Predicting absolute aqueous solubility by applying a machine learning model for an artificially liquid-state as proxy for the solid-state

Chung TDY, Terry DB, Smith LH (2004) In vitro and in vivo assessment of ADME and PK properties during lead selection and lead optimization—guidelines, benchmarks and rules of thumb. In: Markossian S, Grossman A, Brimacombe K, Arkin M, Auld D, Austin C, Baell J, Chung TDY, Coussens NP, Dahlin JL, Devanarayan V, Foley TL, Glicksman M, Haas JV, Hall MD, Hoare S, Inglese J, Iversen PW, Kales SC, Lal-Nag M, Li Z, McGee J, McManus O, Riss T, Saradjian P, Sittampalam GS, Tarselli M, Trask OJ Jr, Wang Y, Weidner JR, Wildey MJ, Wilson K, Xia M, Xu X (eds) Assay guidance manual. Bethesda

Google Scholar 

Clark DE, Grootenhuis PD (2002) Progress in computational methods for the prediction of ADMET properties. Curr Opin Drug Discov Devel 5(3):382–390

CAS  PubMed  Google Scholar 

Dearden JC (2007) In silico prediction of ADMET properties: how far have we come? Expert Opin Drug Metab Toxicol 3(5):635–639

Article  CAS  PubMed  Google Scholar 

Göller AH, Kuhnke L, Montanari F, Bonin A, Schneckener S, ter Laak A, Wichard J, Lobell M, Hillisch A (2020) Bayer’s in silico ADMET platform: a journey of machine learning over the past two decades. Drug Discov Today 25(9):1702–1709

Article  PubMed  Google Scholar 

Göller AH, Kuhnke L, ter Laak A, Meier K, Hillisch A (2022) Machine learning applied to the modeling of pharmacological and ADMET absorption, distribution, metabolism, excretion and toxicity (ADMET) endpoints. In: Heifetz A (ed) Artificial intelligence in drug design. New York, Springer, pp 61–101

Chapter  Google Scholar 

Kier LB, Hall LH (2005) The prediction of ADMET properties using structure information representations. Chem Biodivers 2(11):1428–1437

Article  CAS  PubMed  Google Scholar 

Lucas AJ, Sproston JL, Barton P, Riley RJ (2019) Estimating human ADME properties, pharmacokinetic parameters and likely clinical dose in drug discovery. Expert Opin Drug Discov 14(12):1313–1327

Article  CAS  PubMed  Google Scholar 

Norinder U, Bergstrom CA (2006) Prediction of ADMET properties. ChemMedChem 1(9):920–937

Article  CAS  PubMed  Google Scholar 

Oliferenko PV, Oliferenko AA, Poda G, Palyulin VA, Zefirov NS, Katritzky AR (2009) New developments in hydrogen bonding acidity and basicity of small organic molecules for the prediction of physical and ADMET properties: part 2—the universal solvation equation. J Chem Inf Model 49(3):634–646

Article  CAS  PubMed  Google Scholar 

Zhou SF, Zhong WZ (2017) Drug design and discovery: principles and applications. Molecules 22(2):279

Article  PubMed  PubMed Central  Google Scholar 

Eleftheriadou D, Luette S, Kneuer C (2019) In silico prediction of dermal absorption of pesticides—an evaluation of selected models against results from in vitro testing. SAR QSAR Environ Res 30(8):561–585

Article  CAS  PubMed  Google Scholar 

Elliott JR, Compton RG (2022) Modeling transcuticular uptake from particle-based formulations of lipophilic products. ACS Agric Sci Technol 2(3):603–614

Article  CAS  PubMed  PubMed Central  Google Scholar 

Khayet M, Fernandez V (2012) Estimation of the solubility parameters of model plant surfaces and agrochemicals: a valuable tool for understanding plant surface interactions. Theor Biol Med Model 9:45

Article  CAS  PubMed  PubMed Central  Google Scholar 

Xiao S, Gong Y, Li Z, Fantke P (2021) Improving pesticide uptake modeling into potatoes: considering tuber growth dynamics. J Agric Food Chem 69(12):3607–3616

Article  CAS  PubMed  Google Scholar 

Avdeef A, Fuguet E, Llinàs A, Ràfols C, Bosch E, Völgyi G, Verbić T, Boldyreva E, Takács-Novák K (2016) Equilibrium solubility measurement of ionizable drugs–consensus recommendations for improving data quality. ADMET and DMPK 4(2):117–178

Article  Google Scholar 

Fink C, Sun DJ, Wagner K, Schneider M, Bauer H, Dolgos H, Mader K, Peters SA (2020) Evaluating the role of solubility in oral absorption of poorly water-soluble drugs using physiologically-based pharmacokinetic modeling. Clin Pharmacol Ther 107(3):650–661

Article  CAS  PubMed  Google Scholar 

Llinas A, Avdeef A (2019) Solubility challenge revisited after ten years, with multilab shake-flask data, using tight (SD ∼ 0.17 log) and loose (SD ∼ 0.62 log) test sets. J Chem Inf Model 59(6):3036–3040

Article  CAS  PubMed  Google Scholar 

Ono A, Matsumura N, Kimoto T, Akiyama Y, Funaki S, Tamura N, Hayashi S, Kojima Y, Fushimi M, Sudaki H, Aihara R, Haruna Y, Jiko M, Iwasaki M, Fujita T, Sugano K (2019) Harmonizing solubility measurement to lower inter-laboratory variance—progress of consortium of biopharmaceutical tools (CoBiTo) in Japan. ADMET DMPK 7(3):183–195

Article  PubMed  PubMed Central  Google Scholar 

Kuramochi H, Kawamoto K (2006) Modification of UNIFAC parameter table revision 5 for representation of aqueous solubility and 1-octanol/water partition coefficient for POPs. Chemosphere 63(4):698–706

Article  CAS  PubMed  Google Scholar 

Banerjee S, Howard PH (1988) Improved estimation of solubility and partitioning through correction of UNIFAC-derived activity coefficients. Environ Sci Technol 22(7):839–841

Article  CAS  PubMed  Google Scholar 

Arbuckle WB (1986) Using UNIFAC to calculate aqueous solubilities. Environ Sci Technol 20(10):1060–1064

Article  CAS  PubMed  Google Scholar 

Ochsner AB, Sokoloski TD (1985) Prediction of solubility in nonideal multicomponent systems using the UNIFAC group contribution model. J Pharm Sci 74(6):634–637

Article  CAS  PubMed  Google Scholar 

Banerjee S (1985) Calculation of water solubility of organic compounds with UNIFAC-derived parameters. Environ Sci Technol 19(4):369–370

Article  CAS  PubMed  Google Scholar 

Fredenslund A, Jones RL, Prausnitz JM (1975) Group-contribution estimation of activity-coefficients in nonideal liquid-mixtures. Aiche J 21(6):1086–1099

Article  CAS  Google Scholar 

Hildebrand, J. H., Solubility of non-electrolytes. 1936, 2nd ed. Pp. 203. New York: Reinhold Publishing Corp., London: Chapman & Hall, Ltd. 22s. 6d

Hildebrand JH (1949) A critique of the theory of solubility of non-electrolytes. Chem Rev 44(1):37–45

Article  CAS  PubMed  Google Scholar 

Hildebrand JH (1950) Factors determining solubility among non-electrolytes. Proc Natl Acad Sci USA 36(1):7–15

Article  CAS  PubMed  PubMed Central  Google Scholar 

Martin A, Paruta AN, Adjei A (1981) Extended hildebrand solubility approach: methylxanthines in mixed solvents. J Pharm Sci 70(10):1115–1120

Article  CAS  PubMed  Google Scholar 

Martin A, Miralles MJ (1982) Extended Hildebrand solubility approach: solubility of tolbutamide, acetohexamide, and sulfisomidine in binary solvent mixtures. J Pharm Sci 71(4):439–442

Article  CAS  PubMed  Google Scholar 

Martin A, Wu PL, Adjei A, Lindstrom RE, Elworthy PH (1982) Extended Hildebrand solubility approach and the log linear solubility equation. J Pharm Sci 71(8):849–856

Article  CAS  PubMed  Google Scholar 

Bustamante P, Escalera B, Martin A, Selles E (1993) A modification of the extended Hildebrand approach to predict the solubility of structurally related drugs in solvent mixtures. J Pharm Pharmacol 45(4):253–257

Article  CAS  PubMed  Google Scholar 

Lin HM, Nash RA (1993) An experimental method for determining the Hildebrand solubility parameter of organic nonelectrolytes. J Pharm Sci 82(10):1018–1026

Article  CAS  PubMed  Google Scholar 

Jouyban-Gharamaleki A, Romero S, Bustamante P, Clark BJ (2000) Multiple solubility maxima of oxolinic acid in mixed solvents and a new extension of Hildebrand solubility approach. Chem Pharm Bull (Tokyo) 48(2):175–178

Article  CAS  PubMed  Google Scholar 

Wu PL, Beerbower A, Martin A (1982) Extended Hansen approach: calculating partial solubility parameters of solid solutes. J Pharm Sci 71(11):1285–1287

Article  CAS  PubMed  Google Scholar 

Barra J, Lescure F, Doelker E, Bustamante P (1997) The expanded Hansen approach to solubility parameters: Paracetamol and citric acid in individual solvents. J Pharm Pharmacol 49(7):644–651

Article  CAS  PubMed  Google Scholar 

Hansen CM (2007) Hansen solubility parameters: a user’s handbook. CRC Press

Book  Google Scholar 

Louwerse MJ, Maldonado A, Rousseau S, Moreau-Masselon C, Roux B, Rothenberg G (2017) Revisiting Hansen solubility parameters by including thermodynamics. ChemPhysChem 18(21):2999–3006

Article  CAS  PubMed  PubMed Central  Google Scholar 

Famini GR, Headley AD, Wilson L (1994) Using theoretical descriptors in Qsar and Lfer—the role of solute solvent interactions in solubility, acidity and basicity. Abstr Pap Am Chem S 207:96

Google Scholar 

Abraham MH, Green CE, Acree WE, Hernandez CE, Roy LE (1998) Descriptors for solutes from the solubility of solids: trans-stilbene as an example. J Chem Soc Perk T 2 12:2677–2681

Article 

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