Record Information |
---|
Version | 5.0 |
---|
Status | Expected but not Quantified |
---|
Creation Date | 2021-01-04 22:31:36 UTC |
---|
Update Date | 2022-07-12 23:01:06 UTC |
---|
HMDB ID | HMDB0240742 |
---|
Secondary Accession Numbers | None |
---|
Metabolite Identification |
---|
Common Name | Indigo |
---|
Description | 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 | O=C1\C(NC2=CC=CC=C12)=C1/NC2=CC=CC=C2C1=O 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+ |
---|
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 |
---|
Ontology |
---|
Physiological effect | Not Available |
---|
Disposition | Not Available |
---|
Process | Not Available |
---|
Role | Not Available |
---|
Physical Properties |
---|
State | Not Available |
---|
Experimental Molecular Properties | Property | Value | Reference |
---|
Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
|
---|
Experimental Chromatographic Properties | Not Available |
---|
Predicted Molecular Properties | |
---|
Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
---|
Indigo,1TMS,isomer #1 | C[Si](C)(C)N1/C(=C2/NC3=CC=CC=C3C2=O)C(=O)C2=CC=CC=C21 | 2773.0 | Semi standard non polar | 33892256 | Indigo,1TMS,isomer #1 | C[Si](C)(C)N1/C(=C2/NC3=CC=CC=C3C2=O)C(=O)C2=CC=CC=C21 | 2701.1 | Standard non polar | 33892256 | Indigo,1TMS,isomer #1 | C[Si](C)(C)N1/C(=C2/NC3=CC=CC=C3C2=O)C(=O)C2=CC=CC=C21 | 4403.2 | Standard polar | 33892256 | Indigo,2TMS,isomer #1 | C[Si](C)(C)N1/C(=C2\C(=O)C3=CC=CC=C3N2[Si](C)(C)C)C(=O)C2=CC=CC=C21 | 2657.8 | Semi standard non polar | 33892256 | Indigo,2TMS,isomer #1 | C[Si](C)(C)N1/C(=C2\C(=O)C3=CC=CC=C3N2[Si](C)(C)C)C(=O)C2=CC=CC=C21 | 2691.4 | Standard non polar | 33892256 | Indigo,2TMS,isomer #1 | C[Si](C)(C)N1/C(=C2\C(=O)C3=CC=CC=C3N2[Si](C)(C)C)C(=O)C2=CC=CC=C21 | 3369.4 | Standard polar | 33892256 | Indigo,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N1/C(=C2/NC3=CC=CC=C3C2=O)C(=O)C2=CC=CC=C21 | 3068.5 | Semi standard non polar | 33892256 | Indigo,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N1/C(=C2/NC3=CC=CC=C3C2=O)C(=O)C2=CC=CC=C21 | 2915.3 | Standard non polar | 33892256 | Indigo,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N1/C(=C2/NC3=CC=CC=C3C2=O)C(=O)C2=CC=CC=C21 | 4445.3 | Standard polar | 33892256 | Indigo,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N1/C(=C2\C(=O)C3=CC=CC=C3N2[Si](C)(C)C(C)(C)C)C(=O)C2=CC=CC=C21 | 3151.1 | Semi standard non polar | 33892256 | Indigo,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N1/C(=C2\C(=O)C3=CC=CC=C3N2[Si](C)(C)C(C)(C)C)C(=O)C2=CC=CC=C21 | 3080.7 | Standard non polar | 33892256 | Indigo,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N1/C(=C2\C(=O)C3=CC=CC=C3N2[Si](C)(C)C(C)(C)C)C(=O)C2=CC=CC=C21 | 3439.4 | Standard polar | 33892256 |
|
---|
| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - Indigo GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Indigo 10V, Positive-QTOF | splash10-03di-0090000000-790509310d3a9b1089dc | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Indigo 20V, Positive-QTOF | splash10-03di-0290000000-b87193ec33d05c5972bc | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Indigo 40V, Positive-QTOF | splash10-0006-1920000000-06f522bb3b9294630d21 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Indigo 10V, Negative-QTOF | splash10-03di-0090000000-7b4ca08a5827f92042b5 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Indigo 20V, Negative-QTOF | splash10-03di-0290000000-8e31bd790d0c838bafde | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Indigo 40V, Negative-QTOF | splash10-001i-0590000000-1d3c68663ee4df12a0e2 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Indigo 10V, Negative-QTOF | splash10-03di-0090000000-fc429704171183f86ba8 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Indigo 20V, Negative-QTOF | splash10-03di-0290000000-8d486152aa8dcd21f192 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Indigo 40V, Negative-QTOF | splash10-001i-0920000000-4c6f54d2c5462973f105 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Indigo 10V, Positive-QTOF | splash10-03di-0090000000-d2ff69a7f2ebf2ad3717 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Indigo 20V, Positive-QTOF | splash10-03e9-0690000000-024cece7c516595caa9f | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Indigo 40V, Positive-QTOF | splash10-0w30-0960000000-2d6f1d15e9a51ab8b9f5 | 2021-09-25 | Wishart Lab | View Spectrum |
|
---|