Basic information

CPKB ID	CP02428
IUPAC Name	3-butan-2-yl-12-(1-hydroxyethyl)-18-[(4-hydroxyphenyl)methyl]-6-methyl-21-(2-methylsulfinylethyl)-9-propan-2-yl-1,4,7,10,13,16,19,22-octazabicyclo[22.3.0]heptacosane-2,5,8,11,14,17,20,23-octone
Source	Annona squamosa [Division : Plants and Fungi] Taxonomy :301693 (Viridiplantae-Streptophyta-Magnoliales-Magnoliopsida-Annonaceae Annona) Wikipedia: Annona squamosa PubChem
Information	Cyclo[DL-Ala-DL-xiIle-DL-Pro-DL-Met(O)-DL-Tyr-Gly-DL-xiThr-DL-Val] is a natural product found in Annona squamosa with data available. PubChem\|163004895

Legend

Structure

Molecular Formula	C39H60N8O11S
Molecular Weight	848.4102257 g/mol
SMILES RUN SEA Predictions	CCC(C)C1NC(=O)C(C)NC(=O)C(C(C)C)NC(=O)C(C(C)O)NC(=O)CNC(=O)C(Cc2ccc(O)cc2)NC(=O)C(CCS(C)=O)NC(=O)C2CCCN2C1=O PubChem\|163004895
InChI	InChI=1S/C39H60N8O11S/c1-8-21(4)31-39(57)47-16-9-10-28(47)36(54)42-26(15-17-59(7)58)35(53)43-27(18-24-11-13-25(49)14-12-24)34(52)40-19-29(50)44-32(23(6)48)38(56)45-30(20(2)3)37(55)41-22(5)33(51)46-31/h11-14,20-23,26-28,30-32,48-49H,8-10,15-19H2,1-7H3,(H,40,52)(H,41,55)(H,42,54)(H,43,53)(H,44,50)(H,45,56)(H,46,51)
InChIKey	JNUDLAUDDIPWGP-HTKHYRGWNA-N

2D Structure PubChem\|163004895

Sequence

IUPAC Condensed	cyclo[DL-Ala-DL-xiIle-DL-Pro-DL-Met(O)-DL-Tyr-Gly-DL-xiThr-DL-Val] PubChem\|163004895
Amino acid chain	DL-Ala(1)--DL-xiIle--DL-Pro--DL-Met(O)--DL-Tyr--Gly--DL-xiThr--DL-Val(1) CyclicPepedia\|PP
Graph representation	DL-Ala,DL-xiIle,DL-Pro,DL-Met(O),DL-Tyr,Gly,DL-xiThr,DL-Val @0,7 CyclicPepedia\|PP
One letter code from Structure	TVAIPMYG CyclicPepedia\|Struct2seq
Amino acid chain from Structure	Ile(1)--Pro--O-Met--Tyr--Gly--Thr--Val--Ala(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\|163004895

Chemical and Physical Properties

CyclicPepedia|Struc2Seq + PP

Structure Properties

Property Name	Property Value
Exact Mass	848.4102257
Number of Rings	3.0
Complexity	0.762711864
XlogP3 AA	-2.1643
Heavy Atom Count	59.0
Hydrogen Bond Donor Count	9.0
Hydrogen Bond Acceptor Count	11.0
Rotatable Bond Count	9.0

Property Name	Property Value
Formal Charge	0.0
Refractivity	216.3379
Rule_of_Five	0.0
Number of Atoms	59.0
Topological Polar Surface Area	281.54
Refractivity	216.3379
Veber Rule	0.0
Ghose Filter	0.0

Property Name	Property Value
RDKit Fingerprint	01000011100000100101110011011000110000100111010100101010100001101110101111101100100110110010110010000111000001101010011010110010010001001000110101011111100110010100001010100110100110001111100100100100101001001000000100000000010111000101011110001110011100101111000110001000000010001001100000000010011010011010111111000001010100010011111011110110111000000010011001000001000010000000111001100010010100000100000100001100000010100000101000111011111011100000000101010110111000110100000001001010001110110100100000101101110001100100110010010101101110100100100010110110001001000110010010001001000010111100101000110001100010011000100000001011100100111100000111100110001101000110001010100000010101001100011100110000101101100000000100101011011001011001100010001010001110101010001110010000010101110001001010001010111000001000100000001001111011110010010011101101011000110011011100000001010100001100111000001011001101000010111001010110011110011011010001011110101010001011011101010100011000010110001010000001010100000000010000101111011111111111110110111011100000001010010000001110101001100101010001001001110110001011011101010010000000101000000110001001010000010100101000101000101110100110101111001001010010011110000001001000100101001101010111100000011100110111010010010000100101000110001000000000100000110000110001011001011110110001000001101111100001000011111110000001010110110011110010010000100101001000001000000101100101011101000001000111101010001000011011111010001101001011001100000110010000101001010001111111011001000000100100100111000011100000001000010000011110110100010011110000000110100111001001010111100010000001000011100111000000100011110000000100000000100010010010000001010011000100101010000101010010010001011110001100100101000001010111001000100000100011011001010101100010010110100010001100100001010110100001000011111001111100000010110010011110100111110011000000100000000000110011100000010100001101101100000100101101000001010010010101010010100111110110000011011001111011001011110011011001100110000101001000100010010000000011101110000100100100111000010011
Morgan Fingerprint	0100110000100000000100000000000001000000001000010000000000000000010000000000000010000000001000000000010000000100000100000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000001100000000010001000000000100000000100100000000000000000000000000000101001100001000000100000000100110000000000000000000000000100000000100000110000000000000000000000000000000000000000000000000000000000000000000000100001001000010000010000000001010000000000000000000000010000000001000000000010001000000000001100000000000000000000000000000010000000000000000000000001010000000000100000000000000000000000000000000000000000000100000000000000010000000000000010001000000000000001001000000000000000000000000000100001000001000100000000000000100000000100010000000000000000000000000100000000000000000000001000000000000100000000000100000000010000001000000000000000000000000000000000000000000000100000000000000000000000000000010000000010000000000000000001001000000000000000000000100001000000000000000000000000000000000010000
MACCS Keys	00000000000000000000000000000000000000000000000000010110000011000001000001100001001101101111110111001010110000110111111011101001110110001111111100111111111111111111110

Sequence Properties

Property Name	Property Value
Boman Index	-1.41875
Instability	14.7124999999999
Charge	-0.00286611482556564
Aliphatic Index	97.5

Manufacturers

Manufacturers Name	Value
CreativePeptides	Cyclo[Dl-Ala-Dl-Xiile-Dl-Pro-Dl-Met(O)-Dl-Tyr-Gly-Dl-Xithr-Dl-Val]
Bayer healthcare pharmaceuticals	Cyclo[Dl-Ala-Dl-Xiile-Dl-Pro-Dl-Met(O)-Dl-Tyr-Gly-Dl-Xithr-Dl-Val]
Upsher smith laboratories	Cyclo[Dl-Ala-Dl-Xiile-Dl-Pro-Dl-Met(O)-Dl-Tyr-Gly-Dl-Xithr-Dl-Val]
Merck	Cyclo[Dl-Ala-Dl-Xiile-Dl-Pro-Dl-Met(O)-Dl-Tyr-Gly-Dl-Xithr-Dl-Val]

Manufacturers Name	Value
Apotex	Cyclo[Dl-Ala-Dl-Xiile-Dl-Pro-Dl-Met(O)-Dl-Tyr-Gly-Dl-Xithr-Dl-Val]
Baxter Healthcare Corp	Cyclo[Dl-Ala-Dl-Xiile-Dl-Pro-Dl-Met(O)-Dl-Tyr-Gly-Dl-Xithr-Dl-Val]
Pharmasources	Cyclo[Dl-Ala-Dl-Xiile-Dl-Pro-Dl-Met(O)-Dl-Tyr-Gly-Dl-Xithr-Dl-Val]
Novartis	Cyclo[Dl-Ala-Dl-Xiile-Dl-Pro-Dl-Met(O)-Dl-Tyr-Gly-Dl-Xithr-Dl-Val]
AstraZeneca	Cyclo[Dl-Ala-Dl-Xiile-Dl-Pro-Dl-Met(O)-Dl-Tyr-Gly-Dl-Xithr-Dl-Val]

Forecasting tools

Forecasting tools	Value
Structure to Sequence	CCC(C)C1NC(=O)C(C)NC(=O)C(C(C)C)NC(=O)C(C(C)O)NC(=O)CNC(=O)C(Cc2ccc(O)cc2)NC(=O)C(CCS(C)=O)NC(=O)C2CCCN2C1=O
Structure Properties	CCC(C)C1NC(=O)C(C)NC(=O)C(C(C)C)NC(=O)C(C(C)O)NC(=O)CNC(=O)C(Cc2ccc(O)cc2)NC(=O)C(CCS(C)=O)NC(=O)C2CCCN2C1=O
Sequence to Structure	TVAIPMYG
Sequence Properties	TVAIPMYG
Expasy ProtParam Tool	TVAIPMYG
SEA	RUN SEA Predictions

Information Source

Property Name	Property ID
Patents	JNUDLAUDDIPWGP-HTKHYRGWNA-N
pubchem	163004895
Drugbank	Cyclo[Dl-Ala-Dl-Xiile-Dl-Pro-Dl-Met(O)-Dl-Tyr-Gly-Dl-Xithr-Dl-Val]
DRAMP3	Cyclo[Dl-Ala-Dl-Xiile-Dl-Pro-Dl-Met(O)-Dl-Tyr-Gly-Dl-Xithr-Dl-Val]
Uniprot	Cyclo[Dl-Ala-Dl-Xiile-Dl-Pro-Dl-Met(O)-Dl-Tyr-Gly-Dl-Xithr-Dl-Val]
Cybase	Cyclo[Dl-Ala-Dl-Xiile-Dl-Pro-Dl-Met(O)-Dl-Tyr-Gly-Dl-Xithr-Dl-Val]
CONOSERVER	Cyclo[Dl-Ala-Dl-Xiile-Dl-Pro-Dl-Met(O)-Dl-Tyr-Gly-Dl-Xithr-Dl-Val]
BindingDB	CCC(C)C1NC(=O)C(C)NC(=O)C(C(C)C)NC(=O)C(C(C)O)NC(=O)CNC(=O)C(Cc2ccc(O)cc2)NC(=O)C(CCS(C)=O)NC(=O)C2CCCN2C1=O
CHEMBL	Cyclo[Dl-Ala-Dl-Xiile-Dl-Pro-Dl-Met(O)-Dl-Tyr-Gly-Dl-Xithr-Dl-Val]
CTD	Cyclo[Dl-Ala-Dl-Xiile-Dl-Pro-Dl-Met(O)-Dl-Tyr-Gly-Dl-Xithr-Dl-Val]
Wikipedia	Cyclo[Dl-Ala-Dl-Xiile-Dl-Pro-Dl-Met(O)-Dl-Tyr-Gly-Dl-Xithr-Dl-Val]
KEGG Compound/Drug	Cyclo[Dl-Ala-Dl-Xiile-Dl-Pro-Dl-Met(O)-Dl-Tyr-Gly-Dl-Xithr-Dl-Val]
CHEBI	JNUDLAUDDIPWGP-HTKHYRGWNA-N
EPA DSSTox	Cyclo[Dl-Ala-Dl-Xiile-Dl-Pro-Dl-Met(O)-Dl-Tyr-Gly-Dl-Xithr-Dl-Val]
FDA Global Substance Registration System (GSRS)	Cyclo[Dl-Ala-Dl-Xiile-Dl-Pro-Dl-Met(O)-Dl-Tyr-Gly-Dl-Xithr-Dl-Val]
DTP/NCI	Cyclo[Dl-Ala-Dl-Xiile-Dl-Pro-Dl-Met(O)-Dl-Tyr-Gly-Dl-Xithr-Dl-Val]
Chemspider	JNUDLAUDDIPWGP-HTKHYRGWNA-N

Reference

Pubmed_ID	Title	DOI	Journal
12475187	Treatment of amatoxin poisoning: 20-year retrospective analysis	10.1081/clt-120014646.	J Toxicol Clin Toxicol
Treatment of amatoxin poisoning: 20-year retrospective analysis Abstract Amatoxin poisoning is a medical emergency characterized by a long incubation time lag, gastrointestinal and hepatotoxic phases, coma, and death. This mushroom intoxication is ascribed to 35 amatoxin-containing species belonging to three genera: Amanita, Galerina, and Lepiota. The major amatoxins, the alpha-, beta-, and gamma-amanitins, are bicyclic octapeptide derivatives that damage the liver and kidney via irreversible binding to RNA polymerase II. The mycology and clinical syndrome of amatoxin poisoning are reviewed. Clinical data from 2108 hospitalized amatoxin poisoning exposures as reported in the medical literature from North America and Europe over the last 20 years were compiled. Preliminary medical care, supportive measures, specific treatments used singly or in combination, and liver transplantation were characterized. Specific treatments consisted of detoxication procedures (e.g., toxin removal from bile and urine, and extracorporeal purification) and administration of drugs. Chemotherapy included benzylpenicillin or other beta-lactam antibiotics, silymarin complex, thioctic acid, antioxidant drugs, hormones and steroids administered singly, or more usually, in combination. Supportive measures alone and 10 specific treatment regimens were analyzed relative to mortality. Benzylpenicillin (Penicillin G) alone and in association was the mostfrequently utilized chemotherapy but showed little efficacy. No benefit was found for the use of thioctic acid or steroids. Chi-square statistical comparison of survivors and dead vs. treated individuals supported silybin, administered either as mono-chemotherapy or in drug combination and N-acetylcysteine as mono-chemotherapy as the most effective therapeutic modes. Future clinical research should focus on confirming the efficacy of silybin, N-acetylcysteine, and detoxication procedures.
18025465	Gene family encoding the major toxins of lethal Amanita mushrooms	10.1073/pnas.0707340104.	Proc Natl Acad Sci U S A
Gene family encoding the major toxins of lethal Amanita mushrooms Abstract Amatoxins, the lethal constituents of poisonous mushrooms in the genus Amanita, are bicyclic octapeptides. Two genes in A. bisporigera, AMA1 and PHA1, directly encode alpha-amanitin, an amatoxin, and the related bicyclic heptapeptide phallacidin, a phallotoxin, indicating that these compounds are synthesized on ribosomes and not by nonribosomal peptide synthetases. alpha-Amanitin and phallacidin are synthesized as proproteins of 35 and 34 amino acids, respectively, from which they are predicted to be cleaved by a prolyl oligopeptidase. AMA1 and PHA1 are present in other toxic species of Amanita section Phalloidae but are absent from nontoxic species in other sections. The genomes of A. bisporigera and A. phalloides contain multiple sequences related to AMA1 and PHA1. The predicted protein products of this family of genes are characterized by a hypervariable "toxin" region capable of encoding a wide variety of peptides of 7-10 amino acids flanked by conserved sequences. Our results suggest that these fungi have a broad capacity to synthesize cyclic peptides on ribosomes.