Basic information

CPKB ID	CP00595
IUPAC Name	(3S)-3-methylpiperazine-2,5-dione
Synonyms	(3S)-3-Methylpiperazine-2,5-Dione (S)-3-Methylpiperazine-2,5-Dione 2,5-Piperazinedione,-3-Methyl-,-(3S)- 2,5-Piperazinedione,3-Methyl-,-(3S)- 4526-77-6 A872405 Akos006274981 Chembl2229111 Cs-13042 Cs-M0318 Cyclo(Ala-Gly-) Cyclo(-Ala-Gly) Cyclo(L-Ala-L-Gly) Hy-75564 Mfcd00237603 Schembl2872608 Zinc4899706
Source	Aspergillus fumigatus [Division : Plants and Fungi] Taxonomy :746128 (Fungi-Ascomycota-Eurotiales-Eurotiomycetes-Aspergillaceae Aspergillus) Wikipedia: Aspergillus fumigatus PubChem
Information	Cyclo(-ala-gly) is a natural product found in Aspergillus fumigatus with data available. PubChem\|7408474

Legend

Structure

Molecular Formula	C5H8N2O2
Molecular Weight	128.0585775 g/mol
SMILES RUN SEA Predictions	C[C@@H]1NC(=O)CNC1=O PubChem\|7408474
InChI	InChI=1S/C5H8N2O2/c1-3-5(9)6-2-4(8)7-3/h3H,2H2,1H3,(H,6,9)(H,7,8)/t3-/m0/s1
InChIKey	ICCHEGCKVBMSTF-PRLLIMAUNA-N

2D Structure PubChem\|7408474
3D Structure PubChem\|7408474

Sequence

One letter code from Structure	AG CyclicPepedia\|Struct2seq
Amino acid chain from Structure	Ala--Gly 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	128.0585775
Number of Rings	1.0
Complexity	1.555555556
XlogP3 AA	-1.3791
Heavy Atom Count	9.0
Hydrogen Bond Donor Count	2.0
Hydrogen Bond Acceptor Count	2.0
Rotatable Bond Count	0.0

Property Name	Property Value
Formal Charge	0.0
Refractivity	30.6144
Rule_of_Five	1.0
Number of Atoms	9.0
Topological Polar Surface Area	58.2
Refractivity	30.6144
Veber Rule	1.0
Ghose Filter	0.0

Property Name	Property Value
RDKit Fingerprint	01000000000000000000000000010000000000000010000000000010000000000000000000001000100000000000000000000000000001001000000000100000000000000000000000000000000000100100001000000000000110000010000000000000000001001000000000000000000000000100000100000000000100000001000100000000000000000000000000000000000000010000000000000000000100000000000010000000000000000000000000000000000000000000000000000000000100000000000100001100000010000000000000000000100000000000000000000010000000000000000000000010000000000000100000000100000000000000000010000001000000000000000000000100000000000000010010000000000000000000000000000000000010011000000000001000000000000010000000000000000000000110000000000000000100000000011000000000000001000000000000000010000000000000000000000000001100000000000000010000000001000000001000001000001000001000000000000000000000000000000010000000000000000000000000000000000000000000001000000001000100000000001000000000000000000000000000000100000000000000010000010000010000000000001000000000010100000000000000000000001000000010000000000000100000000010000000000000001001100001000000000000100010000000000001000000000000000000000010000000000010000000001000001000000010100000100100000000000000001010000000000000000000010100000010100000011000010010000000000000100100000010000000000000000000000000000000001001000010000000000000000000100000000000000000000000000000000000010000000000000000000000000000000000000000001100000000000000100010000000000000001000000000001011000000000100000000100000000000000001001000000000100100000000000000100000000000010000000000100000000000100000000100000000000001000100000000010000000000000000000000000000000000000000000000000010010000000000000010000100000010000000000000000000010000000000000000000001000000000000100000000001000000000000000000000000100000000000000000010000000000000000100001000000000000000000011000000110010000000000000000000000000000000000000000001001000000000100001100000000010000000000000010000010000000000000000000001000000000000001000000100000000000000000000000000000000000000000000000000000000000000001
Morgan Fingerprint	0000000000100000000000000000000001000000000000000000000000000000000000000000000000000000001000000000010000000000010000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000100000000000000000000000000000000001000000000000000100000000000010000000000000000000000000000000000000000010000000000000000000000000000000000000000000000000000000000000000000000000000000000010000000000000000000000000000000000000000000000000000000000000010000000000000000000000000000000000000000000000010000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000010000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000010000000000000000000000000000000000000000000000000000100000000000000000000100000000010000000000000000000000000001000000000000000000000000000000000000000000000000000000000000000010000
MACCS Keys	00000000000000000000000000000000000000000000000000000010000000000000000000000001001000000001100100101000100010110000010011000001000110001100001100000011011010111101110

Sequence Properties

Property Name	Property Value
Boman Index	-1.375
Charge	-0.00201570060725275
Aliphatic Index	50.0

Manufacturers

Manufacturers Name	Value
CreativePeptides	Cyclo(-Ala-Gly)
Bayer healthcare pharmaceuticals	Cyclo(-Ala-Gly)
Upsher smith laboratories	Cyclo(-Ala-Gly)
Merck	Cyclo(-Ala-Gly)

Manufacturers Name	Value
Apotex	Cyclo(-Ala-Gly)
Baxter Healthcare Corp	Cyclo(-Ala-Gly)
Pharmasources	Cyclo(-Ala-Gly)
Novartis	Cyclo(-Ala-Gly)
AstraZeneca	Cyclo(-Ala-Gly)

Forecasting tools

Forecasting tools	Value
Structure to Sequence	C[C@@H]1NC(=O)CNC1=O
Structure Properties	C[C@@H]1NC(=O)CNC1=O
Sequence to Structure	AG
Sequence Properties	AG
Expasy ProtParam Tool	AG
SEA	RUN SEA Predictions

Information Source

Property Name	Property ID
Patents	ICCHEGCKVBMSTF-PRLLIMAUNA-N
pubchem	7408474
Drugbank	Cyclo(-Ala-Gly)
DRAMP3	Cyclo(-Ala-Gly)
Uniprot	Cyclo(-Ala-Gly)
Cybase	Cyclo(-Ala-Gly)
CONOSERVER	Cyclo(-Ala-Gly)
BindingDB	C[C@@H]1NC(=O)CNC1=O
CHEMBL	CHEMBL2229111
CTD	Cyclo(-Ala-Gly)
Wikipedia	Cyclo(-Ala-Gly)
KEGG Compound/Drug	Cyclo(-Ala-Gly)
CHEBI	ICCHEGCKVBMSTF-PRLLIMAUNA-N
EPA DSSTox	Cyclo(-Ala-Gly)
FDA Global Substance Registration System (GSRS)	Cyclo(-Ala-Gly)
DTP/NCI	Cyclo(-Ala-Gly)
Chemspider	ICCHEGCKVBMSTF-PRLLIMAUNA-N

Reference

Pubmed_ID	Title	DOI	Journal
11594819	Atom-economical synthesis of the N(10)-C(17) fragment of cyclotheonamides via a novel Passerini reaction-deprotection-acyl migration strategy	10.1021/ol0165239.	Org Lett
Atom-economical synthesis of the N(10)-C(17) fragment of cyclotheonamides via a novel Passerini reaction-deprotection-acyl migration strategy Abstract [reaction: see text]. A novel variant of the atom-economical Passerini reaction between suitably protected argininal, dipeptide isonitrile, and proline components afforded adduct 13. Orthogonal N-deprotection of 13 led, via a smooth O- to N-acyl migration, to 14, which constitutes the N(10)-C(17) fragment of the cyclotheonamide family of serine protease inhibitors. Each reaction in this three-step protocol proceeds in good yield and under very mild conditions.
11908961	Cyclotheonamide E4 and E5, new potent tryptase inhibitors from an Ircinia species of sponge	10.1021/np010304e.	J Nat Prod
Cyclotheonamide E4 and E5, new potent tryptase inhibitors from an Ircinia species of sponge Abstract Tryptase is a protease released from mast cells and is believed to contribute to the inflammatory process in allergic diseases including asthma. In the course of screening to find tryptase inhibitors, we isolated two new tryptase inhibitors, cyclotheonamide E4 (3) and E5 (4), from a marine sponge of the genus Ircinia. The structures of these molecules were determined by interpretation of 1H and 13C NMR spectra, and they were shown to be closely related to the previously reported cyclotheonamides E (1), E2, and E3 (2). These molecules contain two unusual amino acids, vinylogous tyrosine and alpha-ketohomoarginine, which are involved in strong activities against serine proteases. Cyclotheonamide E4 showed potent inhibitory activity against human tryptase (IC50 5.1 nM). Therefore, cyclotheonamide E4 may be useful as a therapeutic agent in the treatment of allergic diseases including asthma.
9599274	Cyclotheonamides E2 and E3, new potent serine protease inhibitors from the marine sponge of the genus Theonella	10.1021/np970544n.	J Nat Prod
Cyclotheonamides E2 and E3, new potent serine protease inhibitors from the marine sponge of the genus Theonella Abstract Two new potent serine protease inhibitors, cyclotheonamides E2 (3) and E3 (4), have been isolated from a marine sponge of the genus Theonella. Their structures were determined by interpretation of spectral data and chemical degradation studies. They are closely related to the previously reported cyclotheonamide E, from which they differ in the N-acyl group of the alanyl side chain. Cyclotheonamides E, E2, and E3 were more active against thrombin than against trypsin.