74440-82-7|3-Iodo-5-methoxybenzoic acid| Ambeed

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Quality Control of [ 74440-82-7 ] Purity: 95% SDS Specification

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Product Details of [ 74440-82-7 ]

CAS No. :	74440-82-7
Formula :	C₈H₇IO₃
M.W :	278.04
SMILES Code :	O=C(O)C1=CC(OC)=CC(I)=C1
MDL No. :	MFCD21607480
InChI Key :	LAGXFKIAZDJQDL-UHFFFAOYSA-N
Pubchem ID :	57905757

Safety of [ 74440-82-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

Computational Chemistry of [ 74440-82-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.12
Num. rotatable bonds	2
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	52.61
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	46.53 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.67
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	2.07
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.0
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.	2.21
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	2.18
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.03

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.11
Solubility	0.218 mg/ml ; 0.000783 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.68
Solubility	0.586 mg/ml ; 0.00211 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	-2.85
Solubility	0.395 mg/ml ; 0.00142 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
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	No
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	No
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	No
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.	-6.53 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	0.0
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	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.56

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<0.0
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)	1.89

Application In Synthesis of [ 74440-82-7 ]

* 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 [ 74440-82-7 ]

[ 74440-82-7 ] Synthesis Path-Downstream 1~21

1
[ 74165-74-5 ]
[ 74440-82-7 ]

Yield	Reaction Conditions	Operation in experiment
60%	With hydrogenchloride; potassium iodide; sodium nitrite; In water;Acidic aqueous solution; Heating / reflux;	3-Amino-5-methoxybenzoic acid (3.1 g) was suspended in 10 mL of water, cooled to O0C and 10 mL of concentrated hydrochloric acid were added, followed by a dropwise addition of a cooled solution of sodium nitrite (2.3 g) in 15 mL water. The resulting solution was stirred for 15 minutes and then a solution of KI (6.1 g) in 10 mL of water was added dropwise. After addition was completed, the reaction mixture was heated to reflux until the production of purple vapor ceased. Then it was diluted with ethyl acetate, washed with 2% sodium bisulfite solution and brine and the organic extracts were filtered through a silica pad. The filtrate was extracted with aqueous bicarbonate solution. The aqueous extracts were washed with ethyl acetate and then acidified with 3N hydrochloric acid. The title product precipitated and was collected by filtration (3.4 g, 60% yield). HRMS calcd for C8H7IO3 M+ 277.9440, observed 277.9439

References: [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 6256 - 6269.
[2]Patent: WO2009/77385,2009,A1 .Location in patent: Page/Page column 36.
[3]Journal of Medicinal Chemistry,2019,vol. 62,p. 1932 - 1958.

2
[ 74440-82-7 ]
C₈H₆ClIO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; for 2.5h;Neat (no solvent); Heating / reflux;	3-Iodo-5-methoxybenzoic acid (4.0 g) was refluxed in thionyl chloride (15 mL) for 2.5 h. Then the excess of thionyl chloride was removed under reduced pressure and the oily residue was taken up in methylene chloride (50 mL) and cooled to O0C. A solution of benzylamine (6.4 mL) in methylene chloride (20 mL) was added dropwise. After 2 h the reaction mixture was diluted with ethyl acetate and washed with water, IN hydrochloric acid, saturated bicarbonate solution and brine. The organic extract was dried over anhydrous sodium sulfate, concentrated and purified on a silica gel column using ethyl acetate and hexanes to yield 4.7 g of yellow oil (90% yield). HRMS calcd for Ci5Hi4INO2 [M+H]+ 368.0142, observed 368.0139

References: [1]Patent: WO2009/77385,2009,A1 .Location in patent: Page/Page column 36.

3
[ 74440-82-7 ]
[ 491839-49-7 ]
N-{4-[(3-iodo-5-methoxybenzene)amido]phenyl}pyridine-2-carboxamide [ No CAS ]