Basic information

CPKB ID	CP00518
IUPAC Name	(5R,8S,11R,15S,18S,19S,22R)-15-[3-(diaminomethylideneamino)propyl]-18-[(1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dienyl]-1,5,19-trimethyl-2-methylidene-8-(2-methylpropyl)-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptazacyclopentacosane-11,22-dicarboxylic acid
Synonyms	(5R,8S,11R,15S,18S,19S,22R)-15-[3-(Diaminomethylideneamino)Propyl]-18-[(1E,3E,5S,6S)-6-Methoxy-3,5-Dimethyl-7-Phenylhepta-1,3-Dienyl]-1,5,19-Trimethyl-2-Methylidene-8-(2-Methylpropyl)-3,6,9,13,16,20,25-Heptaoxo-1,4,7,10,14,17,21-Heptazacyclopentacosane-11,22-Dicarboxylic-Acid (D-Asp3)Microcystin-Lr [D-Asp3]Mc-Lr 120011-66-7 Cyanoginosin-La,-4-D-Beta-Aspartic-Acid-5-L-Arginine- Cyclo-Ala-Leu-Isoasp-Arg-Adda-Isoglu-N-Mdha Dtxsid501016182 Microcystin-[D-Asp3]-Lr Toxin-Ii,-Cyanobacterium
Source	Microcystis aeruginosa [Division : Bacteria] Taxonomy :1126 (Unassigned-Cyanobacteriota-Chroococcales-Cyanophyceae-Microcystaceae Microcystis) Wikipedia: Microcystis aeruginosa PubChem
Information	Toxin II, cyanobacterium is a natural product found in Microcystis aeruginosa with data available. PubChem\|6440025

Legend

Structure

Molecular Formula	C48H72N10O12
Molecular Weight	980.5331177 g/mol
SMILES RUN SEA Predictions	C=C1C(=O)N[C@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(=O)O)CC(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](/C=C/C(C)=C/[C@H](C)[C@H](Cc2ccccc2)OC)[C@H](C)C(=O)N[C@@H](C(=O)O)CCC(=O)N1C PubChem\|6440025
InChI	InChI=1S/C48H72N10O12/c1-26(2)22-36-45(65)57-37(47(68)69)25-39(59)53-34(16-13-21-51-48(49)50)44(64)54-33(18-17-27(3)23-28(4)38(70-9)24-32-14-11-10-12-15-32)29(5)41(61)55-35(46(66)67)19-20-40(60)58(8)31(7)43(63)52-30(6)42(62)56-36/h10-12,14-15,17-18,23,26,28-30,33-38H,7,13,16,19-22,24-25H2,1-6,8-9H3,(H,52,63)(H,53,59)(H,54,64)(H,55,61)(H,56,62)(H,57,65)(H,66,67)(H,68,69)(H4,49,50,51)/b18-17+,27-23+/t28-,29-,30+,33-,34-,35+,36-,37+,38-/m0/s1
InChIKey	VYEBKSHVYPDMQQ-XAPZPTIVNA-N

2D Structure PubChem\|6440025

Sequence

Amino acid chain from Structure

Adda(1)--Asp--Leu--Ala--NMe-Dha--Glu(1)

CyclicPepedia|Struct2seq

Chemical and Physical Properties

Structure Properties

Property Name	Property Value
Exact Mass	980.5331177
Number of Rings	2.0
Complexity	0.871428571
XlogP3 AA	0.3724
Heavy Atom Count	70.0
Hydrogen Bond Donor Count	10.0
Hydrogen Bond Acceptor Count	11.0
Rotatable Bond Count	15.0

Property Name	Property Value
Formal Charge	0.0
Refractivity	259.8246
Rule_of_Five	0.0
Number of Atoms	70.0
Topological Polar Surface Area	343.14
Refractivity	259.8246
Veber Rule	0.0
Ghose Filter	0.0

Property Name	Property Value
RDKit Fingerprint	01110001111000111000110111110001110001010111000000010011101001110110000111101100100000001010100010001101111101001011001011110000010100000110111101001101100011111111101110100101001111000110010110110110011111001011000101000000010001000111111111000111011100101011000111001001000011111001111000000010010011011011101101000100111100110010001111011111000000011011001011000000101000010000001000010011000100011100100111001111000011110110111100110001111011100000001100001110111011010000100010001010100110011101110101101100110001101011011110010101100010100001101010010111101000001100010111001101100010111100101001010001011111011111001000001111100100111111001111101110110011000110101011100001010101001100011111111011100111100000101100110110001011100101011010001010001100110100101101110000000001100001001010011100001110101000110000000011111110100100011010100101001100111010100000110011001100011100111001011011101110001001111110010110011110010110010001111111010110101000111011010100110101010100001010110011110100010100110000110100101110011011000100000011100000100111000011001111111101100111000011011101111010000101010111110010000100101000011111001011110111011101111011101001101111100101100111000001110100011010100001101011110000001111011111101110011101111110011011110110111101101110101101001001010010011001011100111001110110100111000000101101100001100011111110000001011111110011010000010001100100011100011110000010010011101100001011100111100011100000010010101011001001101011101101101110111000100000100001111001111000101101111110010011000001110110001101110010010110110100010010101101001100011111101001011101011010110110111100001011000100100001010000010000100100010010010001011001010111011101000010001001000100011111011100100100111001010001000011111011100010110111101000010001010101011100101010000000100000010011001000000011111101101100101011110011011110110111110000011010000000100011100111101000110010101101101100010110101111000001010110110101010010101111010110000111110011011000001110010101101001100001101111111101100010001110001111101100001100010001001101010011
Morgan Fingerprint	0100000000100000000000000000000101010000001000010001000000000000100000000000000110000000001000000000110000000000000100000100000000001000000010011001000000100000000000000000000100000000000000000000000000001000000000000000000000000001010000010000000000100000000000000000000000000000000101000000000000000100000000000010000001000001000000010000001000000001000110000010000000000000000000000001010000000000000000010100000000000000000000000001001000000000000000000000000000000000000000000000000000000001000000000000000000000000000000000000000000100000010000010100000000000000000000000000000001000000000000000000000000000100000000000000000001000000000000000010000000000000010000000000000000001000000100110000000000000000001100101000011000100100000000000100000000000000000000000000000000000000000000000000001000000001010000000000000100001000100000000100000001001000110000000000000001000000000000010100010001000010000000000000000000000010000000010000000000000000000000000000000000000001001010001001000000000000110000100000000001010000
MACCS Keys	00000000000000000000000001000000001000000001010000100110000000000000000000111111100011000011110101011000101010110001111111110011100110001101111100111111111111111111110

Manufacturers

Manufacturers Name	Value
CreativePeptides	Toxin Ii, Cyanobacterium
Bayer healthcare pharmaceuticals	Toxin Ii, Cyanobacterium
Upsher smith laboratories	Toxin Ii, Cyanobacterium
Merck	Toxin Ii, Cyanobacterium

Manufacturers Name	Value
Apotex	Toxin Ii, Cyanobacterium
Baxter Healthcare Corp	Toxin Ii, Cyanobacterium
Pharmasources	Toxin Ii, Cyanobacterium
Novartis	Toxin Ii, Cyanobacterium
AstraZeneca	Toxin Ii, Cyanobacterium

Forecasting tools

Forecasting tools	Value
Structure to Sequence	C=C1C(=O)N[C@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(=O)O)CC(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](/C=C/C(C)=C/[C@H](C)[C@H](Cc2ccccc2)OC)[C@H](C)C(=O)N[C@@H](C(=O)O)CCC(=O)N1C
Structure Properties	C=C1C(=O)N[C@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(=O)O)CC(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](/C=C/C(C)=C/[C@H](C)[C@H](Cc2ccccc2)OC)[C@H](C)C(=O)N[C@@H](C(=O)O)CCC(=O)N1C
Expasy ProtParam Tool
SEA	RUN SEA Predictions

Information Source

Property Name	Property ID
Patents	VYEBKSHVYPDMQQ-XAPZPTIVNA-N
pubchem	6440025
Drugbank	Toxin Ii, Cyanobacterium
DRAMP3	Toxin Ii, Cyanobacterium
Uniprot	Toxin Ii, Cyanobacterium
Cybase	Toxin Ii, Cyanobacterium
CONOSERVER	Toxin Ii, Cyanobacterium
BindingDB	C=C1C(=O)N[C@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(=O)O)CC(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](/C=C/C(C)=C/[C@H](C)[C@H](Cc2ccccc2)OC)[C@H](C)C(=O)N[C@@H](C(=O)O)CCC(=O)N1C
CHEMBL	Toxin Ii, Cyanobacterium
CTD	Toxin Ii, Cyanobacterium
Wikipedia	Toxin Ii, Cyanobacterium
KEGG Compound/Drug	Toxin Ii, Cyanobacterium
CHEBI	VYEBKSHVYPDMQQ-XAPZPTIVNA-N
EPA DSSTox	DTXSID501016182
FDA Global Substance Registration System (GSRS)	Toxin Ii, Cyanobacterium
DTP/NCI	Toxin Ii, Cyanobacterium
Chemspider	VYEBKSHVYPDMQQ-XAPZPTIVNA-N

Reference

Pubmed_ID

Title

DOI

Journal

10075778

New jaspamide derivatives from the marine sponge Jaspis splendans collected in Vanuatu

10.1021/np9803225.

J Nat Prod

New jaspamide derivatives from the marine sponge Jaspis splendans collected in Vanuatu

Abstract

Two new jaspamide derivatives (1 and 2) along with jaspamide have been isolated from the marine sponge Jaspis splendans collected in Vanuatu. Their chemical structures were determined from 1D and 2D NMR studies and MS data. These two compounds inhibited the in vitro growth of the NSCLC-N6 human tumor cell lines with IC50 values in the microg/mL range.