Indirubin

Details

• Internal ID: 8811868b-21ce-4636-ae3a-ccbe09783073
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Hydroxyindoles
• IUPAC Name: 2-(2-hydroxy-1H-indol-3-yl)indol-3-one
• SMILES (Canonical): C1=CC=C2C(=C1)C(=C(N2)O)C3=NC4=CC=CC=C4C3=O
• SMILES (Isomeric): C1=CC=C2C(=C1)C(=C(N2)O)C3=NC4=CC=CC=C4C3=O
• InChI: InChI=1S/C16H10N2O2/c19-15-10-6-2-4-8-12(10)17-14(15)13-9-5-1-3-7-11(9)18-16(13)20/h1-8,18,20H
• InChI Key: JNLNPCNGMHKCKO-UHFFFAOYSA-N
• Popularity: 509 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

• 479-41-4
• Indigo Red
• Couroupitine B
• Indigopurpurin
• 906748-38-7
• (Z)-[2,3'-biindolinylidene]-2',3-dione
• [2,3'-Biindolinylidene]-2',3-dione
• Isoindirubin
• Isoindirubine
• Isoindogotin
• 397242-72-7
• Indirubin [MI]
• NSC 105327
• NSC-105327
• (E)-[2,3'-biindolinylidene]-2',3-dione
• 2H-Indol-2-one, 3-(1,3-dihydro-3-oxo-2H-indol-2-ylidene)-1,3-dihydro-
• C.I. 73200
• Indirubin 3E-form [MI]
• 3-(3-oxo-1H-indol-2-ylidene)-1H-indol-2-one
• 1LXW6D3W2Z
• V86L8P74GI
• 2-(2-hydroxy-1H-indol-3-yl)indol-3-one
• C.I. 75790
• 3-(1,3-dihydro-3-oxo-2h-indol-2-ylidene)-1,3-dihydro-2h-indol-2-one
• MFCD00956441
• (Z)-[2,3 inverted exclamation mark -Biindolinylidene]-2 inverted exclamation mark ,3-dione
• (3Z)-3-(1,3-Dihydro-3-oxo-2H-indol-2-ylidene)-1,3-dihydro-2H-indol-2-one
• (3E)-3-(1,3-Dihydro-3-oxo-2H-indol-2-ylidene)-1,3-dihydro-2H-indol-2-one
• 2H-Indol-2-one, 3-(1,3-dihydro-3-oxo-2H-indol-2-ylidene)-1,3-dihydro-, (3E)-
• SMR000466311
• BRN 0088279
• UNII-V86L8P74GI
• Indirubin,(S)
• Indirubin- Bio-X
• INDARUBICIN
• (delta2,3'-Biindoline)-2',3-dione
• CPD000466311
• Indirubin derivative, 1
• BiomolKI_000069
• EM-A05-INDIRUBIN
• [.DELTA.2,3-dione
• BiomolKI2_000073
• UNII-1LXW6D3W2Z
• INDIRUBIN [WHO-DD]
• (3Z)-3-(3-oxoindolin-2-ylidene)indolin-2-one
• (delta(sup 2,3')-BIINDOLINE)-2',3-DIONE
• SCHEMBL27678
• BMK1-G9
• BSPBio_001110
• KBioGR_000450
• KBioSS_000450
• 5-24-08-00507 (Beilstein Handbook Reference)
• MLS000759416
• MLS001424211
• MLS002473308
• MLS006010732
• CHEMBL35349
• BDBM7392
• CHEMBL259664
• SCHEMBL9899338
• (3E)-3-(3-oxo-1H-indol-2-ylidene)-1H-indol-2-one
• CHEMBL1276127
• CHEMBL3185783
• CHEBI:92322
• cid_5318433
• KBio2_000450
• KBio2_003018
• KBio2_005586
• KBio3_000839
• KBio3_000840
• EX-A347
• JNLNPCNGMHKCKO-UHFFFAOYSA-N
• Bio2_000395
• Bio2_000875
• DTXSID201026053
• DTXSID501026052
• HMS1362H11
• HMS1792H11
• HMS1990H11
• HMS2051H20
• HMS2234G06
• HMS3369O15
• HMS3393H20
• HMS3403H11
• HMS3656O13
• AMY39890
• BCP28869
• HY-N0117
• AC1180
• BDBM50023867
• BDBM50349806
• FD9058
• MFCD00221745
• NSC105327
• s2386
• 2H-Indol-2-one,3-(1,3-dihydro-3-oxo-2H-indol-2-ylidene)-1,3-dihydro-
• 3-(1,3-dihydro-3-oxo-2h-indol-2-ylidene)-1,3-dihydro-2h-indol-2-on
• AKOS015895136
• AKOS028108775
• AKOS032455876
• AC-8003
• BCP9000788
• CCG-100673
• CCG-101058
• CCG-267073
• CS-3682
• DB12379
• NC00308
• SB64698
• IDI1_002150
• (2'Z)-Indirubin, >=98% (HPLC)
• NCGC00163356-01
• NCGC00163356-02
• NCGC00163356-03
• NCGC00163356-04
• NCGC00179302-02
• (Z)-[2,3-Biindolinylidene]-2,3-dione
• AC-29931
• BI164578
• CS-12423
• LS-14462
• PD003207
• SMR004701694
• SY058396
• 3-(3-oxoindolin-2-ylidene)indolin-2-one
• 3-(3-indolinone-2-ylidene)-indolin-2-one
• UNM-0000305766
• FT-0627199
• I0868
• SW197688-2
• AB00639939-06
• 2-(2-oxo-1H-indol-3-ylidene)-1H-indol-3-one
• A827403
• A922429
• SR-01000759396
• Q-100514
• Q1661452
• SR-01000759396-5
• BRD-K17894950-001-03-6
• BRD-K17894950-001-04-4
• Q27164070
• 3-(3-oxidanylidene-1H-indol-2-ylidene)-1H-indol-2-one
• 2H-Indol-2-one,3-dihydro-3-oxo-2H-indol-2-ylidene)-1,3-dihydro-
• (3E)-3-(3-Oxo-1,3-dihydro-2H-indol-2-ylidene)-1,3-dihydro-2H-indo l-2-one
• (3z)-3-(3-oxo-1,3-dihydro-2h-indol-2-ylidene)-1,3-dihydro-2h-indol-2-one
• (Z)-[2,3invertedexclamationmark-Biindolinylidene]-2invertedexclamationmark,3-dione
• 2-[(3Z)-2-oxo-2,3-dihydro-1H-indol-3-ylidene]-2,3-dihydro-1H-indol-3-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9948	99.48%
Caco-2	+	0.5799	57.99%
Blood Brain Barrier	+	0.8879	88.79%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.4874	48.74%
OATP2B1 inhibitior	-	0.7230	72.30%
OATP1B1 inhibitior	+	0.8836	88.36%
OATP1B3 inhibitior	+	0.9357	93.57%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.4888	48.88%
P-glycoprotein inhibitior	-	0.8218	82.18%
P-glycoprotein substrate	-	0.9170	91.70%
CYP3A4 substrate	+	0.5267	52.67%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8452	84.52%
CYP3A4 inhibition	-	0.8621	86.21%
CYP2C9 inhibition	+	0.6474	64.74%
CYP2C19 inhibition	+	0.6425	64.25%
CYP2D6 inhibition	-	0.8262	82.62%
CYP1A2 inhibition	+	0.9452	94.52%
CYP2C8 inhibition	-	0.7008	70.08%
CYP inhibitory promiscuity	+	0.6157	61.57%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7900	79.00%
Carcinogenicity (trinary)	Non-required	0.6384	63.84%
Eye corrosion	-	0.9943	99.43%
Eye irritation	+	0.5991	59.91%
Skin irritation	-	0.8438	84.38%
Skin corrosion	-	0.9712	97.12%
Ames mutagenesis	+	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8787	87.87%
Micronuclear	+	0.8600	86.00%
Hepatotoxicity	+	0.5303	53.03%
skin sensitisation	-	0.8710	87.10%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	+	0.6465	64.65%
Acute Oral Toxicity (c)	III	0.5452	54.52%
Estrogen receptor binding	+	0.7664	76.64%
Androgen receptor binding	+	0.6086	60.86%
Thyroid receptor binding	+	0.6606	66.06%
Glucocorticoid receptor binding	+	0.8985	89.85%
Aromatase binding	+	0.9228	92.28%
PPAR gamma	+	0.9138	91.38%
Honey bee toxicity	-	0.8646	86.46%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.6802	68.02%

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	97.59%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.31%	95.56%
CHEMBL2581	P07339	Cathepsin D	94.61%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	93.69%	99.23%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.08%	91.11%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	90.22%	96.67%
CHEMBL2535	P11166	Glucose transporter	87.51%	98.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.20%	89.00%
CHEMBL1937	Q92769	Histone deacetylase 2	85.95%	94.75%
CHEMBL2708	Q16584	Mitogen-activated protein kinase kinase kinase 11	84.72%	81.14%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	83.89%	92.67%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	83.29%	96.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	83.14%	94.62%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	82.81%	96.39%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.75%	93.03%
CHEMBL1781	P11387	DNA topoisomerase I	81.51%	97.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.28%	94.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.19%	82.69%
CHEMBL5979	P05186	Alkaline phosphatase, tissue-nonspecific isozyme	80.78%	85.40%
CHEMBL3310	Q96DB2	Histone deacetylase 11	80.51%	88.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.28%	85.14%

Plants that contains it

• Calanthe discolor
• Couroupita guianensis
• Isatis tinctoria

Cross-Links

• PubChem: 10177
• LOTUS: LTS0207407
• wikiData: Q104389757