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

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:44 UTC

HMDB ID

HMDB0014754

Secondary Accession Numbers

HMDB14754

Metabolite Identification

Common Name

Candoxatril

Description

Candoxatril is only found in individuals that have used or taken this drug. It is the orally-active prodrug of candoxatrilat (UK-73967), the active enantiomer of candoxatrilat (UK-69578), a potent neutral endopeptidase (NEP) inhibitor used in the treatment of chronic heart failure.Neutral endopeptidase inhibitors such as Candoxatril have a dual mechanism of action. They inhibit two metalloprotease enzymes, neutral endopeptidase and ACE, resulting in an increased availability of natriuretic peptides that exhibit vasodilatory effects and, possibly, tissue protective effects.

Structure

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


  Mrv0541 04191212132D          

 37 40  0  0  1  0            999 V2000
   12.3382   -8.0488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4842   -8.0571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6322   -8.4687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2071   -8.4690    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.9175   -8.0564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0570   -8.4537    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8854   -6.7615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7824   -8.4819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0591   -8.0574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1875   -7.1810    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.3299   -7.2238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4883   -7.2319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6124   -7.1661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4610   -6.7890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2  4  1  0  0  0  0
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  4  5  1  0  0  0  0
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  6  1  1  0  0  0  0
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  4 20  1  1  0  0  0
 21  3  1  0  0  0  0
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 35 33  1  0  0  0  0
 36 35  1  0  0  0  0
 37 34  1  0  0  0  0
 37 36  1  0  0  0  0
M  END

HMDB0014754
     RDKit          3D
Candoxatril
 78 81  0  0  0  0  0  0  0  0999 V2000
    2.7665    5.4930    1.5014 C   0  0  0  0  0  0  0  0  0  0  0  0
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 37 78  1  0
M  END


  Mrv0541 04191212132D          

 37 40  0  0  1  0            999 V2000
   12.3382   -8.0488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4842   -8.0571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3606   -7.6449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8454   -8.3124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0  0  0  0
  3  1  1  0  0  0  0
  4  5  1  0  0  0  0
  5  3  1  0  0  0  0
  6  1  1  0  0  0  0
 10  7  1  1  0  0  0
  8  2  1  0  0  0  0
  9  8  1  0  0  0  0
 10 15  1  0  0  0  0
 11  1  2  0  0  0  0
 12  2  2  0  0  0  0
 13  7  1  0  0  0  0
 14 18  1  0  0  0  0
 15 19  1  0  0  0  0
 16  6  1  1  0  0  0
 17  7  2  0  0  0  0
 18 16  1  0  0  0  0
 19 16  1  0  0  0  0
  4 20  1  1  0  0  0
 21  3  1  0  0  0  0
 22  3  1  0  0  0  0
 23 20  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 23  1  0  0  0  0
 27 24  1  0  0  0  0
 28 21  1  0  0  0  0
 29 22  1  0  0  0  0
 28 29  1  0  0  0  0
 10 14  1  0  0  0  0
  9 30  1  0  0  0  0
 31 30  2  0  0  0  0
 32  9  2  0  0  0  0
 33 31  1  0  0  0  0
 34 32  1  0  0  0  0
 34 33  2  0  0  0  0
 35 33  1  0  0  0  0
 36 35  1  0  0  0  0
 37 34  1  0  0  0  0
 37 36  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014754

> <DATABASE_NAME>
hmdb

> <SMILES>
COCCOC[C@H](CC1(CCCC1)C(=O)N[C@H]1CC[C@H](CC1)C(O)=O)C(=O)OC1=CC2=C(CCC2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H41NO7/c1-35-15-16-36-19-23(27(33)37-25-12-9-20-5-4-6-22(20)17-25)18-29(13-2-3-14-29)28(34)30-24-10-7-21(8-11-24)26(31)32/h9,12,17,21,23-24H,2-8,10-11,13-16,18-19H2,1H3,(H,30,34)(H,31,32)/t21-,23-,24+/m0/s1

> <INCHI_KEY>
ZTWZVMIYIIVABD-OEMFJLHTSA-N

> <FORMULA>
C29H41NO7

> <MOLECULAR_WEIGHT>
515.6383

> <EXACT_MASS>
515.288302671

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
57.195570395513165

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1s,4s)-4-{1-[(2S)-3-(2,3-dihydro-1H-inden-5-yloxy)-2-[(2-methoxyethoxy)methyl]-3-oxopropyl]cyclopentaneamido}cyclohexane-1-carboxylic acid

> <ALOGPS_LOGP>
3.55

> <JCHEM_LOGP>
4.679150365000001

> <ALOGPS_LOGS>
-5.36

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.236390919782128

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.28541382443718

> <JCHEM_PKA_STRONGEST_BASIC>
1.3153504645056517

> <JCHEM_POLAR_SURFACE_AREA>
111.16

> <JCHEM_REFRACTIVITY>
138.15810000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.25e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
candoxatril

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014754
     RDKit          3D
Candoxatril
 78 81  0  0  0  0  0  0  0  0999 V2000
    2.7665    5.4930    1.5014 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0414    5.0103    1.5377 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3075    3.8683    2.1933 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5708    2.6170    1.6857 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2613    2.8336    1.8095 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3141    1.9298    1.4827 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1765    1.4670    0.0858 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1267    0.4962   -0.2430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3030    0.6965   -0.0785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0353   -0.5391   -0.6073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3887   -1.4755   -1.0974 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4338   -0.5948   -0.5297 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2019   -1.7438   -1.0147 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9230   -2.3603    0.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2710   -1.7867    0.4072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1100   -1.8012   -0.8525 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.4525   -1.2450   -0.5846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4852   -1.9533   -0.7651 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6462    0.0440   -0.1345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4089   -0.8783   -1.8387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0501   -1.3872   -2.1993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7059    0.7255    1.3787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4546    1.9821    1.6459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2409    2.8541    0.4466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9153    1.9060   -0.6524 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4526    0.7309   -0.3008 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1042    0.9976   -1.3332 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9357   -0.2882    0.4965 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0676   -1.0212    0.2035 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2882   -0.6707    0.6926 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4448   -1.4099    0.3999 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3530   -2.5262   -0.4063 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1449   -2.8982   -0.9087 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0069   -2.1590   -0.6119 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2793   -4.1310   -1.7600 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7677   -4.2326   -1.9677 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4203   -3.4741   -0.8582 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3649    5.6673    2.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0924    4.8761    0.8982 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7407    6.5145    0.9841 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4014    3.6572    2.1761 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0308    4.0141    3.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8715    2.5673    0.6132 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9576    1.7193    2.2217 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3631    1.0855    2.2212 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3285    2.4534    1.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2026    2.3413   -0.6404 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4678   -0.4920    0.2449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2805    0.2089   -1.3464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9454    0.2223   -0.1053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4519   -2.4752   -1.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2815   -2.1838    1.0469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9950   -3.4523    0.0310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7671   -2.4249    1.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2249   -0.7343    0.7489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2120   -2.8376   -1.2391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8692    0.6977   -0.0761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3865    0.1211   -1.3595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0369   -0.8335   -2.7515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5268   -0.5895   -2.7703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1749   -2.2393   -2.9099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3921   -0.1628    1.6129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8945    0.5878    2.0954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5398    1.7329    1.7798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0486    2.4539    2.5712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2169    3.3611    0.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4457    3.5963    0.6622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8973    1.6231   -1.1361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3535    2.3673   -1.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4728    0.1806    1.3289 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4033   -1.1367    0.7834 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0427   -2.4609   -1.0165 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8215   -5.0179   -1.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8327   -3.8710   -2.7569 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0817   -5.3026   -1.9390 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1028   -3.7627   -2.9320 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6542   -4.1814   -0.0162 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3432   -2.9661   -1.1507 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 16 20  1  0
 20 21  1  0
  9 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
  7 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 33 35  1  0
 35 36  1  0
 36 37  1  0
 25  9  1  0
 34 29  1  0
 21 13  1  0
 37 32  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  3 41  1  0
  3 42  1  0
  4 43  1  0
  4 44  1  0
  6 45  1  0
  6 46  1  0
  7 47  1  6
  8 48  1  0
  8 49  1  0
 12 50  1  0
 13 51  1  6
 14 52  1  0
 14 53  1  0
 15 54  1  0
 15 55  1  0
 16 56  1  6
 19 57  1  0
 20 58  1  0
 20 59  1  0
 21 60  1  0
 21 61  1  0
 22 62  1  0
 22 63  1  0
 23 64  1  0
 23 65  1  0
 24 66  1  0
 24 67  1  0
 25 68  1  0
 25 69  1  0
 30 70  1  0
 31 71  1  0
 34 72  1  0
 35 73  1  0
 35 74  1  0
 36 75  1  0
 36 76  1  0
 37 77  1  0
 37 78  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      23.031 -15.024   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      17.704 -15.040   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      21.713 -15.808   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      19.053 -15.809   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      20.379 -15.039   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      24.373 -15.780   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      29.653 -12.622   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      16.394 -15.833   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      15.044 -15.041   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      28.350 -13.405   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      23.016 -13.484   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      17.712 -13.500   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      31.010 -13.377   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      26.994 -12.673   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      28.350 -14.945   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      25.715 -14.995   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      29.645 -11.081   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      25.691 -13.456   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      27.033 -15.752   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      19.063 -17.348   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      20.462 -16.695   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      22.973 -16.695   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      17.723 -18.126   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      13.723 -17.383   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      15.057 -18.144   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      16.389 -17.365   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.399 -18.161   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      20.928 -18.164   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      22.467 -18.164   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      15.044 -13.501   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.710 -12.730   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      13.710 -15.811   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.376 -13.501   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.376 -15.041   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.912 -13.025   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      10.006 -14.271   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      10.911 -15.516   0.000  0.00  0.00           C+0
CONECT    1    3    6   11                                                  
CONECT    2    4    8   12                                                  
CONECT    3    1    5   21   22                                             
CONECT    4    2    5   20                                                  
CONECT    5    4    3                                                       
CONECT    6    1   16                                                       
CONECT    7   10   13   17                                                  
CONECT    8    2    9                                                       
CONECT    9    8   30   32                                                  
CONECT   10    7   15   14                                                  
CONECT   11    1                                                            
CONECT   12    2                                                            
CONECT   13    7                                                            
CONECT   14   18   10                                                       
CONECT   15   10   19                                                       
CONECT   16    6   18   19                                                  
CONECT   17    7                                                            
CONECT   18   14   16                                                       
CONECT   19   15   16                                                       
CONECT   20    4   23                                                       
CONECT   21    3   28                                                       
CONECT   22    3   29                                                       
CONECT   23   20   26                                                       
CONECT   24   25   27                                                       
CONECT   25   24   26                                                       
CONECT   26   25   23                                                       
CONECT   27   24                                                            
CONECT   28   21   29                                                       
CONECT   29   22   28                                                       
CONECT   30    9   31                                                       
CONECT   31   30   33                                                       
CONECT   32    9   34                                                       
CONECT   33   31   34   35                                                  
CONECT   34   32   33   37                                                  
CONECT   35   33   36                                                       
CONECT   36   35   37                                                       
CONECT   37   34   36                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

COMPND    HMDB0014754
HETATM    1  C1  UNL     1       2.767   5.493   1.501  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.041   5.010   1.538  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.307   3.868   2.193  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.571   2.617   1.686  1.00  0.00           C  
HETATM    5  O2  UNL     1       2.261   2.834   1.809  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.314   1.930   1.483  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.177   1.467   0.086  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.127   0.496  -0.243  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.303   0.696  -0.078  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.035  -0.539  -0.607  1.00  0.00           C  
HETATM   11  O3  UNL     1      -1.389  -1.475  -1.097  1.00  0.00           O  
HETATM   12  N1  UNL     1      -3.434  -0.595  -0.530  1.00  0.00           N  
HETATM   13  C9  UNL     1      -4.202  -1.744  -1.015  1.00  0.00           C  
HETATM   14  C10 UNL     1      -4.923  -2.360   0.132  1.00  0.00           C  
HETATM   15  C11 UNL     1      -6.271  -1.787   0.407  1.00  0.00           C  
HETATM   16  C12 UNL     1      -7.110  -1.801  -0.853  1.00  0.00           C  
HETATM   17  C13 UNL     1      -8.452  -1.245  -0.585  1.00  0.00           C  
HETATM   18  O4  UNL     1      -9.485  -1.953  -0.765  1.00  0.00           O  
HETATM   19  O5  UNL     1      -8.646   0.044  -0.135  1.00  0.00           O  
HETATM   20  C14 UNL     1      -6.409  -0.878  -1.839  1.00  0.00           C  
HETATM   21  C15 UNL     1      -5.050  -1.387  -2.199  1.00  0.00           C  
HETATM   22  C16 UNL     1      -1.706   0.725   1.379  1.00  0.00           C  
HETATM   23  C17 UNL     1      -2.455   1.982   1.646  1.00  0.00           C  
HETATM   24  C18 UNL     1      -2.241   2.854   0.447  1.00  0.00           C  
HETATM   25  C19 UNL     1      -1.915   1.906  -0.652  1.00  0.00           C  
HETATM   26  C20 UNL     1       2.453   0.731  -0.301  1.00  0.00           C  
HETATM   27  O6  UNL     1       3.104   0.998  -1.333  1.00  0.00           O  
HETATM   28  O7  UNL     1       2.936  -0.288   0.496  1.00  0.00           O  
HETATM   29  C21 UNL     1       4.068  -1.021   0.203  1.00  0.00           C  
HETATM   30  C22 UNL     1       5.288  -0.671   0.693  1.00  0.00           C  
HETATM   31  C23 UNL     1       6.445  -1.410   0.400  1.00  0.00           C  
HETATM   32  C24 UNL     1       6.353  -2.526  -0.406  1.00  0.00           C  
HETATM   33  C25 UNL     1       5.145  -2.898  -0.909  1.00  0.00           C  
HETATM   34  C26 UNL     1       4.007  -2.159  -0.612  1.00  0.00           C  
HETATM   35  C27 UNL     1       5.279  -4.131  -1.760  1.00  0.00           C  
HETATM   36  C28 UNL     1       6.768  -4.233  -1.968  1.00  0.00           C  
HETATM   37  C29 UNL     1       7.420  -3.474  -0.858  1.00  0.00           C  
HETATM   38  H1  UNL     1       2.365   5.667   2.521  1.00  0.00           H  
HETATM   39  H2  UNL     1       2.092   4.876   0.898  1.00  0.00           H  
HETATM   40  H3  UNL     1       2.741   6.515   0.984  1.00  0.00           H  
HETATM   41  H4  UNL     1       5.401   3.657   2.176  1.00  0.00           H  
HETATM   42  H5  UNL     1       4.031   4.014   3.279  1.00  0.00           H  
HETATM   43  H6  UNL     1       3.872   2.567   0.613  1.00  0.00           H  
HETATM   44  H7  UNL     1       3.958   1.719   2.222  1.00  0.00           H  
HETATM   45  H8  UNL     1       1.363   1.086   2.221  1.00  0.00           H  
HETATM   46  H9  UNL     1       0.328   2.453   1.740  1.00  0.00           H  
HETATM   47  H10 UNL     1       1.203   2.341  -0.640  1.00  0.00           H  
HETATM   48  H11 UNL     1       0.468  -0.492   0.245  1.00  0.00           H  
HETATM   49  H12 UNL     1       0.281   0.209  -1.346  1.00  0.00           H  
HETATM   50  H13 UNL     1      -3.945   0.222  -0.105  1.00  0.00           H  
HETATM   51  H14 UNL     1      -3.452  -2.475  -1.384  1.00  0.00           H  
HETATM   52  H15 UNL     1      -4.281  -2.184   1.047  1.00  0.00           H  
HETATM   53  H16 UNL     1      -4.995  -3.452   0.031  1.00  0.00           H  
HETATM   54  H17 UNL     1      -6.767  -2.425   1.166  1.00  0.00           H  
HETATM   55  H18 UNL     1      -6.225  -0.734   0.749  1.00  0.00           H  
HETATM   56  H19 UNL     1      -7.212  -2.838  -1.239  1.00  0.00           H  
HETATM   57  H20 UNL     1      -7.869   0.698  -0.076  1.00  0.00           H  
HETATM   58  H21 UNL     1      -6.387   0.121  -1.360  1.00  0.00           H  
HETATM   59  H22 UNL     1      -7.037  -0.834  -2.752  1.00  0.00           H  
HETATM   60  H23 UNL     1      -4.527  -0.590  -2.770  1.00  0.00           H  
HETATM   61  H24 UNL     1      -5.175  -2.239  -2.910  1.00  0.00           H  
HETATM   62  H25 UNL     1      -2.392  -0.163   1.613  1.00  0.00           H  
HETATM   63  H26 UNL     1      -0.894   0.588   2.095  1.00  0.00           H  
HETATM   64  H27 UNL     1      -3.540   1.733   1.780  1.00  0.00           H  
HETATM   65  H28 UNL     1      -2.049   2.454   2.571  1.00  0.00           H  
HETATM   66  H29 UNL     1      -3.217   3.361   0.247  1.00  0.00           H  
HETATM   67  H30 UNL     1      -1.446   3.596   0.662  1.00  0.00           H  
HETATM   68  H31 UNL     1      -2.897   1.623  -1.136  1.00  0.00           H  
HETATM   69  H32 UNL     1      -1.353   2.367  -1.490  1.00  0.00           H  
HETATM   70  H33 UNL     1       5.473   0.181   1.329  1.00  0.00           H  
HETATM   71  H34 UNL     1       7.403  -1.137   0.783  1.00  0.00           H  
HETATM   72  H35 UNL     1       3.043  -2.461  -1.017  1.00  0.00           H  
HETATM   73  H36 UNL     1       4.822  -5.018  -1.307  1.00  0.00           H  
HETATM   74  H37 UNL     1       4.833  -3.871  -2.757  1.00  0.00           H  
HETATM   75  H38 UNL     1       7.082  -5.303  -1.939  1.00  0.00           H  
HETATM   76  H39 UNL     1       7.103  -3.763  -2.932  1.00  0.00           H  
HETATM   77  H40 UNL     1       7.654  -4.181  -0.016  1.00  0.00           H  
HETATM   78  H41 UNL     1       8.343  -2.966  -1.151  1.00  0.00           H  
CONECT    1    2   38   39   40
CONECT    2    3
CONECT    3    4   41   42
CONECT    4    5   43   44
CONECT    5    6
CONECT    6    7   45   46
CONECT    7    8   26   47
CONECT    8    9   48   49
CONECT    9   10   22   25
CONECT   10   11   11   12
CONECT   12   13   50
CONECT   13   14   21   51
CONECT   14   15   52   53
CONECT   15   16   54   55
CONECT   16   17   20   56
CONECT   17   18   18   19
CONECT   19   57
CONECT   20   21   58   59
CONECT   21   60   61
CONECT   22   23   62   63
CONECT   23   24   64   65
CONECT   24   25   66   67
CONECT   25   68   69
CONECT   26   27   27   28
CONECT   28   29
CONECT   29   30   30   34
CONECT   30   31   70
CONECT   31   32   32   71
CONECT   32   33   37
CONECT   33   34   34   35
CONECT   34   72
CONECT   35   36   73   74
CONECT   36   37   75   76
CONECT   37   77   78
END

HMDB0014754
     RDKit          3D
Candoxatril
 78 81  0  0  0  0  0  0  0  0999 V2000
    2.7665    5.4930    1.5014 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0414    5.0103    1.5377 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3075    3.8683    2.1933 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5708    2.6170    1.6857 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2613    2.8336    1.8095 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3141    1.9298    1.4827 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1765    1.4670    0.0858 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1267    0.4962   -0.2430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3030    0.6965   -0.0785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0353   -0.5391   -0.6073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3887   -1.4755   -1.0974 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4338   -0.5948   -0.5297 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2019   -1.7438   -1.0147 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9230   -2.3603    0.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2710   -1.7867    0.4072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1100   -1.8012   -0.8525 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.4525   -1.2450   -0.5846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4852   -1.9533   -0.7651 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6462    0.0440   -0.1345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4089   -0.8783   -1.8387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0501   -1.3872   -2.1993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7059    0.7255    1.3787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4546    1.9821    1.6459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2409    2.8541    0.4466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9153    1.9060   -0.6524 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4526    0.7309   -0.3008 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1042    0.9976   -1.3332 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9357   -0.2882    0.4965 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0676   -1.0212    0.2035 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2882   -0.6707    0.6926 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4448   -1.4099    0.3999 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3530   -2.5262   -0.4063 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1449   -2.8982   -0.9087 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0069   -2.1590   -0.6119 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2793   -4.1310   -1.7600 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7677   -4.2326   -1.9677 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4203   -3.4741   -0.8582 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3649    5.6673    2.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0924    4.8761    0.8982 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7407    6.5145    0.9841 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4014    3.6572    2.1761 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0308    4.0141    3.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8715    2.5673    0.6132 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9576    1.7193    2.2217 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3631    1.0855    2.2212 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3285    2.4534    1.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2026    2.3413   -0.6404 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4678   -0.4920    0.2449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2805    0.2089   -1.3464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9454    0.2223   -0.1053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4519   -2.4752   -1.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2815   -2.1838    1.0469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9950   -3.4523    0.0310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7671   -2.4249    1.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2249   -0.7343    0.7489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2120   -2.8376   -1.2391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8692    0.6977   -0.0761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3865    0.1211   -1.3595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0369   -0.8335   -2.7515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5268   -0.5895   -2.7703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1749   -2.2393   -2.9099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3921   -0.1628    1.6129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8945    0.5878    2.0954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5398    1.7329    1.7798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0486    2.4539    2.5712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2169    3.3611    0.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4457    3.5963    0.6622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8973    1.6231   -1.1361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3535    2.3673   -1.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4728    0.1806    1.3289 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4033   -1.1367    0.7834 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0427   -2.4609   -1.0165 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8215   -5.0179   -1.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8327   -3.8710   -2.7569 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0817   -5.3026   -1.9390 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1028   -3.7627   -2.9320 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6542   -4.1814   -0.0162 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3432   -2.9661   -1.1507 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 16 20  1  0
 20 21  1  0
  9 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
  7 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 33 35  1  0
 35 36  1  0
 36 37  1  0
 25  9  1  0
 34 29  1  0
 21 13  1  0
 37 32  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  3 41  1  0
  3 42  1  0
  4 43  1  0
  4 44  1  0
  6 45  1  0
  6 46  1  0
  7 47  1  6
  8 48  1  0
  8 49  1  0
 12 50  1  0
 13 51  1  6
 14 52  1  0
 14 53  1  0
 15 54  1  0
 15 55  1  0
 16 56  1  6
 19 57  1  0
 20 58  1  0
 20 59  1  0
 21 60  1  0
 21 61  1  0
 22 62  1  0
 22 63  1  0
 23 64  1  0
 23 65  1  0
 24 66  1  0
 24 67  1  0
 25 68  1  0
 25 69  1  0
 30 70  1  0
 31 71  1  0
 34 72  1  0
 35 73  1  0
 35 74  1  0
 36 75  1  0
 36 76  1  0
 37 77  1  0
 37 78  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-({1-[(S)-2-(indan-5-yloxycarbonyl)-3-(2-methoxy-ethoxy)-propyl]-cyclopentanecarbonyl}-amino)-cyclohexanecarboxylic acid	ChEBI
[4(S)-cis]-4-[[[1-[3-[(2,3-Dihydro-1H-indeb5-yl)oxy]-2-[(2-methoxyethoxy)methyl]-3-oxopropyl]cyclopentyl]carbonyl]amino]cyclohexanecarboxylic acid	ChEBI
4-({1-[(S)-2-(indan-5-yloxycarbonyl)-3-(2-methoxy-ethoxy)-propyl]-cyclopentanecarbonyl}-amino)-cyclohexanecarboxylate	Generator
[4(S)-cis]-4-[[[1-[3-[(2,3-Dihydro-1H-indeb5-yl)oxy]-2-[(2-methoxyethoxy)methyl]-3-oxopropyl]cyclopentyl]carbonyl]amino]cyclohexanecarboxylate	Generator

Chemical Formula

C₂₉H₄₁NO₇

Average Molecular Weight

515.6383

Monoisotopic Molecular Weight

515.288302671

IUPAC Name

(1s,4s)-4-{1-[(2S)-3-(2,3-dihydro-1H-inden-5-yloxy)-2-[(2-methoxyethoxy)methyl]-3-oxopropyl]cyclopentaneamido}cyclohexane-1-carboxylic acid

Traditional Name

candoxatril

CAS Registry Number

118785-03-8

SMILES

COCCOC[C@H](CC1(CCCC1)C(=O)N[C@H]1CC[C@H](CC1)C(O)=O)C(=O)OC1=CC2=C(CCC2)C=C1

InChI Identifier

InChI=1S/C29H41NO7/c1-35-15-16-36-19-23(27(33)37-25-12-9-20-5-4-6-22(20)17-25)18-29(13-2-3-14-29)28(34)30-24-10-7-21(8-11-24)26(31)32/h9,12,17,21,23-24H,2-8,10-11,13-16,18-19H2,1H3,(H,30,34)(H,31,32)/t21-,23-,24+/m0/s1

InChI Key

ZTWZVMIYIIVABD-OEMFJLHTSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indanes. Indanes are compounds containing an indane moiety, which consists of a cyclopentane fused to a benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Indanes

Sub Class

Not Available

Direct Parent

Indanes

Alternative Parents

Substituents

Indane
Fatty acid ester
Dicarboxylic acid or derivatives
Fatty amide
Fatty acyl
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid ester
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

dicarboxylic acid monoester (CHEBI:3353 )
monocarboxylic acid (CHEBI:3353 )
monocarboxylic acid amide (CHEBI:3353 )

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

Extracellular (HMDB: HMDB0014754)
Membrane (HMDB: HMDB0014754)

Source

Exogenous

Exogenous (HMDB: HMDB0014754)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0022 g/L	Not Available
LogP	3.7	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0022 g/L	ALOGPS
logP	3.55	ALOGPS
logP	4.68	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	4.29	ChemAxon
pKa (Strongest Basic)	1.32	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	111.16 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	138.16 m³·mol⁻¹	ChemAxon
Polarizability	57.2 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	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]+	219.29	31661259
DarkChem	[M-H]-	220.798	31661259
DeepCCS	[M+H]+	221.983	30932474
DeepCCS	[M-H]-	219.588	30932474
DeepCCS	[M-2H]-	252.745	30932474
DeepCCS	[M+Na]+	227.946	30932474
AllCCS	[M+H]+	219.8	32859911
AllCCS	[M+H-H2O]+	218.6	32859911
AllCCS	[M+NH4]+	220.9	32859911
AllCCS	[M+Na]+	221.3	32859911
AllCCS	[M-H]-	203.4	32859911
AllCCS	[M+Na-2H]-	205.3	32859911
AllCCS	[M+HCOO]-	207.6	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.	7.8 minutes	32390414
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.	6.98 minutes	32390414
Predicted by Siyang on May 30, 2022	18.3396 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.3 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	45.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3345.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	260.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	248.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	183.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	392.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	734.2 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	746.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	117.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1730.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	710.4 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	1923.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	469.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	479.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	248.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	195.9 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	10.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Candoxatril	COCCOC[C@H](CC1(CCCC1)C(=O)N[C@H]1CC[C@H](CC1)C(O)=O)C(=O)OC1=CC2=C(CCC2)C=C1	4811.4	Standard polar	33892256
Candoxatril	COCCOC[C@H](CC1(CCCC1)C(=O)N[C@H]1CC[C@H](CC1)C(O)=O)C(=O)OC1=CC2=C(CCC2)C=C1	3973.4	Standard non polar	33892256
Candoxatril	COCCOC[C@H](CC1(CCCC1)C(=O)N[C@H]1CC[C@H](CC1)C(O)=O)C(=O)OC1=CC2=C(CCC2)C=C1	3922.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Candoxatril,1TMS,isomer #1	COCCOC[C@H](CC1(C(=O)N[C@H]2CC[C@@H](C(=O)O[Si](C)(C)C)CC2)CCCC1)C(=O)OC1=CC=C2CCCC2=C1	3935.2	Semi standard non polar	33892256
Candoxatril,1TMS,isomer #2	COCCOC[C@H](CC1(C(=O)N([C@H]2CC[C@@H](C(=O)O)CC2)[Si](C)(C)C)CCCC1)C(=O)OC1=CC=C2CCCC2=C1	4063.8	Semi standard non polar	33892256
Candoxatril,2TMS,isomer #1	COCCOC[C@H](CC1(C(=O)N([C@H]2CC[C@@H](C(=O)O[Si](C)(C)C)CC2)[Si](C)(C)C)CCCC1)C(=O)OC1=CC=C2CCCC2=C1	3960.0	Semi standard non polar	33892256
Candoxatril,2TMS,isomer #1	COCCOC[C@H](CC1(C(=O)N([C@H]2CC[C@@H](C(=O)O[Si](C)(C)C)CC2)[Si](C)(C)C)CCCC1)C(=O)OC1=CC=C2CCCC2=C1	3752.0	Standard non polar	33892256
Candoxatril,2TMS,isomer #1	COCCOC[C@H](CC1(C(=O)N([C@H]2CC[C@@H](C(=O)O[Si](C)(C)C)CC2)[Si](C)(C)C)CCCC1)C(=O)OC1=CC=C2CCCC2=C1	4730.7	Standard polar	33892256
Candoxatril,1TBDMS,isomer #1	COCCOC[C@H](CC1(C(=O)N[C@H]2CC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)CC2)CCCC1)C(=O)OC1=CC=C2CCCC2=C1	4177.0	Semi standard non polar	33892256
Candoxatril,1TBDMS,isomer #2	COCCOC[C@H](CC1(C(=O)N([C@H]2CC[C@@H](C(=O)O)CC2)[Si](C)(C)C(C)(C)C)CCCC1)C(=O)OC1=CC=C2CCCC2=C1	4288.4	Semi standard non polar	33892256
Candoxatril,2TBDMS,isomer #1	COCCOC[C@H](CC1(C(=O)N([C@H]2CC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)CC2)[Si](C)(C)C(C)(C)C)CCCC1)C(=O)OC1=CC=C2CCCC2=C1	4408.7	Semi standard non polar	33892256
Candoxatril,2TBDMS,isomer #1	COCCOC[C@H](CC1(C(=O)N([C@H]2CC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)CC2)[Si](C)(C)C(C)(C)C)CCCC1)C(=O)OC1=CC=C2CCCC2=C1	4132.6	Standard non polar	33892256
Candoxatril,2TBDMS,isomer #1	COCCOC[C@H](CC1(C(=O)N([C@H]2CC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)CC2)[Si](C)(C)C(C)(C)C)CCCC1)C(=O)OC1=CC=C2CCCC2=C1	4847.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Candoxatril GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-8903400000-268da98bf001b2697ad3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Candoxatril GC-MS (1 TMS) - 70eV, Positive	splash10-00ea-9701230000-415d420bb3afba46e038	2017-10-06	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Candoxatril 90V, Positive-QTOF	splash10-00pl-9200000000-bc11c66d3ece45e09e88	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Candoxatril 75V, Positive-QTOF	splash10-00pi-9600000000-83441da8ede7797f50e7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Candoxatril 45V, Positive-QTOF	splash10-057r-2900000000-60fd63861087a3fe92d9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Candoxatril 60V, Positive-QTOF	splash10-057i-6900000000-d1197406ad3d8cefddfa	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Candoxatril 45V, Positive-QTOF	splash10-057r-2900000000-0e86e71ecc29989958e8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Candoxatril 15V, Positive-QTOF	splash10-053r-0009000000-f592f37f904e3e76bf19	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Candoxatril 30V, Positive-QTOF	splash10-0569-1986000000-e7ba3bddb330c80b7ce9	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Candoxatril 10V, Positive-QTOF	splash10-014i-0714950000-0d88710626c10ccc6895	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Candoxatril 20V, Positive-QTOF	splash10-014i-1924400000-1212988199020b7a6e78	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Candoxatril 40V, Positive-QTOF	splash10-015c-4951100000-c7b3c19e54fc433cebc6	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Candoxatril 10V, Negative-QTOF	splash10-03di-2302690000-82a62f70e9d322ce04e4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Candoxatril 20V, Negative-QTOF	splash10-0h60-1409510000-c92b3392f22113ddb47a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Candoxatril 40V, Negative-QTOF	splash10-001i-6910000000-a9c7701cff60595f6454	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Candoxatril 10V, Positive-QTOF	splash10-014i-0001390000-c54e9b5c348fb0757710	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Candoxatril 20V, Positive-QTOF	splash10-017i-3386960000-eb7472fe7ae253206129	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Candoxatril 40V, Positive-QTOF	splash10-0170-6921420000-e5f0c1c9c0d663cf9dff	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Candoxatril 10V, Negative-QTOF	splash10-0bt9-0010910000-64ff1f2df639c0ba09b2	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Candoxatril 20V, Negative-QTOF	splash10-000f-0736910000-09ca3f3a4172911e6edc	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Candoxatril 40V, Negative-QTOF	splash10-01ox-8912370000-d08f092f5a2aef1c655f	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
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 DB00616	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00616	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00616

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

16736409

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Candoxatril

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

3353

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

Not Available

Enzymes

Enzyme Details

1. Angiotensin-converting enzyme

General function:: Involved in metallopeptidase activity
Specific function:: Converts angiotensin I to angiotensin II by release of the terminal His-Leu, this results in an increase of the vasoconstrictor activity of angiotensin. Also able to inactivate bradykinin, a potent vasodilator. Has also a glycosidase activity which releases GPI-anchored proteins from the membrane by cleaving the mannose linkage in the GPI moiety
Gene Name:: ACE
Uniprot ID:: P12821
Molecular weight:: 149713.7

References

Dumoulin MJ, Adam A, Rouleau JL, Lamontagne D: Comparison of a vasopeptidase inhibitor with neutral endopeptidase and angiotensin-converting enzyme inhibitors on bradykinin metabolism in the rat coronary bed. J Cardiovasc Pharmacol. 2001 Apr;37(4):359-66. [PubMed:11300648 ]
Kostova E, Jovanoska E, Zafirov D, Jakovski K, Maleska V, Slaninka-Miceska M: Dual inhibition of angiotensin converting enzyme and neutral endopeptidase produces effective blood pressure control in spontaneously hypertensive rats. Bratisl Lek Listy. 2005;106(12):407-11. [PubMed:16642666 ]

Enzyme Details

2. Neprilysin

General function:: Involved in metalloendopeptidase activity
Specific function:: Thermolysin-like specificity, but is almost confined on acting on polypeptides of up to 30 amino acids. Biologically important in the destruction of opioid peptides such as Met- and Leu-enkephalins by cleavage of a Gly-Phe bond. Able to cleave angiotensin-1, angiotensin-2 and angiotensin 1-9. Involved in the degradation of atrial natriuretic factor (ANF)
Gene Name:: MME
Uniprot ID:: P08473
Molecular weight:: 85513.2

References

O'Connell JE, Jardine AG, Davidson G, Connell JM: Candoxatril, an orally active neutral endopeptidase inhibitor, raises plasma atrial natriuretic factor and is natriuretic in essential hypertension. J Hypertens. 1992 Mar;10(3):271-7. [PubMed:1315825 ]
Elsner D, Muntze A, Kromer EP, Riegger GA: Effectiveness of endopeptidase inhibition (candoxatril) in congestive heart failure. Am J Cardiol. 1992 Aug 15;70(4):494-8. [PubMed:1386491 ]
Plamboeck A, Holst JJ, Carr RD, Deacon CF: Neutral endopeptidase 24.11 and dipeptidyl peptidase IV are both mediators of the degradation of glucagon-like peptide 1 in the anaesthetised pig. Diabetologia. 2005 Sep;48(9):1882-90. Epub 2005 Jul 16. [PubMed:16025254 ]
Sansoe G, Aragno M, Mastrocola R, Cutrin JC, Silvano S, Mengozzi G, Smedile A, Rosina F, Danni O, Rizzetto M: Overexpression of kidney neutral endopeptidase (EC 3.4.24.11) and renal function in experimental cirrhosis. Am J Physiol Renal Physiol. 2006 Jun;290(6):F1337-43. Epub 2006 Jan 31. [PubMed:16449355 ]
Hirata Y, Suzuki E, Hayakawa H, Matsuoka H, Sugimoto T, Kangawa K, Matsuo H: Mechanisms of the natriuretic effects of neutral endopeptidase inhibition in Dahl salt-sensitive and salt-resistant rats. J Cardiovasc Pharmacol. 1994 Feb;23(2):283-90. [PubMed:7511759 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Candoxatril (HMDB0014754)

MOL for HMDB0014754 (Candoxatril)

3D MOL for HMDB0014754 (Candoxatril)

3D SDF for HMDB0014754 (Candoxatril)

3D-SDF for HMDB0014754 (Candoxatril)

PDB for HMDB0014754 (Candoxatril)

3D PDB for HMDB0014754 (Candoxatril)

SMILES for HMDB0014754 (Candoxatril)

INCHI for HMDB0014754 (Candoxatril)

Structure for HMDB0014754 (Candoxatril)

3D Structure for HMDB0014754 (Candoxatril)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References