U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C16H10N2O2
Molecular Weight 262.2628
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of INDIGO

SMILES

O=C1C2=C(N\C1=C3\NC4=C(C=CC=C4)C3=O)C=CC=C2

InChI

InChIKey=COHYTHOBJLSHDF-BUHFOSPRSA-N
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+

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including http://faculty.bennington.edu/~bullock/Chem1/indigo%20lab.pdf

Indigo, or indigotin, is a dyestuff originally extracted from the varieties of the indigo and woad plants. Indigo was known throughout the ancient world for its ability to color fabrics a deep blue. Egyptian artifacts suggest that indigo was employed as early as 1600 B.C. and it has been found in Africa, India, Indonesia, and China. Indigo is unique in its ability to impart surface color while only partially penetrating fibers. When yarn died with indigo is untwisted, it can be seen that the inner layers remain uncolored. The dye also fades to give a characteristic wom look and for this reason it is commonly used to color denim.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Expression of naphthalene oxidation genes in Escherichia coli results in the biosynthesis of indigo.
1983 Oct 14
Indirubin and indigo are potent aryl hydrocarbon receptor ligands present in human urine.
2001 Aug 24
Aryl hydrocarbon receptor response to indigoids in vitro and in vivo.
2004 Mar 15
A novel combinatorial biocatalytic approach for producing antibacterial compounds effective against Mycobacterium tuberculosis (TB).
2013 Aug
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Name Type Language
INDIGO
HPUS   HSDB   MI  
Common Name English
D&C BLUE NO. 6
II  
Preferred Name English
2,2'-BIINDOLE-3,3'(1H,1'H)-DIONE
Systematic Name English
(.DELTA.(SUP 2,2')-BIINDOLINE)-3,3'-DIONE
Common Name English
AO201
INCI  
INCI  
Official Name English
C.I.73000
Code English
INDIGO BLUE
Common Name English
INDIGO [HSDB]
Common Name English
INDIGOTIN
Common Name English
CI 73000
INCI  
INCI  
Official Name English
D&C BLUE NO. 6 [II]
Common Name English
Indigo [WHO-DD]
Common Name English
AO201 [INCI]
Common Name English
INDIGO [MI]
Common Name English
CI 73000 [INCI]
Common Name English
INDIGO [HPUS]
Common Name English
NSC-8645
Code English
Classification Tree Code System Code
NCI_THESAURUS C461
Created by admin on Fri Dec 15 15:35:27 GMT 2023 , Edited by admin on Fri Dec 15 15:35:27 GMT 2023
Code System Code Type Description
CAS
64784-13-0
Created by admin on Fri Dec 15 15:35:27 GMT 2023 , Edited by admin on Fri Dec 15 15:35:27 GMT 2023
PRIMARY
SMS_ID
100000076182
Created by admin on Fri Dec 15 15:35:27 GMT 2023 , Edited by admin on Fri Dec 15 15:35:27 GMT 2023
PRIMARY
EPA CompTox
DTXSID3026279
Created by admin on Fri Dec 15 15:35:27 GMT 2023 , Edited by admin on Fri Dec 15 15:35:27 GMT 2023
PRIMARY
ECHA (EC/EINECS)
207-586-9
Created by admin on Fri Dec 15 15:35:27 GMT 2023 , Edited by admin on Fri Dec 15 15:35:27 GMT 2023
PRIMARY
DAILYMED
1G5BK41P4F
Created by admin on Fri Dec 15 15:35:27 GMT 2023 , Edited by admin on Fri Dec 15 15:35:27 GMT 2023
PRIMARY
EVMPD
SUB16081MIG
Created by admin on Fri Dec 15 15:35:27 GMT 2023 , Edited by admin on Fri Dec 15 15:35:27 GMT 2023
PRIMARY
RXCUI
1426889
Created by admin on Fri Dec 15 15:35:27 GMT 2023 , Edited by admin on Fri Dec 15 15:35:27 GMT 2023
PRIMARY RxNorm
FDA UNII
1G5BK41P4F
Created by admin on Fri Dec 15 15:35:27 GMT 2023 , Edited by admin on Fri Dec 15 15:35:27 GMT 2023
PRIMARY
NCI_THESAURUS
C71644
Created by admin on Fri Dec 15 15:35:27 GMT 2023 , Edited by admin on Fri Dec 15 15:35:27 GMT 2023
PRIMARY
HSDB
482-89-3
Created by admin on Fri Dec 15 15:35:27 GMT 2023 , Edited by admin on Fri Dec 15 15:35:27 GMT 2023
PRIMARY
WIKIPEDIA
Indigo dye
Created by admin on Fri Dec 15 15:35:27 GMT 2023 , Edited by admin on Fri Dec 15 15:35:27 GMT 2023
PRIMARY
PUBCHEM
5318432
Created by admin on Fri Dec 15 15:35:27 GMT 2023 , Edited by admin on Fri Dec 15 15:35:27 GMT 2023
PRIMARY
CAS
482-89-3
Created by admin on Fri Dec 15 15:35:27 GMT 2023 , Edited by admin on Fri Dec 15 15:35:27 GMT 2023
NON-SPECIFIC STEREOCHEMISTRY
MESH
C008114
Created by admin on Fri Dec 15 15:35:27 GMT 2023 , Edited by admin on Fri Dec 15 15:35:27 GMT 2023
PRIMARY
NSC
8645
Created by admin on Fri Dec 15 15:35:27 GMT 2023 , Edited by admin on Fri Dec 15 15:35:27 GMT 2023
PRIMARY
MERCK INDEX
m6251
Created by admin on Fri Dec 15 15:35:27 GMT 2023 , Edited by admin on Fri Dec 15 15:35:27 GMT 2023
PRIMARY Merck Index