Molecule

Prodigiosin

AlkaPlorer ID: AK325372

Synonym: None

IUPAC Name: 3-methoxy-2-[(5-methyl-4-pentyl-1H-pyrrol-2-yl)methylidene]-5-(1H-pyrrol-2-yl)pyrrole

Structure

SMILES: CCCCCC1=C/C(=C/C2=C(OC)C=C(C3=CC=CN3)N2)N=C1C

InChI: InChI=1S/C20H25N3O/c1-4-5-6-8-15-11-16(22-14(15)2)12-19-20(24-3)13-18(23-19)17-9-7-10-21-17/h7,9-13,21,23H,4-6,8H2,1-3H3/b16-12-

InChIKey: SZXDNGVQRDTJSD-VBKFSLOCSA-N

Reference

A 2-Substituted Prodiginine, 2-(<i>p</i>-Hydroxybenzyl)prodigiosin, from<i>Pseudoalteromonas rubra</i>

CAS: 82-89-3

LOTUS: LTS0154862

NPASS: NPC84853

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Serratia marcescens	Serratia	Yersiniaceae	Enterobacterales	Gammaproteobacteria	Pseudomonadota	None	Bacteria

Properties Information

Molecule Weight: 323.44

TPSA？: 53.17

MolLogP？: 5.340500000000005

Number of H-Donors: 2

Number of H-Acceptors: 2

RingCount: 3

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Escherichia coli	Escherichia coli	MIC	1.0	ug.mL-1	10.1021/jm501552x
Escherichia coli	Escherichia coli	MIC	2.0	ug.mL-1	10.1021/jm501552x
Escherichia coli	Escherichia coli	MIC	32.0	ug.mL-1	10.1021/jm501552x
Escherichia coli	Escherichia coli	Ratio	2.0	None	10.1021/jm501552x
Homo sapiens	A549	IC50	77.0	nM	10.1016/j.bmcl.2005.10.027
Homo sapiens	DLD-1	IC50	79.0	nM	10.1016/j.bmcl.2005.10.027
Homo sapiens	DNA topoisomerase I	Inhibition	nan	%	10.1021/np800493p
Homo sapiens	HT-29	IC50	173.0	nM	10.1016/j.bmcl.2005.10.027
Homo sapiens	MDA-MB-231	IC50	213.0	nM	10.1016/j.bmcl.2005.10.027
Homo sapiens	NCI-H460	IC50	32.0	nM	10.1016/j.bmcl.2005.10.027
Homo sapiens	SK-OV-3	IC50	1300.0	nM	10.1021/np800493p
Mycobacterium tuberculosis	Probable low molecular weight protein-tyrosine-phosphatase	IC50	8800.0	nM	10.1021/jm2012062
Plasmodium falciparum	Plasmodium falciparum	IC50	8.0	nM	10.1021/jm200543y
Staphylococcus aureus	Staphylococcus aureus	MIC	2.0	ug.mL-1	10.1021/jm501552x
Staphylococcus aureus	Staphylococcus aureus	MIC	16.0	ug.mL-1	10.1021/jm501552x
Staphylococcus aureus	Staphylococcus aureus	Ratio	8.0	None	10.1021/jm501552x
None	ADMET	Drug uptake	nan	None	10.1007/s00044-005-0133-z
None	Molecular identity unknown	Activity	nan	None	10.1007/s00044-005-0133-z
None	NON-PROTEIN TARGET	Activity	5.6	%	10.1007/s00044-005-0133-z
None	NON-PROTEIN TARGET	Activity	28.0	%	10.1007/s00044-005-0133-z
None	NON-PROTEIN TARGET	Activity	34.0	%	10.1007/s00044-005-0133-z
None	NON-PROTEIN TARGET	Activity	nan	None	10.1007/s00044-005-0133-z
None	NON-PROTEIN TARGET	IC50	75000.0	nM	10.1007/s00044-005-0133-z
None	Unchecked	Activity	nan	None	10.1007/s00044-005-0133-z

Metabolism Information

AKRT ID	Reaction	Reaction Link ID
AKRT009433	CCCCCc1cc[nH]c1C.COc1cc(-c2ccc[nH]2)[nH]c1C=O>>CCCCCC1=C/C(=C/c2[nH]c(-c3ccc[nH]3)cc2OC)N=C1C	RXN-15787