Indigocarmine (CED0003697)

Record Information

Version

1.0

Creation Date

2016-05-22 04:43:54 UTC

Update Date

2026-05-14 19:10:37 UTC

Accession Number

CHEM017907

Identification

Common Name

Indigocarmine

Class

Small Molecule

Description

Indigocarmine is an organic compound with the formula C16H10N2O8S2 and an average molecular weight of 422.39 g/mol. Indigocarmine belongs to the indolines, a subclass of indoles and derivatives within the organic compounds. It is categorized as an organoheterocyclic compound. Regarding its pharmacological profile, there are six recorded protein targets for this substance. It acts as an agonist of the Alpha-1D adrenergic receptor (ADRA1D) as well as the Alpha-2A, Alpha-2B, and Alpha-2C adrenergic receptors (ADRA2A, ADRA2B, and ADRA2C). Additionally, two other proteins are recorded as targets. Indigocarmine is found in or released from one recorded source: unclassified diagnostic agents within healthcare, pharmaceuticals, and veterinary products. The recorded exposure routes for this compound are intravenous and intramuscular.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-(1,3-Dihydro-3-oxo-5-sulphO-2H-indol-2-ylidene)-3-oxoindoline-5-sulphonic acid	ChEBI
Indigo carmine free acid	ChEBI
Indigo-5,5'-disulfonic acid	ChEBI
Indigotindisulfonate	ChEBI
Indigotindisulfonic acid	ChEBI
2-(1,3-Dihydro-3-oxo-5-sulfO-2H-indol-2-ylidene)-3-oxoindoline-5-sulfonate	Generator
2-(1,3-Dihydro-3-oxo-5-sulfO-2H-indol-2-ylidene)-3-oxoindoline-5-sulfonic acid	Generator
2-(1,3-Dihydro-3-oxo-5-sulphO-2H-indol-2-ylidene)-3-oxoindoline-5-sulphonate	Generator
Indigo-5,5'-disulfonate	Generator
Indigo-5,5'-disulphonate	Generator
Indigo-5,5'-disulphonic acid	Generator
Indigotindisulphonate	Generator
Indigotindisulphonic acid	Generator
Indigo blue	HMDB
Indigo	HMDB
(delta-2,2'-Biindole)-3,3'-dione	HMDB
Carmine, indigo	HMDB
Indigo disulfonate	HMDB
Soluble indigo blue	HMDB
Indigotin	HMDB
2-(1,3-Dihydro-3-oxo-5-sulphO-2H-indol-2-ylidene)-3- oxoindoline-5-sulphonic acid	HMDB
D And C blue no. 6	HMDB
Disulfonate, indigo	HMDB
FD And C blue no. 2	HMDB
Indigo blue, soluble	HMDB
Indigotindisulfonate sodium	HMDB
indigo Carmine	MeSH, HMDB

Chemical Formula

C₁₆H₁₀N₂O₈S₂

Average Molecular Mass

422.389 g/mol

Monoisotopic Mass

421.988 g/mol

CAS Registry Number

483-20-5

IUPAC Name

(E)-3,3'-dioxo-1H,1'H,3H,3'H-[2,2'-biindolylidene]-5,5'-disulfonic acid

Traditional Name

(E)-3,3'-dioxo-1H,1'H-[2,2'-biindolylidene]-5,5'-disulfonic acid

SMILES

OS(=O)(=O)C1=CC2=C(N\C(C2=O)=C2\NC3=C(C=C(C=C3)S(O)(=O)=O)C2=O)C=C1

InChI Identifier

InChI=1S/C16H10N2O8S2/c19-15-9-5-7(27(21,22)23)1-3-11(9)17-13(15)14-16(20)10-6-8(28(24,25)26)2-4-12(10)18-14/h1-6,17-18H,(H,21,22,23)(H,24,25,26)/b14-13+

InChI Key

CFZXDJWFRVEWSR-BUHFOSPRSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolines. Indolines are compounds containing an indole moiety, which consists of pyrrolidine ring fused to benzene to form 2,3-dihydroindole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolines

Direct Parent

Indolines

Alternative Parents

Substituents

Arylsulfonic acid or derivatives
Dihydroindole
1-sulfo,2-unsubstituted aromatic compound
Aryl ketone
Secondary aliphatic/aromatic amine
Benzenoid
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Organosulfonic acid
Sulfonyl
Vinylogous amide
Ketone
Secondary amine
Enamine
Azacycle
Organic nitrogen compound
Amine
Organopnictogen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.1 g/L	ALOGPS
logP	-0.94	ALOGPS
logP	1.01	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	-2.8	ChemAxon
pKa (Strongest Basic)	-7.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	166.94 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	101.29 m³·mol⁻¹	ChemAxon
Polarizability	39.65 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0006-2749500000-b7042c12e11418d21015	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0000900000-89f2c2f53b28e59acf74	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00dl-0027900000-c2c2a2e9e311e0feddd3	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03fr-0196000000-f4880a3747eaf442484e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0000900000-fe6eb7fd27b8a2dc7f5d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-2021900000-791a8c28c1e7d0e8afa9	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-9011000000-cc798298986c0c283422	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0000900000-0e8ef1c067d34847e6ed	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0w90-0040900000-a8583f2fc19fed114773	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0459-0494000000-e16ae6e2b829c58ccb6a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0020900000-b512a7deb96bf33b61ec	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0010900000-ea73187868f67cd3d3e4	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-9310000000-99a09e8e374d610b7052	Not Available	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
3125.0	Log mg/kg	[1800:5600]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
411	Unclassified diagnostic agents	Healthcare, pharmaceuticals & veterinary products	Not Available

Pathways

0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Cyclin-dependent kinase 1	P06493	Humans	Predicted (SEA)	143.087
Click to view 3D structure	Caspase-3	P42574	Humans	Predicted (SEA)	18.2946
Click to view 3D structure	Glycogen synthase kinase-3 beta	P49841	Humans	Predicted (SEA)	380.916
Click to view 3D structure	Cyclin-dependent kinase 2	P24941	Humans	Predicted (SEA)	570.946
Click to view 3D structure	Receptor-type tyrosine-protein kinase FLT3	P36888	Humans	Predicted (SEA)	949.683
Click to view 3D structure	Carbonic anhydrase 2	P00918	Humans	Predicted (SEA)	359.196
Click to view 3D structure	Carbonic anhydrase 1	P00915	Humans	Predicted (SEA)	297.384
Click to view 3D structure	Serine/threonine-protein kinase 17B	O94768	Humans	Predicted (SEA)	131.487
Click to view 3D structure	Carbonic anhydrase 12	O43570	Humans	Predicted (SEA)	311.397
Click to view 3D structure	Carbonic anhydrase 9	Q16790	Humans	Predicted (SEA)	372.976
Click to view 3D structure	Caspase-7	P55210	Humans	Predicted (SEA)	67.3396
Click to view 3D structure	High affinity nerve growth factor receptor	P04629	Humans	Predicted (SEA)	1178.01
Click to view 3D structure	Diacylglycerol O-acyltransferase 1	O75907	Humans	Predicted (SEA)	31.4511
Click to view 3D structure	Diacylglycerol O-acyltransferase 2	Q96PD7	Humans	Predicted (SEA)	8.32987
Click to view 3D structure	Alpha-1,6-mannosyl-glycoprotein 2-beta-N-acetylglucosaminyltransferase	Q10469	Humans	Predicted (SEA)	10.8989
Click to view 3D structure	Cyclin-dependent kinase 5	Q00535	Humans	Predicted (SEA)	1187.43
Click to view 3D structure	Aurora kinase A	O14965	Humans	Predicted (SEA)	1467.46
Click to view 3D structure	Caspase-9	P55211	Humans	Predicted (SEA)	110.312
Click to view 3D structure	Cruzipain	P25779	Trypanosoma cruzi	Predicted (SEA)	128.218
Click to view 3D structure	Tyrosine-protein kinase SYK	P43405	Humans	Predicted (SEA)	1158.08
Click to view 3D structure	Dual specificity tyrosine-phosphorylation-regulated kinase 1A	Q63470	Rattus norvegicus	Predicted (SEA)	99.2578
Click to view 3D structure	Vascular endothelial growth factor receptor 2	P35968	Humans	Predicted (SEA)	2100.29
Click to view 3D structure	Proto-oncogene tyrosine-protein kinase Src	P12931	Humans	Predicted (SEA)	1731.68
Click to view 3D structure	Hepatocyte growth factor receptor	P08581	Humans	Predicted (SEA)	1638.8
Click to view 3D structure	Fibroblast growth factor receptor 1	P11362	Humans	Predicted (SEA)	1770.99