ChemFOnt: Showing chemical card for Indigo Carmine (CFc000040381)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:41:50 UTC

Chemfont ID

CFc000040381

Molecule Identification

Common Name

Indigo Carmine

Definition

Indigo carmine, also known as C.I. Pigment Blue 63, or indigo blue, 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. Indigo carmine is an indigo derivative that is produced by sulfonation of indigo, which makes the compound water soluble (up to 10 g/L). Indigo carmine exists as a bright purple solid and is an extremely weak basic (essentially neutral) compound (based on its pKa). It is approved for use as a food colorant in the U.S and E.U. It is also used as a medical dye. In obstetric surgery, indigo carmine solutions are sometimes employed to detect amniotic fluid leaks. In urologic surgery, intravenous injection of indigo carmine is often used to highlight portions of the urinary tract. The dye is filtered rapidly by the kidneys from the blood, and colors the urine blue. This enables structures of the urinary tract to be seen in the surgical field and demonstrates if there is a leak. A frequently encountered cardiovascular effect of intravenous indigo carmine administration is temporary alpha-receptor stimulation. Skin discoloration may occur at high doses. According to one study, the primary action of indigo carmine appears to be at the level of nitric oxide generation and/or its release from the endothelium. In addition to this, indigo carmine appears to inhibit vascular smooth muscle guanylyl cyclase. Therefore, indigo carmine may increase blood pressure by interfering with these nitric oxide-mediated vasodilatory mechanisms. Moreover, incubation of isotopically labeled indigo carmine with intestinal contents of rats for 48 h suggested that isatin-5-sulphonic acid and 5-sulphoanthranilic acid may possibly be metabolites formed by intestinal bacterial metabolism of the drug.

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 Weight

422.389

Monoisotopic Molecular Weight

421.987856686

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

CAS Registry Number

16521-38-3

SMILES

[H]N1C2=C(C=C(C=C2)S(O)(=O)=O)C(=O)\C1=C1/N([H])C2=C(C=C(C=C2)S(O)(=O)=O)C1=O

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

Functional Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

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

External Links

HMDB ID

HMDB0059912

DrugBank ID

DB11577

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4445584

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Indigo_carmine

METLIN ID

Not Available

PubChem Compound

5282430

PDB ID

Not Available

ChEBI ID

90117

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Indigo Carmine (CFc000040381)

MOL for CFc000040381 (Indigo Carmine)

3D MOL for CFc000040381 (Indigo Carmine)

3D SDF for CFc000040381 (Indigo Carmine)

3D-SDF for CFc000040381 (Indigo Carmine)

PDB for CFc000040381 (Indigo Carmine)

3D PDB for CFc000040381 (Indigo Carmine)

SMILES for CFc000040381 (Indigo Carmine)

INCHI for CFc000040381 (Indigo Carmine)

Structure for CFc000040381 (Indigo Carmine)

3D Structure for CFc000040381 (Indigo Carmine)