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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:53 UTC

HMDB ID

HMDB0015163

Secondary Accession Numbers

HMDB15163

Metabolite Identification

Common Name

Irbesartan

Description

Irbesartan is an angiotensin receptor blocker (ARB) used mainly for the treatment of hypertension. It competes with angiotensin II for binding at the AT1 receptor subtype. Unlike ACE inhibitors, ARBs do not have the adverse effect of dry cough. The use of ARBs is pending revision due to findings from several clinical trials suggesting that this class of drugs may be associated with a small increased risk of cancer.

Structure

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

1029
  Mrv0541 02231215112D          

 32 36  0  0  0  0            999 V2000
    2.6582   -2.3648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7777   -2.1099    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6977   -1.3252    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8371    2.2237    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6976    3.5512    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0301    2.3952    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9439    3.2157    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1102   -2.5947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7777   -3.0797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4427   -3.0797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5227   -3.8643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6977   -3.8643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4427   -2.1099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5227   -1.3252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0076   -0.6578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2128   -0.6578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8282   -0.7440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5483    0.0959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3130   -0.0766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3688    0.1822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0634    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1336   -0.1628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7044    0.9358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3989    1.5170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2195    1.6033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5550    2.3570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0701    3.0244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3755    2.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4057    3.7781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7111    3.1969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2496    2.9382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2262    3.8643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 13  2  0  0  0  0
  2  8  1  0  0  0  0
  2 14  2  0  0  0  0
  3 13  1  0  0  0  0
  3 14  1  0  0  0  0
  3 16  1  0  0  0  0
  4  6  1  0  0  0  0
  4 31  2  0  0  0  0
  5  7  2  0  0  0  0
  5 31  1  0  0  0  0
  6  7  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 13  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 12  1  0  0  0  0
 14 15  1  0  0  0  0
 15 17  1  0  0  0  0
 16 18  1  0  0  0  0
 17 19  1  0  0  0  0
 18 20  2  0  0  0  0
 18 21  1  0  0  0  0
 19 22  1  0  0  0  0
 20 23  1  0  0  0  0
 21 24  2  0  0  0  0
 23 25  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 27 29  2  0  0  0  0
 27 31  1  0  0  0  0
 28 30  1  0  0  0  0
 29 32  1  0  0  0  0
 30 32  2  0  0  0  0
M  END

HMDB0015163
     RDKit          3D
Irbesartan
 60 64  0  0  0  0  0  0  0  0999 V2000
   -0.9055    2.7512    1.7569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9808    1.9497    1.1031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0121    2.1332   -0.4139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1318    1.3006   -0.9452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9776   -0.1698   -0.6546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6733   -0.8256    0.2044 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2903   -2.1842    0.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8093   -2.6433    1.6033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0485   -3.1815    2.2757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0236   -3.5579    1.1987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4300   -3.1154   -0.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2458   -2.3172   -0.7889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6261   -3.3571   -1.1539 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0446   -1.0191   -1.3337 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1101   -0.6692   -2.3760 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2545   -0.3508   -1.9133 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9459    0.6907   -2.5523 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2305    1.0456   -2.2197 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9099    0.3662   -1.2103 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2838    0.7449   -0.9050 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2064    0.5297   -1.9421 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5280    0.8332   -1.7947 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9568    1.3572   -0.6107 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0752    1.5749    0.4114 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7272    1.2667    0.2645 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8056    1.5047    1.3614 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4943    1.2895    1.3864 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0612    1.6402    2.5794 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0730    2.0726    3.3075 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1519    1.9916    2.5617 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2362   -0.6489   -0.5854 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9355   -1.0070   -0.9226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3636    3.7418    2.0375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0477    2.8620    1.0809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6545    2.2807    2.7386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9980    2.2494    1.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8730    0.8544    1.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3060    3.2139   -0.5474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0454    1.9980   -0.8888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1126    1.6750   -0.6076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1663    1.3579   -2.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9959   -3.3850    1.5473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4258   -1.7771    2.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5089   -2.3486    2.8714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8588   -4.0493    2.9115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0115   -3.0810    1.3130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1952   -4.6502    1.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1423   -2.5298   -0.7334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0887   -3.9662   -0.7449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0820   -1.4653   -3.1768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5712    0.2064   -2.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4281    1.2259   -3.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7546    1.8553   -2.7233 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8503    0.1096   -2.8843 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1807    0.6371   -2.6452 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0214    1.5849   -0.5381 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4192    1.9892    1.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0483    2.4247    4.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7313   -1.1990    0.1958 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4470   -1.8105   -0.3986 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
  8  9  1  0
  9 10  1  0
 10 11  1  0
  7 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  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  2  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  1  0
 19 31  1  0
 31 32  2  0
 14  5  1  0
 32 16  1  0
 11  7  1  0
 25 20  1  0
 30 26  2  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  0
  2 37  1  0
  3 38  1  0
  3 39  1  0
  4 40  1  0
  4 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  0
 10 47  1  0
 11 48  1  0
 11 49  1  0
 15 50  1  0
 15 51  1  0
 17 52  1  0
 18 53  1  0
 21 54  1  0
 22 55  1  0
 23 56  1  0
 24 57  1  0
 29 58  1  0
 31 59  1  0
 32 60  1  0
M  END

1029
  Mrv0541 02231215112D          

 32 36  0  0  0  0            999 V2000
    2.6582   -2.3648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7777   -2.1099    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6977   -1.3252    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8371    2.2237    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6976    3.5512    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0301    2.3952    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9439    3.2157    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1102   -2.5947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7777   -3.0797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4427   -3.0797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5227   -3.8643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6977   -3.8643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4427   -2.1099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5227   -1.3252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0076   -0.6578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2128   -0.6578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8282   -0.7440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5483    0.0959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3130   -0.0766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3688    0.1822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0634    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1336   -0.1628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7044    0.9358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3989    1.5170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2195    1.6033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5550    2.3570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0701    3.0244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3755    2.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4057    3.7781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7111    3.1969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2496    2.9382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2262    3.8643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 13  2  0  0  0  0
  2  8  1  0  0  0  0
  2 14  2  0  0  0  0
  3 13  1  0  0  0  0
  3 14  1  0  0  0  0
  3 16  1  0  0  0  0
  4  6  1  0  0  0  0
  4 31  2  0  0  0  0
  5  7  2  0  0  0  0
  5 31  1  0  0  0  0
  6  7  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 13  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 12  1  0  0  0  0
 14 15  1  0  0  0  0
 15 17  1  0  0  0  0
 16 18  1  0  0  0  0
 17 19  1  0  0  0  0
 18 20  2  0  0  0  0
 18 21  1  0  0  0  0
 19 22  1  0  0  0  0
 20 23  1  0  0  0  0
 21 24  2  0  0  0  0
 23 25  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 27 29  2  0  0  0  0
 27 31  1  0  0  0  0
 28 30  1  0  0  0  0
 29 32  1  0  0  0  0
 30 32  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015163

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC1=NC2(CCCC2)C(=O)N1CC1=CC=C(C=C1)C1=CC=CC=C1C1=NNN=N1

> <INCHI_IDENTIFIER>
InChI=1S/C25H28N6O/c1-2-3-10-22-26-25(15-6-7-16-25)24(32)31(22)17-18-11-13-19(14-12-18)20-8-4-5-9-21(20)23-27-29-30-28-23/h4-5,8-9,11-14H,2-3,6-7,10,15-17H2,1H3,(H,27,28,29,30)

> <INCHI_KEY>
YOSHYTLCDANDAN-UHFFFAOYSA-N

> <FORMULA>
C25H28N6O

> <MOLECULAR_WEIGHT>
428.5294

> <EXACT_MASS>
428.232459548

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
47.58732346937174

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-butyl-3-({4-[2-(2H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1,3-diazaspiro[4.4]non-1-en-4-one

> <ALOGPS_LOGP>
4.51

> <JCHEM_LOGP>
5.495261916666666

> <ALOGPS_LOGS>
-4.69

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.399455602678195

> <JCHEM_PKA_STRONGEST_BASIC>
4.116176027401369

> <JCHEM_POLAR_SURFACE_AREA>
87.13000000000001

> <JCHEM_REFRACTIVITY>
136.71609999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.84e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
irbesartan

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015163
     RDKit          3D
Irbesartan
 60 64  0  0  0  0  0  0  0  0999 V2000
   -0.9055    2.7512    1.7569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9808    1.9497    1.1031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0121    2.1332   -0.4139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1318    1.3006   -0.9452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9776   -0.1698   -0.6546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6733   -0.8256    0.2044 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2903   -2.1842    0.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8093   -2.6433    1.6033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0485   -3.1815    2.2757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0236   -3.5579    1.1987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4300   -3.1154   -0.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2458   -2.3172   -0.7889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6261   -3.3571   -1.1539 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0446   -1.0191   -1.3337 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1101   -0.6692   -2.3760 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2545   -0.3508   -1.9133 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9459    0.6907   -2.5523 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2305    1.0456   -2.2197 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9099    0.3662   -1.2103 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2838    0.7449   -0.9050 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2064    0.5297   -1.9421 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5280    0.8332   -1.7947 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9568    1.3572   -0.6107 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0752    1.5749    0.4114 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7272    1.2667    0.2645 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8056    1.5047    1.3614 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4943    1.2895    1.3864 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0612    1.6402    2.5794 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0730    2.0726    3.3075 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1519    1.9916    2.5617 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2362   -0.6489   -0.5854 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9355   -1.0070   -0.9226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3636    3.7418    2.0375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0477    2.8620    1.0809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6545    2.2807    2.7386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9980    2.2494    1.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8730    0.8544    1.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3060    3.2139   -0.5474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0454    1.9980   -0.8888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1126    1.6750   -0.6076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1663    1.3579   -2.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9959   -3.3850    1.5473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4258   -1.7771    2.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5089   -2.3486    2.8714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8588   -4.0493    2.9115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0115   -3.0810    1.3130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1952   -4.6502    1.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1423   -2.5298   -0.7334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0887   -3.9662   -0.7449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0820   -1.4653   -3.1768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5712    0.2064   -2.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4281    1.2259   -3.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7546    1.8553   -2.7233 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8503    0.1096   -2.8843 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1807    0.6371   -2.6452 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0214    1.5849   -0.5381 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4192    1.9892    1.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0483    2.4247    4.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7313   -1.1990    0.1958 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4470   -1.8105   -0.3986 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
  8  9  1  0
  9 10  1  0
 10 11  1  0
  7 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  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  2  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  1  0
 19 31  1  0
 31 32  2  0
 14  5  1  0
 32 16  1  0
 11  7  1  0
 25 20  1  0
 30 26  2  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  0
  2 37  1  0
  3 38  1  0
  3 39  1  0
  4 40  1  0
  4 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  0
 10 47  1  0
 11 48  1  0
 11 49  1  0
 15 50  1  0
 15 51  1  0
 17 52  1  0
 18 53  1  0
 21 54  1  0
 22 55  1  0
 23 56  1  0
 24 57  1  0
 29 58  1  0
 31 59  1  0
 32 60  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1029                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       4.962  -4.414   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       8.918  -3.938   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       6.902  -2.474   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       5.296   4.151   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       5.036   6.629   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       3.790   4.471   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       3.629   6.003   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       7.672  -4.843   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.918  -5.749   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.426  -5.749   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.442  -7.213   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.902  -7.213   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.426  -3.938   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.442  -2.474   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.348  -1.228   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.997  -1.228   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.879  -1.389   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.623   0.179   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.784  -0.143   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.155   0.340   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.718   1.425   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.316  -0.304   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.782   1.747   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.345   2.832   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.876   2.993   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.503   4.400   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.598   5.646   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.034   4.561   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.224   7.052   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.661   5.968   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.066   5.485   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.756   7.213   0.000  0.00  0.00           C+0
CONECT    1   13                                                            
CONECT    2    8   14                                                       
CONECT    3   13   14   16                                                  
CONECT    4    6   31                                                       
CONECT    5    7   31                                                       
CONECT    6    4    7                                                       
CONECT    7    5    6                                                       
CONECT    8    2    9   10   13                                             
CONECT    9    8   11                                                       
CONECT   10    8   12                                                       
CONECT   11    9   12                                                       
CONECT   12   10   11                                                       
CONECT   13    1    3    8                                                  
CONECT   14    2    3   15                                                  
CONECT   15   14   17                                                       
CONECT   16    3   18                                                       
CONECT   17   15   19                                                       
CONECT   18   16   20   21                                                  
CONECT   19   17   22                                                       
CONECT   20   18   23                                                       
CONECT   21   18   24                                                       
CONECT   22   19                                                            
CONECT   23   20   25                                                       
CONECT   24   21   25                                                       
CONECT   25   23   24   26                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26   29   31                                                  
CONECT   28   26   30                                                       
CONECT   29   27   32                                                       
CONECT   30   28   32                                                       
CONECT   31    4    5   27                                                  
CONECT   32   29   30                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

COMPND    HMDB0015163
HETATM    1  C1  UNL     1      -0.906   2.751   1.757  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.981   1.950   1.103  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.012   2.133  -0.414  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.132   1.301  -0.945  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.978  -0.170  -0.655  1.00  0.00           C  
HETATM    6  N1  UNL     1      -3.673  -0.826   0.204  1.00  0.00           N  
HETATM    7  C6  UNL     1      -3.290  -2.184   0.246  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.809  -2.643   1.603  1.00  0.00           C  
HETATM    9  C8  UNL     1      -4.049  -3.182   2.276  1.00  0.00           C  
HETATM   10  C9  UNL     1      -5.024  -3.558   1.199  1.00  0.00           C  
HETATM   11  C10 UNL     1      -4.430  -3.115  -0.122  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.246  -2.317  -0.789  1.00  0.00           C  
HETATM   13  O1  UNL     1      -1.626  -3.357  -1.154  1.00  0.00           O  
HETATM   14  N2  UNL     1      -2.045  -1.019  -1.334  1.00  0.00           N  
HETATM   15  C12 UNL     1      -1.110  -0.669  -2.376  1.00  0.00           C  
HETATM   16  C13 UNL     1       0.254  -0.351  -1.913  1.00  0.00           C  
HETATM   17  C14 UNL     1       0.946   0.691  -2.552  1.00  0.00           C  
HETATM   18  C15 UNL     1       2.230   1.046  -2.220  1.00  0.00           C  
HETATM   19  C16 UNL     1       2.910   0.366  -1.210  1.00  0.00           C  
HETATM   20  C17 UNL     1       4.284   0.745  -0.905  1.00  0.00           C  
HETATM   21  C18 UNL     1       5.206   0.530  -1.942  1.00  0.00           C  
HETATM   22  C19 UNL     1       6.528   0.833  -1.795  1.00  0.00           C  
HETATM   23  C20 UNL     1       6.957   1.357  -0.611  1.00  0.00           C  
HETATM   24  C21 UNL     1       6.075   1.575   0.411  1.00  0.00           C  
HETATM   25  C22 UNL     1       4.727   1.267   0.265  1.00  0.00           C  
HETATM   26  C23 UNL     1       3.806   1.505   1.361  1.00  0.00           C  
HETATM   27  N3  UNL     1       2.494   1.289   1.386  1.00  0.00           N  
HETATM   28  N4  UNL     1       2.061   1.640   2.579  1.00  0.00           N  
HETATM   29  N5  UNL     1       3.073   2.073   3.307  1.00  0.00           N  
HETATM   30  N6  UNL     1       4.152   1.992   2.562  1.00  0.00           N  
HETATM   31  C24 UNL     1       2.236  -0.649  -0.585  1.00  0.00           C  
HETATM   32  C25 UNL     1       0.935  -1.007  -0.923  1.00  0.00           C  
HETATM   33  H1  UNL     1      -1.364   3.742   2.038  1.00  0.00           H  
HETATM   34  H2  UNL     1      -0.048   2.862   1.081  1.00  0.00           H  
HETATM   35  H3  UNL     1      -0.654   2.281   2.739  1.00  0.00           H  
HETATM   36  H4  UNL     1      -2.998   2.249   1.478  1.00  0.00           H  
HETATM   37  H5  UNL     1      -1.873   0.854   1.272  1.00  0.00           H  
HETATM   38  H6  UNL     1      -2.306   3.214  -0.547  1.00  0.00           H  
HETATM   39  H7  UNL     1      -1.045   1.998  -0.889  1.00  0.00           H  
HETATM   40  H8  UNL     1      -4.113   1.675  -0.608  1.00  0.00           H  
HETATM   41  H9  UNL     1      -3.166   1.358  -2.073  1.00  0.00           H  
HETATM   42  H10 UNL     1      -1.996  -3.385   1.547  1.00  0.00           H  
HETATM   43  H11 UNL     1      -2.426  -1.777   2.178  1.00  0.00           H  
HETATM   44  H12 UNL     1      -4.509  -2.349   2.871  1.00  0.00           H  
HETATM   45  H13 UNL     1      -3.859  -4.049   2.912  1.00  0.00           H  
HETATM   46  H14 UNL     1      -6.011  -3.081   1.313  1.00  0.00           H  
HETATM   47  H15 UNL     1      -5.195  -4.650   1.125  1.00  0.00           H  
HETATM   48  H16 UNL     1      -5.142  -2.530  -0.733  1.00  0.00           H  
HETATM   49  H17 UNL     1      -4.089  -3.966  -0.745  1.00  0.00           H  
HETATM   50  H18 UNL     1      -1.082  -1.465  -3.177  1.00  0.00           H  
HETATM   51  H19 UNL     1      -1.571   0.206  -2.916  1.00  0.00           H  
HETATM   52  H20 UNL     1       0.428   1.226  -3.340  1.00  0.00           H  
HETATM   53  H21 UNL     1       2.755   1.855  -2.723  1.00  0.00           H  
HETATM   54  H22 UNL     1       4.850   0.110  -2.884  1.00  0.00           H  
HETATM   55  H23 UNL     1       7.181   0.637  -2.645  1.00  0.00           H  
HETATM   56  H24 UNL     1       8.021   1.585  -0.538  1.00  0.00           H  
HETATM   57  H25 UNL     1       6.419   1.989   1.346  1.00  0.00           H  
HETATM   58  H26 UNL     1       3.048   2.425   4.307  1.00  0.00           H  
HETATM   59  H27 UNL     1       2.731  -1.199   0.196  1.00  0.00           H  
HETATM   60  H28 UNL     1       0.447  -1.810  -0.399  1.00  0.00           H  
CONECT    1    2   33   34   35
CONECT    2    3   36   37
CONECT    3    4   38   39
CONECT    4    5   40   41
CONECT    5    6    6   14
CONECT    6    7
CONECT    7    8   11   12
CONECT    8    9   42   43
CONECT    9   10   44   45
CONECT   10   11   46   47
CONECT   11   48   49
CONECT   12   13   13   14
CONECT   14   15
CONECT   15   16   50   51
CONECT   16   17   17   32
CONECT   17   18   52
CONECT   18   19   19   53
CONECT   19   20   31
CONECT   20   21   21   25
CONECT   21   22   54
CONECT   22   23   23   55
CONECT   23   24   56
CONECT   24   25   25   57
CONECT   25   26
CONECT   26   27   30   30
CONECT   27   28   28
CONECT   28   29
CONECT   29   30   58
CONECT   31   32   32   59
CONECT   32   60
END

HMDB0015163
     RDKit          3D
Irbesartan
 60 64  0  0  0  0  0  0  0  0999 V2000
   -0.9055    2.7512    1.7569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9808    1.9497    1.1031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0121    2.1332   -0.4139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1318    1.3006   -0.9452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9776   -0.1698   -0.6546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6733   -0.8256    0.2044 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2903   -2.1842    0.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8093   -2.6433    1.6033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0485   -3.1815    2.2757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0236   -3.5579    1.1987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4300   -3.1154   -0.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2458   -2.3172   -0.7889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6261   -3.3571   -1.1539 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0446   -1.0191   -1.3337 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1101   -0.6692   -2.3760 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2545   -0.3508   -1.9133 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9459    0.6907   -2.5523 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2305    1.0456   -2.2197 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9099    0.3662   -1.2103 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2838    0.7449   -0.9050 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2064    0.5297   -1.9421 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5280    0.8332   -1.7947 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9568    1.3572   -0.6107 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0752    1.5749    0.4114 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7272    1.2667    0.2645 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8056    1.5047    1.3614 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4943    1.2895    1.3864 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0612    1.6402    2.5794 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0730    2.0726    3.3075 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1519    1.9916    2.5617 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2362   -0.6489   -0.5854 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9355   -1.0070   -0.9226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3636    3.7418    2.0375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0477    2.8620    1.0809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6545    2.2807    2.7386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9980    2.2494    1.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8730    0.8544    1.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3060    3.2139   -0.5474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0454    1.9980   -0.8888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1126    1.6750   -0.6076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1663    1.3579   -2.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9959   -3.3850    1.5473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4258   -1.7771    2.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5089   -2.3486    2.8714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8588   -4.0493    2.9115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0115   -3.0810    1.3130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1952   -4.6502    1.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1423   -2.5298   -0.7334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0887   -3.9662   -0.7449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0820   -1.4653   -3.1768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5712    0.2064   -2.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4281    1.2259   -3.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7546    1.8553   -2.7233 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8503    0.1096   -2.8843 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1807    0.6371   -2.6452 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0214    1.5849   -0.5381 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4192    1.9892    1.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0483    2.4247    4.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7313   -1.1990    0.1958 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4470   -1.8105   -0.3986 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
  8  9  1  0
  9 10  1  0
 10 11  1  0
  7 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  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  2  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  1  0
 19 31  1  0
 31 32  2  0
 14  5  1  0
 32 16  1  0
 11  7  1  0
 25 20  1  0
 30 26  2  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  0
  2 37  1  0
  3 38  1  0
  3 39  1  0
  4 40  1  0
  4 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  0
 10 47  1  0
 11 48  1  0
 11 49  1  0
 15 50  1  0
 15 51  1  0
 17 52  1  0
 18 53  1  0
 21 54  1  0
 22 55  1  0
 23 56  1  0
 24 57  1  0
 29 58  1  0
 31 59  1  0
 32 60  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Butyl-3-{[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1,3-diazaspiro[4.4]non-1-en-4-one	ChEBI
Avapro	ChEBI
BMS 186295	ChEBI
Aprovel	HMDB
2-N-Butyl-3-((2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl)-1,3-diazaspiro(4,4)non-1-en-4-one	HMDB
Karvea	HMDB

Chemical Formula

C₂₅H₂₈N₆O

Average Molecular Weight

428.5294

Monoisotopic Molecular Weight

428.232459548

IUPAC Name

2-butyl-3-({4-[2-(2H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1,3-diazaspiro[4.4]non-1-en-4-one

Traditional Name

irbesartan

CAS Registry Number

138402-11-6

SMILES

CCCCC1=NC2(CCCC2)C(=O)N1CC1=CC=C(C=C1)C1=CC=CC=C1C1=NNN=N1

InChI Identifier

InChI=1S/C25H28N6O/c1-2-3-10-22-26-25(15-6-7-16-25)24(32)31(22)17-18-11-13-19(14-12-18)20-8-4-5-9-21(20)23-27-29-30-28-23/h4-5,8-9,11-14H,2-3,6-7,10,15-17H2,1H3,(H,27,28,29,30)

InChI Key

YOSHYTLCDANDAN-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
Alpha-amino acid or derivatives
Imidazolinone
Azole
2-imidazoline
Heteroaromatic compound
Tetrazole
Amidine
Carboxylic acid amidine
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Carboximidamide
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Organopnictogen compound
Carbonyl group
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

azaspiro compound (CHEBI:5959 )
biphenylyltetrazole (CHEBI:5959 )

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

Cytoplasm (HMDB: HMDB0015163)
Membrane (HMDB: HMDB0015163)

Source

Exogenous

Exogenous (HMDB: HMDB0015163)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Irbesartan Action Pathway (PathBank: SMP0000161)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	180 - 181 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0088 g/L	Not Available
LogP	6	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	200.8	30932474
[M+H]+	Not Available	201.235	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000842

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0088 g/L	ALOGPS
logP	4.51	ALOGPS
logP	5.5	ChemAxon
logS	-4.7	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	1	ChemAxon
Polar Surface Area	87.13 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	136.72 m³·mol⁻¹	ChemAxon
Polarizability	47.59 Å³	ChemAxon
Number of Rings	5	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
DarkChem	[M+H]+	201.673	31661259
DarkChem	[M-H]-	201.04	31661259
DeepCCS	[M+H]+	198.068	30932474
DeepCCS	[M-H]-	195.71	30932474
DeepCCS	[M-2H]-	229.374	30932474
DeepCCS	[M+Na]+	204.844	30932474
AllCCS	[M+H]+	205.6	32859911
AllCCS	[M+H-H2O]+	203.4	32859911
AllCCS	[M+NH4]+	207.6	32859911
AllCCS	[M+Na]+	208.2	32859911
AllCCS	[M-H]-	201.3	32859911
AllCCS	[M+Na-2H]-	201.9	32859911
AllCCS	[M+HCOO]-	202.6	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.	4.9 minutes	32390414
Predicted by Siyang on May 30, 2022	16.8562 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.84 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2998.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	338.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	236.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	200.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	463.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	661.5 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	604.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	81.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1687.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	607.0 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	1607.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	478.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	392.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	266.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	162.1 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	7.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Irbesartan	CCCCC1=NC2(CCCC2)C(=O)N1CC1=CC=C(C=C1)C1=CC=CC=C1C1=NNN=N1	4415.8	Standard polar	33892256
Irbesartan	CCCCC1=NC2(CCCC2)C(=O)N1CC1=CC=C(C=C1)C1=CC=CC=C1C1=NNN=N1	3922.0	Standard non polar	33892256
Irbesartan	CCCCC1=NC2(CCCC2)C(=O)N1CC1=CC=C(C=C1)C1=CC=CC=C1C1=NNN=N1	3923.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Irbesartan,1TMS,isomer #1	CCCCC1=NC2(CCCC2)C(=O)N1CC1=CC=C(C2=CC=CC=C2C2=NN([Si](C)(C)C)N=N2)C=C1	3905.7	Semi standard non polar	33892256
Irbesartan,1TMS,isomer #1	CCCCC1=NC2(CCCC2)C(=O)N1CC1=CC=C(C2=CC=CC=C2C2=NN([Si](C)(C)C)N=N2)C=C1	3803.0	Standard non polar	33892256
Irbesartan,1TMS,isomer #1	CCCCC1=NC2(CCCC2)C(=O)N1CC1=CC=C(C2=CC=CC=C2C2=NN([Si](C)(C)C)N=N2)C=C1	5262.8	Standard polar	33892256
Irbesartan,1TBDMS,isomer #1	CCCCC1=NC2(CCCC2)C(=O)N1CC1=CC=C(C2=CC=CC=C2C2=NN([Si](C)(C)C(C)(C)C)N=N2)C=C1	4032.6	Semi standard non polar	33892256
Irbesartan,1TBDMS,isomer #1	CCCCC1=NC2(CCCC2)C(=O)N1CC1=CC=C(C2=CC=CC=C2C2=NN([Si](C)(C)C(C)(C)C)N=N2)C=C1	4038.6	Standard non polar	33892256
Irbesartan,1TBDMS,isomer #1	CCCCC1=NC2(CCCC2)C(=O)N1CC1=CC=C(C2=CC=CC=C2C2=NN([Si](C)(C)C(C)(C)C)N=N2)C=C1	5282.4	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Irbesartan 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 DB01029	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01029	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01029

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3618

KEGG Compound ID

C07469

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Irbesartan

METLIN ID

Not Available

PubChem Compound

3749

PDB ID

Not Available

ChEBI ID

5959

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

Adams MA, Trudeau L: Irbesartan: review of pharmacology and comparative properties. Can J Clin Pharmacol. 2000 Spring;7(1):22-31. [PubMed:10822210 ]
Croom KF, Curran MP, Goa KL, Perry CM: Irbesartan: a review of its use in hypertension and in the management of diabetic nephropathy. Drugs. 2004;64(9):999-1028. [PubMed:15101793 ]
Lewis EJ, Hunsicker LG, Clarke WR, Berl T, Pohl MA, Lewis JB, Ritz E, Atkins RC, Rohde R, Raz I: Renoprotective effect of the angiotensin-receptor antagonist irbesartan in patients with nephropathy due to type 2 diabetes. N Engl J Med. 2001 Sep 20;345(12):851-60. [PubMed:11565517 ]

Showing metabocard for Irbesartan (HMDB0015163)

MOL for HMDB0015163 (Irbesartan)

3D MOL for HMDB0015163 (Irbesartan)

3D SDF for HMDB0015163 (Irbesartan)

3D-SDF for HMDB0015163 (Irbesartan)

PDB for HMDB0015163 (Irbesartan)

3D PDB for HMDB0015163 (Irbesartan)

SMILES for HMDB0015163 (Irbesartan)

INCHI for HMDB0015163 (Irbesartan)

Structure for HMDB0015163 (Irbesartan)

3D Structure for HMDB0015163 (Irbesartan)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized