4654-08-4|5-(4-Hydroxyphenyl)pentanoic acid| Ambeed

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Quality Control of [ 4654-08-4 ] Purity: 98% SDS Specification

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Product Details of [ 4654-08-4 ]

CAS No. :	4654-08-4
Formula :	C₁₁H₁₄O₃
M.W :	194.23
SMILES Code :	O=C(O)CCCCC1=CC=C(O)C=C1
MDL No. :	MFCD04039777
InChI Key :	YSSJQFONKASLKM-UHFFFAOYSA-N
Pubchem ID :	7016423

Safety of [ 4654-08-4 ]

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

Computational Chemistry of [ 4654-08-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	6
Fraction Csp3	0.36
Num. rotatable bonds	5
Num. H-bond acceptors	3.0
Num. H-bond donors	2.0
Molar Refractivity	54.43
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	57.53 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.62
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	2.34
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.19
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.	1.96
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	2.13
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.05

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.51
Solubility	0.606 mg/ml ; 0.00312 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.	-3.19
Solubility	0.126 mg/ml ; 0.000649 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	-2.82
Solubility	0.295 mg/ml ; 0.00152 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.	-5.82 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	1.0
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	0.0 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)	1.28

Application In Synthesis of [ 4654-08-4 ]

* 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 [ 4654-08-4 ]

[ 4654-08-4 ] Synthesis Path-Downstream 1~36

1
[ 4648-94-6 ]
[ 4654-08-4 ]

References: [1]Chemische Berichte,1954,vol. 87,p. 345,348.

2
[ 4654-08-4 ]
5-(4-hydroxy-3,5-diiodo-phenyl)-valeric acid [ No CAS ]

References: [1]Journal of Organic Chemistry,1948,vol. 13,p. 576,578.

3
[ 7508-04-5 ]
[ 4654-08-4 ]

References: [1]Journal of Organic Chemistry,1948,vol. 13,p. 576,578.
[2]Journal of the American Chemical Society,1992,vol. 114,p. 3429 - 3441.
[3]Bioscience, Biotechnology and Biochemistry,1999,vol. 63,p. 958 - 960.
[4]Organic and Biomolecular Chemistry,2015,vol. 13,p. 9977 - 9983.

4
[ 103856-01-5 ]
[ 4654-08-4 ]

References: [1]Archives of Biochemistry,1945,vol. 7,p. 415,422.

5
[ 4654-08-4 ]
[ 77-78-1 ]
[ 7508-04-5 ]

References: [1]Chemische Berichte,1954,vol. 87,p. 345,348.

6
[ 4654-08-4 ]
[ 100-39-0 ]
[ 197796-01-3 ]

References: [1]Monatshefte fur Chemie,1997,vol. 128,p. 863 - 879.

7
[ 199444-26-3 ]
[ 87-86-5 ]
[ 4654-08-4 ]

References: [1]Gazzetta Chimica Italiana,1997,vol. 127,p. 269 - 272.

9
[ 4654-08-4 ]
[ 192717-28-5 ]
5-(4-hydroxy-phenyl)-pentanoic acid {2-[2-(3,5-dimethyl-phenyl)-1H-indol-3-yl]-ethyl}-amide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 509 - 513.

10
[ 64201-30-5 ]
[ 4654-08-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 509 - 513.

11
[ 4654-08-4 ]
[ 95426-76-9 ]
5-(4-hydroxy-phenyl)-pentanoic acid {2-[2-(3,4-dimethoxy-phenyl)-1H-indol-3-yl]-ethyl}-amide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 509 - 513.

12
[ 64-17-5 ]
[ 4654-08-4 ]
[ 154044-13-0 ]

References: [1]Molecular Pharmacology,2006,vol. 70,p. 259 - 266.
[2]Organic and Biomolecular Chemistry,2015,vol. 13,p. 9977 - 9983.

13
[ 501-97-3 ]
potash [ No CAS ]
[ 4654-08-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 509 - 513.

14
[ 4654-08-4 ]
4-(5-{2-[2-(3,5-dimethyl-phenyl)-1H-indol-3-yl]-ethylamino}-pentyl)-phenol [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 509 - 513.

15
[ 4654-08-4 ]
4-(5-{2-[2-(3,4-dimethoxy-phenyl)-1H-indol-3-yl]-ethylamino}-pentyl)-phenol [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 509 - 513.

16
[ 50463-48-4 ]
[ 4654-08-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 509 - 513.

17
[ 68486-77-1 ]
[ 4654-08-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 509 - 513.

18
[ 129649-59-8 ]
[ 4654-08-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 509 - 513.

19
[ 4654-08-4 ]
[ 142516-74-3 ]

References: [1]Monatshefte fur Chemie,1997,vol. 128,p. 863 - 879.

20
[ 4654-08-4 ]
[ 154044-14-1 ]

References: [1]Monatshefte fur Chemie,1997,vol. 128,p. 863 - 879.

21
[ 4654-08-4 ]
[ 197796-06-8 ]

References: [1]Monatshefte fur Chemie,1997,vol. 128,p. 863 - 879.

22
[ 4654-08-4 ]
[ 197796-04-6 ]

References: [1]Monatshefte fur Chemie,1997,vol. 128,p. 863 - 879.

23
[ 4654-08-4 ]
C₈₄H₁₀₀O₈ [ No CAS ]

References: [1]Monatshefte fur Chemie,1997,vol. 128,p. 863 - 879.

24
[ 4654-08-4 ]
C₉₀H₁₁₂O₈ [ No CAS ]

References: [1]Monatshefte fur Chemie,1997,vol. 128,p. 863 - 879.

25
[ 47172-89-4 ]
[ 4654-08-4 ]

References: [1]Chemische Berichte,1954,vol. 87,p. 345,348.

26
[ 2270-20-4 ]
[ 4654-08-4 ]

References: [1]Archives of Biochemistry,1945,vol. 7,p. 415,422.

27
[ 67-56-1 ]
[ 4654-08-4 ]
[ 64201-30-5 ]

Yield	Reaction Conditions	Operation in experiment
99%	With sulfuric acid; In water; at 65℃;Inert atmosphere;	[0199] Equipment: 500 ml three-necked flask equipped with magnetic agitation and a refrigerant and placed under nitrogen scavenging-Oil bath. [0200] The <strong>[4654-08-4]5-(4-hydroxyphenyl)-pentanoic acid</strong> 1 (25 g) is put in solution in methanol (375 ml) before slowly pouring in a sulphuric acid solution (25 ml). The solution thus obtained is heated at 65 C. for the night. [0201] The advancement of the reaction is monitored by TLC (eluent: heptane/ethyl acetate: 1/1). After a night of agitation under these conditions, the disappearance of the starting acid 1 is observed in favour of a less polar product. [0202] The reaction medium is concentrated dry under reduced pressure. The residue obtained is taken up by dichloromethane (300 ml). The heterogeneous medium is neutralised and basified, carefully, with a saturated sodium hydrogenocarbonate solution (pH 8-9). The aqueous phase is then extracted three times with dichloromethane. Once collected together, the organic phases are washed once with a saturated sodium chloride solution, dried on magnesium sulphate, filtered and then concentrated under reduced pressure in order to provide a pinkish oil (27 g). [0203] Yield 99%.
99%	With sulfuric acid; at 65℃;	Step 1: Esterification (0419) Equipment: 500 ml Three-Necked Flask Equipped with Magnetic Agitation, Coolant and Placed Under a Stream of Nitrogen-Oil Bath. (0420) <strong>[4654-08-4]5-(4-hydroxyphenyl)-pentanoic acid</strong> 1 (25 g) is placed in solution in methanol (37 5 ml) before slow pouring of sulfuric acid (25 ml). The solution obtained is heated to 65 C. overnight. The progress of the reaction is monitored by TLC (eluting with heptane/ethyl Acetate 1:1). After overnight agitation under these conditions the starting acid 1 is seen to disappear to the benefit of a less polar product. (0421) The reaction medium is concentrated to dryness under reduced pressure. The residue obtained is re-dissolved in dichloromethane (300 ml). The heterogeneous medium is neutralised and basified with precaution with saturated sodium hydrogen carbonate solution (pH 8-9). The aqueous phase is then extracted three times with dichloromethane. Once combined, the organic phases are washed once with saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford a pinkish oil (27 g). (0422) Yield: 99%

References: [1]Patent: US2014/155409,2014,A1 .Location in patent: Paragraph 0198; 0199; 0200; 0201; 0202; 0203.
[2]Patent: US2015/297539,2015,A1 .Location in patent: Paragraph 0418-0422.

28
[ 1929-29-9 ]
[ 4654-08-4 ]