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[ CAS No. 479-41-4 ] {[proInfo.proName]}

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Chemical Structure| 479-41-4
Chemical Structure| 479-41-4
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Product Citations

Product Citations

Shriver, James A. ; Kaller, Kaylie S. ; Kinsey, Ally L. , et al. DOI: PubMed ID:

Abstract: The spontaneous conversion of 3-indoxyl to indigo was a well-established process used to produce indigo dyes. It was recently shown that some indoles, when reacted with molybdenum hexacarbonyl and cumyl peroxide, proceed through an indoxyl intermediate to produce significant amounts of indirubin through a competing mechanism. Modulation of this system to lower temperatures allows for careful tuning, leading to selective production of indirubins in a general process. A systematic assay of indoles show that electron deficient indoles work well when substituted at the 5 and 7 positions. In contrast, 6-substituted electron rich indoles give the best results whereas halogeno indoles work well in all cases. This process shows broad functional group tolerance for generally reactive carbonyl-containing compounds such as aldehydes and carboxylic acids.

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Product Details of [ 479-41-4 ]

CAS No. :479-41-4 MDL No. :MFCD00221745
Formula : C16H10N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :JNLNPCNGMHKCKO-UHFFFAOYSA-N
M.W : 262.26 Pubchem ID :10177
Synonyms :
Couroupitine B;Indigo red;C.I. 73200, Couroupitine B, Indigo red, Indigopurpurin, NSC 105327;C.I. 73200;NSC 105327;Indigopurpurin
Chemical Name :[2,3'-Biindolinylidene]-2',3-dione

Calculated chemistry of [ 479-41-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 81.89
TPSA : 58.2 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.25 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.98
Log Po/w (XLOGP3) : 2.32
Log Po/w (WLOGP) : 1.51
Log Po/w (MLOGP) : 1.5
Log Po/w (SILICOS-IT) : 2.81
Consensus Log Po/w : 2.03

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.37
Solubility : 0.111 mg/ml ; 0.000425 mol/l
Class : Soluble
Log S (Ali) : -3.18
Solubility : 0.173 mg/ml ; 0.000659 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.87
Solubility : 0.000354 mg/ml ; 0.00000135 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.89

Safety of [ 479-41-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319 Packing Group:N/A
GHS Pictogram:
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