Arcyriarubin A

Details

• Internal ID: dbc9f641-2d82-4e31-9f5e-4a8495087e08
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Indoles
• IUPAC Name: 3,4-bis(1H-indol-3-yl)pyrrole-2,5-dione
• InChI: InChI=1S/C20H13N3O2/c24-19-17(13-9-21-15-7-3-1-5-11(13)15)18(20(25)23-19)14-10-22-16-8-4-2-6-12(14)16/h1-10,21-22H,(H,23,24,25)
• InChI Key: DQYBRTASHMYDJG-UHFFFAOYSA-N
• Popularity: 507 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₃N₃O₂
• Molecular Weight: 327.30 g/mol
• Exact Mass: 327.100776666 g/mol
• Topological Polar Surface Area (TPSA): 77.80 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 3.22
• H-Bond Acceptor: 2
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

• 119139-23-0
• 3,4-di(1H-indol-3-yl)-1H-pyrrole-2,5-dione
• Arcyriarubin A
• 3,4-Bis(3-indolyl)maleimide
• 3,4-bis(1H-indol-3-yl)pyrrole-2,5-dione
• 3,4-Di-1H-indol-3-yl-1H-pyrrole-2,5-dione
• 1H-Pyrrole-2,5-dione, 3,4-di-1H-indol-3-yl-
• BIM IV
• C20H13N3O2
• MFCD00236432
• MBK3OO5K8T
• CHEMBL266487
• 3,4-bis(3-indolyl)-1H-pyrrole-2,5-dione
• 3,4-bis(1H-indol-3-yl)-2,5-dihydro-1H-pyrrole-2,5-dione
• 3,4-Bis(3-indolyl)maleimide (Arcyriarubin A)
• Ro-31-6233
• UNII-MBK3OO5K8T
• Hedysarimcoumestan E
• Bisindolyl deriv. 3
• Ro 31-6233
• RO-316233
• BIM-4
• Bisindolylmaleimide deriv. 5
• SCHEMBL624896
• bis-indolylmaleimide deriv. 8a
• BDBM2583
• GTPL5937
• CHEBI:92857
• DTXSID30152324
• HMS3229C03
• HMS3401J13
• HMS3648K22
• AMY31773
• BIM 4; 8; bisindolylmaleimide IV
• HB0137
• HSCI1_000388
• NSC767269
• AKOS015920110
• CCG-206739
• DS-0027
• NSC-767269
• NCGC00262009-03
• HY-108254
• B6068
• CS-0027784
• FT-0694431
• S0754
• 3,4-bis(3-indolyl)-1h-pyr-role-2,5-dione
• 3,4-bis-(3-indolyl)-1H-pyrrole-2,5-dione
• 3,4-Di-(1H-indol-3-yl)pyrrole-2,5-dione
• Bisindolylmaleimide IV - CAS 119139-23-0
• Bisindolylmaleimide IV, >=98% (TLC), solid
• K00203
• SR-01000946386
• J-004072
• SR-01000946386-1
• BRD-K49448285-001-01-3
• Q27075304

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.5533	55.33%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	+	0.7571	75.71%
Subcellular localzation	Mitochondria	0.4311	43.11%
OATP2B1 inhibitior	-	0.8616	86.16%
OATP1B1 inhibitior	+	0.9377	93.77%
OATP1B3 inhibitior	+	0.9439	94.39%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.8496	84.96%
P-glycoprotein inhibitior	-	0.7245	72.45%
P-glycoprotein substrate	-	0.9387	93.87%
CYP3A4 substrate	-	0.5176	51.76%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8588	85.88%
CYP3A4 inhibition	+	0.5097	50.97%
CYP2C9 inhibition	+	0.7158	71.58%
CYP2C19 inhibition	-	0.7028	70.28%
CYP2D6 inhibition	-	0.6627	66.27%
CYP1A2 inhibition	+	0.8089	80.89%
CYP2C8 inhibition	-	0.8982	89.82%
CYP inhibitory promiscuity	+	0.6974	69.74%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8943	89.43%
Carcinogenicity (trinary)	Non-required	0.4816	48.16%
Eye corrosion	-	0.9818	98.18%
Eye irritation	-	0.7710	77.10%
Skin irritation	-	0.8587	85.87%
Skin corrosion	-	0.9639	96.39%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	+	0.8500	85.00%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	-	0.9249	92.49%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	-	0.6000	60.00%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	+	0.5529	55.29%
Acute Oral Toxicity (c)	III	0.4333	43.33%
Estrogen receptor binding	+	0.9033	90.33%
Androgen receptor binding	+	0.7674	76.74%
Thyroid receptor binding	+	0.6535	65.35%
Glucocorticoid receptor binding	+	0.8677	86.77%
Aromatase binding	+	0.7655	76.55%
PPAR gamma	+	0.7602	76.02%
Honey bee toxicity	-	0.8714	87.14%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	+	0.8568	85.68%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3045	P05771	Protein kinase C beta	212 nM	IC50	via Super-PRED
CHEMBL2147	P11309	Serine/threonine-protein kinase PIM1	27 nM	Kd	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL299	P17252	Protein kinase C alpha	97.50%	98.03%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.14%	91.11%
CHEMBL2996	Q05655	Protein kinase C delta	96.87%	97.79%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.95%	95.56%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	93.11%	94.62%
CHEMBL262	P49841	Glycogen synthase kinase-3 beta	92.27%	95.72%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	91.85%	80.96%
CHEMBL2581	P07339	Cathepsin D	91.35%	98.95%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	91.25%	92.67%
CHEMBL1951	P21397	Monoamine oxidase A	89.95%	91.49%
CHEMBL2850	P49840	Glycogen synthase kinase-3 alpha	88.38%	88.84%
CHEMBL2708	Q16584	Mitogen-activated protein kinase kinase kinase 11	86.06%	81.14%
CHEMBL3920	Q04759	Protein kinase C theta	85.32%	97.69%
CHEMBL2535	P11166	Glucose transporter	84.81%	98.75%
CHEMBL3310	Q96DB2	Histone deacetylase 11	84.38%	88.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.37%	89.00%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	83.25%	83.00%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	82.67%	94.23%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.50%	93.03%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.23%	94.00%
CHEMBL1937	Q92769	Histone deacetylase 2	80.91%	94.75%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.64%	99.23%
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	80.20%	90.71%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 2399
• LOTUS: LTS0262715
• wikiData: Q27075304