Peptide

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Echinocandin B

Basic information

CPKB ID CP00639
IUPAC Name
(9Z,12Z)-N-[(3S,6S,9S,11R,15S,18S,20R,21R,24S,25S,26S)-6-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-11,20,21,25-tetrahydroxy-3,15-bis[(1R)-1-hydroxyethyl]-26-methyl-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexazatricyclo[22.3.0.09,13]heptacosan-18-yl]octadeca-9,12-dienamide
Synonyms
(1(Z,Z),6(2.Alpha.,3.Beta.,4.Beta.))-(4R,5R)-4,5-Dihydroxy-N2-(1-Oxo-9,12-Octadecadienyl)-L-Ornithyl-L-Threonyl-Trans-4-Hydroxy-L-Prolyl-(S)-4-Hydroxy-4-(4-Hydroxyphenyl)-L-Threonyl-L-Threonyl-3-Hydroxy-4-Methyl-L-Proline-Cyclic-(6->1)-Peptide
(9Z,12Z)-N-((2R,6S,9S,11R,12R,14As,15S,16S,20S,23S,25As)-23-((1S,2S)-1,2-Dihydroxy-2-(4-Hydroxyphenyl)Ethyl)-2,11,12,15-Tetrahydroxy-6,20-Bis((R)-1-Hydroxyethyl)-16-Methyl-5,8,14,19,22,25-Hexaoxotetracosahydro-1H-Dipyrrolo[2,1-C:2',1'-L][1,4,7,10,13,16]Hexaazacyclohenicosin-9-Yl)Octadeca-9,12-Dienamide
(9Z,12Z)-N-[(3S,6S,9S,11R,15S,18S,20R,21R,24S,25S,26S)-6-[(1S,2S)-1,2-Dihydroxy-2-(4-Hydroxyphenyl)Ethyl]-11,20,21,25-Tetrahydroxy-3,15-Bis[(1R)-1-Hydroxyethyl]-26-Methyl-2,5,8,14,17,23-Hexaoxo-1,4,7,13,16,22-Hexazatricyclo[22.3.0.09,13]Heptacosan-18-Yl]Octadeca-9,12-Dienamide
(9Z,12Z)-N-{(2R,6S,9S,11R,12R,14As,15S,16S,20S,23S,25As)-23-[(1S,2S)-1,2-Dihydroxy-2-(4-Hydroxyphenyl)Ethyl]-2,11,12,15-Tetrahydroxy-6,20-Bis[(1R)-1-Hydroxyethyl]-16-Methyl-5,8,14,19,22,25-Hexaoxotetracosahydro-1H-Dipyrrolo[2,1-C:2',1'-L][1,4,7,10,13,16]Hexaazacyclohenicosin-9-Yl}Octadeca-9,12-Dienamide
5.1:6-Anhydro{(4R,5R)-4,5-Dihydroxy-N(2)-[(9Z,12Z)-Octadeca-9,12-Dienoyl]-L-Ornithyl-L-Threonyl-(4R)-4-Hydroxy-L-Prolyl-(4S)-4-Hydroxy-4-(4-Hydroxyphenyl)-L-Threonyl-L-Threonyl-(3S,4S)-3-Hydroxy-4-Methyl-L-Proline}
54651-05-7
A-30912A
A-22082
A-30912-Factor-A
Antibiotic-A-30912A
Antibiotic-A-30912-Factor-A
Antibiotic-Sl-7810
Antibiotic-A-22082
Antibiotic-Sl-7810F
Chebi:315018
Cnw0Zw8Ztq
Dtxsid301027535
Echinocandin-B
Ex-A7012
Nsc-287461
Schembl17951640
Unii-Cnw0Zw8Ztq
Source

Aspergillus nidulans [Division : Plants and Fungi]

Taxonomy :162425 (Fungi-Ascomycota-Eurotiales-Eurotiomycetes-Aspergillaceae Aspergillus)  

Wikipedia: Aspergillus nidulans

Aspergillus spinulosporus [Division : Plants and Fungi]

Taxonomy :1810908 (Fungi-Ascomycota-Eurotiales-Eurotiomycetes-Aspergillaceae Aspergillus)  

Wikipedia: Aspergillus spinulosporus

Streptomyces [Division : Bacteria]

Taxonomy :1883 (Unassigned-Actinomycetota-Kitasatosporales-Actinomycetes-Streptomycetaceae Unassigned)  

Wikipedia: Streptomyces

PubChem  

Family

Lipopeptide   Norine  

Function

Anti-Fungal   Anti-Infective   Norine  

Information

Echinocandin B is a cyclic hexapeptide echinocandin antibiotic isolated from Aspergillus nidulans var. Echinulatus with specific anti-yeast activity. It has a role as an antiinfective agent. Elisidepsin is a synthetic cyclic depsipeptide of the kahalalides family with potential antineoplastic activity. PM02734 is a derivative of a natural marine compound extracted from the sacoglossan sea slug, Elysia rufescens. Although the exact mechanism of action has yet to be elucidated, elisidepsin exhibits anti-proliferative activity in a wide variety of cancer types, such as breast, colon, pancreas, lung, and prostate.

PubChem|9898144   Norine|NOR01469  

Legend

Structure

Download structure
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similarity structure
Molecular Formula

C52H81N7O16
Molecular Weight 1059.57398 g/mol
SMILES

RUN SEA Predictions

 CCCCC/C=C\C/C=C\CCCCCCCC(=O)N[C@H]1C[C@@H](O)[C@@H](O)NC(=O)[C@@H]2[C@@H](O)[C@@H](C)CN2C(=O)[C@H]([C@@H](C)O)NC(=O)[C@H]([C@H](O)[C@@H](O)c2ccc(O)cc2)NC(=O)[C@@H]2C[C@@H](O)CN2C(=O)[C@H]([C@@H](C)O)NC1=O  

PubChem|9898144
InChI
InChI=1S/C52H81N7O16/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-38(65)53-35-26-37(64)48(71)57-50(73)42-43(66)29(2)27-59(42)52(75)40(31(4)61)55-49(72)41(45(68)44(67)32-21-23-33(62)24-22-32)56-47(70)36-25-34(63)28-58(36)51(74)39(30(3)60)54-46(35)69/h9-10,12-13,21-24,29-31,34-37,39-45,48,60-64,66-68,71H,5-8,11,14-20,25-28H2,1-4H3,(H,53,65)(H,54,69)(H,55,72)(H,56,70)(H,57,73)/b10-9-,13-12-/t29-,30+,31+,34+,35-,36-,37+,39-,40-,41-,42-,43-,44-,45-,48+/m0/s1  
InChIKey
FAUOJMHVEYMQQG-IGWFTHQUNA-N
2D Structure
PubChem|9898144

Sequence

Graph alignment
Local alignment
One letter code from Structure
ATPTTT  

CyclicPepedia|Struct2seq
Amino acid chain from Structure
NFo-D-Abu(1)--Thr--4OH-Pro--Hty--Thr--ProC(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 1059.57398
Number of Rings 4.0
Complexity 0.68
XlogP3 AA -1.3304
Heavy Atom Count 75.0
Hydrogen Bond Donor Count 14.0
Hydrogen Bond Acceptor Count 16.0
Rotatable Bond Count 20.0
Property Name Property Value
Formal Charge 0.0
Refractivity 271.0857
Rule_of_Five 0.0
Number of Atoms 75.0
Topological Polar Surface Area 368.19
Refractivity 271.0857
Veber Rule 0.0
Ghose Filter 0.0
Property Name Property Value
RDKit Fingerprint
01001001001011101100110111011000110111000111010001111011101111101110100111111100100110010111111110000111110001001101011010110010000010000110111100001101000110111111001010110110101111011111100111110111101001001010000111000110011101000101001110000000011100101011001111011001000011001011111100010011011011011011101111000001110101011011011111011010111000100010001001001011111110010000111001001011001101100100000110001110000011100110100010111001111011101010001100010111111010110100000010000010000110011101110001101111111101100111011010011101101111100001100010011110101101001110010111101001001110110101101100110001111010111111111110101111100100110110000111100111110011110110001010110001010101011100011100100010100101110011000100111111001110111001111110011010101110101010111111010000000111110001101010001001001110001000101000110001111011111001010011101000011001110010101110101011010100100101111000100011001111001000111000010100111110011010010000011111001010001011011101010100111100110111011010010111010100010101001001100100101111101111110110111011110100001010100000011110111101101001110011001001110111000001101101110010110011110101000111001011010100010100111000001000101111100110101111110011010000001111010111011000010101101101010111100110111101110010011110011011100111010110101000100101010010111101000001111001010110100001001100100011100001000011111110001101110111110011011100110100000101011000111101000001110101001101101001101100101011000000001010101111101101001011001111010111011001101001100000111111111001011100100110100111000111100010001101010100011110100100000010101100000110110111001001110111101010000111010000101011001000110011110000010110000100101110011011000001100010000101100010100101110011111001011100100100100001110111010111111000100100110011001111011001110110010110100110101000100000010110100010001011111101101111000011110010011110101110010001101111100001001010111111100001010000011111101100111110111101010101011011010111001011101111010111010001110001011111011011000011001111100110111111001110100000011110001111111111001100100101011011110111
Morgan Fingerprint
0100010000100000000100000000000001000000010000000000000000000000000000000000000010000000001000000000000000000000000000011000000010001000000000000000000000000000000000000001000000000010000000000000000000000000000000000000100000010000010000000001000000000000000010000000100000000000001101001100001000100100000000000010000000000000100010000000010000000000000010000000000000000000000000000101000000000000010000000000000010001000000000000000000000000000000000000000000100000000000000000010000000001000000000000100000000000001010000000000000000001000000000000000000000000000000000000010000000000011000010000000000000001000000001000000000000000000000000100010000000000000000000000000000000001001000000100000000000000000000000000000001000010000000100000100000000100000000000000010000100000001000000000010000000001001000000000000100000010100000100000000000001000100000000000000000000000000000000110000010000000000000000000000000000000010000000011000000000000000000010000000000000000000100101000000000000000100000000000000000000010000
MACCS Keys
00000000000000000000000000000000000000000001000000000110000000000000000010000001000101000111100111011000110010110111111011100001110111001111111100111111111111111111110

Sequence Properties

Property Name Property Value
Boman Index 1.41166666666666
Instability 8.33333333333333
Charge -0.00201570060725275
Aliphatic Index 16.6666666666666

Binding Target

Detail

Uniprot:  A2QLK4

Kind:  Protein>Synthase

Organism:  Aspergillus niger (strain CBS 513.88 / FGSC A1513)

Evidevce:  PubChem

Sequence:  MSGYPAGHYEDGYGHQEHGGDAYYQDEHGQAYYDPNDYGDSYYDRGNYYNAEGGQAYGQEGGYYDAGHQDDYYGDQYYDQGNGAPRGRRRGDSEEDSETFSDFTMRSETARAADMDYYGRGDERYNSYADSQYAGRGYNGYRPPSSQVSYGANRSSGASTPVYGMDYGSALPGGPRSREPYPAWASDGQVPVSKEEIEDIFIDLVNKFGFQRDSMRNMYDHLMTQLDSRASRMTPNQALLSLHADYIGGDNANYRRWYFAAHLDLDDAVGFANMKLGKADRKTRKARKAAKAAAQQNPENVEENLEAMEGDNSLEAAVYRWKSRMNRMSPHDRVRQLALYMLCWGEANQVRYMPECICFIFKCADDYYSSPECQSRVEPVEEFTYLNEIITPLYQFCRDQGYEILDGKYVRRERDHEKIIGYDDMNQLFWYPEGIERISFEDKTRLVDVPPAERWTKLKDVDWKKAFFKTYRETRSWFHMITNFNRIWVIHLGAFWFFTAYNAPTLYTKNYQQQLDNKPAGSKYWSAVGFGGALVGLIQILATLCEWMYVPRRWAGAQHLSKRLMFLIAVFIVNLAPGVVVFGFNNVLSETICLIIGIVHFFIALATFFFFSVMPLGGLFGSYLKKHGRQYVASQTFTASYPRLNGNDMWMSYGLWICVFGAKLVESYFFLTLSLKDPMRILSPMRIHQCAGVTYIPNSLCHAQPQILLGLMMFMDLTLFFLDSYLWYVICNTIFSVARSFYLGVSIWSPWRNIFSRLPKRIYSKVLATTDMEIKYKPKVLISQVWNAIIISMYREHLLAIDHVQKLLYHQVPSEQEGKRTLRAPTFFVSQEDQSFKTEFFPAGSEAERRISFFAQSVATPMPEPLPVDNMPTFTVLIPHYGEKILLSLREIIREDEPYSRVTLLEYLKQLHPHEWDCFVKDTKILADETSQLNGEPEKNEKDAQKSKIDDLPFYCIGFKSAAPEYTLRTRIWSSLRSQTLYRTISGFMNYSRAIKLLYRVENPEVVQMFGGNSEKLERELERMARRKFKICVSMQRYAKFNKEERENTEFLLRAYPDLQIAYLDEEPPANEGEEPRLYSALIDGHCELLDNGMRKPKFRIQLSGNPILGDGKSDNQNHSIIFYRGEYIQVIDANQDNYLEECLKIRSVLAEFEELTTDNVSPYTPGIATEAETPVAILGAREYIFSENVGVLGDVAASKEQTFGTLFARTLAQIGGKLHYGHPDFLNGIFMTTRGGISKAQKGLHLNEDIYAGMTALCRGGRIKHCEYFQCGKGRDLGFGSILNFTTKIGTGMGEQMLSREYYYLGTQLPLDRFLSFYYAHPGFHLNNMFIMLSVQMFMIVLINLGALKHETITCRYNSNLPITDPLRPTYCADLTPIIAWVNRCVVSIFIVFFISFVPLAVQELTERGLWRMATRLAKHFGSFSFMFEVFVCQIYANAVHQNLSFGGARYIGTGRGFATARIPFGVLYSRFAGPSIYAGSRLLLMLLFATSTVWTPALIWFWVSLLALCISPFLFNPHQFAWHDFFIDYRDYIRWLSRGNSRSHASSWIAFCRLSRTRLTGYKRKLLGVPSEKGSGDVPRAKFTNIFFSEIIAPLVQVAVTLVPYLYINSRTGISNDNERASNAVVRIAIVAFGPIGVNAGVSGMFFGMACCMGPIFGMCCKKFGAVLAAIAHAIAVIILLVIFEVMFFLESWSWPRMVLGMISAAAIQRFIYKLIISLALTREFKHDQSNIAWWTGKWYNMGWHSLSQPGREFLCKITELGYFSADFVLGHILLFVMLPALCIPYVDKFHSVILFWLRPSRQIRPPIYSLKQSKLRKRRVVRFAILYFTMLVLFLILLIAPLVARDEGISVNLNIMSLMQPLDTDNNDTISSYTGNGLPVGYSAWTPSAASASA

General Function:

      1,3-beta-d-glucan synthase activity

Specific Function:

      Catalytic subunit of the 1,3-beta-glucan synthase. Synthesizes 1,3-beta-glucan, a major structural component of the cell wall. Involved in cell wall synthesis, maintenance and cell wall remodeling (By similarity).

Additional database information: TTD[1,3-beta-glucan synthase component FKS1]

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

1281482

 The cyclic peptide synthetase catalyzing HC-toxin production in the filamentous fungus Cochliobolus carbonum is encoded by a 15.7-kilobase open reading frame

None

J Biol Chem

The cyclic peptide synthetase catalyzing HC-toxin production in the filamentous fungus Cochliobolus carbonum is encoded by a 15.7-kilobase open reading frame

Abstract

  • Race 1 of Cochliobolus carbonum, a fungal plant pathogen, owes its exceptional virulence on certain genotypes of maize to the production of HC-toxin, a cyclic tetrapeptide. Production of HC-toxin is controlled by a single known gene, TOX2. Race 1, but not races that do not make HC-toxin, contains two copies of a 22-kilobase (kb) region of chromosomal DNA that is required for HC-toxin biosynthesis and hence virulence. We have sequenced this 22-kb region and here show that it contains an open reading frame of 15.7 kb that encodes a multifunctional cyclic peptide synthetase of potential M(r)574,620. This gene, called HTS1, apparently contains no introns. The predicted gene product, HC-toxin synthetase (HTS), contains four amino acid-binding (adenylate-forming) domains that are highly similar to those found in other cyclic peptide synthetases and other adenylate-binding enzymes. The DNA sequence encodes tryptic peptides derived from two HC-toxin biosynthetic enzymes, HC-toxin synthetase 1 (HTS-1) and HC-toxin synthetase 2 (HTS-2), indicating that these two enzymes exist in vivo as part of a single polypeptide. Consistent with this, in some enzyme preparations antibodies against the enzyme HTS-2, which was originally purified as a protein with a subunit M(r) of 160,000, recognize a protein with an estimated subunit M(r) greater than 480,000.

1359642

 Reductase activity encoded by the HM1 disease resistance gene in maize 10.1126/science.1359642.

Science

Reductase activity encoded by the HM1 disease resistance gene in maize

Abstract

  • The HM1 gene in maize controls both race-specific resistance to the fungus Cochliobolus carbonum race 1 and expression of the NADPH (reduced form of nicotinamide adenine dinucleotide phosphate)-dependent HC toxin reductase (HCTR), which inactivates HC toxin, a cyclic tetrapeptide produced by the fungus to permit infection. Several HM1 alleles were generated and cloned by transposon-induced mutagenesis. The sequence of wild-type HM1 shares homology with dihydroflavonol-4-reductase genes from maize, petunia, and snap-dragon. Sequence homology is greatest in the beta alpha beta-dinucleotide binding fold that is conserved among NADPH- and NADH (reduced form of nicotinamide adenine dinucleotide)-dependent reductases and dehydrogenases. This indicates that HM1 encodes HCTR.

2470418

 Ionic pores formed by cyclic peptides 10.1016/0300-9084(89)90134-x.

Biochimie

Ionic pores formed by cyclic peptides

Abstract

  • It is shown that 2 cyclic tetrapeptides, namely tentoxin and HC toxin, are able to induce the formation of transmembrane ionic channels, although a carrier mechanism could be expected on the basis of their chemical structure (presence of proline or N-methylated residues). Since other cyclic peptides but of larger size, i.e., tyrocidines, gramicidin S (decapeptides) and an octapeptide with a sequence similar to that of HC toxin, are also able to form pores, it appears that this property can be extended to a large number of cyclic peptides. A pore structure based on aggregates is proposed.