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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 02:51:42 UTC

HMDB ID

HMDB0014663

Secondary Accession Numbers

HMDB14663

Metabolite Identification

Common Name

Bentiromide

Description

Bentiromide is a peptide used as a screening test for exocrine pancreatic insufficiency and to monitor the adequacy of supplemental pancreatic therapy. It is given by mouth as a noninvasive test. The amount of 4-aminobenzoic acid and its metabolites excreted in the urine is taken as a measure of the chymotrypsin-secreting activity of the pancreas. Headache and gastrointestinal disturbances have been reported in patients taking bentiromide. Bentiromide is not available in the U.S. or Canada (It was withdrawn in the US in October 1996).

Structure

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

  Mrv0541 04191212132D          

 30 32  0  0  0  0            999 V2000
    4.3618   -5.6354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3618   -4.8103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0780   -4.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7899   -4.8103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7899   -5.6354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0780   -6.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6476   -6.0482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5047   -4.3983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2190   -4.8114    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.9338   -4.3994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6479   -4.8124    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9343   -3.5744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3627   -4.4005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3624   -3.5771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0771   -3.1651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7913   -3.5782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7907   -4.4032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0759   -4.8151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5061   -3.1662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5067   -2.3412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2202   -3.5792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2183   -5.6364    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9325   -6.0494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9319   -6.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6472   -5.6374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6455   -7.2828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6449   -8.1078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9300   -8.5197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2160   -8.1068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2166   -7.2818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  8  1  0  0  0  0
  2  3  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 13  1  0  0  0  0
  8  9  1  0  0  0  0
 16 19  1  0  0  0  0
  3  4  2  0  0  0  0
 19 20  2  0  0  0  0
  9 10  1  0  0  0  0
 19 21  1  0  0  0  0
  4  5  1  0  0  0  0
  9 22  1  1  0  0  0
 10 11  1  0  0  0  0
 22 23  1  0  0  0  0
  5  6  2  0  0  0  0
 23 24  1  0  0  0  0
 10 12  2  0  0  0  0
 23 25  2  0  0  0  0
  6  1  1  0  0  0  0
 11 13  1  0  0  0  0
  1  7  1  0  0  0  0
  1  2  2  0  0  0  0
 24 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 24  1  0  0  0  0
M  END

HMDB0014663
     RDKit          3D
Bentiromide
 50 52  0  0  0  0  0  0  0  0999 V2000
    7.1436   -3.8538   -0.2364 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1162   -2.6033   -0.3069 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2852   -1.8598   -0.2795 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8386   -1.9339   -0.4186 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8122   -0.5437   -0.4970 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6255    0.1056   -0.6021 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4224   -0.6098   -0.6329 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2159    0.0856   -0.7494 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9093   -0.4418   -0.6741 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6468   -1.6378   -0.4874 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2164    0.5706   -0.8408 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0463    1.5753    0.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0455    2.6479    0.2441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1914    2.4729    0.9867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1964    3.4156    1.0591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0497    4.5905    0.3555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0686    5.5307    0.4371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9041    4.7853   -0.3972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9095    3.8307   -0.4575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4425   -0.1899   -0.7242 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7914   -0.9812    0.3697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0427   -1.0926    1.3741 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0490   -1.7146    0.3880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4375   -2.4406    1.5176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6056   -3.1560    1.6066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4443   -3.1594    0.5204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1290   -2.4690   -0.6246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9341   -1.7574   -0.6700 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4731   -1.9686   -0.5551 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6778   -2.6629   -0.4463 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6610   -1.6500    0.6420 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7631   -0.0087   -0.4710 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5724    1.1775   -0.6638 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2972    1.1447   -0.9229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    0.9714   -1.8742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1187    1.0405    1.2223 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9523    2.0501    0.2608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3753    1.5711    1.5704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1007    3.2597    1.6544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0097    6.2237    1.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7982    5.6967   -0.9384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0113    3.9765   -1.0440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1063   -0.1230   -1.5385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7578   -2.4169    2.3510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8698   -3.7066    2.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3548   -3.7201    0.5966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7804   -2.4687   -1.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7293   -1.2361   -1.5814 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5828   -2.5738   -0.5784 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6677   -3.7428   -0.3872 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 11 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
  7 29  1  0
 29 30  2  0
 30  4  1  0
 19 13  1  0
 28 23  1  0
  3 31  1  0
  5 32  1  0
  6 33  1  0
  8 34  1  0
 11 35  1  6
 12 36  1  0
 12 37  1  0
 14 38  1  0
 15 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
 24 44  1  0
 25 45  1  0
 26 46  1  0
 27 47  1  0
 28 48  1  0
 29 49  1  0
 30 50  1  0
M  END

  Mrv0541 04191212132D          

 30 32  0  0  0  0            999 V2000
    4.3618   -5.6354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3618   -4.8103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0780   -4.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7899   -4.8103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7899   -5.6354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0780   -6.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6476   -6.0482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5047   -4.3983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2190   -4.8114    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.9338   -4.3994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6479   -4.8124    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9343   -3.5744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3627   -4.4005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3624   -3.5771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0771   -3.1651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7913   -3.5782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7907   -4.4032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0759   -4.8151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5061   -3.1662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5067   -2.3412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2202   -3.5792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2183   -5.6364    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9325   -6.0494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9319   -6.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6472   -5.6374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6455   -7.2828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6449   -8.1078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9300   -8.5197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2160   -8.1068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2166   -7.2818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  8  1  0  0  0  0
  2  3  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 13  1  0  0  0  0
  8  9  1  0  0  0  0
 16 19  1  0  0  0  0
  3  4  2  0  0  0  0
 19 20  2  0  0  0  0
  9 10  1  0  0  0  0
 19 21  1  0  0  0  0
  4  5  1  0  0  0  0
  9 22  1  1  0  0  0
 10 11  1  0  0  0  0
 22 23  1  0  0  0  0
  5  6  2  0  0  0  0
 23 24  1  0  0  0  0
 10 12  2  0  0  0  0
 23 25  2  0  0  0  0
  6  1  1  0  0  0  0
 11 13  1  0  0  0  0
  1  7  1  0  0  0  0
  1  2  2  0  0  0  0
 24 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014663

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)C1=CC=C(NC(=O)[C@H](CC2=CC=C(O)C=C2)NC(=O)C2=CC=CC=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C23H20N2O5/c26-19-12-6-15(7-13-19)14-20(25-21(27)16-4-2-1-3-5-16)22(28)24-18-10-8-17(9-11-18)23(29)30/h1-13,20,26H,14H2,(H,24,28)(H,25,27)(H,29,30)/t20-/m0/s1

> <INCHI_KEY>
SPPTWHFVYKCNNK-FQEVSTJZSA-N

> <FORMULA>
C23H20N2O5

> <MOLECULAR_WEIGHT>
404.4153

> <EXACT_MASS>
404.13722176

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
42.16284740225868

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(2S)-3-(4-hydroxyphenyl)-2-(phenylformamido)propanamido]benzoic acid

> <ALOGPS_LOGP>
2.99

> <JCHEM_LOGP>
3.5389555783333333

> <ALOGPS_LOGS>
-4.99

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.503912519104427

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.157471380782726

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3006283420418332

> <JCHEM_POLAR_SURFACE_AREA>
115.73000000000002

> <JCHEM_REFRACTIVITY>
112.745

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.12e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bentiromide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014663
     RDKit          3D
Bentiromide
 50 52  0  0  0  0  0  0  0  0999 V2000
    7.1436   -3.8538   -0.2364 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1162   -2.6033   -0.3069 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2852   -1.8598   -0.2795 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8386   -1.9339   -0.4186 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8122   -0.5437   -0.4970 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6255    0.1056   -0.6021 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4224   -0.6098   -0.6329 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2159    0.0856   -0.7494 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9093   -0.4418   -0.6741 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6468   -1.6378   -0.4874 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2164    0.5706   -0.8408 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0463    1.5753    0.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0455    2.6479    0.2441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1914    2.4729    0.9867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1964    3.4156    1.0591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0497    4.5905    0.3555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0686    5.5307    0.4371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9041    4.7853   -0.3972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9095    3.8307   -0.4575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4425   -0.1899   -0.7242 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7914   -0.9812    0.3697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0427   -1.0926    1.3741 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0490   -1.7146    0.3880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4375   -2.4406    1.5176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6056   -3.1560    1.6066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4443   -3.1594    0.5204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1290   -2.4690   -0.6246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9341   -1.7574   -0.6700 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4731   -1.9686   -0.5551 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6778   -2.6629   -0.4463 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6610   -1.6500    0.6420 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7631   -0.0087   -0.4710 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5724    1.1775   -0.6638 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2972    1.1447   -0.9229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    0.9714   -1.8742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1187    1.0405    1.2223 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9523    2.0501    0.2608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3753    1.5711    1.5704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1007    3.2597    1.6544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0097    6.2237    1.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7982    5.6967   -0.9384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0113    3.9765   -1.0440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1063   -0.1230   -1.5385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7578   -2.4169    2.3510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8698   -3.7066    2.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3548   -3.7201    0.5966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7804   -2.4687   -1.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7293   -1.2361   -1.5814 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5828   -2.5738   -0.5784 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6677   -3.7428   -0.3872 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 11 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
  7 29  1  0
 29 30  2  0
 30  4  1  0
 19 13  1  0
 28 23  1  0
  3 31  1  0
  5 32  1  0
  6 33  1  0
  8 34  1  0
 11 35  1  6
 12 36  1  0
 12 37  1  0
 14 38  1  0
 15 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
 24 44  1  0
 25 45  1  0
 26 46  1  0
 27 47  1  0
 28 48  1  0
 29 49  1  0
 30 50  1  0
M  END

HEADER    PROTEIN                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  C   UNK     0       8.142 -10.519   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.142  -8.979   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.479  -8.209   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.808  -8.979   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.808 -10.519   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.479 -11.289   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.809 -11.290   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      12.142  -8.210   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.475  -8.981   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.810  -8.212   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      16.143  -8.983   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0      14.811  -6.672   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      17.477  -8.214   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.476  -6.677   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      18.811  -5.908   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      20.144  -6.679   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      20.143  -8.219   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      18.808  -8.988   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      21.478  -5.910   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      21.479  -4.370   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      22.811  -6.681   0.000  0.00  0.00           O+0
HETATM   22  N   UNK     0      13.474 -10.521   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0      14.807 -11.292   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.806 -12.832   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      16.141 -10.523   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      16.138 -13.595   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      16.137 -15.135   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      14.803 -15.903   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.470 -15.133   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.471 -13.593   0.000  0.00  0.00           C+0
CONECT    1    6    7    2                                                  
CONECT    2    3    1                                                       
CONECT    3    2    4                                                       
CONECT    4    8    3    5                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    1                                                            
CONECT    8    4    9                                                       
CONECT    9    8   10   22                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10   13                                                       
CONECT   12   10                                                            
CONECT   13   14   18   11                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19   16   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22    9   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23   26   30                                                  
CONECT   25   23                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   24                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

COMPND    HMDB0014663
HETATM    1  O1  UNL     1       7.144  -3.854  -0.236  1.00  0.00           O  
HETATM    2  C1  UNL     1       7.116  -2.603  -0.307  1.00  0.00           C  
HETATM    3  O2  UNL     1       8.285  -1.860  -0.280  1.00  0.00           O  
HETATM    4  C2  UNL     1       5.839  -1.934  -0.419  1.00  0.00           C  
HETATM    5  C3  UNL     1       5.812  -0.544  -0.497  1.00  0.00           C  
HETATM    6  C4  UNL     1       4.625   0.106  -0.602  1.00  0.00           C  
HETATM    7  C5  UNL     1       3.422  -0.610  -0.633  1.00  0.00           C  
HETATM    8  N1  UNL     1       2.216   0.086  -0.749  1.00  0.00           N  
HETATM    9  C6  UNL     1       0.909  -0.442  -0.674  1.00  0.00           C  
HETATM   10  O3  UNL     1       0.647  -1.638  -0.487  1.00  0.00           O  
HETATM   11  C7  UNL     1      -0.216   0.571  -0.841  1.00  0.00           C  
HETATM   12  C8  UNL     1      -0.046   1.575   0.240  1.00  0.00           C  
HETATM   13  C9  UNL     1      -1.045   2.648   0.244  1.00  0.00           C  
HETATM   14  C10 UNL     1      -2.191   2.473   0.987  1.00  0.00           C  
HETATM   15  C11 UNL     1      -3.196   3.416   1.059  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.050   4.591   0.356  1.00  0.00           C  
HETATM   17  O4  UNL     1      -4.069   5.531   0.437  1.00  0.00           O  
HETATM   18  C13 UNL     1      -1.904   4.785  -0.397  1.00  0.00           C  
HETATM   19  C14 UNL     1      -0.909   3.831  -0.457  1.00  0.00           C  
HETATM   20  N2  UNL     1      -1.443  -0.190  -0.724  1.00  0.00           N  
HETATM   21  C15 UNL     1      -1.791  -0.981   0.370  1.00  0.00           C  
HETATM   22  O5  UNL     1      -1.043  -1.093   1.374  1.00  0.00           O  
HETATM   23  C16 UNL     1      -3.049  -1.715   0.388  1.00  0.00           C  
HETATM   24  C17 UNL     1      -3.438  -2.441   1.518  1.00  0.00           C  
HETATM   25  C18 UNL     1      -4.606  -3.156   1.607  1.00  0.00           C  
HETATM   26  C19 UNL     1      -5.444  -3.159   0.520  1.00  0.00           C  
HETATM   27  C20 UNL     1      -5.129  -2.469  -0.625  1.00  0.00           C  
HETATM   28  C21 UNL     1      -3.934  -1.757  -0.670  1.00  0.00           C  
HETATM   29  C22 UNL     1       3.473  -1.969  -0.555  1.00  0.00           C  
HETATM   30  C23 UNL     1       4.678  -2.663  -0.446  1.00  0.00           C  
HETATM   31  H1  UNL     1       8.661  -1.650   0.642  1.00  0.00           H  
HETATM   32  H2  UNL     1       6.763  -0.009  -0.471  1.00  0.00           H  
HETATM   33  H3  UNL     1       4.572   1.178  -0.664  1.00  0.00           H  
HETATM   34  H4  UNL     1       2.297   1.145  -0.923  1.00  0.00           H  
HETATM   35  H5  UNL     1      -0.147   0.971  -1.874  1.00  0.00           H  
HETATM   36  H6  UNL     1      -0.119   1.040   1.222  1.00  0.00           H  
HETATM   37  H7  UNL     1       0.952   2.050   0.261  1.00  0.00           H  
HETATM   38  H8  UNL     1      -2.375   1.571   1.570  1.00  0.00           H  
HETATM   39  H9  UNL     1      -4.101   3.260   1.654  1.00  0.00           H  
HETATM   40  H10 UNL     1      -4.010   6.224   1.175  1.00  0.00           H  
HETATM   41  H11 UNL     1      -1.798   5.697  -0.938  1.00  0.00           H  
HETATM   42  H12 UNL     1      -0.011   3.977  -1.044  1.00  0.00           H  
HETATM   43  H13 UNL     1      -2.106  -0.123  -1.538  1.00  0.00           H  
HETATM   44  H14 UNL     1      -2.758  -2.417   2.351  1.00  0.00           H  
HETATM   45  H15 UNL     1      -4.870  -3.707   2.503  1.00  0.00           H  
HETATM   46  H16 UNL     1      -6.355  -3.720   0.597  1.00  0.00           H  
HETATM   47  H17 UNL     1      -5.780  -2.469  -1.475  1.00  0.00           H  
HETATM   48  H18 UNL     1      -3.729  -1.236  -1.581  1.00  0.00           H  
HETATM   49  H19 UNL     1       2.583  -2.574  -0.578  1.00  0.00           H  
HETATM   50  H20 UNL     1       4.668  -3.743  -0.387  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   31
CONECT    4    5    5   30
CONECT    5    6   32
CONECT    6    7    7   33
CONECT    7    8   29
CONECT    8    9   34
CONECT    9   10   10   11
CONECT   11   12   20   35
CONECT   12   13   36   37
CONECT   13   14   14   19
CONECT   14   15   38
CONECT   15   16   16   39
CONECT   16   17   18
CONECT   17   40
CONECT   18   19   19   41
CONECT   19   42
CONECT   20   21   43
CONECT   21   22   22   23
CONECT   23   24   24   28
CONECT   24   25   44
CONECT   25   26   26   45
CONECT   26   27   46
CONECT   27   28   28   47
CONECT   28   48
CONECT   29   30   30   49
CONECT   30   50
END

HMDB0014663
     RDKit          3D
Bentiromide
 50 52  0  0  0  0  0  0  0  0999 V2000
    7.1436   -3.8538   -0.2364 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1162   -2.6033   -0.3069 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2852   -1.8598   -0.2795 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8386   -1.9339   -0.4186 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8122   -0.5437   -0.4970 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6255    0.1056   -0.6021 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4224   -0.6098   -0.6329 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2159    0.0856   -0.7494 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9093   -0.4418   -0.6741 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6468   -1.6378   -0.4874 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2164    0.5706   -0.8408 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0463    1.5753    0.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0455    2.6479    0.2441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1914    2.4729    0.9867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1964    3.4156    1.0591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0497    4.5905    0.3555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0686    5.5307    0.4371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9041    4.7853   -0.3972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9095    3.8307   -0.4575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4425   -0.1899   -0.7242 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7914   -0.9812    0.3697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0427   -1.0926    1.3741 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0490   -1.7146    0.3880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4375   -2.4406    1.5176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6056   -3.1560    1.6066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4443   -3.1594    0.5204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1290   -2.4690   -0.6246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9341   -1.7574   -0.6700 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4731   -1.9686   -0.5551 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6778   -2.6629   -0.4463 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6610   -1.6500    0.6420 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7631   -0.0087   -0.4710 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5724    1.1775   -0.6638 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2972    1.1447   -0.9229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    0.9714   -1.8742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1187    1.0405    1.2223 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9523    2.0501    0.2608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3753    1.5711    1.5704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1007    3.2597    1.6544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0097    6.2237    1.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7982    5.6967   -0.9384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0113    3.9765   -1.0440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1063   -0.1230   -1.5385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7578   -2.4169    2.3510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8698   -3.7066    2.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3548   -3.7201    0.5966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7804   -2.4687   -1.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7293   -1.2361   -1.5814 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5828   -2.5738   -0.5784 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6677   -3.7428   -0.3872 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 11 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
  7 29  1  0
 29 30  2  0
 30  4  1  0
 19 13  1  0
 28 23  1  0
  3 31  1  0
  5 32  1  0
  6 33  1  0
  8 34  1  0
 11 35  1  6
 12 36  1  0
 12 37  1  0
 14 38  1  0
 15 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
 24 44  1  0
 25 45  1  0
 26 46  1  0
 27 47  1  0
 28 48  1  0
 29 49  1  0
 30 50  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(S)-4-((2-(Benzoylamino)-3-(4-hydroxyphenyl)-1-oxopropyl)amino)benzoic acid	ChEBI
(S)-p-(alpha-Benzamido-p-hydroxyhydrocinnamamido)benzoic acid	ChEBI
4-(N-Benzoyl-L-tyrosylamino)benzoic acid	ChEBI
Bentiromido	ChEBI
Bentiromidum	ChEBI
Benzoyltyrosyl-p-aminobenzoic acid	ChEBI
BT-PABA	ChEBI
BTPABA	ChEBI
N-Benzoyl-L-tyrosyl-p-aminobenzoate	ChEBI
N-Benzoyl-L-tyrosyl-p-aminobenzoic acid	ChEBI
PFD	ChEBI
PFT	ChEBI
(S)-4-((2-(Benzoylamino)-3-(4-hydroxyphenyl)-1-oxopropyl)amino)benzoate	Generator
(S)-p-(a-Benzamido-p-hydroxyhydrocinnamamido)benzoate	Generator
(S)-p-(a-Benzamido-p-hydroxyhydrocinnamamido)benzoic acid	Generator
(S)-p-(alpha-Benzamido-p-hydroxyhydrocinnamamido)benzoate	Generator
(S)-p-(Α-benzamido-p-hydroxyhydrocinnamamido)benzoate	Generator
(S)-p-(Α-benzamido-p-hydroxyhydrocinnamamido)benzoic acid	Generator
4-(N-Benzoyl-L-tyrosylamino)benzoate	Generator
Benzoyltyrosyl-p-aminobenzoate	Generator
N-Benzoyl-L-tyrosyl-paba	HMDB
PABA-peptide	HMDB
Benzoyl-tyrosyl-paba	HMDB

Chemical Formula

C₂₃H₂₀N₂O₅

Average Molecular Weight

404.4153

Monoisotopic Molecular Weight

404.13722176

IUPAC Name

4-[(2S)-3-(4-hydroxyphenyl)-2-(phenylformamido)propanamido]benzoic acid

Traditional Name

bentiromide

CAS Registry Number

37106-97-1

SMILES

OC(=O)C1=CC=C(NC(=O)[C@H](CC2=CC=C(O)C=C2)NC(=O)C2=CC=CC=C2)C=C1

InChI Identifier

InChI=1S/C23H20N2O5/c26-19-12-6-15(7-13-19)14-20(25-21(27)16-4-2-1-3-5-16)22(28)24-18-10-8-17(9-11-18)23(29)30/h1-13,20,26H,14H2,(H,24,28)(H,25,27)(H,29,30)/t20-/m0/s1

InChI Key

SPPTWHFVYKCNNK-FQEVSTJZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Tyrosine and derivatives

Alternative Parents

Substituents

Tyrosine or derivatives
Phenylalanine or derivatives
Hippuric acid or derivatives
N-acyl-alpha amino acid or derivatives
Acylaminobenzoic acid or derivatives
Alpha-amino acid amide
Amphetamine or derivatives
Benzoic acid or derivatives
Anilide
Benzoic acid
Benzamide
N-arylamide
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Fatty amide
Secondary carboxylic acid amide
Carboxamide group
Monocarboxylic acid or derivatives
Carboxylic acid
Organic nitrogen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

dipeptide (CHEBI:31263 )

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: HMDB0014663)

Source

Exogenous

Exogenous (HMDB: HMDB0014663)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	241 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0041 g/L	Not Available
LogP	3.3	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0041 g/L	ALOGPS
logP	2.99	ALOGPS
logP	3.54	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	4.16	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	115.73 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	112.74 m³·mol⁻¹	ChemAxon
Polarizability	42.16 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	195.91	31661259
DarkChem	[M-H]-	194.885	31661259
DeepCCS	[M+H]+	196.322	30932474
DeepCCS	[M-H]-	193.926	30932474
DeepCCS	[M-2H]-	226.81	30932474
DeepCCS	[M+Na]+	202.252	30932474
AllCCS	[M+H]+	196.3	32859911
AllCCS	[M+H-H2O]+	193.7	32859911
AllCCS	[M+NH4]+	198.7	32859911
AllCCS	[M+Na]+	199.3	32859911
AllCCS	[M-H]-	193.8	32859911
AllCCS	[M+Na-2H]-	193.6	32859911
AllCCS	[M+HCOO]-	193.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bentiromide	OC(=O)C1=CC=C(NC(=O)[C@H](CC2=CC=C(O)C=C2)NC(=O)C2=CC=CC=C2)C=C1	5350.7	Standard polar	33892256
Bentiromide	OC(=O)C1=CC=C(NC(=O)[C@H](CC2=CC=C(O)C=C2)NC(=O)C2=CC=CC=C2)C=C1	2846.0	Standard non polar	33892256
Bentiromide	OC(=O)C1=CC=C(NC(=O)[C@H](CC2=CC=C(O)C=C2)NC(=O)C2=CC=CC=C2)C=C1	4226.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Bentiromide,1TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=C(NC(=O)[C@H](CC2=CC=C(O)C=C2)NC(=O)C2=CC=CC=C2)C=C1	3931.1	Semi standard non polar	33892256
Bentiromide,1TMS,isomer #2	C[Si](C)(C)OC1=CC=C(C[C@H](NC(=O)C2=CC=CC=C2)C(=O)NC2=CC=C(C(=O)O)C=C2)C=C1	4011.3	Semi standard non polar	33892256
Bentiromide,1TMS,isomer #3	C[Si](C)(C)N(C(=O)[C@H](CC1=CC=C(O)C=C1)NC(=O)C1=CC=CC=C1)C1=CC=C(C(=O)O)C=C1	3821.4	Semi standard non polar	33892256
Bentiromide,1TMS,isomer #4	C[Si](C)(C)N(C(=O)C1=CC=CC=C1)[C@@H](CC1=CC=C(O)C=C1)C(=O)NC1=CC=C(C(=O)O)C=C1	3971.0	Semi standard non polar	33892256
Bentiromide,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=C(NC(=O)[C@H](CC2=CC=C(O[Si](C)(C)C)C=C2)NC(=O)C2=CC=CC=C2)C=C1	3942.1	Semi standard non polar	33892256
Bentiromide,2TMS,isomer #2	C[Si](C)(C)OC(=O)C1=CC=C(N(C(=O)[C@H](CC2=CC=C(O)C=C2)NC(=O)C2=CC=CC=C2)[Si](C)(C)C)C=C1	3674.3	Semi standard non polar	33892256
Bentiromide,2TMS,isomer #3	C[Si](C)(C)OC(=O)C1=CC=C(NC(=O)[C@H](CC2=CC=C(O)C=C2)N(C(=O)C2=CC=CC=C2)[Si](C)(C)C)C=C1	3760.3	Semi standard non polar	33892256
Bentiromide,2TMS,isomer #4	C[Si](C)(C)OC1=CC=C(C[C@@H](C(=O)NC2=CC=C(C(=O)O)C=C2)N(C(=O)C2=CC=CC=C2)[Si](C)(C)C)C=C1	3889.7	Semi standard non polar	33892256
Bentiromide,2TMS,isomer #5	C[Si](C)(C)OC1=CC=C(C[C@H](NC(=O)C2=CC=CC=C2)C(=O)N(C2=CC=C(C(=O)O)C=C2)[Si](C)(C)C)C=C1	3814.1	Semi standard non polar	33892256
Bentiromide,2TMS,isomer #6	C[Si](C)(C)N(C(=O)[C@H](CC1=CC=C(O)C=C1)N(C(=O)C1=CC=CC=C1)[Si](C)(C)C)C1=CC=C(C(=O)O)C=C1	3694.3	Semi standard non polar	33892256
Bentiromide,3TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=C(N(C(=O)[C@H](CC2=CC=C(O[Si](C)(C)C)C=C2)NC(=O)C2=CC=CC=C2)[Si](C)(C)C)C=C1	3771.9	Semi standard non polar	33892256
Bentiromide,3TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=C(N(C(=O)[C@H](CC2=CC=C(O[Si](C)(C)C)C=C2)NC(=O)C2=CC=CC=C2)[Si](C)(C)C)C=C1	3214.7	Standard non polar	33892256
Bentiromide,3TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=C(N(C(=O)[C@H](CC2=CC=C(O[Si](C)(C)C)C=C2)NC(=O)C2=CC=CC=C2)[Si](C)(C)C)C=C1	4214.5	Standard polar	33892256
Bentiromide,3TMS,isomer #2	C[Si](C)(C)OC(=O)C1=CC=C(NC(=O)[C@H](CC2=CC=C(O[Si](C)(C)C)C=C2)N(C(=O)C2=CC=CC=C2)[Si](C)(C)C)C=C1	3782.1	Semi standard non polar	33892256
Bentiromide,3TMS,isomer #2	C[Si](C)(C)OC(=O)C1=CC=C(NC(=O)[C@H](CC2=CC=C(O[Si](C)(C)C)C=C2)N(C(=O)C2=CC=CC=C2)[Si](C)(C)C)C=C1	3468.9	Standard non polar	33892256
Bentiromide,3TMS,isomer #2	C[Si](C)(C)OC(=O)C1=CC=C(NC(=O)[C@H](CC2=CC=C(O[Si](C)(C)C)C=C2)N(C(=O)C2=CC=CC=C2)[Si](C)(C)C)C=C1	4314.9	Standard polar	33892256
Bentiromide,3TMS,isomer #3	C[Si](C)(C)OC(=O)C1=CC=C(N(C(=O)[C@H](CC2=CC=C(O)C=C2)N(C(=O)C2=CC=CC=C2)[Si](C)(C)C)[Si](C)(C)C)C=C1	3582.8	Semi standard non polar	33892256
Bentiromide,3TMS,isomer #3	C[Si](C)(C)OC(=O)C1=CC=C(N(C(=O)[C@H](CC2=CC=C(O)C=C2)N(C(=O)C2=CC=CC=C2)[Si](C)(C)C)[Si](C)(C)C)C=C1	3204.3	Standard non polar	33892256
Bentiromide,3TMS,isomer #3	C[Si](C)(C)OC(=O)C1=CC=C(N(C(=O)[C@H](CC2=CC=C(O)C=C2)N(C(=O)C2=CC=CC=C2)[Si](C)(C)C)[Si](C)(C)C)C=C1	4270.6	Standard polar	33892256
Bentiromide,3TMS,isomer #4	C[Si](C)(C)OC1=CC=C(C[C@@H](C(=O)N(C2=CC=C(C(=O)O)C=C2)[Si](C)(C)C)N(C(=O)C2=CC=CC=C2)[Si](C)(C)C)C=C1	3698.7	Semi standard non polar	33892256
Bentiromide,3TMS,isomer #4	C[Si](C)(C)OC1=CC=C(C[C@@H](C(=O)N(C2=CC=C(C(=O)O)C=C2)[Si](C)(C)C)N(C(=O)C2=CC=CC=C2)[Si](C)(C)C)C=C1	3300.6	Standard non polar	33892256
Bentiromide,3TMS,isomer #4	C[Si](C)(C)OC1=CC=C(C[C@@H](C(=O)N(C2=CC=C(C(=O)O)C=C2)[Si](C)(C)C)N(C(=O)C2=CC=CC=C2)[Si](C)(C)C)C=C1	4219.1	Standard polar	33892256
Bentiromide,4TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=C(N(C(=O)[C@H](CC2=CC=C(O[Si](C)(C)C)C=C2)N(C(=O)C2=CC=CC=C2)[Si](C)(C)C)[Si](C)(C)C)C=C1	3648.8	Semi standard non polar	33892256
Bentiromide,4TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=C(N(C(=O)[C@H](CC2=CC=C(O[Si](C)(C)C)C=C2)N(C(=O)C2=CC=CC=C2)[Si](C)(C)C)[Si](C)(C)C)C=C1	3120.0	Standard non polar	33892256
Bentiromide,4TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=C(N(C(=O)[C@H](CC2=CC=C(O[Si](C)(C)C)C=C2)N(C(=O)C2=CC=CC=C2)[Si](C)(C)C)[Si](C)(C)C)C=C1	4010.8	Standard polar	33892256
Bentiromide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(NC(=O)[C@H](CC2=CC=C(O)C=C2)NC(=O)C2=CC=CC=C2)C=C1	4211.1	Semi standard non polar	33892256
Bentiromide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@H](NC(=O)C2=CC=CC=C2)C(=O)NC2=CC=C(C(=O)O)C=C2)C=C1	4284.3	Semi standard non polar	33892256
Bentiromide,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C(=O)[C@H](CC1=CC=C(O)C=C1)NC(=O)C1=CC=CC=C1)C1=CC=C(C(=O)O)C=C1	4119.2	Semi standard non polar	33892256
Bentiromide,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C(=O)C1=CC=CC=C1)[C@@H](CC1=CC=C(O)C=C1)C(=O)NC1=CC=C(C(=O)O)C=C1	4241.1	Semi standard non polar	33892256
Bentiromide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(NC(=O)[C@H](CC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)NC(=O)C2=CC=CC=C2)C=C1	4474.3	Semi standard non polar	33892256
Bentiromide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(N(C(=O)[C@H](CC2=CC=C(O)C=C2)NC(=O)C2=CC=CC=C2)[Si](C)(C)C(C)(C)C)C=C1	4200.7	Semi standard non polar	33892256
Bentiromide,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(NC(=O)[C@H](CC2=CC=C(O)C=C2)N(C(=O)C2=CC=CC=C2)[Si](C)(C)C(C)(C)C)C=C1	4313.3	Semi standard non polar	33892256
Bentiromide,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@@H](C(=O)NC2=CC=C(C(=O)O)C=C2)N(C(=O)C2=CC=CC=C2)[Si](C)(C)C(C)(C)C)C=C1	4412.2	Semi standard non polar	33892256
Bentiromide,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@H](NC(=O)C2=CC=CC=C2)C(=O)N(C2=CC=C(C(=O)O)C=C2)[Si](C)(C)C(C)(C)C)C=C1	4333.0	Semi standard non polar	33892256
Bentiromide,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N(C(=O)[C@H](CC1=CC=C(O)C=C1)N(C(=O)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C)C1=CC=C(C(=O)O)C=C1	4190.8	Semi standard non polar	33892256
Bentiromide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(N(C(=O)[C@H](CC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)NC(=O)C2=CC=CC=C2)[Si](C)(C)C(C)(C)C)C=C1	4452.9	Semi standard non polar	33892256
Bentiromide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(N(C(=O)[C@H](CC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)NC(=O)C2=CC=CC=C2)[Si](C)(C)C(C)(C)C)C=C1	3756.6	Standard non polar	33892256
Bentiromide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(N(C(=O)[C@H](CC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)NC(=O)C2=CC=CC=C2)[Si](C)(C)C(C)(C)C)C=C1	4382.1	Standard polar	33892256
Bentiromide,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(NC(=O)[C@H](CC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)N(C(=O)C2=CC=CC=C2)[Si](C)(C)C(C)(C)C)C=C1	4520.1	Semi standard non polar	33892256
Bentiromide,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(NC(=O)[C@H](CC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)N(C(=O)C2=CC=CC=C2)[Si](C)(C)C(C)(C)C)C=C1	3984.7	Standard non polar	33892256
Bentiromide,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(NC(=O)[C@H](CC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)N(C(=O)C2=CC=CC=C2)[Si](C)(C)C(C)(C)C)C=C1	4471.0	Standard polar	33892256
Bentiromide,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(N(C(=O)[C@H](CC2=CC=C(O)C=C2)N(C(=O)C2=CC=CC=C2)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	4272.6	Semi standard non polar	33892256
Bentiromide,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(N(C(=O)[C@H](CC2=CC=C(O)C=C2)N(C(=O)C2=CC=CC=C2)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	3672.3	Standard non polar	33892256
Bentiromide,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(N(C(=O)[C@H](CC2=CC=C(O)C=C2)N(C(=O)C2=CC=CC=C2)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	4421.2	Standard polar	33892256
Bentiromide,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@@H](C(=O)N(C2=CC=C(C(=O)O)C=C2)[Si](C)(C)C(C)(C)C)N(C(=O)C2=CC=CC=C2)[Si](C)(C)C(C)(C)C)C=C1	4369.7	Semi standard non polar	33892256
Bentiromide,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@@H](C(=O)N(C2=CC=C(C(=O)O)C=C2)[Si](C)(C)C(C)(C)C)N(C(=O)C2=CC=CC=C2)[Si](C)(C)C(C)(C)C)C=C1	3806.8	Standard non polar	33892256
Bentiromide,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@@H](C(=O)N(C2=CC=C(C(=O)O)C=C2)[Si](C)(C)C(C)(C)C)N(C(=O)C2=CC=CC=C2)[Si](C)(C)C(C)(C)C)C=C1	4373.0	Standard polar	33892256
Bentiromide,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(N(C(=O)[C@H](CC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)N(C(=O)C2=CC=CC=C2)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	4523.3	Semi standard non polar	33892256
Bentiromide,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(N(C(=O)[C@H](CC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)N(C(=O)C2=CC=CC=C2)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	3802.3	Standard non polar	33892256
Bentiromide,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(N(C(=O)[C@H](CC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)N(C(=O)C2=CC=CC=C2)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	4247.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Bentiromide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-0951000000-3408813d239b684fcca1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bentiromide GC-MS (2 TMS) - 70eV, Positive	splash10-0a59-0902130000-2e52e28c1a3b2bc381ce	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bentiromide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bentiromide 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bentiromide 10V, Positive-QTOF	splash10-0a4r-0479500000-9b7d3992e6800b7ec069	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bentiromide 20V, Positive-QTOF	splash10-0a4l-0951000000-0e8e632e5411e48e747e	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bentiromide 40V, Positive-QTOF	splash10-0a4i-2920000000-786eb7e2b52e3322399d	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bentiromide 10V, Negative-QTOF	splash10-0udi-0254900000-a07141fcfe2759e41e1b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bentiromide 20V, Negative-QTOF	splash10-0zg3-3694200000-da9c1e7b3b855e5436e0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bentiromide 40V, Negative-QTOF	splash10-0006-6900000000-d9bd094cd00bd79ca2a7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bentiromide 10V, Positive-QTOF	splash10-0a4i-0020900000-491ed190ebed6003bc34	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bentiromide 20V, Positive-QTOF	splash10-0a59-0970200000-bd7f9a2db2ad1e6443f6	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bentiromide 40V, Positive-QTOF	splash10-056r-5921000000-a21fe0aa532ec26db20f	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bentiromide 10V, Negative-QTOF	splash10-0udi-0000900000-6c33d64e035c215f9b55	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bentiromide 20V, Negative-QTOF	splash10-00to-6972100000-fd8354cac47979662cab	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bentiromide 40V, Negative-QTOF	splash10-00l6-6900000000-655dee2f28414fdf2f97	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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 DB00522	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00522	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00522

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5329364

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bentiromide

METLIN ID

Not Available

PubChem Compound

6957673

PDB ID

Not Available

ChEBI ID

31263

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

Toskes PP: The bentiromide test for pancreatic exocrine insufficiency. Pharmacotherapy. 1984 Mar-Apr;4(2):74-80. [PubMed:6371722 ]

Showing metabocard for Bentiromide (HMDB0014663)

MOL for HMDB0014663 (Bentiromide)

3D MOL for HMDB0014663 (Bentiromide)

3D SDF for HMDB0014663 (Bentiromide)

3D-SDF for HMDB0014663 (Bentiromide)

PDB for HMDB0014663 (Bentiromide)

3D PDB for HMDB0014663 (Bentiromide)

SMILES for HMDB0014663 (Bentiromide)

INCHI for HMDB0014663 (Bentiromide)

Structure for HMDB0014663 (Bentiromide)

3D Structure for HMDB0014663 (Bentiromide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra