Basic information

CPKB ID	CP00010
IUPAC Name	4-butan-2-yl-7-(2-methylpropyl)-10-propan-2-yl-15,16-dithia-2,5,8,11,19-pentazabicyclo[11.4.2]nonadecane-3,6,9,12,18-pentone
Synonyms	11006-42-1 3022-92-2 4-(Butan-2-Yl)-7-(2-Methylpropyl)-10-(Propan-2-Yl)-15,16-Dithia-2,5,8,11,19-Pentaazabicyclo[11.4.2]Nonadeca-2,5,8,11,18-Pentaene-3,6,9,12,18-Pentol 4-Butan-2-Yl-7-(2-Methylpropyl)-10-Propan-2-Yl-15,16-Dithia-2,5,8,11,19-Pentazabicyclo[11.4.2]Nonadecane-3,6,9,12,18-Pentone 4-Sec-Butyl-7-Isobutyl-10-Isopropyl-15,16-Dithia-2,5,8,11,19-Pentaaza-Bicyclo[11.4.2]Nonadecane-3,6,9,12,18-Pentaone 7-Isobutyl-4-Isopropyl-10-Sec-Butyl-15,16-Dithia-3,6,9,12,18-Pentazabicyclo[11.4.2]Nonadecane-2,5,8,11,19-Pentone Akos030213204 Bs-1480 Chebi:193906 Chembl1987208 Cyclic(D-Cysteinyl-D-Cysteinyl-L-Valyl--D-Leucyl-L-Isoleucyl)Cyclic(1-2)-Disulfide,-Malformin-A Cyclic(D-Cysteinyl-D-Cysteinyl-L-Valyl-D-Leucyl-L-Isoleucyl)Cyclic(1-2)-Disulfide Cyclo(D-Cys-D-Cys-Val-D-Leu-Ile)Cyclic(1-2)-Disulfide Dtxsid60911481 Hb3965 Malformin Malformin-A Malformin-A1 Malformins Mfcd00133524 Nci60_002817 Nsc324646 Nsc-324646
Source	Aspergillus niger [Division : Plants and Fungi] Taxonomy :5061 (Fungi-Ascomycota-Eurotiales-Eurotiomycetes-Aspergillaceae Aspergillus) Wikipedia: Aspergillus niger Aspergillus tubingensis [Division : Plants and Fungi] Taxonomy :5068 (Fungi-Ascomycota-Eurotiales-Eurotiomycetes-Aspergillaceae Aspergillus) Wikipedia: Aspergillus tubingensis PubChem
Information	Malformin is a cyclic peptide.Malformin A is a natural product found in Aspergillus niger and Aspergillus tubingensis with data available. PubChem\|4005

Legend

Structure

Molecular Formula	C23H39N5O5S2
Molecular Weight	529.2392613 g/mol
SMILES RUN SEA Predictions	CCC(C)C1NC(=O)C(CC(C)C)NC(=O)C(C(C)C)NC(=O)C2CSSCC(NC1=O)C(=O)N2 PubChem\|4005
InChI	InChI=1S/C23H39N5O5S2/c1-7-13(6)18-23(33)26-15-9-34-35-10-16(25-20(15)30)21(31)27-17(12(4)5)22(32)24-14(8-11(2)3)19(29)28-18/h11-18H,7-10H2,1-6H3,(H,24,32)(H,25,30)(H,26,33)(H,27,31)(H,28,29)
InChIKey	RNCGDQLZIATDOU-JYSCUBAANA-N

2D Structure PubChem\|4005

Sequence

IUPAC Condensed	cyclo[DL-Cys(1)-DL-Cys(1)-DL-Val-DL-Leu-DL-xiIle] PubChem\|4005
Amino acid chain	DL-Cys(1)(2)--DL-Cys(1)--DL-Val--DL-Leu--DL-xiIle(2) CyclicPepedia\|PP
Graph representation	DL-Cys,DL-Cys,DL-Val,DL-Leu,DL-xiIle @0,1 @0,4 CyclicPepedia\|PP
One letter code from Structure	ICCVL CyclicPepedia\|Struct2seq
Amino acid chain from Structure	Ile(1)--Cys--Cys--Val--Leu(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\|4005

Chemical and Physical Properties

CyclicPepedia|Struc2Seq + PP

Structure Properties

Property Name	Property Value
Exact Mass	529.2392613
Number of Rings	2.0
Complexity	0.685714286
XlogP3 AA	0.5672
Heavy Atom Count	35.0
Hydrogen Bond Donor Count	5.0
Hydrogen Bond Acceptor Count	7.0
Rotatable Bond Count	5.0

Property Name	Property Value
Formal Charge	0.0
Refractivity	138.3175
Rule_of_Five	0.0
Number of Atoms	35.0
Topological Polar Surface Area	145.5
Refractivity	138.3175
Veber Rule	0.0
Ghose Filter	0.0

Property Name	Property Value
RDKit Fingerprint	01000001001000100000000000010000110000000011100000000010100000100100000000101110101100000100100000010100000001001000011000110010010000000000110000011101000010010100001000000110000110000110000100000100001001001000000100000001010000000100010110000010011100001011000100001000000010001001100000000000000000010010100011010000010100000001001010110000000000000000001001001001000000000010000000100010000100000000000110001100000010100000100000100001101000000000100000000010011000000000000100001010000000000100100000100110110000010010001010001101000000001000100000000100001000100100010010000000000010110000101000000001001010011000000000001101000100111000000110110111001000000110000010000000010101000000011100000010101001100000000011000010001000000000000000111010001100101001000000011000000001000001001000011000001000001001000000000100110000010000001010010100000000000011000000110000000100000000001000000001000100100000001001010110010010110000010001011101101000001001111100010000011000010010001010000000010100000001010000000000001001000010100100000010100000000010010100000000001001100001110000000001110010001001000001001010000000000001100010001001110010000000001000011000101010100100100101000000000001101110011010000000100001000100100110100100011100010011010010010000101110000010000000000000100001100000100000001001010110100000000000010101101000000010110000010000011000010001010000010000100100011000001000000001000001011100000010000001101011001000010000001000000000001011100100001100010001100000100000010001001010010000100100000010010011100000001000010100000100100000110001100000100100000001001001000110000010000000000001000001000000000000010000000000000000100000010000000000001010000100000010000000000000010000010100000100100000000001010011100000100000100011001000000000110000010000100000001000000000010000000011010001111001000100000000010000011000000110010000000000100000000000000000100000010100001001101010000100101101000010010000010101001010010110010110100010010001001000000000000001000100100001000101001100110000001000000001101000000000000000000000000011
Morgan Fingerprint	0100000000100000000000000000010001000000001000000000010000000000000000000000000010000000001000000000000000000100000100000000000000100000000000000000000000000000000000000000000000000000000000000010000000000000000000001000000000000000000000000000000000000100000000000000000000000000000100000000001000000100000000000010000001000000000000010000000000000100000010000000000000000000000000000000000000000000000000000000000000000000000000000001000000000000000000000000000000000000000000100010000000001000000000000000000000000001100000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000010000000000000010001000001000000000000000000100000000000000000010000000000000000000000000000000000000000000000000000000000000000000000000000000000000000001000000000000000000100000000000000001000000000001000000000000000000000000000000000000000000000010000000000000000000000000010000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000010000
MACCS Keys	00000000000000100000000000000000000010000000000000000010000000000001000000100001000000001011100100000100110000110011010011001001010100001110111100100111011110111100110

Sequence Properties

Property Name	Property Value
Boman Index	-3.288
Instability	-7.08
Charge	-0.125965132457968
Aliphatic Index	214.0

Manufacturers

Manufacturers Name	Value
CreativePeptides	Malformin A
Bayer healthcare pharmaceuticals	Malformin A
Upsher smith laboratories	Malformin A
Merck	Malformin A

Manufacturers Name	Value
Apotex	Malformin A
Baxter Healthcare Corp	Malformin A
Pharmasources	Malformin A
Novartis	Malformin A
AstraZeneca	Malformin A

Forecasting tools

Forecasting tools	Value
Structure to Sequence	CCC(C)C1NC(=O)C(CC(C)C)NC(=O)C(C(C)C)NC(=O)C2CSSCC(NC1=O)C(=O)N2
Structure Properties	CCC(C)C1NC(=O)C(CC(C)C)NC(=O)C(C(C)C)NC(=O)C2CSSCC(NC1=O)C(=O)N2
Sequence to Structure	ICCVL
Sequence Properties	ICCVL
Expasy ProtParam Tool	ICCVL
SEA	RUN SEA Predictions

Information Source

Property Name	Property ID
Patents	RNCGDQLZIATDOU-JYSCUBAANA-N
pubchem	4005
Drugbank	Malformin A
DRAMP3	Malformin A
Uniprot	Malformin A
Cybase	Malformin A
CONOSERVER	Malformin A
BindingDB	CCC(C)C1NC(=O)C(CC(C)C)NC(=O)C(C(C)C)NC(=O)C2CSSCC(NC1=O)C(=O)N2
CHEMBL	CHEMBL1987208
CTD	Malformin A
Wikipedia	Malformin A
KEGG Compound/Drug	Malformin A
CHEBI	CHEBI:193906
EPA DSSTox	DTXSID60911481
FDA Global Substance Registration System (GSRS)	Malformin A
DTP/NCI
Chemspider	RNCGDQLZIATDOU-JYSCUBAANA-N

Reference

Pubmed_ID	Title	DOI	Journal
4528068	The structure and synthesis of malformin A	10.1073/pnas.71.7.2791.	Proc Natl Acad Sci U S A
The structure and synthesis of malformin A Abstract A structure (the disulfide form of cyclo-D-cysteinyl-L-valyl-D-cysteinyl-D-leucyl-L-isoleucyl), previously proposed for malformin A, was reexamined. On the basis of chemical degradations, a different structure (the disulfide form of cyclo-D-cysteinyl-D-cysteinyl-L-valyl-D-leucyl-L-isoleucyl) was established. Accordingly, a compound with this structure was synthesized and was found to be identical with malformin A. The synthetic product causes curvatures on corn roots; maximum effect was seen at a concentration of 0.1 mug/ml, the optimal concentration for malformin A.
7118425	Allomalformin	None	Int J Pept Protein Res
Allomalformin Abstract In an attempt to find explanation for the initial erroneous sequence assignment for malformin, a sequence-isomer of the natural product, 3-isoleucine-5-valine malformin or briefly "allomalformin" that on partial acid hydrolysis could have given rise to misleading fragments, was synthesized and compared with both natural and synthetic preparations of malformin. Allomalformin is identical to the parent microbial peptide (malformin A, or briefly malformin) with respect to biological activity and conformation (ORD and CD spectra) and is indistinguishable from it by high pressure liquid chromatography. Yet, the two isomers have slightly different Rf values on thin-layer chromatograms and by this method no allomalformin could be detected in samples of the natural product. On the other hand both high pressure liquid chromatography and thin-layer chromatography demonstrated the presence of the lower homolog, 5-valine malformin, in the samples examined. On partial acid hydrolysis this natural analog should liberate Val-Cys, while Cys-Val forms from malformin itself. Similarly, the corresponding desthio cyclopentapeptides should give rise to Val-Ala and Ala-Val respectively; the former being more resistant to further hydrolysis persists in the partial hydrolysates. The presence of Val-Cys in partial hydrolysates of malformin and of Val-Ala in the partial hydrolysates of desthiomalformin, both originating from the accompanying lower homolog rather than from malformin itself, is likely to have led to the postulation of the erroneous Cys-Val-Cys partial sequence.
7531879	Malformin A prevents IL-1 induced endothelial changes by inhibition of protein synthesis	None	Thromb Haemost
Malformin A prevents IL-1 induced endothelial changes by inhibition of protein synthesis Abstract No profile to view
7763777	Structure of malformin B, a phytotoxic metabolite produced by Aspergillus niger	10.1271/bbb.57.787.	Biosci Biotechnol Biochem
Structure of malformin B, a phytotoxic metabolite produced by Aspergillus niger Abstract Malformin B, produced by Aspergillus niger, was separated into six compounds by HPLC. Their structures were determined by amino acid analyses, and by mass spectral and two-dimensional NMR experiments to be cyclic pentapeptides structurally related to malformin A1. Both the NMR and MS/MS experiments suggest cyclo-D-cysteinyl-D-cysteinyl-L-amino acid-D-amino acid-L-amino acid as the essential structure of malformins.