Arcyriarubin A

HCID 2399CAS 119139-23-0

Substructure search Find similar structures

Basic information

Standard SMILES: O=C1NC(=O)C(c2c[nH]c3ccccc23)=C1c1c[nH]c2ccccc12
InChIKey: DQYBRTASHMYDJG-UHFFFAOYSA-N
Molecular formula: C20H13N3O2
Average molar mass: 327.3 g/mol
Monoisotopic mass: 327.10077667

Names & identifiers

Preferred name: Arcyriarubin A
IUPAC: 3,4-bis(1H-indol-3-yl)pyrrole-2,5-dione
English name: 3,4-Di-1H-indol-3-yl-1H-pyrrole-2,5-dione
Molecular formula: C20H13N3O2
Molecular weight: 327.34

Names & synonyms

119139-23-0Arcyriarubin ABisindolylmaleimide3,4-Di-1H-indol-3-yl-1H-pyrrole-2,5-dioneMBK3OO5K8TDTXSID30152324bis-indolylmaleimidebis(indolyl)maleimideRefChem:916128DTXCID8074815bisindolylmaleimide iv3,4-di(1H-indol-3-yl)-1H-pyrrole-2,5-dione

Show more names

RO 31-62333,4-Di(1H-indol-3-yl)BISINDOLYMALEIMIDE IVSotrastaurin Impurity 132,3-BIS(1H-INDOL-3-YL)MALEIMIDEBisindolylMaleiMide IV [Ro 31-6233]Bisindolylmaleimide IV, PKC inhibitor

3,4-Bis(3-indolyl)maleimide3,4-bis(1H-indol-3-yl)pyrrole-2,5-dione1H-Pyrrole-2,5-dione, 3,4-di-1H-indol-3-yl-MFCD002364323,4-bis(1H-indol-3-yl)-2,5-dihydro-1H-pyrrole-2,5-dioneBIM IVCHEMBL2664873,4-bis(3-indolyl)-1H-pyrrole-2,5-dione

Database identifiers

CAS: 119139-23-0
PubChem CID: 2399
DTXSID: DTXSID30152324
ChEMBL: CHEMBL266487
ChEBI: CHEBI:92857
UNII: MBK3OO5K8T
Nikkaji: J442.995H

Properties

Computed structural properties

XLogP: 2.8
Topological polar surface area: 77.8 Å²
Hydrogen bond donors: 3
Hydrogen bond acceptors: 2
Rotatable bonds: 2
Heavy atoms: 25
Formal charge: 0
Complexity: 576

Physicochemical properties

Melting point: 161 °C · 161 °C
Boiling point: 690.1 · 690.1±55.0 °C(Predicted)
Density: 1.486 · 1.486±0.06 g/cm3(Predicted)
storage temp.: -20 °C · -20°C
solubility: DMSO: soluble
form: solid
pka: 8.44 · 8.44±0.60(Predicted)
color: dark red
biological source: synthetic (organic)
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)
InChIKey: DQYBRTASHMYDJG-UHFFFAOYSA-N
SMILES: O=C1NC(=O)C(c2c[nH]c3ccccc23)=C1c4c[nH]c5ccccc45
FDA UNII: 3 OO5K8T · MBK3OO5K8T
UNSPSC Code: 12352111 · 12352111
NACRES: 77 · NA.77
PPE: 95 · Eyeshields, Gloves, type N95 (US)
WGK Germany: 3 · 3
HS Code: 2933.99 · 2933.99.8290
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

Safety data

PPE: Eyeshields, Gloves, type N95 (US)
wgk: 3
hs_code: 2933.99.8290
Storage Class: 11 - Combustible Solids

Chemistry & industry

Applications

General DescriptionA potent, cell permeable, and selective inhibitor of protein kinase C (IC50 = 87 nM). Inhibits protein kinase A at much higher concentrations (IC50 = 2.7 μM).