62162-97-4|2-Bromophenanthrene| Ambeed

CAS No. :	62162-97-4
Formula :	C₁₄H₉Br
M.W :	257.13
SMILES Code :	BrC1=CC=C2C(C=CC3=C2C=CC=C3)=C1
MDL No. :	MFCD13191756
InChI Key :	SQTPFYJEKHTINP-UHFFFAOYSA-N
Pubchem ID :	12491433

Safety of [ 62162-97-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 62162-97-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	15
Num. arom. heavy atoms	14
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	0.0
Num. H-bond donors	0.0
Molar Refractivity	69.15
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	0.0 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.74
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	5.22
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	4.76
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	4.9
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	4.72
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	4.47

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-5.41
Solubility	0.000992 mg/ml ; 0.00000386 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-4.97
Solubility	0.00277 mg/ml ; 0.0000108 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-6.6
Solubility	0.000064 mg/ml ; 0.000000249 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Poorly soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	Low
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	Yes
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	Yes
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-4.16 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	1.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	2.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.46

Application In Synthesis of [ 62162-97-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 62162-97-4 ]

[ 62162-97-4 ] Synthesis Path-Downstream 1~54

1
[ 109-72-8 ]
[ 60-29-7 ]
[ 62162-97-4 ]
[ 40452-20-8 ]

References: [1]Journal of the American Chemical Society,1940,vol. 62,p. 2813,2815.

2
[ 62162-97-4 ]
[ 40452-20-8 ]

References: [1]Journal of the American Chemical Society,1940,vol. 62,p. 2813,2815.

3
[ 3366-65-2 ]
[ 62162-97-4 ]

References: [1]Journal of the American Chemical Society,1936,vol. 58,p. 1838,1841.

4
[ 56988-45-5 ]
[ 62162-97-4 ]

References: [1]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1980,vol. 29,p. 1789 - 1792.
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1980,p. 2530 - 2534.

5
[ 54888-78-7 ]
[ 62162-97-4 ]

Yield	Reaction Conditions	Operation in experiment
67%	With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; at 100℃; for 24h;	5.1g (20 mmol) 27 is dissolved in 100ml dioxane and 14.9g (65 mmol) DDQ (4,5-dichloro- S.psi-dioxo-i^-cyclohexadiene-i ^-dicarbonitrile) is added. A black suspension is formed and the reaction mixture is heated up to T= 100°C and stirred for 24 hours. The reaction mixture is cooled down to room temperature and filtrated. Product 28 is isolated by evaporation and purified by column chromatography (silica gel, heptane as eluant). Product 28 is isolated in 67percent yield as colorless crystals. M.p.28: 84-88°C

References: [1]Patent: WO2006/131466,2006,A1 .Location in patent: Page/Page column 58-59.
[2]Australian Journal of Chemistry,1975,vol. 28,p. 65 - 80.

6
7-Bromo-2,3,4,4a,10,10a-hexahydro-1H-phenanthren-9-one [ No CAS ]
[ 62162-97-4 ]

References: [1]Journal of Chemical Research, Miniprint,1996,p. 979 - 994.

10
[ 62325-30-8 ]
[ 62162-97-4 ]