ChemFOnt: Showing chemical card for Indigo (CFc000220995)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 01:40:31 UTC

Chemfont ID

CFc000220995

Molecule Identification

Common Name

Indigo

Definition

Indigo (indigo dye or indigotin) is an organic compound with a distinctive blue color. It is an oxindole dimer consisting of two fused oxindole rings. Indoles are compounds which consist of a pyrrole ring fused to benzene to form 2,3-benzopyrrole. Indigo is found in both plants and animals and has been detected in human urine and human tissues (PMID: 11076521 ; PMID: 8667928 ). The natural precursor to indigo is indican, a colorless, water-soluble derivative of the amino acid tryptophan. Indican readily hydrolyzes to release β-D-glucose and indoxyl. Oxidation of indoxyl by CYP450 enzymes in the liver or kidneys can convert indoxyl to indigo (PMID: 11076521 ). Likewise, exposure to air can convert indoxyl to indigo. In addition to the mammalian production of minute amounts of indigo, this chemical can also be recovered in far larger amounts from plants. Historically, indigo has been extracted from the leaves of certain plants of the Indigofera genus, in particular Indigofera tinctoria. Indigofera plants were commonly grown and used throughout the world for the production of indigo dyestuff. This was economically important due to the previous rarity of some blue dyestuffs historically. India was the primary supplier of indigo to Europe as early as the Greco-Roman era. The association of India with indigo is reflected in the Greek word for the dye, indikón. The Romans latinized the term to indicum, which passed into Italian dialect and eventually into English as the word indigo. Most indigo dye produced today is synthetic, constituting several thousand tons each year. It is most commonly associated with the production of denim cloth and blue jeans.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Indigotin	HMDB
Cystoceva	HMDB
Diindogen	HMDB
Vulcafix blue R	HMDB
Indigotindisulfonic acid	HMDB
Indigo carmine	HMDB
Indigotindisulfonate	HMDB
Soluble indigo blue	HMDB
Disulfonate, indigo	HMDB
2-(1,3-Dihydro-3-oxo-5-sulphO-2H-indol-2-ylidene)-3- oxoindoline-5-sulphonic acid	HMDB
FD And C blue no. 2	HMDB
Indigo blue, soluble	HMDB
(delta-2,2'-Biindole)-3,3'-dione	HMDB
D And C blue no. 6	HMDB
Carmine, indigo	HMDB
Indigo disulfonate	HMDB
Indigo blue	HMDB
Indigotindisulfonate sodium	HMDB
Indigo	MeSH

Chemical Formula

C₁₆H₁₀N₂O₂

Average Molecular Weight

262.268

Monoisotopic Molecular Weight

262.07422757

IUPAC Name

(E)-1H,1'H,3H,3'H-[2,2'-biindolylidene]-3,3'-dione

Traditional Name

(E)-1H,1'H-[2,2'-biindolylidene]-3,3'-dione

CAS Registry Number

Not Available

SMILES

O=C1\C(NC2=CC=CC=C12)=C1/NC2=CC=CC=C2C1=O

InChI Identifier

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

InChI Key

COHYTHOBJLSHDF-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

Dihydroindole
Aryl ketone
Secondary aliphatic/aromatic amine
Benzenoid
Vinylogous amide
Ketone
Secondary amine
Enamine
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Amine
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0240742)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.04 g/L	ALOGPS
logP	2.76	ALOGPS
logP	2.65	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	8.18	ChemAxon
pKa (Strongest Basic)	-7.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.2 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	80.04 m³·mol⁻¹	ChemAxon
Polarizability	27.82 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

HMDB0240742

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00000126

Chemspider ID

4477009

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Indigo

METLIN ID

Not Available

PubChem Compound

5318432

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Indigo (CFc000220995)

MOL for CFc000220995 (Indigo)

3D MOL for CFc000220995 (Indigo)

3D SDF for CFc000220995 (Indigo)

3D-SDF for CFc000220995 (Indigo)

PDB for CFc000220995 (Indigo)

3D PDB for CFc000220995 (Indigo)

SMILES for CFc000220995 (Indigo)

INCHI for CFc000220995 (Indigo)

Structure for CFc000220995 (Indigo)

3D Structure for CFc000220995 (Indigo)