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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2)transporters (1) Show 3 proteins XML

enzymes (2)transporters (1) Show 3 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:49 UTC

HMDB ID

HMDB0015014

Secondary Accession Numbers

HMDB15014

Metabolite Identification

Common Name

Eprosartan

Description

Eprosartan, also known as SK and F 108566 or teveten, belongs to the class of organic compounds known as benzoic acids. These are organic Compounds containing a benzene ring which bears at least one carboxyl group. Eprosartan is sometimes paired with hydrochlorothiazide, whereupon it is marketed in the US as Teveten HCT and elsewhere as Teveten Plus. Eprosartan is a drug which is used for the management of hypertension alone or in combination with other classes of antihypertensive agents. also used as a first-line agent in the treatment of diabetic nephropathy, as well as a second-line agent in the treatment of congestive heart failure (only in those intolerant of ace inhibitors). As with other angiotensin II receptor antagonists, eprosartan is generally better tolerated than enalapril (an ACE inhibitor), especially among the elderly. It is marketed in the United States as Teveten by Abbvie, the spin-off of the pharmaceutical discovery division of Abbott Laboratories; it is marketed as Eprozar by Intas Pharmaceuticals in India, and by Abbott Laboratories elsewhere. The compound came into the Abbott Laboratories cardiovascular pipeline with its acquisition of Kos Pharmaceuticals in 2006, which had licensed it, along with "a range of hypertensive treatments", from the Biovail Corporation. Eprosartan is a very strong basic compound (based on its pKa). The drug acts on the renin–angiotensin system to decrease total peripheral resistance in two ways. In humans, eprosartan is involved in eprosartan action pathway. Second, it inhibits sympathetic norepinephrine production, further reducing blood pressure. First, it blocks the binding of angiotensin II to AT1 receptors in vascular smooth muscle, causing vascular dilatation. Eprosartan is an angiotensin II receptor antagonist used for the treatment of high blood pressure.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 04191212152D          

 30 32  0  0  0  0            999 V2000
   -0.7145   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1433   -0.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290    0.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0001    1.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7146    2.0624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7146    2.8874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290    1.6498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578    0.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8580    1.6498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5723    0.4122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4989    0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9839    0.0001    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4991   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7541   -1.4520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5610   -1.6235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8159   -2.4082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6228   -2.5797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7143    2.0624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7142    2.8874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0467    3.3723    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3015    4.1569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1265    4.1570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3816    3.3724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 20  1  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  7  2  0  0  0  0
  3  4  1  0  0  0  0
  4 10  2  0  0  0  0
  5 11  2  0  0  0  0
  1  6  1  0  0  0  0
  6  5  1  0  0  0  0
  6 18  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 15  1  0  0  0  0
 10  9  1  0  0  0  0
 11 25  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 18 19  1  0  0  0  0
 20 19  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 26 27  1  0  0  0  0
 26 30  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 30 29  1  0  0  0  0
 25 26  1  0  0  0  0
M  END

HMDB0015014
     RDKit          3D
Eprosartan
 54 56  0  0  0  0  0  0  0  0999 V2000
   -4.9644   -3.7362    0.4044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5206   -3.1998   -0.9378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0335   -2.9124   -0.9075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7127   -1.8704    0.1729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2376   -1.6754    0.1066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3623   -2.3931    0.8390 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8968   -2.0229    0.5767 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8435   -1.0228   -0.3641 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9160   -0.2706   -1.0003 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8908    0.3012   -0.3288 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9911    0.2387    1.1404 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2921   -0.4433    1.4902 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4645    0.1182    1.9246 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4958   -0.7125    2.1586 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2970   -2.0440    1.9475 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6770   -2.1139    1.4263 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.8889    1.0179   -1.1324 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8296    1.0852   -2.3863 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9489    1.6560   -0.5190 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4928   -0.8347   -0.6302 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9632    0.1362   -1.5644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2910    1.4610   -1.0357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4013    2.4289   -0.6814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8503    3.6597   -0.2066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1701    3.9636   -0.0708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6861    5.2361    0.4262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9138    5.4677    0.5256 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8088    6.2535    0.8132 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0760    2.9879   -0.4283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6526    1.7654   -0.9001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1168   -4.0096    1.0563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5743   -4.6739    0.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6041   -2.9694    0.8815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6833   -3.9837   -1.7000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1062   -2.2913   -1.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7141   -2.5310   -1.8990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5180   -3.8713   -0.6936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9840   -2.2899    1.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2866   -0.9837   -0.0585 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7606   -2.4727    1.0388 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053   -0.1772   -2.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1046    1.2771    1.5791 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2019   -0.2862    1.6579 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5242    1.2281    2.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4864   -0.3536    2.5126 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0372   -2.8584    2.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9199    1.4551   -0.6986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1729    0.2942   -2.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8416   -0.3038   -2.0900 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6546    2.2305   -0.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1192    4.4040    0.0655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6075    6.4584    1.7841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1641    3.1547   -0.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3969    1.0285   -1.1827 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 10 17  1  0
 17 18  2  0
 17 19  1  0
  8 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 25 29  1  0
 29 30  2  0
 20  5  1  0
 30 22  1  0
 16 12  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  4 39  1  0
  7 40  1  0
  9 41  1  0
 11 42  1  0
 11 43  1  0
 13 44  1  0
 14 45  1  0
 15 46  1  0
 19 47  1  0
 21 48  1  0
 21 49  1  0
 23 50  1  0
 24 51  1  0
 28 52  1  0
 29 53  1  0
 30 54  1  0
M  END


  Mrv0541 04191212152D          

 30 32  0  0  0  0            999 V2000
   -0.7145   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1433   -0.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290    0.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0001    1.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7146    2.0624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7146    2.8874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290    1.6498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578    0.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8580    1.6498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5723    0.4122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4989    0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9839    0.0001    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4991   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7541   -1.4520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5610   -1.6235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8159   -2.4082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6228   -2.5797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7143    2.0624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7142    2.8874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0467    3.3723    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3015    4.1569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1265    4.1570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3816    3.3724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 20  1  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  7  2  0  0  0  0
  3  4  1  0  0  0  0
  4 10  2  0  0  0  0
  5 11  2  0  0  0  0
  1  6  1  0  0  0  0
  6  5  1  0  0  0  0
  6 18  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 15  1  0  0  0  0
 10  9  1  0  0  0  0
 11 25  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 18 19  1  0  0  0  0
 20 19  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 26 27  1  0  0  0  0
 26 30  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 30 29  1  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015014

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC1=NC=C(\C=C(/CC2=CC=CS2)C(O)=O)N1CC1=CC=C(C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H24N2O4S/c1-2-3-6-21-24-14-19(12-18(23(28)29)13-20-5-4-11-30-20)25(21)15-16-7-9-17(10-8-16)22(26)27/h4-5,7-12,14H,2-3,6,13,15H2,1H3,(H,26,27)(H,28,29)/b18-12+

> <INCHI_KEY>
OROAFUQRIXKEMV-LDADJPATSA-N

> <FORMULA>
C23H24N2O4S

> <MOLECULAR_WEIGHT>
424.513

> <EXACT_MASS>
424.145677956

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
45.29168425040713

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-({2-butyl-5-[(1E)-2-carboxy-2-(thiophen-2-ylmethyl)eth-1-en-1-yl]-1H-imidazol-1-yl}methyl)benzoic acid

> <ALOGPS_LOGP>
3.57

> <JCHEM_LOGP>
3.797230393590431

> <ALOGPS_LOGS>
-4.69

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.311688293613994

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6324817466992205

> <JCHEM_PKA_STRONGEST_BASIC>
6.932609566145001

> <JCHEM_POLAR_SURFACE_AREA>
92.42

> <JCHEM_REFRACTIVITY>
117.02430000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.66e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
eprosartan

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015014
     RDKit          3D
Eprosartan
 54 56  0  0  0  0  0  0  0  0999 V2000
   -4.9644   -3.7362    0.4044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5206   -3.1998   -0.9378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0335   -2.9124   -0.9075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7127   -1.8704    0.1729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2376   -1.6754    0.1066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3623   -2.3931    0.8390 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8968   -2.0229    0.5767 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8435   -1.0228   -0.3641 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9160   -0.2706   -1.0003 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8908    0.3012   -0.3288 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9911    0.2387    1.1404 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2921   -0.4433    1.4902 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4645    0.1182    1.9246 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4958   -0.7125    2.1586 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2970   -2.0440    1.9475 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6770   -2.1139    1.4263 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.8889    1.0179   -1.1324 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8296    1.0852   -2.3863 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9489    1.6560   -0.5190 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4928   -0.8347   -0.6302 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9632    0.1362   -1.5644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2910    1.4610   -1.0357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4013    2.4289   -0.6814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8503    3.6597   -0.2066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1701    3.9636   -0.0708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6861    5.2361    0.4262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9138    5.4677    0.5256 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8088    6.2535    0.8132 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0760    2.9879   -0.4283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6526    1.7654   -0.9001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1168   -4.0096    1.0563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5743   -4.6739    0.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6041   -2.9694    0.8815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6833   -3.9837   -1.7000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1062   -2.2913   -1.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7141   -2.5310   -1.8990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5180   -3.8713   -0.6936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9840   -2.2899    1.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2866   -0.9837   -0.0585 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7606   -2.4727    1.0388 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053   -0.1772   -2.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1046    1.2771    1.5791 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2019   -0.2862    1.6579 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5242    1.2281    2.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4864   -0.3536    2.5126 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0372   -2.8584    2.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9199    1.4551   -0.6986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1729    0.2942   -2.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8416   -0.3038   -2.0900 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6546    2.2305   -0.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1192    4.4040    0.0655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6075    6.4584    1.7841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1641    3.1547   -0.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3969    1.0285   -1.1827 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 10 17  1  0
 17 18  2  0
 17 19  1  0
  8 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 25 29  1  0
 29 30  2  0
 20  5  1  0
 30 22  1  0
 16 12  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  4 39  1  0
  7 40  1  0
  9 41  1  0
 11 42  1  0
 11 43  1  0
 13 44  1  0
 14 45  1  0
 15 46  1  0
 19 47  1  0
 21 48  1  0
 21 49  1  0
 23 50  1  0
 24 51  1  0
 28 52  1  0
 29 53  1  0
 30 54  1  0
M  END

HEADER    PROTEIN                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  N   UNK     0      -1.334  -0.770   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -0.771   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.334   5.390   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       2.667   3.080   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.335   3.080   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       6.668   0.769   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.798   1.246   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0      -3.703   0.000   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0      -2.798  -1.246   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.274  -2.710   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.781  -3.031   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.256  -4.495   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -6.763  -4.815   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.333   3.850   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.333   5.390   0.000  0.00  0.00           C+0
HETATM   27  S   UNK     0      -0.087   6.295   0.000  0.00  0.00           S+0
HETATM   28  C   UNK     0      -0.563   7.760   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.103   7.760   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.579   6.295   0.000  0.00  0.00           C+0
CONECT    1   20    2    6                                                  
CONECT    2    1    3                                                       
CONECT    3    2    7    4                                                  
CONECT    4    3   10                                                       
CONECT    5   11    6                                                       
CONECT    6    1    5   18                                                  
CONECT    7    3    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   15   10                                                  
CONECT   10    4    9                                                       
CONECT   11    5   25   12                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    9   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    6   19                                                       
CONECT   19   18   20                                                       
CONECT   20    1   19   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   11   26                                                       
CONECT   26   27   30   25                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   26   29                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

COMPND    HMDB0015014
HETATM    1  C1  UNL     1      -4.964  -3.736   0.404  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.521  -3.200  -0.938  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.034  -2.912  -0.907  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.713  -1.870   0.173  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.238  -1.675   0.107  1.00  0.00           C  
HETATM    6  N1  UNL     1      -0.362  -2.393   0.839  1.00  0.00           N  
HETATM    7  C6  UNL     1       0.897  -2.023   0.577  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.843  -1.023  -0.364  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.916  -0.271  -1.000  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.891   0.301  -0.329  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.991   0.239   1.140  1.00  0.00           C  
HETATM   12  C11 UNL     1       4.292  -0.443   1.490  1.00  0.00           C  
HETATM   13  C12 UNL     1       5.464   0.118   1.925  1.00  0.00           C  
HETATM   14  C13 UNL     1       6.496  -0.713   2.159  1.00  0.00           C  
HETATM   15  C14 UNL     1       6.297  -2.044   1.948  1.00  0.00           C  
HETATM   16  S1  UNL     1       4.677  -2.114   1.426  1.00  0.00           S  
HETATM   17  C15 UNL     1       3.889   1.018  -1.132  1.00  0.00           C  
HETATM   18  O1  UNL     1       3.830   1.085  -2.386  1.00  0.00           O  
HETATM   19  O2  UNL     1       4.949   1.656  -0.519  1.00  0.00           O  
HETATM   20  N2  UNL     1      -0.493  -0.835  -0.630  1.00  0.00           N  
HETATM   21  C16 UNL     1      -0.963   0.136  -1.564  1.00  0.00           C  
HETATM   22  C17 UNL     1      -1.291   1.461  -1.036  1.00  0.00           C  
HETATM   23  C18 UNL     1      -0.401   2.429  -0.681  1.00  0.00           C  
HETATM   24  C19 UNL     1      -0.850   3.660  -0.207  1.00  0.00           C  
HETATM   25  C20 UNL     1      -2.170   3.964  -0.071  1.00  0.00           C  
HETATM   26  C21 UNL     1      -2.686   5.236   0.426  1.00  0.00           C  
HETATM   27  O3  UNL     1      -3.914   5.468   0.526  1.00  0.00           O  
HETATM   28  O4  UNL     1      -1.809   6.253   0.813  1.00  0.00           O  
HETATM   29  C22 UNL     1      -3.076   2.988  -0.428  1.00  0.00           C  
HETATM   30  C23 UNL     1      -2.653   1.765  -0.900  1.00  0.00           C  
HETATM   31  H1  UNL     1      -4.117  -4.010   1.056  1.00  0.00           H  
HETATM   32  H2  UNL     1      -5.574  -4.674   0.264  1.00  0.00           H  
HETATM   33  H3  UNL     1      -5.604  -2.969   0.882  1.00  0.00           H  
HETATM   34  H4  UNL     1      -4.683  -3.984  -1.700  1.00  0.00           H  
HETATM   35  H5  UNL     1      -5.106  -2.291  -1.234  1.00  0.00           H  
HETATM   36  H6  UNL     1      -2.714  -2.531  -1.899  1.00  0.00           H  
HETATM   37  H7  UNL     1      -2.518  -3.871  -0.694  1.00  0.00           H  
HETATM   38  H8  UNL     1      -2.984  -2.290   1.170  1.00  0.00           H  
HETATM   39  H9  UNL     1      -3.287  -0.984  -0.059  1.00  0.00           H  
HETATM   40  H10 UNL     1       1.761  -2.473   1.039  1.00  0.00           H  
HETATM   41  H11 UNL     1       1.905  -0.177  -2.115  1.00  0.00           H  
HETATM   42  H12 UNL     1       3.105   1.277   1.579  1.00  0.00           H  
HETATM   43  H13 UNL     1       2.202  -0.286   1.658  1.00  0.00           H  
HETATM   44  H14 UNL     1       5.524   1.228   2.077  1.00  0.00           H  
HETATM   45  H15 UNL     1       7.486  -0.354   2.513  1.00  0.00           H  
HETATM   46  H16 UNL     1       7.037  -2.858   2.092  1.00  0.00           H  
HETATM   47  H17 UNL     1       5.920   1.455  -0.699  1.00  0.00           H  
HETATM   48  H18 UNL     1      -0.173   0.294  -2.361  1.00  0.00           H  
HETATM   49  H19 UNL     1      -1.842  -0.304  -2.090  1.00  0.00           H  
HETATM   50  H20 UNL     1       0.655   2.231  -0.778  1.00  0.00           H  
HETATM   51  H21 UNL     1      -0.119   4.404   0.065  1.00  0.00           H  
HETATM   52  H22 UNL     1      -1.608   6.458   1.784  1.00  0.00           H  
HETATM   53  H23 UNL     1      -4.164   3.155  -0.349  1.00  0.00           H  
HETATM   54  H24 UNL     1      -3.397   1.028  -1.183  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3   34   35
CONECT    3    4   36   37
CONECT    4    5   38   39
CONECT    5    6    6   20
CONECT    6    7
CONECT    7    8    8   40
CONECT    8    9   20
CONECT    9   10   10   41
CONECT   10   11   17
CONECT   11   12   42   43
CONECT   12   13   13   16
CONECT   13   14   44
CONECT   14   15   15   45
CONECT   15   16   46
CONECT   17   18   18   19
CONECT   19   47
CONECT   20   21
CONECT   21   22   48   49
CONECT   22   23   23   30
CONECT   23   24   50
CONECT   24   25   25   51
CONECT   25   26   29
CONECT   26   27   27   28
CONECT   28   52
CONECT   29   30   30   53
CONECT   30   54
END

HMDB0015014
     RDKit          3D
Eprosartan
 54 56  0  0  0  0  0  0  0  0999 V2000
   -4.9644   -3.7362    0.4044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5206   -3.1998   -0.9378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0335   -2.9124   -0.9075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7127   -1.8704    0.1729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2376   -1.6754    0.1066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3623   -2.3931    0.8390 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8968   -2.0229    0.5767 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8435   -1.0228   -0.3641 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9160   -0.2706   -1.0003 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8908    0.3012   -0.3288 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9911    0.2387    1.1404 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2921   -0.4433    1.4902 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4645    0.1182    1.9246 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4958   -0.7125    2.1586 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2970   -2.0440    1.9475 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6770   -2.1139    1.4263 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.8889    1.0179   -1.1324 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8296    1.0852   -2.3863 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9489    1.6560   -0.5190 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4928   -0.8347   -0.6302 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9632    0.1362   -1.5644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2910    1.4610   -1.0357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4013    2.4289   -0.6814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8503    3.6597   -0.2066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1701    3.9636   -0.0708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6861    5.2361    0.4262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9138    5.4677    0.5256 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8088    6.2535    0.8132 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0760    2.9879   -0.4283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6526    1.7654   -0.9001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1168   -4.0096    1.0563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5743   -4.6739    0.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6041   -2.9694    0.8815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6833   -3.9837   -1.7000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1062   -2.2913   -1.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7141   -2.5310   -1.8990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5180   -3.8713   -0.6936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9840   -2.2899    1.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2866   -0.9837   -0.0585 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7606   -2.4727    1.0388 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053   -0.1772   -2.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1046    1.2771    1.5791 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2019   -0.2862    1.6579 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5242    1.2281    2.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4864   -0.3536    2.5126 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0372   -2.8584    2.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9199    1.4551   -0.6986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1729    0.2942   -2.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8416   -0.3038   -2.0900 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6546    2.2305   -0.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1192    4.4040    0.0655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6075    6.4584    1.7841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1641    3.1547   -0.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3969    1.0285   -1.1827 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 10 17  1  0
 17 18  2  0
 17 19  1  0
  8 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 25 29  1  0
 29 30  2  0
 20  5  1  0
 30 22  1  0
 16 12  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  4 39  1  0
  7 40  1  0
  9 41  1  0
 11 42  1  0
 11 43  1  0
 13 44  1  0
 14 45  1  0
 15 46  1  0
 19 47  1  0
 21 48  1  0
 21 49  1  0
 23 50  1  0
 24 51  1  0
 28 52  1  0
 29 53  1  0
 30 54  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(e)-2-Butyl-1-(p-carboxybenzyl)-alpha-2-thenylimidazole-5-acrylic acid	ChEBI
(e)-3-[2-N-Butyl-1-{(4-carboxyphenyl)methyl}-1H-imidazol-5-yl]-2-(2-thienyl)methyl-2-propenoic acid	ChEBI
(e)-Alpha{[2-butyl-1-[(4-carboxyphenyl)methyl]-1H-imidazole-5-yl]methylene}-2-thiopheneproprionic acid	ChEBI
(e)-2-Butyl-1-(p-carboxybenzyl)-a-2-thenylimidazole-5-acrylate	Generator
(e)-2-Butyl-1-(p-carboxybenzyl)-a-2-thenylimidazole-5-acrylic acid	Generator
(e)-2-Butyl-1-(p-carboxybenzyl)-alpha-2-thenylimidazole-5-acrylate	Generator
(e)-2-Butyl-1-(p-carboxybenzyl)-α-2-thenylimidazole-5-acrylate	Generator
(e)-2-Butyl-1-(p-carboxybenzyl)-α-2-thenylimidazole-5-acrylic acid	Generator
(e)-3-[2-N-Butyl-1-{(4-carboxyphenyl)methyl}-1H-imidazol-5-yl]-2-(2-thienyl)methyl-2-propenoate	Generator
(e)-Alpha{[2-butyl-1-[(4-carboxyphenyl)methyl]-1H-imidazole-5-yl]methylene}-2-thiopheneproprionate	Generator
SK And F 108566	HMDB
Teveten	HMDB

Chemical Formula

C₂₃H₂₄N₂O₄S

Average Molecular Weight

424.513

Monoisotopic Molecular Weight

424.145677956

IUPAC Name

4-({2-butyl-5-[(1E)-2-carboxy-2-(thiophen-2-ylmethyl)eth-1-en-1-yl]-1H-imidazol-1-yl}methyl)benzoic acid

Traditional Name

eprosartan

CAS Registry Number

133040-01-4

SMILES

CCCCC1=NC=C(\C=C(/CC2=CC=CS2)C(O)=O)N1CC1=CC=C(C=C1)C(O)=O

InChI Identifier

InChI=1S/C23H24N2O4S/c1-2-3-6-21-24-14-19(12-18(23(28)29)13-20-5-4-11-30-20)25(21)15-16-7-9-17(10-8-16)22(26)27/h4-5,7-12,14H,2-3,6,13,15H2,1H3,(H,26,27)(H,28,29)/b18-12+

InChI Key

OROAFUQRIXKEMV-LDADJPATSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoic acids. These are organic Compounds containing a benzene ring which bears at least one carboxyl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acids

Alternative Parents

Substituents

Benzoic acid
1,2,5-trisubstituted-imidazole
Benzoyl
Imidazolyl carboxylic acid derivative
Trisubstituted imidazole
Dicarboxylic acid or derivatives
N-substituted imidazole
Azole
Heteroaromatic compound
Imidazole
Thiophene
Carboxylic acid derivative
Carboxylic acid
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Organic oxide
Organic oxygen compound
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

imidazoles (CHEBI:4814 )
thiophenes (CHEBI:4814 )
dicarboxylic acid (CHEBI:4814 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015014)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Eprosartan Action Pathway (PathBank: SMP0000159)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	248 - 250 °C (mesylate form)	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0087 g/L	Not Available
LogP	3.9	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0087 g/L	ALOGPS
logP	3.57	ALOGPS
logP	3.8	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	3.63	ChemAxon
pKa (Strongest Basic)	6.93	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	92.42 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	117.02 m³·mol⁻¹	ChemAxon
Polarizability	45.29 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	196.487	30932474
DeepCCS	[M-H]-	194.129	30932474
DeepCCS	[M-2H]-	227.667	30932474
DeepCCS	[M+Na]+	202.896	30932474
AllCCS	[M+H]+	201.0	32859911
AllCCS	[M+H-H2O]+	198.7	32859911
AllCCS	[M+NH4]+	203.2	32859911
AllCCS	[M+Na]+	203.8	32859911
AllCCS	[M-H]-	198.8	32859911
AllCCS	[M+Na-2H]-	199.1	32859911
AllCCS	[M+HCOO]-	199.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Eprosartan	CCCCC1=NC=C(\C=C(/CC2=CC=CS2)C(O)=O)N1CC1=CC=C(C=C1)C(O)=O	5413.8	Standard polar	33892256
Eprosartan	CCCCC1=NC=C(\C=C(/CC2=CC=CS2)C(O)=O)N1CC1=CC=C(C=C1)C(O)=O	2901.2	Standard non polar	33892256
Eprosartan	CCCCC1=NC=C(\C=C(/CC2=CC=CS2)C(O)=O)N1CC1=CC=C(C=C1)C(O)=O	3645.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Eprosartan,1TMS,isomer #1	CCCCC1=NC=C(/C=C(\CC2=CC=CS2)C(=O)O[Si](C)(C)C)N1CC1=CC=C(C(=O)O)C=C1	3795.6	Semi standard non polar	33892256
Eprosartan,1TMS,isomer #2	CCCCC1=NC=C(/C=C(\CC2=CC=CS2)C(=O)O)N1CC1=CC=C(C(=O)O[Si](C)(C)C)C=C1	3804.6	Semi standard non polar	33892256
Eprosartan,2TMS,isomer #1	CCCCC1=NC=C(/C=C(\CC2=CC=CS2)C(=O)O[Si](C)(C)C)N1CC1=CC=C(C(=O)O[Si](C)(C)C)C=C1	3640.6	Semi standard non polar	33892256
Eprosartan,1TBDMS,isomer #1	CCCCC1=NC=C(/C=C(\CC2=CC=CS2)C(=O)O[Si](C)(C)C(C)(C)C)N1CC1=CC=C(C(=O)O)C=C1	4047.4	Semi standard non polar	33892256
Eprosartan,1TBDMS,isomer #2	CCCCC1=NC=C(/C=C(\CC2=CC=CS2)C(=O)O)N1CC1=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C1	4049.4	Semi standard non polar	33892256
Eprosartan,2TBDMS,isomer #1	CCCCC1=NC=C(/C=C(\CC2=CC=CS2)C(=O)O[Si](C)(C)C(C)(C)C)N1CC1=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C1	4052.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Eprosartan GC-MS (Non-derivatized) - 70eV, Positive	splash10-0570-3319300000-aac3fe556775bf3acc88	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Eprosartan GC-MS (2 TMS) - 70eV, Positive	splash10-0ufr-5011890000-afa379b8ab766fe48b4b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Eprosartan GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Eprosartan GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eprosartan LC-ESI-ITFT , negative-QTOF	splash10-004i-0009000000-fa421ee23b907968b800	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eprosartan LC-ESI-ITFT , negative-QTOF	splash10-00di-0002900000-694c481f9555295f9426	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eprosartan LC-ESI-ITFT , negative-QTOF	splash10-004u-0289000000-647b9ea41a7a812dea66	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eprosartan LC-ESI-ITFT , negative-QTOF	splash10-00kg-0290000000-08e189bdaeb9c6af3b4f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eprosartan LC-ESI-ITFT , negative-QTOF	splash10-014j-1290000000-e8207e65f017389d706f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eprosartan LC-ESI-ITFT , negative-QTOF	splash10-00lr-9260000000-7b844b75045cf89e145e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eprosartan LC-ESI-ITFT , negative-QTOF	splash10-001i-9100000000-f49fc8384f38dc7b6e3b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eprosartan LC-ESI-ITFT , negative-QTOF	splash10-00di-0002900000-e62e6d74d830487d0954	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eprosartan LC-ESI-ITFT , negative-QTOF	splash10-002u-0198000000-d571b7bcdbe9e3f7e69f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eprosartan LC-ESI-ITFT , negative-QTOF	splash10-00kp-0290000000-0b7c3fe664812ce51596	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eprosartan LC-ESI-ITFT , negative-QTOF	splash10-014j-1090000000-85f4ee357273ee0268c0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eprosartan LC-ESI-ITFT , negative-QTOF	splash10-001i-9240000000-8ed6c4fadafd173a2579	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eprosartan LC-ESI-ITFT , negative-QTOF	splash10-001i-9400000000-81bd0b20c45458b1bdec	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eprosartan LC-ESI-ITFT , negative-QTOF	splash10-004i-0009000000-0333ac2f95788dceda2c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eprosartan LC-ESI-ITFT , positive-QTOF	splash10-0a4l-0196300000-c2476723863e5584d7e8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eprosartan LC-ESI-ITFT , positive-QTOF	splash10-004i-0000900000-a93af7ff9cf5786971d0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eprosartan LC-ESI-ITFT , positive-QTOF	splash10-056r-0171900000-4a8d34412967af4cbf35	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eprosartan LC-ESI-ITFT , positive-QTOF	splash10-052r-1971000000-ee85641cdce897ab6693	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Eprosartan LC-ESI-ITFT , positive-QTOF	splash10-052r-1920000000-282ecc38e7c0c6cbefef	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eprosartan 10V, Positive-QTOF	splash10-056r-0007900000-af8b26b78a7236bf49dd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eprosartan 20V, Positive-QTOF	splash10-0bwd-0039200000-2d604267275eb14f1e11	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eprosartan 40V, Positive-QTOF	splash10-001i-3079000000-c55b0efc1b2e86cb7aec	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eprosartan 10V, Negative-QTOF	splash10-00fr-1008900000-930173837879467b7cbf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eprosartan 20V, Negative-QTOF	splash10-0059-2019200000-79382deb0cfe4928da7a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eprosartan 40V, Negative-QTOF	splash10-0a4j-9001000000-775d3beb00a39b27ce48	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Eprosartan Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00876	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00876	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00876

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4444504

KEGG Compound ID

C07467

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Eprosartan

METLIN ID

Not Available

PubChem Compound

5281037

PDB ID

Not Available

ChEBI ID

4814

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Hedner T: The clinical profile of the angiotensin II receptor blocker eprosartan. J Hypertens Suppl. 2002 Jun;20(5):S33-8. [PubMed:12184062 ]
Puig JG, Lopez MA, Bueso TS, Bernardino JI, Jimenez RT: Clinical profile of eprosartan. Cardiovasc Drugs Ther. 2002 Dec;16(6):543-9. [PubMed:12766389 ]
Ruilope L, Jager B: Eprosartan for the treatment of hypertension. Expert Opin Pharmacother. 2003 Jan;4(1):107-14. [PubMed:12517247 ]
de la Sierra A, Ram CV: Introduction: The pharmacological profile of eprosartan--implications for cerebrovascular and cardiovascular risk reduction. Curr Med Res Opin. 2007 Nov;23 Suppl 5:S1-3. doi: 10.1185/030079907X260692. [PubMed:18093407 ]
Ruilope L, Jager B, Prichard B: Eprosartan versus enalapril in elderly patients with hypertension: a double-blind, randomized trial. Blood Press. 2001;10(4):223-9. [PubMed:11800061 ]
Blankestijn PJ, Rupp H: Clinical profile of eprosartan: a different angiotensin II receptor blocker. Cardiovasc Hematol Agents Med Chem. 2008 Oct;6(4):253-7. [PubMed:18855637 ]

Enzymes

Enzyme Details

1. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Type-1 angiotensin II receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Receptor for angiotensin II. Mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system
Gene Name:: AGTR1
Uniprot ID:: P30556
Molecular weight:: 41060.5

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Heusser K, Vitkovsky J, Schmieder RE, Schobel HP: AT1 antagonism by eprosartan lowers heart rate variability and baroreflex gain. Auton Neurosci. 2003 Aug 29;107(1):45-51. [PubMed:12927226 ]
Gremmler B, Kunert M, Schleiting H, Ulbricht LJ: Improvement of cardiac output in patients with severe heart failure by use of ACE-inhibitors combined with the AT1-antagonist eprosartan. Eur J Heart Fail. 2000 Jun;2(2):183-7. [PubMed:10856732 ]
Suzuki G, Mishima T, Tanhehco EJ, Sharov VG, Todor A, Rostogi S, Gupta RC, Chaudhry PA, Anagnostopoulos PV, Nass O, Goldstein S, Sabbah HN: Effects of the AT1-receptor antagonist eprosartan on the progression of left ventricular dysfunction in dogs with heart failure. Br J Pharmacol. 2003 Jan;138(2):301-9. [PubMed:12540520 ]
Ilson BE, Martin DE, Boike SC, Jorkasky DK: The effects of eprosartan, an angiotensin II AT1 receptor antagonist, on uric acid excretion in patients with mild to moderate essential hypertension. J Clin Pharmacol. 1998 May;38(5):437-41. [PubMed:9602957 ]
Nap A, Mathy MJ, Balt JC, Pfaffendorf M, van Zwieten PA: Pre- and postsynaptic inhibitory potencies of the angiotensin AT1 receptor antagonists eprosartan and candesartan. Eur J Pharmacol. 2003 May 23;469(1-3):117-24. [PubMed:12782193 ]
Hedner T: The clinical profile of the angiotensin II receptor blocker eprosartan. J Hypertens Suppl. 2002 Jun;20(5):S33-8. [PubMed:12184062 ]
Puig JG, Lopez MA, Bueso TS, Bernardino JI, Jimenez RT: Clinical profile of eprosartan. Cardiovasc Drugs Ther. 2002 Dec;16(6):543-9. [PubMed:12766389 ]
Ruilope L, Jager B: Eprosartan for the treatment of hypertension. Expert Opin Pharmacother. 2003 Jan;4(1):107-14. [PubMed:12517247 ]
de la Sierra A, Ram CV: Introduction: The pharmacological profile of eprosartan--implications for cerebrovascular and cardiovascular risk reduction. Curr Med Res Opin. 2007 Nov;23 Suppl 5:S1-3. doi: 10.1185/030079907X260692. [PubMed:18093407 ]
Murdoch DR, McDonagh TA, Farmer R, Morton JJ, McMurray JJ, Dargie HJ: ADEPT: Addition of the AT1 receptor antagonist eprosartan to ACE inhibitor therapy in chronic heart failure trial: hemodynamic and neurohormonal effects. Am Heart J. 2001 May;141(5):800-7. [PubMed:11320369 ]

Transporters

Enzyme Details

1. Canalicular multispecific organic anion transporter 1

General function:: Involved in ATP binding
Specific function:: Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter
Gene Name:: ABCC2
Uniprot ID:: Q92887
Molecular weight:: 174205.6

References

Weiss J, Sauer A, Divac N, Herzog M, Schwedhelm E, Boger RH, Haefeli WE, Benndorf RA: Interaction of angiotensin receptor type 1 blockers with ATP-binding cassette transporters. Biopharm Drug Dispos. 2010 Mar;31(2-3):150-61. doi: 10.1002/bdd.699. [PubMed:20222053 ]

Showing metabocard for Eprosartan (HMDB0015014)

MOL for HMDB0015014 (Eprosartan)

3D MOL for HMDB0015014 (Eprosartan)

3D SDF for HMDB0015014 (Eprosartan)

3D-SDF for HMDB0015014 (Eprosartan)

PDB for HMDB0015014 (Eprosartan)

3D PDB for HMDB0015014 (Eprosartan)

SMILES for HMDB0015014 (Eprosartan)

INCHI for HMDB0015014 (Eprosartan)

Structure for HMDB0015014 (Eprosartan)

3D Structure for HMDB0015014 (Eprosartan)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

Transporters

References