Basic information

CPKB ID	CP02423
IUPAC Name	(3S,9S,12S,15S,18R,21S,24S)-12,15-bis[(1S)-1-hydroxyethyl]-9-[(4-hydroxyphenyl)methyl]-3,21-dimethyl-18-(2-methylpropyl)-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[Ala-D-Leu-aThr-aThr-Tyr-Gly-Ala-Pro] is a natural product found in Annona squamosa with data available. PubChem\|162999804

Legend

Structure

Molecular Formula	C36H54N8O11
Molecular Weight	774.3912045 g/mol
SMILES RUN SEA Predictions	CC(C)C[C@H]1NC(=O)[C@H](C)NC(=O)[C@@H]2CCCN2C(=O)[C@H](C)NC(=O)CNC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)[C@H]([C@H](C)O)NC(=O)[C@H]([C@H](C)O)NC1=O PubChem\|162999804
InChI	InChI=1S/C36H54N8O11/c1-17(2)14-24-32(51)42-29(21(6)46)35(54)43-28(20(5)45)34(53)41-25(15-22-9-11-23(47)12-10-22)31(50)37-16-27(48)38-19(4)36(55)44-13-7-8-26(44)33(52)39-18(3)30(49)40-24/h9-12,17-21,24-26,28-29,45-47H,7-8,13-16H2,1-6H3,(H,37,50)(H,38,48)(H,39,52)(H,40,49)(H,41,53)(H,42,51)(H,43,54)/t18-,19-,20-,21-,24+,25-,26-,28-,29-/m0/s1
InChIKey	XLTMDOFLUKZVOQ-VRKCIBGFNA-N

2D Structure PubChem\|162999804

Sequence

IUPAC Condensed	cyclo[Ala-D-Leu-aThr-aThr-Tyr-Gly-Ala-Pro] PubChem\|162999804
Amino acid chain	Ala(1)--D-Leu--aThr--aThr--Tyr--Gly--Ala--Pro(1) CyclicPepedia\|PP
Graph representation	Ala,D-Leu,aThr,aThr,Tyr,Gly,Ala,Pro @0,7 CyclicPepedia\|PP
One letter code from Structure	APALTTYG CyclicPepedia\|Struct2seq
Amino acid chain from Structure	Leu(1)--Thr--Thr--Tyr--Gly--Ala--Pro--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\|162999804

Chemical and Physical Properties

CyclicPepedia|Struc2Seq + PP

Structure Properties

Property Name	Property Value
Exact Mass	774.3912045
Number of Rings	3.0
Complexity	0.672727273
XlogP3 AA	-3.1882
Heavy Atom Count	55.0
Hydrogen Bond Donor Count	10.0
Hydrogen Bond Acceptor Count	11.0
Rotatable Bond Count	6.0

Property Name	Property Value
Formal Charge	0.0
Refractivity	195.3043
Rule_of_Five	0.0
Number of Atoms	55.0
Topological Polar Surface Area	284.7
Refractivity	195.3043
Veber Rule	0.0
Ghose Filter	0.0

Property Name	Property Value
RDKit Fingerprint	01000010101000100100100011011000110000100111010000101010100001101110101111101100100110010010110010000101000001001010001000110010000001001100110100001111000110000100001010100110100110001111100100100100101001001000000100000000010101000101001110001100011100101111000110001000000010001001100000000010011010011010101101000001010100000010111011010110111000000010011000000001000010000000101001000010010100000100000110001100000010100000101000111011110011100000000100010110111000010100000000000010001110010100100000101101110001100100111010010101101110100100100010010110001001000110010010001001000010111100101000110001101010011000100000001011100100110100000011100110000001000110001010000000010101001100011100110010100101100000000100101011001001011001100010001010001110101010001110010000000001100001001010001000001000001000100000001001111011110000010011101001011000110010011100100001010100000100111000000011001101000010111000010100011110011010000000011110001010001011011101010000011000010110001010000001010100000000000000101101001111110011110110111011100000001010000000001110101001100001000001001001110110000001001101010010000000101000000110001001010000010100101000001000100110100110101111001001010010001110000001001000000101001101010011100000011100110111000010010000100101000110001000000100000000110000110001011001011010100001000001100010100001000011111110000001010110110011010000010000000101011000001000000101100101001100000001000101100011001000001011111010001101001011001100000110010000100001110000111111011001000000100100100111000011100000001000010000011110100100000010100000000110100111001001010101100010000001000010100001000000100010110000000100000000100010010010000001000011000100101010000101000010000001011110100100100101000001010110001000100000100011011001010101010010010110100010000000100001010110100000000011111101101100000010110010011110100111110011000000100000000000110011100000010000001101101100000100101101000001010010010101000010000111110110000001011001011011001001000011001001100110000101001000100010010000000011101110000100100100111000010011
Morgan Fingerprint	0100110000100000000100000000000001000000000000010000000000000000000000000000000010000000001000100000010000000000010100000000000000000000000000000000000000000000000000000000000000000000000000000000001000000000000000000000000000010001000000000000000000100000000000000000000000000000000101001100000000000100000000100010000001000000000000010000100000000000000010000000000000000000000000000000000000000000000000000000000000000000000000001001000010000010000000001010000000000000000000000010000000001000000000010001000000000001000000000000000000000000000000010000000000000000000000000010000000000000000000000000000000000000000000000000000000100000000000000010000000000000010000000000000000001001000000100000000000000000000100000000001000100000000000000100000000100010000000000000000000000000000000000000000000000001000000000000100100000000000000000010000001001000000000000000000000000000000000000000000100000000000000000000000000000010000000010000000000000000001001000000000000000000000000001000000000000000000000000000000000010000
MACCS Keys	00000000000000000000000000000000000000000000000000000110000000000000000000100001001101000111100111001000110010110101011011100001110110001111111100111111111111111111110

Sequence Properties

Property Name	Property Value
Boman Index	-0.525
Instability	46.2875
Charge	-0.00286611482556564
Aliphatic Index	73.75

Manufacturers

Manufacturers Name	Value
CreativePeptides	Cyclo[Ala-D-Leu-Athr-Athr-Tyr-Gly-Ala-Pro]
Bayer healthcare pharmaceuticals	Cyclo[Ala-D-Leu-Athr-Athr-Tyr-Gly-Ala-Pro]
Upsher smith laboratories	Cyclo[Ala-D-Leu-Athr-Athr-Tyr-Gly-Ala-Pro]
Merck	Cyclo[Ala-D-Leu-Athr-Athr-Tyr-Gly-Ala-Pro]

Manufacturers Name	Value
Apotex	Cyclo[Ala-D-Leu-Athr-Athr-Tyr-Gly-Ala-Pro]
Baxter Healthcare Corp	Cyclo[Ala-D-Leu-Athr-Athr-Tyr-Gly-Ala-Pro]
Pharmasources	Cyclo[Ala-D-Leu-Athr-Athr-Tyr-Gly-Ala-Pro]
Novartis	Cyclo[Ala-D-Leu-Athr-Athr-Tyr-Gly-Ala-Pro]
AstraZeneca	Cyclo[Ala-D-Leu-Athr-Athr-Tyr-Gly-Ala-Pro]

Forecasting tools

Forecasting tools	Value
Structure to Sequence	CC(C)C[C@H]1NC(=O)[C@H](C)NC(=O)[C@@H]2CCCN2C(=O)[C@H](C)NC(=O)CNC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)[C@H]([C@H](C)O)NC(=O)[C@H]([C@H](C)O)NC1=O
Structure Properties	CC(C)C[C@H]1NC(=O)[C@H](C)NC(=O)[C@@H]2CCCN2C(=O)[C@H](C)NC(=O)CNC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)[C@H]([C@H](C)O)NC(=O)[C@H]([C@H](C)O)NC1=O
Sequence to Structure	APALTTYG
Sequence Properties	APALTTYG
Expasy ProtParam Tool	APALTTYG
SEA	RUN SEA Predictions

Information Source

Property Name	Property ID
Patents	XLTMDOFLUKZVOQ-VRKCIBGFNA-N
pubchem	162999804
Drugbank	Cyclo[Ala-D-Leu-Athr-Athr-Tyr-Gly-Ala-Pro]
DRAMP3	Cyclo[Ala-D-Leu-Athr-Athr-Tyr-Gly-Ala-Pro]
Uniprot	Cyclo[Ala-D-Leu-Athr-Athr-Tyr-Gly-Ala-Pro]
Cybase	Cyclo[Ala-D-Leu-Athr-Athr-Tyr-Gly-Ala-Pro]
CONOSERVER	Cyclo[Ala-D-Leu-Athr-Athr-Tyr-Gly-Ala-Pro]
BindingDB	CC(C)C[C@H]1NC(=O)[C@H](C)NC(=O)[C@@H]2CCCN2C(=O)[C@H](C)NC(=O)CNC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)[C@H]([C@H](C)O)NC(=O)[C@H]([C@H](C)O)NC1=O
CHEMBL	Cyclo[Ala-D-Leu-Athr-Athr-Tyr-Gly-Ala-Pro]
CTD	Cyclo[Ala-D-Leu-Athr-Athr-Tyr-Gly-Ala-Pro]
Wikipedia	Cyclo[Ala-D-Leu-Athr-Athr-Tyr-Gly-Ala-Pro]
KEGG Compound/Drug	Cyclo[Ala-D-Leu-Athr-Athr-Tyr-Gly-Ala-Pro]
CHEBI	XLTMDOFLUKZVOQ-VRKCIBGFNA-N
EPA DSSTox	Cyclo[Ala-D-Leu-Athr-Athr-Tyr-Gly-Ala-Pro]
FDA Global Substance Registration System (GSRS)	Cyclo[Ala-D-Leu-Athr-Athr-Tyr-Gly-Ala-Pro]
DTP/NCI	Cyclo[Ala-D-Leu-Athr-Athr-Tyr-Gly-Ala-Pro]
Chemspider	XLTMDOFLUKZVOQ-VRKCIBGFNA-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.
24613547	The molecular diversity of toxin gene families in lethal Amanita mushrooms	10.1016/j.toxicon.2014.02.020.	Toxicon
The molecular diversity of toxin gene families in lethal Amanita mushrooms Abstract Mushrooms in lethal Amanita species are responsible for a large number of food poisoning cases and deaths. However, the diversity of the toxins in these mushrooms remains largely unknown. This study analyzed the gene families of toxins found in 6 lethal Amanitae from Asia and Europe. Fifty-four gene sequences were obtained, accounting for 70.1% of the known MSDIN family members. Of the 54 gene sequences, 20 encode α-amanitin, 5 encode β-amanitin, 16 encode phallacidin, and 13 encode peptides of unknown functions. Bayesian analysis of MSDIN family members identified differences in the number of toxin genes in different toxin families among the Amanita species. Ten of the 13 peptides of unknown functions were closely related to known phallotoxins, while the remaining 3 were similar to amatoxins. The α-AMA tree indicated that there were significant differences between the Amanita and Galerina species. However, both the α-AMA and PHA trees showed that these toxin genes have similar upstream and downstream motif sequences among the Amanita species. This study greatly enriches the available diversity information regarding toxin gene families in lethal Amanita mushrooms, and could lay a strong foundation for further research about the evolution of Amanita toxin genes.