000000001011000010001000100001001000100000000000000001000001010000000000000000000000000000010000010000010000000000000100010000000010000000000000000000000000000001000000001000000000100001000000000000000000000000100000000001010000
MACCS Keys
00000000000000100000000000000000000010000000000000000110000000000101000000000001001110001111100111001100110001110000111011011101010101001111111101110111111111111111111

Sequence Properties

Property Name Property Value
Boman Index -0.39
Instability 8.57142857142857
Charge 0.873739833690026

Binding Target

Other evidence

Property Name Property ID
TTD D02XIY
DrugMAP DMHIDCJ

Manufacturers

Manufacturers Name Value
CreativePeptides
Bayer healthcare pharmaceuticals
Upsher smith laboratories
Merck
Manufacturers Name Value
Apotex
Baxter Healthcare Corp
Pharmasources
Novartis
AstraZeneca

Forecasting tools

Information Source

Reference

Pubmed_ID Title DOI Journal

15497957

 Cyanopeptolin 963A, a chymotrypsin inhibitor of Microcystis PCC 7806 10.1021/np049828f.

J Nat Prod

Cyanopeptolin 963A, a chymotrypsin inhibitor of Microcystis PCC 7806

Abstract

  • A new depsipeptide, cyanopeptolin 963 A (1), was isolated from an axenic strain of the toxic freshwater cyanobacterium Microcystis PCC 7806. The structure of this compound was elucidated by chemical and spectroscopic analyses, including high-resolution ESI-FTICR-MS, 2-D NMR, and GC-MS of the hydrolysate. The major structural difference compared to previously characterized cyanopeptolins of this strain is the replacement of the basic amino acid in position 3 by L-tyrosine. Compound 1 displayed inhibitory activity against chymotrypsin with an IC50 value of 0.9 microM.