NP-MRD: Showing NP-Card for Stercobilinogen (NP0136905)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-05-12 15:26:43 UTC

Updated at

2022-05-12 15:26:43 UTC

NP-MRD ID

NP0136905

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Stercobilinogen

Description

Stercobilinogen belongs to the class of organic compounds known as bilirubins. These are organic compounds containing a dicarboxylic acyclic tetrapyrrole derivative. Stercobilinogen is an extremely weak basic (essentially neutral) compound (based on its pKa). It is further processed to become the chemical that gives feces its brown color. It is made of broken-down hemoglobin. Stercobilinogen (fecal urobilinogen) is a chemical created by bacteria in the gut. Bilirubin is a pigment that results from the breakdown of the heme portion of hemoglobin. Stercobilinogen is oxidized to stercobilin, which is responsible for the pigmentation of feces. In the intestine, bilirubin is converted by bacteria to stercobilinogen. Stercobilinogen is absorbed and excreted by either the liver or the kidney. The liver conjugates bilirubin, making it water-soluble; and the conjugated form is then excreted in urine as urobilinogen, giving urine its color. This happens because "Stercobilinogen" is simply the name given to Urobilinogen in the GI tract; and in fact its use as a separate term has fallen out of favor due to the confusion. Stercobilinogen was first documented in 2006 (PMID: 16504607). In early liver disease, impaired biliary excretion causes sterocobilinogen to be absorbed mostly by the kidney, and, therefore, stercobilinogen will appear in the urine in excess as urobilinogen.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304202022172D          

 45 48  0  0  0  0            999 V2000
   -1.8645   -1.4462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846   -2.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0395   -1.4462    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1195   -2.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9041   -2.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4520   -2.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1207    0.9669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2069    0.1464    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8744    1.3024    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0459    2.1094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4264    0.6893    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2469    0.7756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5824    1.5290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4062    1.3794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -2.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8646   -1.4462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0396   -1.4462    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1195   -2.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9042   -2.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4521   -2.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4521   -3.5408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1666   -3.9533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4521   -5.1908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1666   -4.7783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8809   -5.1908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4265    0.6893    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2469    0.7756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8744    1.3024    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0460    2.1094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8306    2.3643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2070    0.1464    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1207    0.9669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4063    1.3794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3495   -0.7788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3495   -0.7788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4520   -3.5408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1665   -3.9533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8809   -5.1908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1665   -4.7783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4520   -5.1908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0139   -0.0251    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8389   -0.0251    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0139   -0.0251    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8390   -0.0251    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 35  1  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  6  2  2  0  0  0  0
  3  2  1  0  0  0  0
  2 26  1  0  0  0  0
  4  6  1  0  0  0  0
  4  5  1  0  0  0  0
  6 37  1  0  0  0  0
 14  7  2  0  0  0  0
  7  8  1  0  0  0  0
  9  7  1  0  0  0  0
 42 35  1  0  0  0  0
  8 42  1  0  0  0  0
 11 42  1  0  0  0  0
  9 11  1  0  0  0  0
  9 10  1  1  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 15 26  1  0  0  0  0
 17 15  1  0  0  0  0
 20 15  2  0  0  0  0
 36 16  1  0  0  0  0
 17 16  1  0  0  0  0
 18 16  2  0  0  0  0
 18 20  1  0  0  0  0
 18 19  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 24  1  0  0  0  0
 24 23  2  0  0  0  0
 24 25  1  0  0  0  0
 44 32  1  0  0  0  0
 27 44  1  0  0  0  0
 36 44  1  0  0  0  0
 29 27  1  0  0  0  0
 27 28  1  1  0  0  0
 29 33  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 37 38  1  0  0  0  0
 38 40  1  0  0  0  0
 40 39  2  0  0  0  0
 40 41  1  0  0  0  0
 42 43  1  6  0  0  0
 44 45  1  1  0  0  0
M  END

     RDKit          3D

 91 94  0  0  0  0  0  0  0  0999 V2000
    9.4570   -0.8737    1.1961 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1693    0.5958    1.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7753    0.9535    0.7443 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3706    0.4190   -0.6100 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1037    0.0644   -1.5613 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9303    0.3905   -0.6045 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4838    0.4134    0.7243 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4155   -0.5795    1.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2141   -0.3537    0.2945 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2597    0.5436    0.6140 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3295    0.6080   -0.3486 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1794    1.5438   -0.2663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0970    0.8974    0.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0408    0.6598   -0.9297 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0619   -0.0121   -0.3486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2824   -0.4270   -1.0833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4386    0.4840   -0.8692 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8055    0.5446    0.5118 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8140   -0.4477    0.6914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9803   -1.1532    1.7240 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5947   -0.4506   -0.5841 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.9428   -1.8814   -0.9151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6779    0.1019   -1.6321 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.3027    1.3834   -2.1936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5503    1.1070   -2.9713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7690   -0.1973    0.9739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6033   -0.9013    1.9797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5064    0.3847    1.2423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9585    0.4350    2.5906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5264    1.4268    3.5280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4851    2.8333    3.1774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0750    3.3666    2.1411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9835    3.7796    4.1365 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6433   -0.2626   -1.3530 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9191   -0.5452   -2.6054 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0414   -1.7336   -2.6326 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7201   -3.0078   -2.3690 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7113   -3.4037   -1.1521 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3417   -3.7603   -3.3444 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8448   -0.8681   -0.9304 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5888   -1.9147   -1.6715 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7095    0.2913    1.5917 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5168    1.0222    2.9037 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5451   -0.9601    1.4844 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9032   -1.3060    2.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2844   -1.4006    0.2502 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8399    1.0947    0.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4043    1.0645    2.0940 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6699    2.0487    0.7932 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3153    0.3746   -1.4627 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0810    1.4741    0.9272 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7637   -1.6274    0.9663 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1392   -0.4597    2.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2747    1.0992    1.5066 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3843    2.3590    0.4068 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1454    2.0210   -1.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9549    0.9553   -1.9277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4944   -1.4721   -0.7536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0740   -0.4946   -2.1759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1150    1.5097   -1.2067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4054    1.1908    1.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5023    0.1780   -0.4799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9821   -2.1262   -0.5656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2448   -2.5732   -0.3754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8551   -2.0901   -1.9934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4990   -0.5749   -2.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5847    2.0417   -1.3288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5564    1.9745   -2.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3947    0.2454   -3.6594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4192    0.8686   -2.3184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8178    2.0258   -3.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2831   -1.6446    1.4672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1495   -0.2475    2.6573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9595   -1.5698    2.6285 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1598    0.6281    2.5823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0936   -0.6191    3.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5984    1.1653    3.8124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9168    1.3443    4.4941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9904    3.6540    4.2848 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3419    0.3945   -2.8717 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6482   -0.6075   -3.4794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8300   -1.5793   -1.9454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4067   -1.8420   -3.6717 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3130   -3.9744   -3.4186 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6844   -1.8505   -1.5337 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3498   -1.9254   -2.7461 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3491   -2.9403   -1.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9147   -0.7799    1.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4621    1.5265    3.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6571    1.7010    2.8002 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2685    0.2494    3.6742 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0
  8  9  1  0
  9 40  2  0
 40 41  1  0
 40 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 39  1  0
 37 38  2  0
 34 11  2  0
 11 12  1  0
 12 13  1  0
 13 28  2  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 33  1  0
 31 32  2  0
 28 26  1  0
 26 27  1  0
 26 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 15 14  1  0
 11 10  1  0
  7  6  1  0
  6  4  1  0
  4  5  2  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
  3 42  1  0
 42 43  1  0
 42  7  1  0
 10  9  1  0
 14 13  1  0
 23 17  1  0
  7 51  1  1
  8 52  1  0
  8 53  1  0
 41 85  1  0
 41 86  1  0
 41 87  1  0
 35 80  1  0
 35 81  1  0
 36 82  1  0
 36 83  1  0
 39 84  1  0
 12 55  1  0
 12 56  1  0
 29 75  1  0
 29 76  1  0
 30 77  1  0
 30 78  1  0
 33 79  1  0
 27 72  1  0
 27 73  1  0
 27 74  1  0
 16 58  1  0
 16 59  1  0
 17 60  1  6
 18 61  1  0
 21 62  1  1
 22 63  1  0
 22 64  1  0
 22 65  1  0
 23 66  1  6
 24 67  1  0
 24 68  1  0
 25 69  1  0
 25 70  1  0
 25 71  1  0
 14 57  1  0
 10 54  1  0
  6 50  1  0
  3 49  1  6
  2 47  1  0
  2 48  1  0
  1 44  1  0
  1 45  1  0
  1 46  1  0
 42 88  1  1
 43 89  1  0
 43 90  1  0
 43 91  1  0
M  END


  Mrv1652304202022172D          

 45 48  0  0  0  0            999 V2000
   -1.8645   -1.4462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846   -2.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0395   -1.4462    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1195   -2.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9041   -2.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4520   -2.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1207    0.9669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2069    0.1464    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8744    1.3024    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0459    2.1094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4264    0.6893    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2469    0.7756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5824    1.5290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4062    1.3794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -2.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8646   -1.4462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0396   -1.4462    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1195   -2.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9042   -2.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4521   -2.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4521   -3.5408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1666   -3.9533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4521   -5.1908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1666   -4.7783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8809   -5.1908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4265    0.6893    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2469    0.7756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8744    1.3024    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0460    2.1094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8306    2.3643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2070    0.1464    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1207    0.9669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4063    1.3794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3495   -0.7788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3495   -0.7788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4520   -3.5408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1665   -3.9533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8809   -5.1908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1665   -4.7783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4520   -5.1908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0139   -0.0251    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8389   -0.0251    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0139   -0.0251    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8390   -0.0251    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 35  1  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  6  2  2  0  0  0  0
  3  2  1  0  0  0  0
  2 26  1  0  0  0  0
  4  6  1  0  0  0  0
  4  5  1  0  0  0  0
  6 37  1  0  0  0  0
 14  7  2  0  0  0  0
  7  8  1  0  0  0  0
  9  7  1  0  0  0  0
 42 35  1  0  0  0  0
  8 42  1  0  0  0  0
 11 42  1  0  0  0  0
  9 11  1  0  0  0  0
  9 10  1  1  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 15 26  1  0  0  0  0
 17 15  1  0  0  0  0
 20 15  2  0  0  0  0
 36 16  1  0  0  0  0
 17 16  1  0  0  0  0
 18 16  2  0  0  0  0
 18 20  1  0  0  0  0
 18 19  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 24  1  0  0  0  0
 24 23  2  0  0  0  0
 24 25  1  0  0  0  0
 44 32  1  0  0  0  0
 27 44  1  0  0  0  0
 36 44  1  0  0  0  0
 29 27  1  0  0  0  0
 27 28  1  1  0  0  0
 29 33  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 37 38  1  0  0  0  0
 38 40  1  0  0  0  0
 40 39  2  0  0  0  0
 40 41  1  0  0  0  0
 42 43  1  6  0  0  0
 44 45  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0136905

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CC2=C(C)C(CCC(O)=O)=C(CC3=C(CCC(O)=O)C(C)=C(C[C@]4([H])NC(=O)[C@H](C)[C@H]4CC)N3)N2)NC(=O)[C@H](CC)[C@H]1C

> <INCHI_IDENTIFIER>
InChI=1S/C33H48N4O6/c1-7-20-19(6)32(42)37-27(20)14-25-18(5)23(10-12-31(40)41)29(35-25)15-28-22(9-11-30(38)39)17(4)24(34-28)13-26-16(3)21(8-2)33(43)36-26/h16,19-21,26-27,34-35H,7-15H2,1-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/t16-,19-,20-,21-,26+,27+/m1/s1

> <INCHI_KEY>
VKGRRZVYCXLHII-OLFWPHQKSA-N

> <FORMULA>
C33H48N4O6

> <MOLECULAR_WEIGHT>
596.769

> <EXACT_MASS>
596.357385282

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
91

> <JCHEM_AVERAGE_POLARIZABILITY>
68.39767606637673

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(2-{[3-(2-carboxyethyl)-5-{[(2S,3R,4R)-4-ethyl-3-methyl-5-oxopyrrolidin-2-yl]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2S,3R,4R)-3-ethyl-4-methyl-5-oxopyrrolidin-2-yl]methyl}-4-methyl-1H-pyrrol-3-yl)propanoic acid

> <ALOGPS_LOGP>
2.96

> <JCHEM_LOGP>
3.9994254876666675

> <ALOGPS_LOGS>
-4.64

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.649226694644768

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.046446349310869

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8877558453654916

> <JCHEM_POLAR_SURFACE_AREA>
164.38

> <JCHEM_REFRACTIVITY>
164.97719999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.38e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-stercobilinogen

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-20         0                                  
HETATM    1  C   UNK     0      -3.480  -2.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.465  -4.164   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -1.940  -2.700   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -3.956  -4.164   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.421  -4.640   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.710  -5.069   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.092   1.805   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      -2.253   0.273   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -3.499   2.431   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.819   3.938   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.529   1.287   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.061   1.448   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.687   2.854   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.758   2.575   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.465  -4.164   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.481  -2.700   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       1.941  -2.700   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       3.956  -4.164   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.421  -4.640   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.711  -5.069   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.711  -6.609   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.044  -7.379   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.711  -9.689   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.044  -8.919   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.378  -9.689   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.000  -4.640   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.529   1.287   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.061   1.448   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.499   2.431   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.819   3.938   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.284   4.413   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0       2.253   0.273   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0       2.092   1.805   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       0.758   2.575   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -4.386  -1.454   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.386  -1.454   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -2.710  -6.609   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -4.044  -7.379   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -5.378  -9.689   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -4.044  -8.919   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -2.710  -9.689   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -3.759  -0.047   0.000  0.00  0.00           C+0
HETATM   43  H   UNK     0      -5.299  -0.047   0.000  0.00  0.00           H+0
HETATM   44  C   UNK     0       3.759  -0.047   0.000  0.00  0.00           C+0
HETATM   45  H   UNK     0       5.299  -0.047   0.000  0.00  0.00           H+0
CONECT    1   35    3    4                                                  
CONECT    2    6    3   26                                                  
CONECT    3    1    2                                                       
CONECT    4    1    6    5                                                  
CONECT    5    4                                                            
CONECT    6    2    4   37                                                  
CONECT    7   14    8    9                                                  
CONECT    8    7   42                                                       
CONECT    9    7   11   10                                                  
CONECT   10    9                                                            
CONECT   11   42    9   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14    7                                                            
CONECT   15   26   17   20                                                  
CONECT   16   36   17   18                                                  
CONECT   17   15   16                                                       
CONECT   18   16   20   19                                                  
CONECT   19   18                                                            
CONECT   20   15   18   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   24                                                       
CONECT   23   24                                                            
CONECT   24   22   23   25                                                  
CONECT   25   24                                                            
CONECT   26    2   15                                                       
CONECT   27   44   29   28                                                  
CONECT   28   27                                                            
CONECT   29   27   33   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32   44   33                                                       
CONECT   33   29   32   34                                                  
CONECT   34   33                                                            
CONECT   35    1   42                                                       
CONECT   36   16   44                                                       
CONECT   37    6   38                                                       
CONECT   38   37   40                                                       
CONECT   39   40                                                            
CONECT   40   38   39   41                                                  
CONECT   41   40                                                            
CONECT   42   35    8   11   43                                             
CONECT   43   42                                                            
CONECT   44   32   27   36   45                                             
CONECT   45   44                                                            
MASTER        0    0    0    0    0    0    0    0   45    0   96    0
END

View in JSmol

Synonyms

Value	Source
(2R,3R,4S,16S,17R,18R)-2,17-Diethyl-1,2,3,4,5,10,15,16,17,18,19,22,23,24-tetradecahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoic acid	ChEBI
L-Stercobilinogen	ChEBI
(2R,3R,4S,16S,17R,18R)-2,17-Diethyl-1,2,3,4,5,10,15,16,17,18,19,22,23,24-tetradecahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoate	Generator
Stercobilinogen ixα	HMDB
(-)-2,17-Diethyl-1,2,3,4,5,10,15,16,17,18,19,22,23,24-tetradecahydro-3,7,13,18-tetramethyl-1,19-dioxo-biline-8,12-dipropionic acid	HMDB
(-)-Stercobilinogen	HMDB
L-Urobilinogen	HMDB
Stercobilinogen ixalpha	HMDB
Stercobilinogen	ChEBI

Chemical Formula

C₃₃H₄₈N₄O₆

Average Mass

596.7690 Da

Monoisotopic Mass

596.35739 Da

IUPAC Name

3-(2-{[3-(2-carboxyethyl)-5-{[(2S,3R,4R)-4-ethyl-3-methyl-5-oxopyrrolidin-2-yl]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2S,3R,4R)-3-ethyl-4-methyl-5-oxopyrrolidin-2-yl]methyl}-4-methyl-1H-pyrrol-3-yl)propanoic acid

Traditional Name

(-)-stercobilinogen

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC2=C(C)C(CCC(O)=O)=C(CC3=C(CCC(O)=O)C(C)=C(C[C@]4([H])NC(=O)[C@H](C)[C@H]4CC)N3)N2)NC(=O)[C@H](CC)[C@H]1C

InChI Identifier

InChI=1S/C33H48N4O6/c1-7-20-19(6)32(42)37-27(20)14-25-18(5)23(10-12-31(40)41)29(35-25)15-28-22(9-11-30(38)39)17(4)24(34-28)13-26-16(3)21(8-2)33(43)36-26/h16,19-21,26-27,34-35H,7-15H2,1-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/t16-,19-,20-,21-,26+,27+/m1/s1

InChI Key

VKGRRZVYCXLHII-OLFWPHQKSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bilirubins. These are organic compounds containing a dicarboxylic acyclic tetrapyrrole derivative.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrapyrroles and derivatives

Sub Class

Bilirubins

Direct Parent

Bilirubins

Alternative Parents

Substituents

Bilirubin skeleton
Dicarboxylic acid or derivatives
Substituted pyrrole
2-pyrrolidone
Pyrrolidone
Pyrrole
Heteroaromatic compound
Pyrrolidine
Carboxamide group
Lactam
Secondary carboxylic acid amide
Carboxylic acid derivative
Carboxylic acid
Azacycle
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

stercobilinogen (CHEBI:6320 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.96	ALOGPS
logP	4	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	4.05	ChemAxon
pKa (Strongest Basic)	-0.89	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	164.38 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	164.98 m³·mol⁻¹	ChemAxon
Polarizability	68.4 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

External Links

HMDB ID

HMDB0004157

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023322

KNApSAcK ID

Not Available

Chemspider ID

7827641

KEGG Compound ID

C05789

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Stercobilinogen

METLIN ID

Not Available

PubChem Compound

9548718

PDB ID

Not Available

ChEBI ID

6320

Good Scents ID

Not Available

References

General References

Vitek L, Majer F, Muchova L, Zelenka J, Jiraskova A, Branny P, Malina J, Ubik K: Identification of bilirubin reduction products formed by Clostridium perfringens isolated from human neonatal fecal flora. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Apr 3;833(2):149-57. doi: 10.1016/j.jchromb.2006.01.032. Epub 2006 Feb 28. [PubMed:16504607 ]

Showing NP-Card for Stercobilinogen (NP0136905)

MOL for NP0136905 (Stercobilinogen)

3D MOL for NP0136905 (Stercobilinogen)

3D SDF for NP0136905 (Stercobilinogen)

3D-SDF for NP0136905 (Stercobilinogen)

PDB for NP0136905 (Stercobilinogen)

3D PDB for NP0136905 (Stercobilinogen)

SMILES for NP0136905 (Stercobilinogen)

INCHI for NP0136905 (Stercobilinogen)

Structure for NP0136905 (Stercobilinogen)

3D Structure for NP0136905 (Stercobilinogen)