Indigo

Details

• Internal ID: 65f58c1d-f0a9-4c23-a407-8a36b7a415dd
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Hydroxyindoles
• IUPAC Name: 2-(3-hydroxy-1H-indol-2-yl)indol-3-one
• SMILES (Canonical): C1=CC=C2C(=C1)C(=C(N2)C3=NC4=CC=CC=C4C3=O)O
• SMILES (Isomeric): C1=CC=C2C(=C1)C(=C(N2)C3=NC4=CC=CC=C4C3=O)O
• InChI: 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/h1-8,17,19H
• InChI Key: QQILFGKZUJYXGS-UHFFFAOYSA-N
• Popularity: 1,188 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₀N₂O₂
• Molecular Weight: 262.26 g/mol
• Exact Mass: 262.074227566 g/mol
• Topological Polar Surface Area (TPSA): 65.40 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 3.19
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• 482-89-3
• Indigotin
• Indigo Blue
• Vat blue 1
• Cystoceva
• Diindogen
• Vulcafix Blue R
• Indigo Pure BASF
• Indigo Ciba
• Indigo Synthetic
• Synthetic Indigo
• Indigo J
• Indigo N
• Indigo P
• Indigo Powder W
• Vulcafor Blue A
• Vynamon Blue A
• Indigo VS
• Indigo Ciba SL
• Indigo NAC
• Indigo PLN
• Indigo NACCO
• C.I. Vat Blue 1
• Indigo (synthetic)
• Mitsui Indigo Pure
• Mitsui Indigo Paste
• indigo dye
• Synthetic Indigo TS
• Vulcol Fast Blue GL
• Lithosol Deep Blue B
• Vulcanosine Dark Blue L
• D&C Blue No. 6
• Blue No. 201
• D and C Blue No. 6
• Lithosol deep blue V
• Indigo,natural
• Indigo Pure BASF Powder K
• 11669 Blue
• Monolite Fast Navy Blue BV
• Modr kypova 1
• CI 73000
• 3H-Indol-3-one, 2-(1,3-dihydro-3-oxo-2H-indol-2-ylidene)-1,2-dihydro-
• C.I. 73000
• Indigo Naturalis
• NCI-C61392
• (2,2'-Biindoline)-3,3'-dione
• 12626-73-2
• 68651-46-7
• Indigo [HPUS]
• Indigo [HSDB]
• Indigo [MI]
• indigo blue (powder)
• C.I Vat blue 1
• AO201
• D&C Blue No.6
• D&C Blue 6
• D+C Blue No. 6
• NSC 8645
• NSC-8645
• MFCD00005722
• D And C Blue Number 6
• 2-(1,3-Dihydro-3-oxo-2H-indol-2-ylidene)-1,2-dihydro-3H-indol-3-one
• (2E)-2-(3-oxo-1H-indol-2-ylidene)-1H-indol-3-one
• C.I.73000
• D&C Blue No. 6 [II]
• 1G5BK41P4F
• AO201 [INCI]
• CHEMBL599552
• .DELTA.2,2'-Bipseudoindoxyl
• 2-(3-hydroxy-1H-indol-2-yl)indol-3-one
• DTXSID3026279
• CI 73000 [INCI]
• [2,2'-Biindolinylidene]-3,3'-dione
• NCGC00163355-01
• 2,2'-Biindole-3,3'(1H,1'H)-dione
• (delta(sup 2,2')-Biindoline)-3,3'-dione
• (Z)-[2,2'-Biindolinylidene]-3,3'-dione
• 1H,1'H-[2,2']Biindolylidene-3,3'-dione
• 64784-13-0
• Indigo (VAN)
• CI Vat Blue 1
• DTXCID101022739
• Modr Kypova 1 [Czech]
• delta2,2'-Bipseudoindoxyl
• D & C Blue No. 6
• Indigo (dye)
• 2001554-70-5
• CAS-482-89-3
• SMR000857361
• CCRIS 4379
• HSDB 4372
• (2E)-2,2'-biindole-3,3'(1H,1'H)-dione
• delta(sup 2,2')-Bipseudoindoxyl
• EINECS 207-586-9
• BRN 0088275
• UNII-1G5BK41P4F
• Indigoblau
• cis-indigo
• AI3-09080
• indigo B
• Indigo, synthetic
• (delta2,2'(3H,3'H)-Biindole)-3,3'-dione
• Indigotin (natural)
• Indigo,(S)
• (delta2,2'-Biindoline)-3,3'-dione
• D & C blue No 6
• INDIGO [WHO-DD]
• 2-(1,3-Dihydro-3-oxo-2H-indazol-2-ylidene)-1,2-dihydro-3H-indol-3-one
• EC 207-586-9
• [.DELTA.2,3'-dione
• (2E)-2-(3-oxoindolin-2-ylidene)indolin-3-one
• SCHEMBL42280
• SCHEMBL56085
• 5-24-08-00503 (Beilstein Handbook Reference)
• MLS001335921
• MLS001335922
• CHEMBL35479
• MEGxp0_001924
• Indigo (C.I. 73000)
• SCHEMBL23064865
• ACon1_002192
• COHYTHOBJLSHDF-BUHFOSPRSA-
• NSC8645
• CHEBI:177687
• COHYTHOBJLSHDF-BUHFOSPRSA-N
• BCP26169
• HY-N0335
• Tox21_112052
• Tox21_202545
• BDBM50310357
• s3876
• 2-(1,3-Dihydro-3-oxo-2H-indol-2-ylidene)-1,2-dihydro-3H-indol-3-o- ne
• AKOS015900171
• AKOS015955899
• Indigo, synthetic, Dye content 95 %
• Tox21_112052_1
• AC-8002
• CCG-267072
• CID 5354391
• NCGC00091633-01
• NCGC00163355-02
• NCGC00163355-03
• NCGC00163355-04
• NCGC00163355-05
• NCGC00260094-01
• PD100504
• SY108978
• [(D)(2,2')-Biindoline]-3,3'-dione
• 2-(3-oxoindolin-2-ylidene)indolin-3-one
• (.DELTA.2,2'-Biindoline)-3,3'-dione
• (E)-[2,2'-Biindolinylidene]-3,3'-dione
• [.DELTA.2,3'H)-Biindole]-3,3'-dione
• CS-0008896
• FT-0627197
• I0212
• VAT BLUE 1 (INDIGO C.I. 73000)
• Q422662
• SR-01000941903
• (.DELTA.2,2'(3H,3'H)-Biindole)-3,3'-dione
• Indigo, EuropePharmacopoeia (EP) Reference Standard
• J-521528
• SR-01000941903-2
• (.DELTA.(SUP 2,2')-BIINDOLINE)-3,3'-DIONE
• 3-CARBOXY-1,4-DIMETHYL-1H-PYRROLE-2-ACETICACID
• 2-(3-oxo-2,3-dihydro-1h-indol-2-ylidene)-2,3-dihydro-1h-indol-3-one
• (2,2 inverted exclamation mark -biindoline)-3,3 inverted exclamation mark -dione
• InChI=1/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+

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9945	99.45%
Caco-2	+	0.5481	54.81%
Blood Brain Barrier	+	0.6629	66.29%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6866	68.66%
OATP2B1 inhibitior	-	0.8583	85.83%
OATP1B1 inhibitior	+	0.8682	86.82%
OATP1B3 inhibitior	+	0.9361	93.61%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.4510	45.10%
P-glycoprotein inhibitior	-	0.8129	81.29%
P-glycoprotein substrate	-	0.9316	93.16%
CYP3A4 substrate	+	0.5263	52.63%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8275	82.75%
CYP3A4 inhibition	-	0.8077	80.77%
CYP2C9 inhibition	+	0.6377	63.77%
CYP2C19 inhibition	+	0.8276	82.76%
CYP2D6 inhibition	+	0.5000	50.00%
CYP1A2 inhibition	+	0.9130	91.30%
CYP2C8 inhibition	-	0.7411	74.11%
CYP inhibitory promiscuity	+	0.8453	84.53%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8400	84.00%
Carcinogenicity (trinary)	Non-required	0.6638	66.38%
Eye corrosion	-	0.9936	99.36%
Eye irritation	+	0.7396	73.96%
Skin irritation	-	0.8072	80.72%
Skin corrosion	-	0.9556	95.56%
Ames mutagenesis	+	0.8600	86.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8779	87.79%
Micronuclear	+	0.8800	88.00%
Hepatotoxicity	+	0.5803	58.03%
skin sensitisation	-	0.8402	84.02%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	+	0.4729	47.29%
Acute Oral Toxicity (c)	III	0.5443	54.43%
Estrogen receptor binding	-	0.4752	47.52%
Androgen receptor binding	+	0.6471	64.71%
Thyroid receptor binding	+	0.6215	62.15%
Glucocorticoid receptor binding	+	0.8834	88.34%
Aromatase binding	+	0.9208	92.08%
PPAR gamma	+	0.8482	84.82%
Honey bee toxicity	-	0.8997	89.97%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.7019	70.19%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	98.37%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.13%	95.56%
CHEMBL2581	P07339	Cathepsin D	94.45%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	94.31%	99.23%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.65%	91.11%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	89.15%	96.67%
CHEMBL2708	Q16584	Mitogen-activated protein kinase kinase kinase 11	86.51%	81.14%
CHEMBL1937	Q92769	Histone deacetylase 2	86.22%	94.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.77%	89.00%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	85.66%	92.67%
CHEMBL2535	P11166	Glucose transporter	84.63%	98.75%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	84.63%	94.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.29%	94.00%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	84.11%	96.00%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	83.41%	96.39%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.87%	85.14%

Plants that contains it

• Couroupita guianensis
• Isatis tinctoria
• Koanophyllon simillimum

Cross-Links

• PubChem: 10215
• LOTUS: LTS0134142
• wikiData: Q104389767