Molecule

[3,3'-Biindoline]-2,2'-dione

AlkaPlorer ID: AK290612

Synonym: 3-(1,2-Dihydro-2-oxo-3H-indol-3-ylidene)-1,3-dihydro-2H-indol-2-one, Isoindigotin, Isoindigo, Indigo brown

IUPAC Name: 3-(2-hydroxy-1H-indol-3-yl)indol-2-one

Structure

SMILES: OC1=NC2=CC=CC=C2/C1=C1\C(O)=NC2=CC=CC=C12

InChI: InChI=1S/C16H10N2O2/c19-15-13(9-5-1-3-7-11(9)17-15)14-10-6-2-4-8-12(10)18-16(14)20/h1-8H,(H,17,19)(H,18,20)/b14-13+

InChIKey: MLCPSWPIYHDOKG-BUHFOSPRSA-N

Reference

Identification of an indigo precursor from leaves of Isatis tinctoria (Woad)

CAS: 476-34-6

LOTUS: LTS0222556

SuperNatural Ⅲ: SN0228535-01

NPASS: NPC147957

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
None	Indigofera	Fabaceae	Fabales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Persicaria tinctoria	Persicaria	Polygonaceae	Caryophyllales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Isatis tinctoria	Isatis	Brassicaceae	Brassicales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Angelica pubescens	Angelica	Apiaceae	Apiales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Angelica taiwaniana	Angelica	Apiaceae	Apiales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
None	Polygonum	Polygonaceae	Caryophyllales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Hansenia forbesii	Hansenia	Apiaceae	Apiales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota

Properties Information

Molecule Weight: 262.268

TPSA？: 65.18

MolLogP？: 3.800600000000001

Number of H-Donors: 2

Number of H-Acceptors: 2

RingCount: 4

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Homo sapiens	786-0	GI50	9418.9	nM	None
Homo sapiens	A498	GI50	20941.12	nM	None
Homo sapiens	A549	GI50	27415.74	nM	None
Homo sapiens	ACHN	GI50	12560.3	nM	None
Homo sapiens	BT-549	GI50	25644.84	nM	None
Homo sapiens	CAKI-1	GI50	19724.23	nM	None
Homo sapiens	CCRF-CEM	GI50	2897.34	nM	None
Homo sapiens	COLO 205	GI50	21877.62	nM	None
Homo sapiens	Cyclin-dependent kinase 2/cyclin A	Inhibition	nan	%	10.1016/j.bmc.2009.09.008
Homo sapiens	DU-145	GI50	12912.19	nM	None
Homo sapiens	EKVX	GI50	20653.8	nM	None
Homo sapiens	HCC 2998	GI50	23173.95	nM	None
Homo sapiens	HCT-116	GI50	16982.44	nM	None
Homo sapiens	HCT-116	IC50	30000.0	nM	10.1016/j.bmc.2009.09.008
Homo sapiens	HCT-15	GI50	3837.07	nM	None
Homo sapiens	HL-60	IC50	16600.0	nM	10.1016/j.bmc.2009.09.008
Homo sapiens	HL-60	Inhibition	53.0	%	10.1016/j.ejmech.2007.05.012
Homo sapiens	HOP-62	GI50	25003.45	nM	None
Homo sapiens	HOP-92	GI50	20558.91	nM	None
Homo sapiens	Hs-578T	GI50	49203.95	nM	None
Homo sapiens	HT-29	GI50	4977.37	nM	None
Homo sapiens	Huh-7	IC50	28900.0	nM	10.1016/j.bmc.2009.09.008
Homo sapiens	IGROV-1	GI50	10280.16	nM	None
Homo sapiens	K562	GI50	7481.7	nM	None
Homo sapiens	K562	IC50	6700.0	nM	10.1016/j.bmc.2009.09.008
Homo sapiens	K562	Inhibition	64.0	%	10.1016/j.ejmech.2007.05.012
Homo sapiens	KB	IC50	1600.0	nM	10.1016/j.ejmech.2007.05.012
Homo sapiens	KB	Inhibition	92.0	%	10.1016/j.ejmech.2007.05.012
Homo sapiens	KM12	GI50	21627.19	nM	None
Homo sapiens	LOX IMVI	GI50	18620.87	nM	None
Homo sapiens	M14	GI50	32062.69	nM	None
Homo sapiens	Malme-3M	GI50	13182.57	nM	None
Homo sapiens	MCF7	GI50	4518.56	nM	None
Homo sapiens	MDA-MB-231	GI50	27797.13	nM	None
Homo sapiens	MDA-MB-435	GI50	11939.88	nM	None
Homo sapiens	MDA-N	GI50	24547.09	nM	None
Homo sapiens	MOLT-4	GI50	3589.22	nM	None
Homo sapiens	NCI/ADR-RES	GI50	17258.38	nM	None
Homo sapiens	NCI-H226	GI50	100000.0	nM	None
Homo sapiens	NCI-H23	GI50	20892.96	nM	None
Homo sapiens	NCI-H322M	GI50	36475.39	nM	None
Homo sapiens	NCI-H460	GI50	21577.44	nM	None
Homo sapiens	NCI-H522	GI50	10327.61	nM	None
Homo sapiens	OVCAR-3	GI50	19319.68	nM	None
Homo sapiens	OVCAR-4	GI50	10023.05	nM	None
Homo sapiens	OVCAR-5	GI50	3475.36	nM	None
Homo sapiens	OVCAR-8	GI50	18793.17	nM	None
Homo sapiens	PC-3	GI50	9749.9	nM	None
Homo sapiens	Protein-glutamine gamma-glutamyltransferase	IC50	8000.0	nM	10.1016/j.bmcl.2010.12.037
Homo sapiens	Protein-glutamine gamma-glutamyltransferase	Ki	41000.0	nM	10.1016/j.bmcl.2010.12.037
Homo sapiens	RPMI-8226	GI50	17258.38	nM	None
Homo sapiens	RXF 393	GI50	3556.31	nM	None
Homo sapiens	SF-268	GI50	31188.9	nM	None
Homo sapiens	SF-295	GI50	60255.96	nM	None
Homo sapiens	SK-MEL-2	GI50	18450.15	nM	None
Homo sapiens	SK-MEL-28	GI50	91201.08	nM	None
Homo sapiens	SK-MEL-5	GI50	59703.53	nM	None
Homo sapiens	SK-OV-3	GI50	59703.53	nM	None
Homo sapiens	SN12C	GI50	18967.06	nM	None
Homo sapiens	SNB-19	GI50	22490.55	nM	None
Homo sapiens	SNB-75	GI50	14092.89	nM	None
Homo sapiens	SR	GI50	2818.38	nM	None
Homo sapiens	SW-620	GI50	4570.88	nM	None
Homo sapiens	T47D	GI50	1345.86	nM	None
Homo sapiens	TK-10	GI50	31550.05	nM	None
Homo sapiens	U-251	GI50	11402.5	nM	None
Homo sapiens	UACC-257	GI50	31117.16	nM	None
Homo sapiens	UACC-62	GI50	17258.38	nM	None
Homo sapiens	UO-31	GI50	13645.83	nM	None
Mus musculus	Cytochrome P450 1A1	Ratio	1.44	None	10.1016/j.bmc.2008.12.052
Mus musculus	NAD(P)H dehydrogenase [quinone] 1	Ratio	0.025	None	10.1016/j.bmc.2008.12.052
Mus musculus	NAD(P)H dehydrogenase [quinone] 1	Ratio	2.8	None	10.1016/j.bmc.2008.12.052
Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	27000.0	nM	10.1016/j.bmcl.2013.11.024
None	ADMET	IC50	16300.0	nM	10.1016/j.bmc.2009.09.008
None	ADMET	Ratio	25.0	None	10.1016/j.bmc.2008.12.052
None	Unchecked	Ratio	1.94	None	10.1016/j.bmc.2008.12.052