Indigo (CHEM012469)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 03:56:16 UTC
Update Date2016-11-09 01:14:35 UTC
Accession NumberCHEM012469
Identification
Common NameIndigo
ClassSmall Molecule
DescriptionIndigo (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.
Contaminant Sources
  • HPV EPA Chemicals
  • OECD HPV Chemicals
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
IndigotinHMDB
CystocevaHMDB
DiindogenHMDB
Vulcafix blue RHMDB
Indigotindisulfonic acidHMDB
Indigo carmineHMDB
IndigotindisulfonateHMDB
Soluble indigo blueHMDB
Disulfonate, indigoHMDB
2-(1,3-Dihydro-3-oxo-5-sulphO-2H-indol-2-ylidene)-3- oxoindoline-5-sulphonic acidHMDB
FD And C blue no. 2HMDB
Indigo blue, solubleHMDB
(delta-2,2'-Biindole)-3,3'-dioneHMDB
D And C blue no. 6HMDB
Carmine, indigoHMDB
Indigo disulfonateHMDB
Indigo blueHMDB
Indigotindisulfonate sodiumHMDB
IndigoMeSH
Chemical FormulaC16H10N2O2
Average Molecular Mass262.268 g/mol
Monoisotopic Mass262.074 g/mol
CAS Registry Number482-89-3
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
SMILESO=C1\C(NC2=CC=CC=C12)=C1/NC2=CC=CC=C2C1=O
InChI IdentifierInChI=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 KeyCOHYTHOBJLSHDF-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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndolines
Direct ParentIndolines
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 FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.04 g/LALOGPS
logP2.76ALOGPS
logP2.65ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)8.18ChemAxon
pKa (Strongest Basic)-7.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.2 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity80.04 m³·mol⁻¹ChemAxon
Polarizability27.82 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0090000000-790509310d3a9b1089dcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0290000000-b87193ec33d05c5972bcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-1920000000-06f522bb3b9294630d21Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0090000000-7b4ca08a5827f92042b5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0290000000-8e31bd790d0c838bafdeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0590000000-1d3c68663ee4df12a0e2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0090000000-fc429704171183f86ba8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0290000000-8d486152aa8dcd21f192Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0920000000-4c6f54d2c5462973f105Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0090000000-d2ff69a7f2ebf2ad3717Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-0690000000-024cece7c516595caa9fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0w30-0960000000-2d6f1d15e9a51ab8b9f5Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0240742
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00000126
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkIndigo
Chemspider ID4477009
ChEBI IDNot Available
PubChem Compound ID5318432
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Gillam EM, Notley LM, Cai H, De Voss JJ, Guengerich FP: Oxidation of indole by cytochrome P450 enzymes. Biochemistry. 2000 Nov 14;39(45):13817-24. doi: 10.1021/bi001229u.
2. Arnold WN: King George III's urine and indigo blue. Lancet. 1996 Jun 29;347(9018):1811-3. doi: 10.1016/s0140-6736(96)91622-0.