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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:45 UTC

HMDB ID

HMDB0014816

Secondary Accession Numbers

HMDB14816

Metabolite Identification

Common Name

Losartan

Description

Losartan is an angiotensin-receptor blocker (ARB) that may be used alone or with other agents to treat hypertension. Losartan and its longer acting metabolite, E-3174, lower blood pressure by antagonizing the renin-angiotensin-aldosterone system (RAAS); they compete with angiotensin II for binding to the type-1 angiotensin II receptor (AT1) subtype and prevents the blood pressure increasing effects of angiotensin II. Unlike angiotensin-converting enzyme (ACE) inhibitors, ARBs do not have the adverse effect of dry cough. Losartan may be used to treat hypertension, isolated systolic hypertension, left ventricular hypertrophy and diabetic nephropathy. It may also be used as an alternative agent for the treatment of systolic dysfunction, myocardial infarction, coronary artery disease, and heart failure.

Structure

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

678
  Mrv0541 02231214552D          

 30 33  0  0  0  0            999 V2000
    3.0873   -1.7146    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.6714   -2.1483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3161    0.0312    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0103   -0.2464    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9355    0.5161    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2705    0.5161    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1905    1.3007    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0155    1.3007    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5623    0.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3908    1.1738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0305    0.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6062    1.4287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2299   -0.7893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7450    0.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4347    2.2356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4228   -0.9608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8429   -1.3414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7450   -0.7938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4596    0.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1740   -0.7938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4596   -1.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1740    0.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.4906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8885   -1.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6030   -0.7938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8885   -2.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3175   -1.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6030   -2.4439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6030    0.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3175   -2.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 16  1  0  0  0  0
  2 17  1  0  0  0  0
  3  9  1  0  0  0  0
  3 11  1  0  0  0  0
  3 13  1  0  0  0  0
  4  9  2  0  0  0  0
  4 16  1  0  0  0  0
  5  7  1  0  0  0  0
  5 29  2  0  0  0  0
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  6 29  1  0  0  0  0
  7  8  1  0  0  0  0
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 10 12  1  0  0  0  0
 11 14  1  0  0  0  0
 12 15  1  0  0  0  0
 13 16  2  0  0  0  0
 13 17  1  0  0  0  0
 14 18  2  0  0  0  0
 14 19  1  0  0  0  0
 15 23  1  0  0  0  0
 18 21  1  0  0  0  0
 19 22  2  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 20 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 25 27  2  0  0  0  0
 25 29  1  0  0  0  0
 26 28  1  0  0  0  0
 27 30  1  0  0  0  0
 28 30  2  0  0  0  0
M  END

HMDB0014816
     RDKit          3D
Losartan
 53 56  0  0  0  0  0  0  0  0999 V2000
    5.9974    1.7315   -0.5008 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0356    2.5365    0.2777 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8737    1.7499    0.8750 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1295    1.0654   -0.2185 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4613   -0.3549   -0.3219 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4946   -1.0089   -0.8524 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2702   -2.3199   -0.8486 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3157   -3.6349   -1.4424 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.9919   -2.4783   -0.2730 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3944   -3.8205   -0.0034 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1266   -3.8628   -0.7304 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5090   -1.2978    0.0640 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3717   -1.0156    0.8328 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0627   -0.7275    0.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7119   -0.0161    1.3476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9591    0.4636    1.1196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5590    0.2493   -0.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7753    1.0518   -0.3594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4006    2.4183   -0.6038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4177    3.3442   -0.7482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7581    2.9586   -0.6618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0874    1.6669   -0.4300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0127    0.6755   -0.2560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3917   -0.7126   -0.0986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6385   -1.7487    0.2677 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3841   -2.8623    0.1669 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6295   -2.4337   -0.2759 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5882   -1.1813   -0.4202 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8285   -0.4330   -1.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5239   -0.9289   -0.8507 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3486    0.8517    0.0129 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9105    2.3848   -0.6767 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5825    1.4886   -1.5189 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5624    3.0376    1.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5524    3.3366   -0.3879 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3258    1.0129    1.6151 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2261    2.4017    1.4685 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0413    1.2530   -0.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5272    1.4649   -1.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9560   -3.7631    1.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9534   -4.6844   -0.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4783   -3.9971   -1.7289 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6857   -0.1243    1.5669 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2423   -1.8238    1.6883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2761    0.1556    2.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5388    0.9756    1.8626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3738    2.6951   -0.6742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2289    4.3913   -0.9561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5309    3.7077   -0.7661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0879    1.3054   -0.3125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4139   -3.1255   -0.4494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3067   -0.5755   -2.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0036   -1.4424   -1.5863 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  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 17 29  1  0
 29 30  2  0
 12  5  1  0
 30 14  1  0
 23 18  1  0
 28 24  2  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
 10 40  1  0
 10 41  1  0
 11 42  1  0
 13 43  1  0
 13 44  1  0
 15 45  1  0
 16 46  1  0
 19 47  1  0
 20 48  1  0
 21 49  1  0
 22 50  1  0
 27 51  1  0
 29 52  1  0
 30 53  1  0
M  END

678
  Mrv0541 02231214552D          

 30 33  0  0  0  0            999 V2000
    3.0873   -1.7146    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.6714   -2.1483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3161    0.0312    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0103   -0.2464    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9355    0.5161    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2705    0.5161    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1905    1.3007    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0155    1.3007    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5623    0.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3908    1.1738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0305    0.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6062    1.4287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2299   -0.7893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7450    0.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4347    2.2356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4228   -0.9608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8429   -1.3414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7450   -0.7938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4596    0.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1740   -0.7938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4596   -1.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1740    0.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.4906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8885   -1.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6030   -0.7938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8885   -2.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3175   -1.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6030   -2.4439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6030    0.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3175   -2.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 16  1  0  0  0  0
  2 17  1  0  0  0  0
  3  9  1  0  0  0  0
  3 11  1  0  0  0  0
  3 13  1  0  0  0  0
  4  9  2  0  0  0  0
  4 16  1  0  0  0  0
  5  7  1  0  0  0  0
  5 29  2  0  0  0  0
  6  8  2  0  0  0  0
  6 29  1  0  0  0  0
  7  8  1  0  0  0  0
  9 10  1  0  0  0  0
 10 12  1  0  0  0  0
 11 14  1  0  0  0  0
 12 15  1  0  0  0  0
 13 16  2  0  0  0  0
 13 17  1  0  0  0  0
 14 18  2  0  0  0  0
 14 19  1  0  0  0  0
 15 23  1  0  0  0  0
 18 21  1  0  0  0  0
 19 22  2  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 20 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 25 27  2  0  0  0  0
 25 29  1  0  0  0  0
 26 28  1  0  0  0  0
 27 30  1  0  0  0  0
 28 30  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014816

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=C1)C1=CC=CC=C1C1=NNN=N1

> <INCHI_IDENTIFIER>
InChI=1S/C22H23ClN6O/c1-2-3-8-20-24-21(23)19(14-30)29(20)13-15-9-11-16(12-10-15)17-6-4-5-7-18(17)22-25-27-28-26-22/h4-7,9-12,30H,2-3,8,13-14H2,1H3,(H,25,26,27,28)

> <INCHI_KEY>
PSIFNNKUMBGKDQ-UHFFFAOYSA-N

> <FORMULA>
C22H23ClN6O

> <MOLECULAR_WEIGHT>
422.911

> <EXACT_MASS>
422.162187095

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
44.86091696292752

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[2-butyl-4-chloro-1-({4-[2-(2H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1H-imidazol-5-yl]methanol

> <ALOGPS_LOGP>
4.50

> <JCHEM_LOGP>
5.084907282333333

> <ALOGPS_LOGS>
-4.95

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.273295264842385

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.399772178569369

> <JCHEM_PKA_STRONGEST_BASIC>
4.122062660199966

> <JCHEM_POLAR_SURFACE_AREA>
92.51

> <JCHEM_REFRACTIVITY>
131.8496

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.70e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
losartan

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014816
     RDKit          3D
Losartan
 53 56  0  0  0  0  0  0  0  0999 V2000
    5.9974    1.7315   -0.5008 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0356    2.5365    0.2777 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8737    1.7499    0.8750 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1295    1.0654   -0.2185 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4613   -0.3549   -0.3219 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4946   -1.0089   -0.8524 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2702   -2.3199   -0.8486 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3157   -3.6349   -1.4424 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.9919   -2.4783   -0.2730 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3944   -3.8205   -0.0034 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1266   -3.8628   -0.7304 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5090   -1.2978    0.0640 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3717   -1.0156    0.8328 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0627   -0.7275    0.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7119   -0.0161    1.3476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9591    0.4636    1.1196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5590    0.2493   -0.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7753    1.0518   -0.3594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4006    2.4183   -0.6038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4177    3.3442   -0.7482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7581    2.9586   -0.6618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0874    1.6669   -0.4300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0127    0.6755   -0.2560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3917   -0.7126   -0.0986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6385   -1.7487    0.2677 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3841   -2.8623    0.1669 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6295   -2.4337   -0.2759 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5882   -1.1813   -0.4202 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8285   -0.4330   -1.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5239   -0.9289   -0.8507 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3486    0.8517    0.0129 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9105    2.3848   -0.6767 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5825    1.4886   -1.5189 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5624    3.0376    1.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5524    3.3366   -0.3879 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3258    1.0129    1.6151 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2261    2.4017    1.4685 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0413    1.2530   -0.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5272    1.4649   -1.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9560   -3.7631    1.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9534   -4.6844   -0.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4783   -3.9971   -1.7289 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6857   -0.1243    1.5669 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2423   -1.8238    1.6883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2761    0.1556    2.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5388    0.9756    1.8626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3738    2.6951   -0.6742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2289    4.3913   -0.9561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5309    3.7077   -0.7661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0879    1.3054   -0.3125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4139   -3.1255   -0.4494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3067   -0.5755   -2.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0036   -1.4424   -1.5863 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  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 17 29  1  0
 29 30  2  0
 12  5  1  0
 30 14  1  0
 23 18  1  0
 28 24  2  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
 10 40  1  0
 10 41  1  0
 11 42  1  0
 13 43  1  0
 13 44  1  0
 15 45  1  0
 16 46  1  0
 19 47  1  0
 20 48  1  0
 21 49  1  0
 22 50  1  0
 27 51  1  0
 29 52  1  0
 30 53  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 678                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       5.763  -3.201   0.000  0.00  0.00          Cl+0
HETATM    2  O   UNK     0       8.720  -4.010   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       8.057   0.058   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       5.619  -0.460   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      14.813   0.963   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      17.305   0.963   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      15.289   2.428   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      16.829   2.428   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       6.650   0.685   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.329   2.191   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.390   0.828   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.865   2.667   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.896  -1.473   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.724   0.058   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.545   4.173   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.389  -1.793   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.040  -2.504   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.724  -1.482   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.058   0.828   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.391  -1.482   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.058  -2.252   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.391   0.058   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.080   4.649   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.725  -2.252   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.059  -1.482   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.725  -3.792   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      17.393  -2.252   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      16.059  -4.562   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      16.059   0.058   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      17.393  -3.792   0.000  0.00  0.00           C+0
CONECT    1   16                                                            
CONECT    2   17                                                            
CONECT    3    9   11   13                                                  
CONECT    4    9   16                                                       
CONECT    5    7   29                                                       
CONECT    6    8   29                                                       
CONECT    7    5    8                                                       
CONECT    8    6    7                                                       
CONECT    9    3    4   10                                                  
CONECT   10    9   12                                                       
CONECT   11    3   14                                                       
CONECT   12   10   15                                                       
CONECT   13    3   16   17                                                  
CONECT   14   11   18   19                                                  
CONECT   15   12   23                                                       
CONECT   16    1    4   13                                                  
CONECT   17    2   13                                                       
CONECT   18   14   21                                                       
CONECT   19   14   22                                                       
CONECT   20   21   22   24                                                  
CONECT   21   18   20                                                       
CONECT   22   19   20                                                       
CONECT   23   15                                                            
CONECT   24   20   25   26                                                  
CONECT   25   24   27   29                                                  
CONECT   26   24   28                                                       
CONECT   27   25   30                                                       
CONECT   28   26   30                                                       
CONECT   29    5    6   25                                                  
CONECT   30   27   28                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

COMPND    HMDB0014816
HETATM    1  C1  UNL     1       5.997   1.731  -0.501  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.036   2.536   0.278  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.874   1.750   0.875  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.129   1.065  -0.218  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.461  -0.355  -0.322  1.00  0.00           C  
HETATM    6  N1  UNL     1       4.495  -1.009  -0.852  1.00  0.00           N  
HETATM    7  C6  UNL     1       4.270  -2.320  -0.849  1.00  0.00           C  
HETATM    8 CL1  UNL     1       5.316  -3.635  -1.442  1.00  0.00          CL  
HETATM    9  C7  UNL     1       2.992  -2.478  -0.273  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.394  -3.821  -0.003  1.00  0.00           C  
HETATM   11  O1  UNL     1       1.127  -3.863  -0.730  1.00  0.00           O  
HETATM   12  N2  UNL     1       2.509  -1.298   0.064  1.00  0.00           N  
HETATM   13  C9  UNL     1       1.372  -1.016   0.833  1.00  0.00           C  
HETATM   14  C10 UNL     1       0.063  -0.727   0.391  1.00  0.00           C  
HETATM   15  C11 UNL     1      -0.712  -0.016   1.348  1.00  0.00           C  
HETATM   16  C12 UNL     1      -1.959   0.464   1.120  1.00  0.00           C  
HETATM   17  C13 UNL     1      -2.559   0.249  -0.144  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.775   1.052  -0.359  1.00  0.00           C  
HETATM   19  C15 UNL     1      -3.401   2.418  -0.604  1.00  0.00           C  
HETATM   20  C16 UNL     1      -4.418   3.344  -0.748  1.00  0.00           C  
HETATM   21  C17 UNL     1      -5.758   2.959  -0.662  1.00  0.00           C  
HETATM   22  C18 UNL     1      -6.087   1.667  -0.430  1.00  0.00           C  
HETATM   23  C19 UNL     1      -5.013   0.676  -0.256  1.00  0.00           C  
HETATM   24  C20 UNL     1      -5.392  -0.713  -0.099  1.00  0.00           C  
HETATM   25  N3  UNL     1      -4.638  -1.749   0.268  1.00  0.00           N  
HETATM   26  N4  UNL     1      -5.384  -2.862   0.167  1.00  0.00           N  
HETATM   27  N5  UNL     1      -6.630  -2.434  -0.276  1.00  0.00           N  
HETATM   28  N6  UNL     1      -6.588  -1.181  -0.420  1.00  0.00           N  
HETATM   29  C21 UNL     1      -1.829  -0.433  -1.039  1.00  0.00           C  
HETATM   30  C22 UNL     1      -0.524  -0.929  -0.851  1.00  0.00           C  
HETATM   31  H1  UNL     1       6.349   0.852   0.013  1.00  0.00           H  
HETATM   32  H2  UNL     1       6.910   2.385  -0.677  1.00  0.00           H  
HETATM   33  H3  UNL     1       5.583   1.489  -1.519  1.00  0.00           H  
HETATM   34  H4  UNL     1       5.562   3.038   1.114  1.00  0.00           H  
HETATM   35  H5  UNL     1       4.552   3.337  -0.388  1.00  0.00           H  
HETATM   36  H6  UNL     1       4.326   1.013   1.615  1.00  0.00           H  
HETATM   37  H7  UNL     1       3.226   2.402   1.468  1.00  0.00           H  
HETATM   38  H8  UNL     1       2.041   1.253  -0.198  1.00  0.00           H  
HETATM   39  H9  UNL     1       3.527   1.465  -1.250  1.00  0.00           H  
HETATM   40  H10 UNL     1       1.956  -3.763   1.079  1.00  0.00           H  
HETATM   41  H11 UNL     1       2.953  -4.684  -0.171  1.00  0.00           H  
HETATM   42  H12 UNL     1       1.478  -3.997  -1.729  1.00  0.00           H  
HETATM   43  H13 UNL     1       1.686  -0.124   1.567  1.00  0.00           H  
HETATM   44  H14 UNL     1       1.242  -1.824   1.688  1.00  0.00           H  
HETATM   45  H15 UNL     1      -0.276   0.156   2.352  1.00  0.00           H  
HETATM   46  H16 UNL     1      -2.539   0.976   1.863  1.00  0.00           H  
HETATM   47  H17 UNL     1      -2.374   2.695  -0.674  1.00  0.00           H  
HETATM   48  H18 UNL     1      -4.229   4.391  -0.956  1.00  0.00           H  
HETATM   49  H19 UNL     1      -6.531   3.708  -0.766  1.00  0.00           H  
HETATM   50  H20 UNL     1      -7.088   1.305  -0.313  1.00  0.00           H  
HETATM   51  H21 UNL     1      -7.414  -3.126  -0.449  1.00  0.00           H  
HETATM   52  H22 UNL     1      -2.307  -0.575  -2.042  1.00  0.00           H  
HETATM   53  H23 UNL     1      -0.004  -1.442  -1.586  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   12
CONECT    6    7
CONECT    7    8    9    9
CONECT    9   10   12
CONECT   10   11   40   41
CONECT   11   42
CONECT   12   13
CONECT   13   14   43   44
CONECT   14   15   15   30
CONECT   15   16   45
CONECT   16   17   17   46
CONECT   17   18   29
CONECT   18   19   19   23
CONECT   19   20   47
CONECT   20   21   21   48
CONECT   21   22   49
CONECT   22   23   23   50
CONECT   23   24
CONECT   24   25   28   28
CONECT   25   26   26
CONECT   26   27
CONECT   27   28   51
CONECT   29   30   30   52
CONECT   30   53
END

HMDB0014816
     RDKit          3D
Losartan
 53 56  0  0  0  0  0  0  0  0999 V2000
    5.9974    1.7315   -0.5008 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0356    2.5365    0.2777 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8737    1.7499    0.8750 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1295    1.0654   -0.2185 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4613   -0.3549   -0.3219 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4946   -1.0089   -0.8524 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2702   -2.3199   -0.8486 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3157   -3.6349   -1.4424 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.9919   -2.4783   -0.2730 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3944   -3.8205   -0.0034 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1266   -3.8628   -0.7304 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5090   -1.2978    0.0640 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3717   -1.0156    0.8328 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0627   -0.7275    0.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7119   -0.0161    1.3476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9591    0.4636    1.1196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5590    0.2493   -0.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7753    1.0518   -0.3594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4006    2.4183   -0.6038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4177    3.3442   -0.7482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7581    2.9586   -0.6618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0874    1.6669   -0.4300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0127    0.6755   -0.2560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3917   -0.7126   -0.0986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6385   -1.7487    0.2677 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3841   -2.8623    0.1669 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6295   -2.4337   -0.2759 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5882   -1.1813   -0.4202 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8285   -0.4330   -1.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5239   -0.9289   -0.8507 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3486    0.8517    0.0129 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9105    2.3848   -0.6767 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5825    1.4886   -1.5189 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5624    3.0376    1.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5524    3.3366   -0.3879 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3258    1.0129    1.6151 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2261    2.4017    1.4685 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0413    1.2530   -0.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5272    1.4649   -1.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9560   -3.7631    1.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9534   -4.6844   -0.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4783   -3.9971   -1.7289 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6857   -0.1243    1.5669 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2423   -1.8238    1.6883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2761    0.1556    2.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5388    0.9756    1.8626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3738    2.6951   -0.6742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2289    4.3913   -0.9561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5309    3.7077   -0.7661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0879    1.3054   -0.3125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4139   -3.1255   -0.4494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3067   -0.5755   -2.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0036   -1.4424   -1.5863 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  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 17 29  1  0
 29 30  2  0
 12  5  1  0
 30 14  1  0
 23 18  1  0
 28 24  2  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
 10 40  1  0
 10 41  1  0
 11 42  1  0
 13 43  1  0
 13 44  1  0
 15 45  1  0
 16 46  1  0
 19 47  1  0
 20 48  1  0
 21 49  1  0
 22 50  1  0
 27 51  1  0
 29 52  1  0
 30 53  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2-Butyl-4-chloro-1-{[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-imidazol-5-yl)methanol	ChEBI
2-N-Butyl-4-chloro-5-hydroxymethyl-1-[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl]imidazole	ChEBI
Losartic	Kegg
DUP 89	HMDB
Losartan potassium	HMDB
DuP 753	HMDB
Potassium, losartan	HMDB
2-Butyl-4-chloro-1-((2'-(1H-etrazol-5-yl) (1,1'-biphenyl)-4-yl)methyl)-1H-imidazole-5-methanol	HMDB
DuP-753	HMDB
Cozaar	HMDB
Losartan monopotassium salt	HMDB
Monopotassium salt, losartan	HMDB
Salt, losartan monopotassium	HMDB

Chemical Formula

C₂₂H₂₃ClN₆O

Average Molecular Weight

422.911

Monoisotopic Molecular Weight

422.162187095

IUPAC Name

[2-butyl-4-chloro-1-({4-[2-(2H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1H-imidazol-5-yl]methanol

Traditional Name

losartan

CAS Registry Number

114798-26-4

SMILES

CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=C1)C1=CC=CC=C1C1=NNN=N1

InChI Identifier

InChI=1S/C22H23ClN6O/c1-2-3-8-20-24-21(23)19(14-30)29(20)13-15-9-11-16(12-10-15)17-6-4-5-7-18(17)22-25-27-28-26-22/h4-7,9-12,30H,2-3,8,13-14H2,1H3,(H,25,26,27,28)

InChI Key

PSIFNNKUMBGKDQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Biphenyls and derivatives

Direct Parent

Biphenyls and derivatives

Alternative Parents

Substituents

Biphenyl
Phenyltetrazole
1,2,4,5-tetrasubstituted imidazole
Aryl chloride
Aryl halide
N-substituted imidazole
Azole
Heteroaromatic compound
Imidazole
Tetrazole
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Organochloride
Organohalogen compound
Aromatic alcohol
Alcohol
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Primary alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

imidazoles (CHEBI:6541 )
biphenylyltetrazole (CHEBI:6541 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014816)

Source

Exogenous

Exogenous (HMDB: HMDB0014816)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Losartan Action Pathway (PathBank: SMP0000162)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	183.5 - 184.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0047 g/L	Not Available
LogP	6.1	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	200.3	30932474
[M+H]+	Not Available	199.228	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000749

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0047 g/L	ALOGPS
logP	4.5	ALOGPS
logP	5.08	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	7.4	ChemAxon
pKa (Strongest Basic)	4.12	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	92.51 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	131.85 m³·mol⁻¹	ChemAxon
Polarizability	44.86 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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]+	197.222	30932474
DeepCCS	[M-H]-	194.847	30932474
DeepCCS	[M-2H]-	229.155	30932474
DeepCCS	[M+Na]+	204.888	30932474
AllCCS	[M+H]+	201.5	32859911
AllCCS	[M+H-H2O]+	199.1	32859911
AllCCS	[M+NH4]+	203.8	32859911
AllCCS	[M+Na]+	204.4	32859911
AllCCS	[M-H]-	199.5	32859911
AllCCS	[M+Na-2H]-	199.7	32859911
AllCCS	[M+HCOO]-	200.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.56 minutes	32390414
Predicted by Siyang on May 30, 2022	16.5923 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.28 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	41.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2738.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	385.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	224.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	214.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	348.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	631.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	619.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	99.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1514.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	595.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1675.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	442.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	433.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	272.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	185.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	21.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Losartan	CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=C1)C1=CC=CC=C1C1=NNN=N1	4513.0	Standard polar	33892256
Losartan	CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=C1)C1=CC=CC=C1C1=NNN=N1	3657.5	Standard non polar	33892256
Losartan	CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=C1)C1=CC=CC=C1C1=NNN=N1	3930.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Losartan,1TMS,isomer #1	CCCCC1=NC(Cl)=C(CO[Si](C)(C)C)N1CC1=CC=C(C2=CC=CC=C2C2=N[NH]N=N2)C=C1	3623.1	Semi standard non polar	33892256
Losartan,1TMS,isomer #2	CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C2=CC=CC=C2C2=NN([Si](C)(C)C)N=N2)C=C1	3781.5	Semi standard non polar	33892256
Losartan,2TMS,isomer #1	CCCCC1=NC(Cl)=C(CO[Si](C)(C)C)N1CC1=CC=C(C2=CC=CC=C2C2=NN([Si](C)(C)C)N=N2)C=C1	3785.9	Semi standard non polar	33892256
Losartan,2TMS,isomer #1	CCCCC1=NC(Cl)=C(CO[Si](C)(C)C)N1CC1=CC=C(C2=CC=CC=C2C2=NN([Si](C)(C)C)N=N2)C=C1	3723.0	Standard non polar	33892256
Losartan,2TMS,isomer #1	CCCCC1=NC(Cl)=C(CO[Si](C)(C)C)N1CC1=CC=C(C2=CC=CC=C2C2=NN([Si](C)(C)C)N=N2)C=C1	4606.0	Standard polar	33892256
Losartan,1TBDMS,isomer #1	CCCCC1=NC(Cl)=C(CO[Si](C)(C)C(C)(C)C)N1CC1=CC=C(C2=CC=CC=C2C2=N[NH]N=N2)C=C1	3792.0	Semi standard non polar	33892256
Losartan,1TBDMS,isomer #2	CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C2=CC=CC=C2C2=NN([Si](C)(C)C(C)(C)C)N=N2)C=C1	3906.6	Semi standard non polar	33892256
Losartan,2TBDMS,isomer #1	CCCCC1=NC(Cl)=C(CO[Si](C)(C)C(C)(C)C)N1CC1=CC=C(C2=CC=CC=C2C2=NN([Si](C)(C)C(C)(C)C)N=N2)C=C1	4050.6	Semi standard non polar	33892256
Losartan,2TBDMS,isomer #1	CCCCC1=NC(Cl)=C(CO[Si](C)(C)C(C)(C)C)N1CC1=CC=C(C2=CC=CC=C2C2=NN([Si](C)(C)C(C)(C)C)N=N2)C=C1	4171.2	Standard non polar	33892256
Losartan,2TBDMS,isomer #1	CCCCC1=NC(Cl)=C(CO[Si](C)(C)C(C)(C)C)N1CC1=CC=C(C2=CC=CC=C2C2=NN([Si](C)(C)C(C)(C)C)N=N2)C=C1	4609.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Losartan GC-MS (Non-derivatized) - 70eV, Positive	splash10-002r-4089100000-3b72c4e0ebc46e6402a9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Losartan GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9002300000-8cb18ee6a14e321f81eb	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Losartan 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 - Losartan LC-ESI-QFT , negative-QTOF	splash10-00di-0000900000-657db16bb4bfe9184114	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Losartan LC-ESI-QFT , negative-QTOF	splash10-056r-0900000000-43bb8508cd1dbc71bcee	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Losartan LC-ESI-QFT , negative-QTOF	splash10-004i-0900000000-55368087829d113fdb7b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Losartan LC-ESI-QFT , negative-QTOF	splash10-004i-0900000000-af470646c547613f82a0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Losartan LC-ESI-QFT , negative-QTOF	splash10-004i-0900000000-746dcf7a43a3f8839c1d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Losartan LC-ESI-QFT , negative-QTOF	splash10-004i-0900000000-0bee80f7ccbc4b68eee0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Losartan LC-ESI-QFT , negative-QTOF	splash10-004i-0900000000-d845ae166a10faff242a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Losartan LC-ESI-QFT , negative-QTOF	splash10-004i-2900000000-d39a309c02e1aaa956b0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Losartan LC-ESI-QFT , negative-QTOF	splash10-004i-7900000000-d27d10ab008deb157e7a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Losartan LC-ESI-QFT , negative-QTOF	splash10-00fr-0900700000-fef78a7f52d4aa515bb4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Losartan LC-ESI-QFT , negative-QTOF	splash10-00fr-0900600000-c62f0db44e17f79e0c70	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Losartan LC-ESI-QFT , positive-QTOF	splash10-0a4i-0034900000-22ba49ec64d374c8965e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Losartan LC-ESI-QFT , positive-QTOF	splash10-0a4i-0191000000-8ff1b5a21f6ef4a462cd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Losartan LC-ESI-QFT , positive-QTOF	splash10-0a4i-0590000000-9841ff7f881c3e9c11b9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Losartan LC-ESI-QFT , positive-QTOF	splash10-0a59-0960000000-a24e287a018dae01dd0d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Losartan LC-ESI-QFT , positive-QTOF	splash10-0a5c-0930000000-ff3e675bd445225bf04e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Losartan LC-ESI-QFT , positive-QTOF	splash10-0pxu-0920000000-9adf4aef59fc1545fea6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Losartan LC-ESI-QFT , positive-QTOF	splash10-0v00-1900000000-3591888cf5831cbe3d11	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Losartan LC-ESI-QFT , positive-QTOF	splash10-0wmi-2900000000-ab9304c8cebc201d0178	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Losartan 10V, Positive-QTOF	splash10-05fr-0021900000-2c231055acd0a8f296d3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Losartan 20V, Positive-QTOF	splash10-052r-0195400000-b093eaecc05008eba3de	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Losartan 40V, Positive-QTOF	splash10-01p9-8392000000-dc1eae529c5259d2591b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Losartan 10V, Negative-QTOF	splash10-00di-0304900000-071c5333315e558faa09	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Losartan 20V, Negative-QTOF	splash10-0a73-0709200000-be33ec2e3b5adaf0fb63	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Losartan 40V, Negative-QTOF	splash10-0v03-2900000000-2cc4dbb7931105738ba5	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
Losartan 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 DB00678	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00678	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00678

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3824

KEGG Compound ID

C07072

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Losartan

METLIN ID

Not Available

PubChem Compound

3961

PDB ID

Not Available

ChEBI ID

6541

Food Biomarker Ontology

Not Available

VMH ID

LSTN

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Sica DA, Gehr TW, Ghosh S: Clinical pharmacokinetics of losartan. Clin Pharmacokinet. 2005;44(8):797-814. [PubMed:16029066 ]
Dahlof B, Devereux RB, Kjeldsen SE, Julius S, Beevers G, de Faire U, Fyhrquist F, Ibsen H, Kristiansson K, Lederballe-Pedersen O, Lindholm LH, Nieminen MS, Omvik P, Oparil S, Wedel H: Cardiovascular morbidity and mortality in the Losartan Intervention For Endpoint reduction in hypertension study (LIFE): a randomised trial against atenolol. Lancet. 2002 Mar 23;359(9311):995-1003. [PubMed:11937178 ]
Guo ZX, Qiu MC: [Losartan downregulates the expression of transforming growth factor beta type I and type II receptors in kidney of diabetic rat]. Zhonghua Nei Ke Za Zhi. 2003 Jun;42(6):403-8. [PubMed:12895325 ]
Habashi JP, Judge DP, Holm TM, Cohn RD, Loeys BL, Cooper TK, Myers L, Klein EC, Liu G, Calvi C, Podowski M, Neptune ER, Halushka MK, Bedja D, Gabrielson K, Rifkin DB, Carta L, Ramirez F, Huso DL, Dietz HC: Losartan, an AT1 antagonist, prevents aortic aneurysm in a mouse model of Marfan syndrome. Science. 2006 Apr 7;312(5770):117-21. [PubMed:16601194 ]
(). Bader, M. (2004). Renin-angiotensin-aldosterone system. In S. Offermanns, & W. Rosenthal (Eds.). Encyclopedic reference of molecular pharmacology_ (pp. 810-814). Berlin, Germany: Springer. . .
(). FDA label . .
(). Stanfield, C.L., & Germann, W.J. (2008). Principles of human physiology (3rd ed.). San Francisco, CA: Pearson Education, Inc.. .

Showing metabocard for Losartan (HMDB0014816)

MOL for HMDB0014816 (Losartan)

3D MOL for HMDB0014816 (Losartan)

3D SDF for HMDB0014816 (Losartan)

3D-SDF for HMDB0014816 (Losartan)

PDB for HMDB0014816 (Losartan)

3D PDB for HMDB0014816 (Losartan)

SMILES for HMDB0014816 (Losartan)

INCHI for HMDB0014816 (Losartan)

Structure for HMDB0014816 (Losartan)

3D Structure for HMDB0014816 (Losartan)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra