Peptide

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Cyclosporin A

Basic information

CPKB ID CP00007
IUPAC Name
30-ethyl-33-(1-hydroxy-2-methylhex-4-enyl)-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21-di(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone
Synonyms
5-(N-Methyl-D-Valine)-Cyclosporin-A
59865-13-3
83602-39-5
Akos024456385
C62H111N11O12
Cyclosporin-A
Divk1C_000871
Ft-0603155
Ft-0603156
Ft-0701261
Hb0220
Hms3267I20
Hms3372A06
Hms3651O16
Hms3654L18
Kbio1_000871
Kbio2_000780
Kbio2_003348
Kbio2_005916
Kbio3_002686
Kbiogr_001898
Kbioss_000780
Mfcd00274558
Ncgc00093704-11
Ninds_000871
Spbio_001467
Spectrum_000300
Spectrum2_001484
Spectrum3_001593
Spectrum4_001279
Sy012000
Source

Tolypocladium inflatum [Division : Plants and Fungi]

Taxonomy :29910 (Fungi-Ascomycota-Hypocreales-Sordariomycetes-Ophiocordycipitaceae Tolypocladium)  

Wikipedia: Tolypocladium inflatum

Mycale hentscheli [Division : Invertebrates]

Taxonomy :659499 (Metazoa-Porifera-Poecilosclerida-Demospongiae-Mycalidae Mycale)  

Wikipedia: Mycale hentscheli

PubChem  

Family

Cyclosporins   Norine  

Function

Anti-Microbial   Immunomodulating   Norine  

Information

Cyclosporin a appears as white prismatic needles (from acetone) or white powder. (NTP, 1992) Cyclosporin A is a natural product found in Tolypocladium inflatum and Mycale hentscheli with data available. A cyclic undecapeptide from an extract of soil fungi. It is a powerful immunosupressant with a specific action on T-lymphocytes. It is used for the prophylaxis of graft rejection in organ and tissue transplantation. (From Martindale, The Extra Pharmacopoeia, 30th ed).

PubChem|2909   Norine|NOR00033  

Legend

Structure

Download structure
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similarity structure
Molecular Formula

C62H111N11O12
Molecular Weight 1201.841368 g/mol
SMILES

RUN SEA Predictions

 CC=CCC(C)C(O)C1C(=O)NC(CC)C(=O)N(C)CC(=O)N(C)C(CC(C)C)C(=O)NC(C(C)C)C(=O)N(C)C(CC(C)C)C(=O)NC(C)C(=O)NC(C)C(=O)N(C)C(CC(C)C)C(=O)N(C)C(CC(C)C)C(=O)N(C)C(C(C)C)C(=O)N1C  

PubChem|2909
InChI
InChI=1S/C62H111N11O12/c1-25-27-28-40(15)52(75)51-56(79)65-43(26-2)58(81)67(18)33-48(74)68(19)44(29-34(3)4)55(78)66-49(38(11)12)61(84)69(20)45(30-35(5)6)54(77)63-41(16)53(76)64-42(17)57(80)70(21)46(31-36(7)8)59(82)71(22)47(32-37(9)10)60(83)72(23)50(39(13)14)62(85)73(51)24/h25,27,34-47,49-52,75H,26,28-33H2,1-24H3,(H,63,77)(H,64,76)(H,65,79)(H,66,78)  
InChIKey
PMATZTZNYRCHOR-FQWWPSEDNA-N
2D Structure
PubChem|2909

Sequence

Graph alignment
Local alignment
One letter code from Structure
LVLAALLVTAG  

CyclicPepedia|Struct2seq
Amino acid chain from Structure
Abu(1)--NMe-Gly--NMe-Leu--Val--NMe-Leu--Ala--Ala--NMe-Leu--NMe-Leu--NMe-Val--NMe-Bmt(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 1201.841368
Number of Rings 1.0
Complexity 0.458823529
XlogP3 AA 3.269
Heavy Atom Count 85.0
Hydrogen Bond Donor Count 5.0
Hydrogen Bond Acceptor Count 12.0
Rotatable Bond Count 15.0
Property Name Property Value
Formal Charge 0.0
Refractivity 328.4446
Rule_of_Five 0.0
Number of Atoms 85.0
Topological Polar Surface Area 278.8
Refractivity 328.4446
Veber Rule 0.0
Ghose Filter 0.0
Property Name Property Value
RDKit Fingerprint
01000000001000100100100011011000110000000011000000100010100001101100110101111100100000010010110010000110000001001000001010110000010000000010110100011101100010010110001010010100000110000110101111000000001001001000000100000000010001000100111100000010011100111011000111001000000010000001000000000001011000011010101111000000010100010000001011011000010000000010101001000000010000000000111001001010010100000000000110011110000010100000100000101001100010000101000100010010011000000100000000001010000110011101110001100101110101100000011010011101001100100000100010010100001001011110010010001001001010110100101100100001001010011100011000001111000101100110000011100111000000000110001000100000010101011100011100100010000101100000000100101010001000000001100000011010001101110000101100010000000001100001001000001000001110001000000100000001110001000000010011001100001000010010000100101011000100100000111001001011001100000000111000000110010110011000000001011110100010001001011001010000011000010011011010010001110100010100000000100000001010001011000100110011100000000010000000000100001101100001010000001001110010001001100001010010000010100000000111001001010000010100001000101000101110100100101101010001010000011010000001001100110101100100000111100000011100010010011110000000100100001110100000000000100010100000000001011001110111100001000100101101100000010001110100000001010001110011010000010000100100010000001100000001110101001100101000100101100011000000011010001111001000001011001101000100010000100001100000010111011000000000100100100111000011110000001000010000001100100100010011101000000100100011011001000101100010000001000000100011000000000010100000010011000000000010010011000001100010000100000010000001000000010000011100100100100000000001000010000000101000100011001110000001010010010000100010000000000000010101101000001001111101000100000011011010011010100110010000000110100000000010010000100000010000011001101100000100101101000000010010110101000010000110000110010010110001111011000011010001001101100000100101001100100000000000000011101001100100100100010000010011
Morgan Fingerprint
0100010000100000000100000000000001000010000000010000000000000000000000000000000010000000001000100000010000000000000100000100001000001100000000000000000000000000000000100000000000000000001000000000001000000000100000000001000000010000000000000000000000100100000000000000010000000000000101000000001010000100000000000010000000000000000010010000000000000100000010000000000000100000000000000000000000000000000000000000000000000000000000100000000000000000000000000000000000000001000010000010000000001000000000000000000000000000000000000000000000001000000000001000000000000000000000000000000000000100000010000000000000000000000000000000000000000010000000000010000010000000010001000001000000000100000000100000000000000000000000000000010000000000000000010000010000000000010000000000000000000000000000000000001000000001000000000000000100100000000000000000100000000000000000000000000000000010000000000000010000000000000000000000000100100010000000110000000000000000000000000000000000000000000000001000000000000000000000000000000000010000
MACCS Keys
00000000000000000000000000000000000000000000000000000110000000000000000000110001000001100111110101011000100010110011110011100001100110001101111100101111111111111100110

Sequence Properties

Property Name Property Value
Boman Index -2.8690909090909
Instability 1.37272727272727
Charge -0.00201570060725275
Aliphatic Index 221.818181818181

Binding Target

Other evidence

Property Name Property ID
TTD D0O3YF
DrugMAP DMAZJFX DMT2KRV DMP6BU3

Biologic Description

Toxicity PubChem|2909

Cyclosporin A: known to be a human carcinogen.

Metabolism PubChem|2909

Cyclosporine is extensively metabolized in the liver by the cytochrome-P450 3A (CYP3A) enzyme system & to a lesser degree by the GI tract & kidneys. At least 25 metabolites have been identified in human bile, feces, blood, & urine. Although the cyclic peptide structure of cyclosporine is relatively resistant to metab, the side chains are extensively metabolized. All of the metabolites have both reduced biological activity & toxicity compared to the parent drug.

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

2358465

 Cyclosporin synthetase. The most complex peptide synthesizing multienzyme polypeptide so far described

None

J Biol Chem

Cyclosporin synthetase. The most complex peptide synthesizing multienzyme polypeptide so far described

Abstract

  • Cyclosporin A and its homologues are synthesized by a single multifunctional enzyme from their precursor amino acids. Cyclosporin synthetase is a polypeptide chain with a molecular mass of approximately 800 kDa. In 3% polyacrylamide-sodium dodecyl sulfate gels it shows a single band of approximately 650 kDa, which appears to not be glycosylated. The enzyme could be purified to near-homogeneity in five steps. A 72-fold purification was obtained. All constitutive amino acids of cyclosporins are activated as thioesters via aminoadenylation by the same enzyme. Then N-methylation of the thioester-bound amino acids which are present in methylated form in the cyclosporin molecule takes place, whereby S-adenosyl-L-methionine serves as the methyl group donor. Methyltransferase activity is an integral entity of the enzyme; this could be shown by a photoaffinity labeling method. 4'-Phosphopantetheine is a prosthetic group of cyclosporin synthetase similar to other peptide and depsipeptide synthetases. Cyclosporin synthetase shows cross-reactions with monoclonal antibodies directed against enniatin synthetase."