Molecule

Indole

AlkaPlorer ID: AK008871

Synonym: None

IUPAC Name: 1H-indol-1-ium

Structure

SMILES: C1=CC2=CC=CC=C2[NH2+]1

InChI: InChI=1S/C8H7N/c1-2-4-8-7(3-1)5-6-9-8/h1-6,9H/p+1

InChIKey: SIKJAQJRHWYJAI-UHFFFAOYSA-O

Reference

Antimicrobial activities of indole.

PubChem CID: 22035206

CAS: 120-72-9

LOTUS: LTS0185357

NPASS: NPC117652

COCONUT: CNP0118430

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Camellia sinensis	Camellia	Theaceae	Ericales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Citrus sp.	Citrus	Rutaceae	Sapindales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Viverra zibetha	Viverra	Viverridae	Carnivora	Mammalia	Chordata	Metazoa	Eukaryota
Sauromatum venosum	Sauromatum	Araceae	Alismatales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota

Properties Information

Molecule Weight: 118.15899999999998

TPSA？: 16.61

MolLogP？: 0.8657999999999999

Number of H-Donors: 1

Number of H-Acceptors: 0

RingCount: 2

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Bos taurus	Carbonic anhydrase 3	Ki	17600.0	nM	10.1016/j.ejmech.2011.12.022
Bos taurus	Serum albumin	Log 1/C	4.07	None	10.1021/jm00118a010
Cutibacterium acnes	Cutibacterium acnes	MIC	200.0	ug.mL-1	10.1021/np50103a002
Enterobacteria phage T4	Lysozyme	Kd	290000.0	nM	10.1021/jm0491187
Hepacivirus hominis	Hepatitis C virus	FC	10.0	None	10.1128/aac.00669-08
Homo sapiens	A549	IC50	100000.0	nM	10.1016/j.bmcl.2012.02.011
Homo sapiens	Acyl coenzyme A:cholesterol acyltransferase	Activity	nan	None	10.1021/jm061471k
Homo sapiens	Adenosine kinase	Kd	3000000.0	nM	10.1021/jm000373a
Homo sapiens	Adenosine kinase	Kd	3000000.0	nM	10.1021/jm040031v
Homo sapiens	Carbonic anhydrase I	Ki	27400.0	nM	10.1016/j.ejmech.2011.12.022
Homo sapiens	Carbonic anhydrase II	Ki	32500.0	nM	10.1016/j.ejmech.2011.12.022
Homo sapiens	Carbonic anhydrase IV	Ki	2330.0	nM	10.1016/j.ejmech.2011.12.022
Homo sapiens	Carbonic anhydrase VI	Ki	3630.0	nM	10.1016/j.ejmech.2011.12.022
Homo sapiens	Cyclin-dependent kinase 5/CDK5 activator 1	Inhibition	78.0	%	10.1021/jm030561b
Homo sapiens	Cyclin-dependent kinase 5/CDK5 activator 1	Inhibition	81.0	%	10.1021/jm030561b
Homo sapiens	Glycogen synthase kinase-3	Inhibition	68.0	%	10.1021/jm030561b
Homo sapiens	Glycogen synthase kinase-3	Inhibition	76.0	%	10.1021/jm030561b
Homo sapiens	Intercellular adhesion molecule (ICAM-1), Integrin alpha-L/beta-2	Kd	300000.0	nM	10.1021/jm000503f
Homo sapiens	Intercellular adhesion molecule (ICAM-1), Integrin alpha-L/beta-2	Kd	300000.0	nM	10.1021/jm040031v
Homo sapiens	MCF7	IC50	nan	None	10.1016/j.ejmech.2016.04.039
Homo sapiens	MDA-MB-231	IC50	100000.0	nM	10.1016/j.bmcl.2012.02.011
Homo sapiens	MRC5	IC50	15580.0	nM	10.1016/j.bmcl.2012.02.011
Homo sapiens	NCI-H292	IC50	50000.0	nM	10.1016/j.ejmech.2016.04.039
Homo sapiens	SK-N-SH	IC50	1780.0	nM	10.1016/j.bmcl.2012.02.011
Homo sapiens	Transient receptor potential cation channel subfamily A member 1	Activity	111.0	%	10.1016/j.bmcl.2020.127639
Homo sapiens	Transient receptor potential cation channel subfamily A member 1	EC50	75200.0	nM	10.1016/j.bmcl.2020.127639
Homo sapiens	U-251	EC50	625000.0	nM	10.1039/C8MD00436F
Homo sapiens	U-251	EC50	nan	None	10.1016/j.bmcl.2017.02.033
Homo sapiens	U-87 MG	EC50	625000.0	nM	10.1039/C8MD00436F
Oryctolagus cuniculus	Glycogen phosphorylase, muscle form	Activity	nan	None	10.1021/acs.jmedchem.5b01114
Plutella xylostella	Phenol oxidase	IC50	78320.0	nM	10.1128/aem.00301-12
Plutella xylostella	Phenol oxidase	Inhibition	nan	%	10.1128/aem.00301-12
Plutella xylostella	Plutella xylostella	Activity	nan	None	10.1128/aem.00301-12
Plutella xylostella	Plutella xylostella	LC50	6274.3	ppm	10.1128/aem.00301-12
Rattus norvegicus	INS1	Activity	nan	None	10.1016/j.bmcl.2021.128096
Rattus norvegicus	INS1	Activity_index	3.31	None	10.1016/j.bmcl.2021.128096
Rattus norvegicus	INS1	Activity_index	7.72	None	10.1016/j.bmcl.2021.128096
Rattus norvegicus	Rattus norvegicus	Inhibition	nan	%	10.1021/jm00214a015
Saccharomyces cerevisiae	Saccharomyces cerevisiae	EC50	300000.0	nM	10.1016/j.ejmech.2022.114845
Spodoptera exigua	Spodoptera exigua	IC50	52920.0	nM	10.1128/aem.00301-12
None	ADMET	Log k' w	2.014	None	10.1021/jm00118a010
None	ADMET	LogP app	-4.5	None	10.1016/j.bmc.2007.03.040
None	ADMET	Ratio	85.7	None	10.1021/acs.jmedchem.2c00444
None	NON-PROTEIN TARGET	IC50	50000.0	nM	10.1016/j.ejmech.2016.04.039
None	NON-PROTEIN TARGET	Inhibition	25.0	%	10.1016/j.bmc.2013.05.044
None	NON-PROTEIN TARGET	Inhibition	25.6	%	10.1016/j.bmc.2013.12.040
None	NON-PROTEIN TARGET	Inhibition	nan	%	10.1016/j.bmc.2013.05.044
None	NON-PROTEIN TARGET	Inhibition	nan	%	10.1016/j.bmc.2013.12.040
None	No relevant target	CHI	69.15	None	10.1016/j.ejmech.2019.111770
None	No relevant target	LogD	0.66	None	10.1021/jm701549s
None	No relevant target	LogD	2.24	None	10.1021/jm701549s
None	No relevant target	LogP	2.14	None	10.1016/j.bmc.2007.03.040
None	No relevant target	LogP	2.14	None	10.1016/j.bmcl.2005.04.064
None	No relevant target	LogP	2.14	None	10.1021/jm00118a010
None	No relevant target	LogP	2.14	None	10.1021/jm00171a043
None	No relevant target	Log PNalk	0.68	None	10.1021/jm048980b
None	No relevant target	Log S	-1.21	None	10.1016/s0960-894x(00)00172-4
None	No relevant target	pKa	-2.4	None	10.1021/acs.jmedchem.2c00444
None	No relevant target	Retention_time	10.27	min	10.1016/j.ejmech.2019.111770
None	Unchecked	Activity	nan	None	10.1016/j.bmcl.2009.07.082
None	Unchecked	Activity	nan	None	10.1016/j.bmcl.2021.128096
None	Unchecked	Activity	nan	None	10.1021/jm061471k
None	Unchecked	EC50	625000.0	nM	10.1039/C8MD00436F
None	Unchecked	EC50	nan	None	10.1016/j.bmcl.2017.02.033
None	Unchecked	IC50	64900.0	nM	10.1128/aem.00301-12
None	Unchecked	IC50	10000000.0	nM	10.1016/S0960-894X(00)80378-9
None	Unchecked	Inhibition	nan	%	10.1016/j.bmcl.2009.07.082
None	Unchecked	Inhibition	nan	%	10.1128/aem.00301-12

Metabolism Information

AKRT ID	Reaction	Reaction Link ID
AKRT004115	CC(=O)O.c1ccc2[nH]ccc2c1>>O=C(O)Cc1c[nH]c2ccccc12	MNXR176713
AKRT012952	C[C@@H](O)[C@H](N)C(=O)O.c1ccc2[nH]ccc2c1>>C[C@@H](c1c[nH]c2ccccc12)[C@H](N)C(=O)O	enzymemap_83787
AKRT019501	N[C@@H](CO)C(=O)O.c1ccc2[nH]ccc2c1>>N[C@@H](Cc1c[nH]c2ccccc12)C(=O)O	RXN0-2382
AKRT019530	N[C@@H](COP(=O)(O)O)C(=O)O.c1ccc2[nH]ccc2c1>>N[C@@H](Cc1c[nH]c2ccccc12)C(=O)O	MNXR172579
AKRT019810	N[C@@H](Cc1c[nH]c2ccccc12)C(=O)O>>c1ccc2[nH]ccc2c1	RXN-15578
AKRT020286	N[C@H](CO)C(=O)O.c1ccc2[nH]ccc2c1>>N[C@H](Cc1c[nH]c2ccccc12)C(=O)O	enzymemap_83450
AKRT022966	O=C(O)Cc1c[nH]c2ccccc12>>c1ccc2[nH]ccc2c1	RXN-1408
AKRT023273	O=C(O)c1c[nH]c2ccccc12>>c1ccc2[nH]ccc2c1	RXN-12341
AKRT023491	O=C1/C(=C2\Nc3ccccc3C2=O)Nc2ccccc21>>c1ccc2[nH]ccc2c1	MNXR141390
AKRT023653	O=C=O.c1ccc2[nH]ccc2c1>>O=C(O)c1c[nH]c2ccccc12	RXN-12341
AKRT023744	O=C[C@H](O)COP(=O)(O)O.c1ccc2[nH]ccc2c1>>O=P(O)(O)OC[C@@H](O)[C@@H](O)c1c[nH]c2ccccc12	R02340
AKRT023745	O=C[C@H](O)COP(=O)(O)O.c1ccc2[nH]ccc2c1>>O=P(O)(O)OC[C@@H](O)[C@H](O)c1c[nH]c2ccccc12	enzymemap_84087
AKRT023806	O=P(O)(O)OC[C@@H](O)CO.c1ccc2[nH]ccc2c1>>O=P(O)(O)OC[C@@H](O)[C@@H](O)c1c[nH]c2ccccc12	MNXR179414
AKRT023808	O=P(O)(O)OC[C@@H](O)[C@@H](O)c1c[nH]c2ccccc12>>O=CC(O)COP(=O)(O)O.c1ccc2[nH]ccc2c1	None
AKRT023810	O=P(O)(O)OC[C@@H](O)[C@@H](O)c1c[nH]c2ccccc12>>c1ccc2[nH]ccc2c1	RXN0-2381
AKRT023816	O=P(O)(O)OC[C@H](O)CO.c1ccc2[nH]ccc2c1>>O=P(O)(O)OC[C@@H](O)[C@@H](O)c1c[nH]c2ccccc12	MNXR178235
AKRT023819	O=P(O)(O)OC[C@H](O)[C@H](O)c1c[nH]c2ccccc12>>O=C[C@@H](O)COP(=O)(O)O.c1ccc2[nH]ccc2c1	None
AKRT023820	O=P(O)(O)OC[C@H](O)[C@H](O)c1c[nH]c2ccccc12>>c1ccc2[nH]ccc2c1	enzymemap_84041
AKRT024971	c1ccc2[nH]ccc2c1>>N[C@@H](Cc1c[nH]c2ccccc12)C(=O)O	retrobiocat_337
AKRT024972	c1ccc2[nH]ccc2c1>>O=C1CNc2ccccc21	RXN-16824
AKRT024973	c1ccc2[nH]ccc2c1>>O=C1Cc2ccccc2N1	RXN-6681
AKRT024974	c1ccc2[nH]ccc2c1>>O=CNc1ccccc1C=O	INDOLE-23-DIOXYGENASE-RXN
AKRT024975	c1ccc2[nH]ccc2c1>>O[C@@H]1Nc2ccccc2[C@@H]1O	enzymemap_11269
AKRT024976	c1ccc2[nH]ccc2c1>>O[C@H]1Nc2ccccc2[C@H]1O	RXN-9819
AKRT024977	c1ccc2[nH]ccc2c1>>Oc1c[nH]c2ccccc12	R02339
AKRT024978	c1ccc2[nH]ccc2c1>>Oc1cccc2cc[nH]c12	enzymemap_12507