Peptide

CyclicPepedia Knowledge Base

Visitor
Visitor
Status Profile

Oacsa

Basic information

CPKB ID CP00515
IUPAC Name
[(E,1R,2R)-1-[(2S,5S,11S,14S,17S,20S,23R,26S,29S,32S)-5-ethyl-1,7,10,16,20,23,25,26,31-nonamethyl-11,17,26,29-tetrakis(2-methylpropyl)-3,6,9,12,15,18,21,24,27,30,33-undecaoxo-14,32-di(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacont-2-yl]-2-methylhex-4-enyl] acetate
Synonyms
[(E,1R,2R)-1-[(2S,5S,11S,14S,17S,20S,23R,26S,29S,32S)-5-Ethyl-1,7,10,16,20,23,25,26,31-Nonamethyl-11,17,26,29-Tetrakis(2-Methylpropyl)-3,6,9,12,15,18,21,24,27,30,33-Undecaoxo-14,32-Di(Propan-2-Yl)-1,4,7,10,13,16,19,22,25,28,31-Undecazacyclotritriacont-2-Yl]-2-Methylhex-4-Enyl]-Acetate
6-[(2S,3R,4R,6E)-3-(Acetyloxy)-4-Methyl-2-(Methylamino)-6-Octenoic-Acid]-Cyclosporin-A
B-3-243
B3-243
Cyclosporin-A,-6-Acetate
O-Acetyl-C(9)-Cyclosporin-A
Oacsa
Sdz-33-243

Legend

Structure

Download structure
2D img
300x300 pixels
100x100 pixels
500x500 pixels
file
similarity structure
Molecular Formula

C64H113N11O13
Molecular Weight 1243.851933 g/mol
SMILES

RUN SEA Predictions

 C/C=C/C[C@@H](C)[C@@H](OC(C)=O)[C@H]1C(=O)N[C@@H](CC)C(=O)N(C)CC(=O)N(C)[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N(C)[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@H](C)C(=O)N(C)[C@@](C)(CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N(C)[C@@H](C(C)C)C(=O)N1C  

PubChem|6438472
InChI
InChI=1S/C64H113N11O13/c1-26-28-29-41(15)53(88-44(18)76)52-57(81)67-45(27-2)59(83)70(20)34-49(77)71(21)47(31-36(5)6)56(80)69-50(39(11)12)61(85)72(22)48(32-37(7)8)55(79)65-42(16)54(78)66-43(17)58(82)75(25)64(19,33-38(9)10)63(87)68-46(30-35(3)4)60(84)73(23)51(40(13)14)62(86)74(52)24/h26,28,35-43,45-48,50-53H,27,29-34H2,1-25H3,(H,65,79)(H,66,78)(H,67,81)(H,68,87)(H,69,80)/b28-26+/t41-,42+,43-,45+,46+,47+,48+,50+,51+,52+,53-,64+/m1/s1  
InChIKey
SNGZGZKWJAWNLP-XIHGQEFNNA-N
2D Structure
PubChem|6438472

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--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 1243.851933
Number of Rings 1.0
Complexity 0.556818182
XlogP3 AA 3.8877
Heavy Atom Count 88.0
Hydrogen Bond Donor Count 5.0
Hydrogen Bond Acceptor Count 13.0
Rotatable Bond Count 16.0
Property Name Property Value
Formal Charge 0.0
Refractivity 337.9815
Rule_of_Five 0.0
Number of Atoms 88.0
Topological Polar Surface Area 293.66
Refractivity 337.9815
Veber Rule 0.0
Ghose Filter 0.0
Property Name Property Value
RDKit Fingerprint
01010001001000100100100011011000110000001011100000100110110101101110110101111100100011010010110011000111000001111000001011110000010000100110110100011101100010011110001010010100010110000110101111000100001001001000000101001010010011100100111100000010011101111011010111001000000010000011001100000001011000011111111111010010010100010100111011011010010000000011101001100000010000000000111001001011010100000011000110011110001010100010100100111001101110000101001100010110011110010110010000001010001110011101110101100101110101100110011110011101001100100001100010010111001001111110010010001001111110110100101100100001001010011110111100011111010111100110000011101111010000000110001000100000010101011100011100100110010101100000010100101010001010000101100100011010001101110010101101010000001001101011001010001000001110001000000100110001110001000010111011001111011000010011000100101111000100101000111001101011101100100000111101000110010110011110000001011110101110001101011011010010011100011011011010011011110100011110000000101010001010001011000100111011110000100110110000100100011101100001010000001101110010001001100101010010000010110000001111001001010000011100001001101000111110100100101101010001011000011011000001101100110111100100000111101000011101010010011111000001100100001110100001010000100010100001010001111001110111100001000101101111100000010001110100100111010101110011010000010000100100010010111100000111110101001100111010100101100011000010011011001111011010111011111101000101010011100101100000010111011100000000100100111111000011110000101100010000001100110100010011101000101110100111011101010101100010000001000000100011010000010010111000010011000000000010010011000101100010000100000010010101000001011000011100100100101000000001000111001100101000100011001110000001010111010001101010000110000000011101101000001001111101001100001011011010011010110110010000000111100001010010010000100000010100011001101100100101101101001010010010110101100010010110010111010010110011111011000011010001001101100010110101011100100000010000000011101001100110101100010001011011
Morgan Fingerprint
0100010000110000000100000000000001001010000000010000000000000000000001000000000010000001001000100000010000000000000100000100001000001100000000000000000000000000000000100001000000000000001010000000001000000000100000000001000010000000000000010000000000100110000000000000010000000000000101000000001010000100000000000010000000000000000010010000000000000100000010000000000000100000000000000000000000000000000000000000001000000010000000100000000000000000000000000100000000000001000000000010000000001000000000000000000000000000000000010000000000001000000000001000000000000000000000000000000000000110000010000000000000000000000000000010000000000000000000000010000000000000010001000001000000000100000000110000000000000000010000000000010000000000000000000000000000000001010000000010000000000000000000000000001000000001000000000000000100000000000000000000100000001000000000000000001000000010000000000000010000000000100000000000000100100010000000110000000000000000000000000000000000000000000000001000000000000001000000000000000001010000
MACCS Keys
00000000000000000000000000000000000000000000000000000010000000000010000000110001000001100111110101011000100010111011110011110011100110001100111100101111111111111100110

Sequence Properties

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

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

11895390

 Kulokekahilide-1, a cytotoxic depsipeptide from the cephalaspidean mollusk Philinopsis speciosa 10.1021/jo010176z.

J Org Chem

Kulokekahilide-1, a cytotoxic depsipeptide from the cephalaspidean mollusk Philinopsis speciosa

Abstract

  • The cytotoxic depsipeptide kulokekahilide-1, which contains two unusual amino acids, 4-phenylvaline and 3-amino-2-methylhexanoic acid, was isolated from the cephalaspidean mollusk Philinopsis speciosa. Structure elucidation of kulokekahilide-1 was carried out by spectroscopic analysis and chemical degradation. The absolute stereochemistry was determined by Marfey analysis for amino acids and chiral HPLC analysis for hydroxy acids. All four stereoisomers of 4-phenylvaline and 3-amino-2-methylhexanoic acid, which were necessary for Marfey analysis, were synthesized by use of the Heck reaction and Evans's method, respectively. Kulokekahilide-1 showed cytotoxicity against P388 murine leukemia cells with an IC(50) value of 2.1 microg/mL.