TABLE 2

Endogeneous compounds, including metabolites and nontoxic nutrient components that are transported by human organic cation transporters

Charge of major microspecies at pH 7.4 was calculated with program MarvinSketch of ChemAxon. Acetylcholine: Lips et al., 2005; Pochini et al., 2012, acetyl-L-carnitine: Ohashi et al., 1999, agmatine: Gründemann et al., 2003; Astorga et al., 2012, amoxicillin: Parvez et al., 2018, betaine: Wu et al., 1999; Wagner et al., 2000; Urban et al., 2007, L-carnitine: Tamai et al., 1998; Seth et al., 1999; Yabuuchi et al., 1999; Wagner et al., 2000; Ohashi et al., 2002; Peltekova et al., 2004; Grube et al., 2006; Masuda et al., 2006, D-carnitine: Ohashi et al., 1999; Wagner et al., 2000, choline: Gorboulev et al., 1997; Wu et al., 1999; Wagner et al., 2000; Bednarczyk et al., 2003; Peltekova et al., 2004; Otsuka et al., 2005; Chen et al., 2014; Pochini et al., 2015; Severance et al., 2017; Visentin et al., 2018, creatinine: Urakami et al., 2004; Masuda et al., 2006; Tanihara et al., 2007; Imamura et al., 2011; Astorga et al., 2012; Ciarimboli et al., 2012; Lepist et al., 2014, cyclo(His-Pro): Taubert et al., 2007; Tanihara et al., 2009, 2′deoxycytidine: Drenberg et al., 2017, dopamine: Busch et al., 1998; Bednarczyk et al., 2003; Amphoux et al., 2006; Zolk et al., 2009a; Zhu et al., 2010; Chen et al., 2014, ergothioneine: Gründemann et al., 2005; Grigat et al., 2009; Futatsugi et al., 2016, estrone sulfate: Tanihara et al., 2007; Lechner et al., 2016, epinephrine: Gründemann et al., 1998; Amphoux et al., 2006; Chen et al., 2014, guanidine: Ohashi et al., 1999; Wu et al., 1999, 2000; Urakami et al., 2004; Masuda et al., 2006; Tanihara et al., 2007; Kimura et al., 2009, histamine: Busch et al., 1998; Gründemann et al., 1998; Bednarczyk et al., 2003; Amphoux et al., 2006; Astorga et al., 2012; Chen et al., 2014, 6-β-hydroxycortisol: Imamura et al., 2013, lysine: Wagner et al., 2000, methionine: Wagner et al., 2000, N-1-methylnicotinamide: Gorboulev et al., 1997; Zhang et al., 1998; Wu et al., 1999; Bednarczyk et al., 2003; Peltekova et al., 2004; Masuda et al., 2006; Sakata et al., 2010; Ito et al., 2012a, norepinephrine: Busch et al., 1998; Gründemann et al., 1998; Amphoux et al., 2006; Zolk et al., 2009a; Zhu et al., 2010; Chen et al., 2014; Song et al., 2019, salsolinol: Taubert et al., 2007, serotonin: Busch et al., 1998; Otsuka et al., 2005; Amphoux et al., 2006; Zhu et al., 2010; Astorga et al., 2012; Boxberger et al., 2014; Chen et al., 2014, stachydrine: Gründemann et al., 2005, thiamine: Dutta et al., 1999; Bednarczyk et al., 2003; Masuda et al., 2006; Tanihara et al., 2007; Astorga et al., 2012; Chen et al., 2014; Kato et al., 2014; Lechner et al., 2016, trimethylamine N-oxide: Miyake et al., 2017; Teft et al., 2017, tyramine: Gründemann et al., 1998; Bednarczyk et al., 2003; Chen et al., 2014, quercetin: Lee et al., 2014b.

Compound (Charge of Major Microspecies at pH 7.4)Km (IC50) [µM]
hOCT1hOCT2hOCT3hOCTN1hOCTN2hMATE1hMATE2-K
Acetylcholine (+)(580)1171000
Acetyl-L-carnitine (+/−)8.5
Agmatine (++)t (24,000)14002500(54a)(61a)
Betaine (+/−)tt
Choline (+)t (3540)210–404t (231)t (>2000)(>5000a)
Creatinine (+)t1820, 4000 (580)1320n.t.d.n.t.d.>2000 (195a)>2000 (150a)
Cyclo (His-Pro) (0)65574126
D-Carnitine (+/−)11, 98
L-Carnitine (+/−)5713.5–7.7n.t.d.
2′Deoxycytidine (0)t
Dopamine (+)t (487)390–1400800.
Epinephrine (+)t420240
Ergothioneine (+/−)21, 85n.t.d.
Estrone 3-sulfate (−)470a850a
Guanidine (+)(2200, 3030)(6201)n.t.d., n.i.d.2100a4200a
6-β-Hydroxycortisol (0)tt
Histamine (+)t (3007)940, 1300180, 220(761a)(775a)
Lysine (++/−)t
Methionine (+/−)t
N-1-methylnicotinamide (0)(1035, 7700)318 (266–1000)(77)i.n.f.t.301422
Norepinephrine (+)t1500–5450182–2630
Salsolinol (+)440130139
Serotonin (+)197 (>20,000)80, 290900 (1000)(29a)(18a)
Stachydrine (+/−)270
Thiamine (+)780 (434)60, 750t3.5a,b, 313.9a,b, 23
Trimethylamine-N-oxide (+/−)33,9007370, 74,000n.t.d.
Tyramine (+)t (107)t(87a)(138a)
Quercetin (0)t
  • i.n.f.t., inhibition, not tested for transport; n.i.d., no inhibition detected; n.t.d., no transport detected; t, transported.

  • a Uptake measurements performed in presence of an outwardly directed proton gradient.

  • b Determination of the low apparent Km values is supposed to be due to the fact that only thiamine concentrations up to 100 µM were tested and the Km of an apparent high-affinity transport site was obtained.