Hmdb loader

Showing metabocard for Urobilin (HMDB0004160)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-13 13:18:56 UTC
Update Date2022-09-22 18:34:18 UTC
HMDB IDHMDB0004160
Secondary Accession Numbers
  • HMDB0004159
  • HMDB0004161
  • HMDB04159
  • HMDB04160
  • HMDB04161
Metabolite Identification
Common NameUrobilin
DescriptionUrobilin, also known as urochrome, is the tetrapyrrole chemical compound that is primarily responsible for the yellow color of urine. Urobilin is formed through the oxidation of its parent compound uroblinogen. Urobilin is actually generated through the degradation of heme, the red pigment in haemoglobin and red blood cells (RBCs). RBCs have a life span of about 120 days. When the RBCs have reached the end of their useful lifespan, the cells are engulfed by macrophages and their constituents recycled or disposed of. Heme is broken down when the heme ring is opened by the enzyme known as heme oxygenase, which is found in the endoplasmic reticulum of the macrophages. The oxidation process produces the linear tetrapyrrole known as biliverdin along with ferric iron (Fe3+), and carbon monoxide (CO). In the next reaction, a second methylene group (located between rings III and IV of the porphyrin ring) is reduced by the enzyme known as biliverdin reductase, producing bilirubin. Bilirubin is significantly less extensively conjugated than biliverdin. This reduction causes a change in the color of the biliverdin molecule from blue-green (vert or verd for green) to yellow-red, which is the color of bilirubin (ruby or rubi for red). In plasma virtually all the bilirubin is tightly bound to plasma proteins, largely albumin, because it is only sparingly soluble in aqueous solutions at physiological pH. In the sinusoids unconjugated bilirubin dissociates from albumin, enters the liver cells across the cell membrane through non-ionic diffusion to the smooth endoplasmatic reticulum. In hepatocytes, bilirubin-UDP-glucuronyltransferase (bilirubin-UGT) adds 2 additional glucuronic acid molecules to bilirubin to produce the more water-soluble version of the molecule known as bilirubin diglucuronide. The bilirubin diglucuronide is transferred rapidly across the canalicular membrane into the bile canaliculi where it is then excreted as bile into the large intestine. The bilirubin is further degraded (reduced) by microbes present in the large intestine to form a colorless product known as urobilinogen. Some of the urobilinogen produced by the gut bacteria is reabsorbed and re-enters the enterohepatic circulation. These urobilinogens are oxidized and converted to urobilin. The urobilin is processed through the kidneys and then excreted in the urine, which causes the yellowish color in urine. Many urine tests monitor the amount of urobilin in urine, as this provides some useful insight into urinary tract function. Normally, urine would appear as either light yellow or colorless. A lack of water intake, for example following sleep or dehydration, reduces the water content of urine, thereby concentrating urobilin and producing a darker color of urine. Obstructive jaundice reduces biliary bilirubin excretion, which is then excreted directly from the blood stream into the urine, giving a dark-colored urine. This dark colored urine has a paradoxically low urobilin concentration.
Structure
Data?1582752301
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0004160 (Urobilin)


  Mrv1652304062012592D          

 44 47  0  0  0  0            999 V2000
   -1.8645   -1.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846   -2.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0395   -1.3329    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1195   -2.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9041   -2.3725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4520   -2.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1207    1.0802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0139    0.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2069    0.2597    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8744    1.4156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0459    2.2227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4264    0.8026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2469    0.8889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5824    1.6425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4062    1.4927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -2.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8646   -1.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0396   -1.3329    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1195   -2.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9042   -2.3725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4521   -2.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4521   -3.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1666   -3.8400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4521   -5.0775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1666   -4.6650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8809   -5.0775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0139    0.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4265    0.8026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2469    0.8889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8744    1.4156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0460    2.2227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8306    2.4775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2070    0.2597    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1207    1.0802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4063    1.4927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3495   -0.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3495   -0.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4520   -3.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1665   -3.8400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8809   -5.0775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1665   -4.6650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4520   -5.0775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.3725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.1974    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 36  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 43  1  0  0  0  0
  4  6  1  0  0  0  0
  4  5  1  0  0  0  0
  6 38  1  0  0  0  0
 15  7  2  0  0  0  0
  7  9  1  0  0  0  0
 10  7  1  0  0  0  0
  8 36  1  0  0  0  0
  9  8  1  0  0  0  0
 12  8  1  0  0  0  0
 10 12  2  0  0  0  0
 10 11  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 16 43  2  0  0  0  0
 18 16  1  0  0  0  0
 21 16  1  0  0  0  0
 37 17  1  0  0  0  0
 18 17  2  0  0  0  0
 19 17  1  0  0  0  0
 19 21  2  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 25  1  0  0  0  0
 25 24  2  0  0  0  0
 25 26  1  0  0  0  0
 27 33  1  0  0  0  0
 28 27  1  0  0  0  0
 37 27  1  0  0  0  0
 30 28  2  0  0  0  0
 28 29  1  0  0  0  0
 30 34  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 38 39  1  0  0  0  0
 39 41  1  0  0  0  0
 41 40  2  0  0  0  0
 41 42  1  0  0  0  0
 43 44  1  4  0  0  0
M  END
Download

3D MOL for HMDB0004160 (Urobilin)

HMDB0004160
     RDKit          3D
Urobilin
 85 88  0  0  0  0  0  0  0  0999 V2000
    8.9204    3.2160    2.1963 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8000    2.6923    0.7824 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4441    2.2154    0.4888 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0898    1.0200    0.1158 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0200   -0.1329   -0.0899 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6156    0.9420   -0.1094 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0299   -0.1476    0.7230 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5540   -0.2525    0.5166 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7070   -0.1088    1.4551 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3599   -0.2780    0.8810 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2805   -0.1940    1.6315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1103   -0.3070    1.3444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8710    0.3088    0.4642 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1635   -0.1188    0.4897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2229    0.4035   -0.3638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0978    1.4644    0.2327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7811    1.0368    1.4101 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1632    0.9702    1.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1104    0.6203    1.8881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3643    1.3842   -0.2768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6858    1.4398   -0.9449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2078    1.6727   -0.7927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8362    2.1714   -2.1273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9420    2.4787   -3.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1895   -1.0883    1.4843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4158   -1.8425    1.8975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9305   -1.2234    2.0282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5121   -2.1011    3.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5352   -3.1479    2.7217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9554   -4.0768    1.6796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0474   -3.9966    1.1102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1172   -5.1250    1.2707 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5821   -0.5367   -0.5013 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6074   -0.7677   -1.5735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0364   -2.1242   -1.4413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0360   -2.3288   -2.5367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2374   -1.4462   -3.4003 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7276   -3.5126   -2.5683 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9113   -0.5226   -0.7312 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5727   -0.7622   -2.0572 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1242    2.2487    0.2584 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2442    3.0393    0.5956 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1809    4.2657    0.9321 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5203    2.4864    2.9186 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9940    3.4014    2.3912 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4244    4.2120    2.2480 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0460    3.5283    0.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5476    1.8671    0.6655 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5947   -0.7599   -0.9175 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1671   -0.7148    0.8441 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0069    0.2172   -0.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5070    0.7629   -1.2043 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2828    0.0649    1.7817 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5141   -1.1163    0.4504 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4737    0.0128    2.7265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5401    1.0733   -0.1882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7525    0.7577   -1.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8633   -0.4703   -0.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5539    2.4285    0.3692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3867    0.8182    2.3359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1698    2.4405   -0.8460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3821    0.7733   -0.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7247    0.9982   -1.9409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2902    3.1446   -1.9361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0411    1.5423   -2.6259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7715    3.0387   -2.6383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2224    1.5660   -3.6454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5533    3.1709   -3.8925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2196   -2.9066    2.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2177   -1.6809    1.1394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8071   -1.3841    2.8553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4212   -2.5936    3.5725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0729   -1.4425    3.9445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4210   -2.5993    2.4196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2042   -3.7398    3.6229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2961   -6.0626    1.6125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1173    0.0575   -1.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1331   -0.7311   -2.5855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7716   -2.9156   -1.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5278   -2.2361   -0.4812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3131   -4.3559   -2.9846 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6439    0.1564   -2.6343 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9724   -1.5044   -2.6323 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5563   -1.2886   -1.9009 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1246    2.5353    0.2674 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  3
 11 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  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  1  0
 14 25  2  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 10 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  2  0
 36 38  1  0
 33 39  2  0
 39 40  1  0
  6 41  1  0
 41 42  1  0
 42 43  2  0
 42  3  1  0
 39  8  1  0
 27 12  2  0
 22 16  1  0
  1 44  1  0
  1 45  1  0
  1 46  1  0
  2 47  1  0
  2 48  1  0
  5 49  1  0
  5 50  1  0
  5 51  1  0
  6 52  1  0
  7 53  1  0
  7 54  1  0
 11 55  1  0
 13 56  1  0
 15 57  1  0
 15 58  1  0
 16 59  1  0
 17 60  1  0
 21 61  1  0
 21 62  1  0
 21 63  1  0
 23 64  1  0
 23 65  1  0
 24 66  1  0
 24 67  1  0
 24 68  1  0
 26 69  1  0
 26 70  1  0
 26 71  1  0
 28 72  1  0
 28 73  1  0
 29 74  1  0
 29 75  1  0
 32 76  1  0
 34 77  1  0
 34 78  1  0
 35 79  1  0
 35 80  1  0
 38 81  1  0
 40 82  1  0
 40 83  1  0
 40 84  1  0
 41 85  1  0
M  END
Download

3D SDF for HMDB0004160 (Urobilin)


  Mrv1652304062012592D          

 44 47  0  0  0  0            999 V2000
   -1.8645   -1.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846   -2.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0395   -1.3329    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1195   -2.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9041   -2.3725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4520   -2.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1207    1.0802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0139    0.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2069    0.2597    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8744    1.4156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0459    2.2227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4264    0.8026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2469    0.8889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5824    1.6425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4062    1.4927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -2.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8646   -1.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0396   -1.3329    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1195   -2.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9042   -2.3725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4521   -2.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4521   -3.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1666   -3.8400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4521   -5.0775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1666   -4.6650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8809   -5.0775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0139    0.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4265    0.8026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2469    0.8889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8744    1.4156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0460    2.2227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8306    2.4775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2070    0.2597    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1207    1.0802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4063    1.4927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3495   -0.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3495   -0.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4520   -3.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1665   -3.8400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8809   -5.0775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1665   -4.6650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4520   -5.0775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.3725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.1974    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 36  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 43  1  0  0  0  0
  4  6  1  0  0  0  0
  4  5  1  0  0  0  0
  6 38  1  0  0  0  0
 15  7  2  0  0  0  0
  7  9  1  0  0  0  0
 10  7  1  0  0  0  0
  8 36  1  0  0  0  0
  9  8  1  0  0  0  0
 12  8  1  0  0  0  0
 10 12  2  0  0  0  0
 10 11  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 16 43  2  0  0  0  0
 18 16  1  0  0  0  0
 21 16  1  0  0  0  0
 37 17  1  0  0  0  0
 18 17  2  0  0  0  0
 19 17  1  0  0  0  0
 19 21  2  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 25  1  0  0  0  0
 25 24  2  0  0  0  0
 25 26  1  0  0  0  0
 27 33  1  0  0  0  0
 28 27  1  0  0  0  0
 37 27  1  0  0  0  0
 30 28  2  0  0  0  0
 28 29  1  0  0  0  0
 30 34  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 38 39  1  0  0  0  0
 39 41  1  0  0  0  0
 41 40  2  0  0  0  0
 41 42  1  0  0  0  0
 43 44  1  4  0  0  0
M  END
> <DATABASE_ID>
HMDB0004160

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]C(C1=C(CCC(O)=O)C(C)=C(CC2NC(=O)C(C)=C2CC)N1)=C1N=C(CC2NC(=O)C(CC)=C2C)C(C)=C1CCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C33H42N4O6/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/h15,26-27,35H,7-14H2,1-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)

> <INCHI_KEY>
KDCCOOGTVSRCHX-UHFFFAOYSA-N

> <FORMULA>
C33H42N4O6

> <MOLECULAR_WEIGHT>
590.721

> <EXACT_MASS>
590.310435088

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
66.88580348882167

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
3.04

> <JCHEM_LOGP>
1.233423460104334

> <ALOGPS_LOGS>
-4.09

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.474284155740964

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8793949820379234

> <JCHEM_PKA_STRONGEST_BASIC>
5.981237510474162

> <JCHEM_POLAR_SURFACE_AREA>
160.95

> <JCHEM_REFRACTIVITY>
166.25980000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.81e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
urobilin

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0004160 (Urobilin)

HMDB0004160
     RDKit          3D
Urobilin
 85 88  0  0  0  0  0  0  0  0999 V2000
    8.9204    3.2160    2.1963 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8000    2.6923    0.7824 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4441    2.2154    0.4888 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0898    1.0200    0.1158 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0200   -0.1329   -0.0899 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6156    0.9420   -0.1094 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0299   -0.1476    0.7230 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5540   -0.2525    0.5166 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7070   -0.1088    1.4551 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3599   -0.2780    0.8810 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2805   -0.1940    1.6315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1103   -0.3070    1.3444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8710    0.3088    0.4642 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1635   -0.1188    0.4897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2229    0.4035   -0.3638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0978    1.4644    0.2327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7811    1.0368    1.4101 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1632    0.9702    1.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1104    0.6203    1.8881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3643    1.3842   -0.2768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6858    1.4398   -0.9449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2078    1.6727   -0.7927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8362    2.1714   -2.1273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9420    2.4787   -3.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1895   -1.0883    1.4843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4158   -1.8425    1.8975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9305   -1.2234    2.0282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5121   -2.1011    3.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5352   -3.1479    2.7217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9554   -4.0768    1.6796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0474   -3.9966    1.1102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1172   -5.1250    1.2707 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5821   -0.5367   -0.5013 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6074   -0.7677   -1.5735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0364   -2.1242   -1.4413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0360   -2.3288   -2.5367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2374   -1.4462   -3.4003 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7276   -3.5126   -2.5683 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9113   -0.5226   -0.7312 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5727   -0.7622   -2.0572 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1242    2.2487    0.2584 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2442    3.0393    0.5956 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1809    4.2657    0.9321 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5203    2.4864    2.9186 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9940    3.4014    2.3912 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4244    4.2120    2.2480 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0460    3.5283    0.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5476    1.8671    0.6655 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5947   -0.7599   -0.9175 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1671   -0.7148    0.8441 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0069    0.2172   -0.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5070    0.7629   -1.2043 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2828    0.0649    1.7817 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5141   -1.1163    0.4504 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4737    0.0128    2.7265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5401    1.0733   -0.1882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7525    0.7577   -1.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8633   -0.4703   -0.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5539    2.4285    0.3692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3867    0.8182    2.3359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1698    2.4405   -0.8460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3821    0.7733   -0.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7247    0.9982   -1.9409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2902    3.1446   -1.9361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0411    1.5423   -2.6259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7715    3.0387   -2.6383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2224    1.5660   -3.6454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5533    3.1709   -3.8925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2196   -2.9066    2.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2177   -1.6809    1.1394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8071   -1.3841    2.8553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4212   -2.5936    3.5725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0729   -1.4425    3.9445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4210   -2.5993    2.4196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2042   -3.7398    3.6229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2961   -6.0626    1.6125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1173    0.0575   -1.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1331   -0.7311   -2.5855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7716   -2.9156   -1.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5278   -2.2361   -0.4812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3131   -4.3559   -2.9846 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6439    0.1564   -2.6343 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9724   -1.5044   -2.6323 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5563   -1.2886   -1.9009 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1246    2.5353    0.2674 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  3
 11 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  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  1  0
 14 25  2  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 10 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  2  0
 36 38  1  0
 33 39  2  0
 39 40  1  0
  6 41  1  0
 41 42  1  0
 42 43  2  0
 42  3  1  0
 39  8  1  0
 27 12  2  0
 22 16  1  0
  1 44  1  0
  1 45  1  0
  1 46  1  0
  2 47  1  0
  2 48  1  0
  5 49  1  0
  5 50  1  0
  5 51  1  0
  6 52  1  0
  7 53  1  0
  7 54  1  0
 11 55  1  0
 13 56  1  0
 15 57  1  0
 15 58  1  0
 16 59  1  0
 17 60  1  0
 21 61  1  0
 21 62  1  0
 21 63  1  0
 23 64  1  0
 23 65  1  0
 24 66  1  0
 24 67  1  0
 24 68  1  0
 26 69  1  0
 26 70  1  0
 26 71  1  0
 28 72  1  0
 28 73  1  0
 29 74  1  0
 29 75  1  0
 32 76  1  0
 34 77  1  0
 34 78  1  0
 35 79  1  0
 35 80  1  0
 38 81  1  0
 40 82  1  0
 40 83  1  0
 40 84  1  0
 41 85  1  0
M  END
Download

PDB for HMDB0004160 (Urobilin)

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  C   UNK     0      -3.480  -2.488   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.465  -3.953   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -1.940  -2.488   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -3.956  -3.953   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.421  -4.429   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.710  -4.858   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.092   2.016   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.759   0.165   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -2.253   0.485   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -3.499   2.642   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.819   4.149   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.529   1.498   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.061   1.659   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.687   3.066   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.758   2.786   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.465  -3.953   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.481  -2.488   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       1.941  -2.488   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       3.956  -3.953   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.421  -4.429   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.711  -4.858   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.711  -6.398   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.044  -7.168   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.711  -9.478   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.044  -8.708   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.378  -9.478   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.759   0.165   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.529   1.498   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.061   1.659   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.499   2.642   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.819   4.149   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.284   4.625   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0       2.253   0.485   0.000  0.00  0.00           N+0
HETATM   34  C   UNK     0       2.092   2.016   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       0.758   2.786   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -4.386  -1.242   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.386  -1.242   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -2.710  -6.398   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -4.044  -7.168   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -5.378  -9.478   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -4.044  -8.708   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -2.710  -9.478   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       0.000  -4.429   0.000  0.00  0.00           C+0
HETATM   44  H   UNK     0       0.000  -5.968   0.000  0.00  0.00           H+0
CONECT    1   36    3    4                                                  
CONECT    2    6    3   43                                                  
CONECT    3    1    2                                                       
CONECT    4    1    6    5                                                  
CONECT    5    4                                                            
CONECT    6    2    4   38                                                  
CONECT    7   15    9   10                                                  
CONECT    8   36    9   12                                                  
CONECT    9    7    8                                                       
CONECT   10    7   12   11                                                  
CONECT   11   10                                                            
CONECT   12    8   10   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15    7                                                            
CONECT   16   43   18   21                                                  
CONECT   17   37   18   19                                                  
CONECT   18   16   17                                                       
CONECT   19   17   21   20                                                  
CONECT   20   19                                                            
CONECT   21   16   19   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   25                                                       
CONECT   24   25                                                            
CONECT   25   23   24   26                                                  
CONECT   26   25                                                            
CONECT   27   33   28   37                                                  
CONECT   28   27   30   29                                                  
CONECT   29   28                                                            
CONECT   30   28   34   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   27   34                                                       
CONECT   34   30   33   35                                                  
CONECT   35   34                                                            
CONECT   36    1    8                                                       
CONECT   37   17   27                                                       
CONECT   38    6   39                                                       
CONECT   39   38   41                                                       
CONECT   40   41                                                            
CONECT   41   39   40   42                                                  
CONECT   42   41                                                            
CONECT   43    2   16   44                                                  
CONECT   44   43                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   94    0
END
Download

3D PDB for HMDB0004160 (Urobilin)

COMPND    HMDB0242265
HETATM    1  C1  UNL     1      -6.858  -4.519   1.833  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.871  -4.506   0.669  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.235  -3.159   0.544  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.286  -2.321  -0.466  1.00  0.00           C  
HETATM    5  C5  UNL     1      -6.031  -2.611  -1.719  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.542  -1.088  -0.186  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.547  -0.762  -1.279  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.777   0.486  -1.003  1.00  0.00           C  
HETATM    9  N1  UNL     1      -1.496   0.563  -0.883  1.00  0.00           N  
HETATM   10  C9  UNL     1      -1.070   1.889  -0.622  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.186   2.296  -0.431  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.222   1.251  -0.500  1.00  0.00           C  
HETATM   13  N2  UNL     1       1.037   0.032   0.022  1.00  0.00           N  
HETATM   14  C12 UNL     1       2.147  -0.748  -0.177  1.00  0.00           C  
HETATM   15  C13 UNL     1       2.347  -2.101   0.253  1.00  0.00           C  
HETATM   16  C14 UNL     1       2.967  -2.468   1.538  1.00  0.00           C  
HETATM   17  N3  UNL     1       2.968  -3.948   1.496  1.00  0.00           N  
HETATM   18  C15 UNL     1       4.285  -4.336   1.728  1.00  0.00           C  
HETATM   19  O1  UNL     1       4.753  -5.535   1.753  1.00  0.00           O  
HETATM   20  C16 UNL     1       5.098  -3.150   1.947  1.00  0.00           C  
HETATM   21  C17 UNL     1       6.578  -3.283   2.259  1.00  0.00           C  
HETATM   22  C18 UNL     1       4.343  -2.089   1.847  1.00  0.00           C  
HETATM   23  C19 UNL     1       4.769  -0.690   2.061  1.00  0.00           C  
HETATM   24  C20 UNL     1       6.221  -0.430   2.172  1.00  0.00           C  
HETATM   25  C21 UNL     1       3.031   0.062  -0.857  1.00  0.00           C  
HETATM   26  C22 UNL     1       4.413  -0.267  -1.353  1.00  0.00           C  
HETATM   27  C23 UNL     1       2.458   1.322  -1.065  1.00  0.00           C  
HETATM   28  C24 UNL     1       3.089   2.463  -1.750  1.00  0.00           C  
HETATM   29  C25 UNL     1       3.595   3.517  -0.776  1.00  0.00           C  
HETATM   30  C26 UNL     1       4.204   4.593  -1.585  1.00  0.00           C  
HETATM   31  O2  UNL     1       4.248   4.564  -2.841  1.00  0.00           O  
HETATM   32  O3  UNL     1       4.759   5.694  -0.949  1.00  0.00           O  
HETATM   33  C27 UNL     1      -2.274   2.699  -0.586  1.00  0.00           C  
HETATM   34  C28 UNL     1      -2.414   4.138  -0.349  1.00  0.00           C  
HETATM   35  C29 UNL     1      -1.763   5.041  -1.336  1.00  0.00           C  
HETATM   36  C30 UNL     1      -2.243   4.885  -2.728  1.00  0.00           C  
HETATM   37  O4  UNL     1      -3.099   4.054  -3.091  1.00  0.00           O  
HETATM   38  O5  UNL     1      -1.685   5.739  -3.678  1.00  0.00           O  
HETATM   39  C31 UNL     1      -3.286   1.834  -0.816  1.00  0.00           C  
HETATM   40  C32 UNL     1      -4.731   2.244  -0.850  1.00  0.00           C  
HETATM   41  N4  UNL     1      -3.933  -1.312   1.098  1.00  0.00           N  
HETATM   42  C33 UNL     1      -4.396  -2.568   1.556  1.00  0.00           C  
HETATM   43  O6  UNL     1      -4.103  -3.074   2.689  1.00  0.00           O  
HETATM   44  H1  UNL     1      -7.226  -5.554   1.928  1.00  0.00           H  
HETATM   45  H2  UNL     1      -7.741  -3.883   1.615  1.00  0.00           H  
HETATM   46  H3  UNL     1      -6.362  -4.255   2.780  1.00  0.00           H  
HETATM   47  H4  UNL     1      -5.067  -5.218   0.939  1.00  0.00           H  
HETATM   48  H5  UNL     1      -6.380  -4.774  -0.261  1.00  0.00           H  
HETATM   49  H6  UNL     1      -6.359  -1.673  -2.218  1.00  0.00           H  
HETATM   50  H7  UNL     1      -5.384  -3.195  -2.413  1.00  0.00           H  
HETATM   51  H8  UNL     1      -6.979  -3.167  -1.477  1.00  0.00           H  
HETATM   52  H9  UNL     1      -5.326  -0.276  -0.120  1.00  0.00           H  
HETATM   53  H10 UNL     1      -4.149  -0.568  -2.197  1.00  0.00           H  
HETATM   54  H11 UNL     1      -2.871  -1.587  -1.499  1.00  0.00           H  
HETATM   55  H12 UNL     1       0.490   3.295  -0.230  1.00  0.00           H  
HETATM   56  H13 UNL     1       0.203  -0.324   0.515  1.00  0.00           H  
HETATM   57  H14 UNL     1       1.305  -2.587   0.270  1.00  0.00           H  
HETATM   58  H15 UNL     1       2.836  -2.736  -0.576  1.00  0.00           H  
HETATM   59  H16 UNL     1       2.272  -2.258   2.417  1.00  0.00           H  
HETATM   60  H17 UNL     1       2.132  -4.536   1.325  1.00  0.00           H  
HETATM   61  H18 UNL     1       6.776  -4.338   2.667  1.00  0.00           H  
HETATM   62  H19 UNL     1       7.183  -3.250   1.349  1.00  0.00           H  
HETATM   63  H20 UNL     1       6.877  -2.652   3.095  1.00  0.00           H  
HETATM   64  H21 UNL     1       4.215   0.071   1.499  1.00  0.00           H  
HETATM   65  H22 UNL     1       4.377  -0.460   3.146  1.00  0.00           H  
HETATM   66  H23 UNL     1       6.633  -0.425   3.210  1.00  0.00           H  
HETATM   67  H24 UNL     1       6.405   0.666   1.867  1.00  0.00           H  
HETATM   68  H25 UNL     1       6.862  -0.985   1.472  1.00  0.00           H  
HETATM   69  H26 UNL     1       5.189   0.345  -0.854  1.00  0.00           H  
HETATM   70  H27 UNL     1       4.657  -1.329  -1.150  1.00  0.00           H  
HETATM   71  H28 UNL     1       4.425  -0.161  -2.467  1.00  0.00           H  
HETATM   72  H29 UNL     1       3.926   2.087  -2.339  1.00  0.00           H  
HETATM   73  H30 UNL     1       2.393   2.965  -2.463  1.00  0.00           H  
HETATM   74  H31 UNL     1       4.320   3.060  -0.072  1.00  0.00           H  
HETATM   75  H32 UNL     1       2.778   3.973  -0.184  1.00  0.00           H  
HETATM   76  H33 UNL     1       4.170   6.396  -0.537  1.00  0.00           H  
HETATM   77  H34 UNL     1      -1.987   4.369   0.661  1.00  0.00           H  
HETATM   78  H35 UNL     1      -3.492   4.449  -0.251  1.00  0.00           H  
HETATM   79  H36 UNL     1      -2.009   6.121  -1.068  1.00  0.00           H  
HETATM   80  H37 UNL     1      -0.650   5.025  -1.281  1.00  0.00           H  
HETATM   81  H38 UNL     1      -2.031   6.693  -3.808  1.00  0.00           H  
HETATM   82  H39 UNL     1      -4.854   3.288  -1.190  1.00  0.00           H  
HETATM   83  H40 UNL     1      -5.228   1.604  -1.601  1.00  0.00           H  
HETATM   84  H41 UNL     1      -5.140   2.090   0.173  1.00  0.00           H  
HETATM   85  H42 UNL     1      -3.270  -0.707   1.640  1.00  0.00           H  
CONECT    1    2   44   45   46
CONECT    2    3   47   48
CONECT    3    4    4   42
CONECT    4    5    6
CONECT    5   49   50   51
CONECT    6    7   41   52
CONECT    7    8   53   54
CONECT    8    9    9   39
CONECT    9   10
CONECT   10   11   11   33
CONECT   11   12   55
CONECT   12   13   27   27
CONECT   13   14   56
CONECT   14   15   25   25
CONECT   15   16   57   58
CONECT   16   17   22   59
CONECT   17   18   60
CONECT   18   19   19   20
CONECT   20   21   22   22
CONECT   21   61   62   63
CONECT   22   23
CONECT   23   24   64   65
CONECT   24   66   67   68
CONECT   25   26   27
CONECT   26   69   70   71
CONECT   27   28
CONECT   28   29   72   73
CONECT   29   30   74   75
CONECT   30   31   31   32
CONECT   32   76
CONECT   33   34   39   39
CONECT   34   35   77   78
CONECT   35   36   79   80
CONECT   36   37   37   38
CONECT   38   81
CONECT   39   40
CONECT   40   82   83   84
CONECT   41   42   85
CONECT   42   43   43
END
Download

SMILES for HMDB0004160 (Urobilin)

[H]C(C1=C(CCC(O)=O)C(C)=C(CC2NC(=O)C(C)=C2CC)N1)=C1N=C(CC2NC(=O)C(CC)=C2C)C(C)=C1CCC(O)=O
Download

INCHI for HMDB0004160 (Urobilin)

InChI=1S/C33H42N4O6/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/h15,26-27,35H,7-14H2,1-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)
Download
View in JSmolView Stereo Labels
Synonyms
ValueSource
3,18-Diethyl-1,4,5,15,16,19,22,24-octahydro-2,7,13,17-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoic acidChEBI
3,18-Diethyl-1,4,5,15,16,19,22,24-octahydro-2,7,13,17-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropionic acidChEBI
8,12-Bis(2-carboxyethyl)-3,18-diethyl-2,7,13,17-tetramethylbilene-b-1,19(4H,16H)-dioneChEBI
I-urobilinChEBI
3,18-Diethyl-1,4,5,15,16,19,22,24-octahydro-2,7,13,17-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoateGenerator
3,18-Diethyl-1,4,5,15,16,19,22,24-octahydro-2,7,13,17-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropionateGenerator
(-)-UrobilinHMDB
3,18-Diethyl-1,4,5,15,16,19,22,24-octahydro-2,7,13,17-tetramethyl-1,19-dioxo-biline-8,12-dipropionic acidHMDB
Urobilin ixαHMDB
Urobilin ixalphaHMDB
UrobilinHMDB
Chemical FormulaC33H42N4O6
Average Molecular Weight590.721
Monoisotopic Molecular Weight590.310435088
IUPAC Name3-(2-{[3-(2-carboxyethyl)-5-[(4-ethyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-yl)methyl]-4-methyl-2H-pyrrol-2-ylidene]methyl}-5-[(3-ethyl-4-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-yl)methyl]-4-methyl-1H-pyrrol-3-yl)propanoic acid
Traditional Nameurobilin
CAS Registry Number1856-98-0
SMILES
[H]C(C1=C(CCC(O)=O)C(C)=C(CC2NC(=O)C(C)=C2CC)N1)=C1N=C(CC2NC(=O)C(CC)=C2C)C(C)=C1CCC(O)=O
InChI Identifier
InChI=1S/C33H42N4O6/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/h15,26-27,35H,7-14H2,1-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)
InChI KeyKDCCOOGTVSRCHX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as bilirubins. These are organic compounds containing a dicarboxylic acyclic tetrapyrrole derivative.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTetrapyrroles and derivatives
Sub ClassBilirubins
Direct ParentBilirubins
Alternative Parents
Substituents
  • Bilirubin skeleton
  • Dipyrrin
  • Dicarboxylic acid or derivatives
  • Substituted pyrrole
  • Pyrrole
  • Pyrroline
  • Heteroaromatic compound
  • Carboxamide group
  • Ketimine
  • Lactam
  • Secondary carboxylic acid amide
  • Azacycle
  • Organic 1,3-dipolar compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Propargyl-type 1,3-dipolar organic compound
  • Hydrocarbon derivative
  • Imine
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.363Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.048 g/LALOGPS
logP3.04ALOGPS
logP1.23ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)3.88ChemAxon
pKa (Strongest Basic)5.98ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area160.95 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity166.26 m³·mol⁻¹ChemAxon
Polarizability66.89 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+234.64430932474
DeepCCS[M-H]-232.74830932474
DeepCCS[M-2H]-265.98930932474
DeepCCS[M+Na]+240.3330932474
AllCCS[M+H]+240.232859911
AllCCS[M+H-H2O]+239.132859911
AllCCS[M+NH4]+241.332859911
AllCCS[M+Na]+241.632859911
AllCCS[M-H]-233.732859911
AllCCS[M+Na-2H]-236.632859911
AllCCS[M+HCOO]-239.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Urobilin[H]C(C1=C(CCC(O)=O)C(C)=C(CC2NC(=O)C(C)=C2CC)N1)=C1N=C(CC2NC(=O)C(CC)=C2C)C(C)=C1CCC(O)=O7127.2Standard polar33892256
Urobilin[H]C(C1=C(CCC(O)=O)C(C)=C(CC2NC(=O)C(C)=C2CC)N1)=C1N=C(CC2NC(=O)C(CC)=C2C)C(C)=C1CCC(O)=O4318.3Standard non polar33892256
Urobilin[H]C(C1=C(CCC(O)=O)C(C)=C(CC2NC(=O)C(C)=C2CC)N1)=C1N=C(CC2NC(=O)C(CC)=C2C)C(C)=C1CCC(O)=O5395.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Urobilin,1TMS,isomer #1CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC4NC(=O)C(C)=C4CC)[NH]3)C(CCC(=O)O)=C2C)NC1=O5165.8Semi standard non polar33892256
Urobilin,1TMS,isomer #1CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC4NC(=O)C(C)=C4CC)[NH]3)C(CCC(=O)O)=C2C)NC1=O4784.8Standard non polar33892256
Urobilin,1TMS,isomer #1CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC4NC(=O)C(C)=C4CC)[NH]3)C(CCC(=O)O)=C2C)NC1=O7041.5Standard polar33892256
Urobilin,1TMS,isomer #2CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4NC(=O)C(C)=C4CC)[NH]3)C(CCC(=O)O[Si](C)(C)C)=C2C)NC1=O5180.6Semi standard non polar33892256
Urobilin,1TMS,isomer #2CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4NC(=O)C(C)=C4CC)[NH]3)C(CCC(=O)O[Si](C)(C)C)=C2C)NC1=O4771.9Standard non polar33892256
Urobilin,1TMS,isomer #2CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4NC(=O)C(C)=C4CC)[NH]3)C(CCC(=O)O[Si](C)(C)C)=C2C)NC1=O7053.9Standard polar33892256
Urobilin,1TMS,isomer #3CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)C(CCC(=O)O)=C2C)NC1=O5070.1Semi standard non polar33892256
Urobilin,1TMS,isomer #3CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)C(CCC(=O)O)=C2C)NC1=O4733.6Standard non polar33892256
Urobilin,1TMS,isomer #3CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)C(CCC(=O)O)=C2C)NC1=O6835.3Standard polar33892256
Urobilin,1TMS,isomer #4CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4NC(=O)C(C)=C4CC)N3[Si](C)(C)C)C(CCC(=O)O)=C2C)NC1=O5236.6Semi standard non polar33892256
Urobilin,1TMS,isomer #4CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4NC(=O)C(C)=C4CC)N3[Si](C)(C)C)C(CCC(=O)O)=C2C)NC1=O4878.0Standard non polar33892256
Urobilin,1TMS,isomer #4CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4NC(=O)C(C)=C4CC)N3[Si](C)(C)C)C(CCC(=O)O)=C2C)NC1=O7104.2Standard polar33892256
Urobilin,1TMS,isomer #5CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4NC(=O)C(C)=C4CC)[NH]3)C(CCC(=O)O)=C2C)N([Si](C)(C)C)C1=O5085.7Semi standard non polar33892256
Urobilin,1TMS,isomer #5CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4NC(=O)C(C)=C4CC)[NH]3)C(CCC(=O)O)=C2C)N([Si](C)(C)C)C1=O4736.1Standard non polar33892256
Urobilin,1TMS,isomer #5CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4NC(=O)C(C)=C4CC)[NH]3)C(CCC(=O)O)=C2C)N([Si](C)(C)C)C1=O6881.7Standard polar33892256
Urobilin,2TMS,isomer #1CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC4NC(=O)C(C)=C4CC)[NH]3)C(CCC(=O)O[Si](C)(C)C)=C2C)NC1=O5068.5Semi standard non polar33892256
Urobilin,2TMS,isomer #1CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC4NC(=O)C(C)=C4CC)[NH]3)C(CCC(=O)O[Si](C)(C)C)=C2C)NC1=O4779.5Standard non polar33892256
Urobilin,2TMS,isomer #1CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC4NC(=O)C(C)=C4CC)[NH]3)C(CCC(=O)O[Si](C)(C)C)=C2C)NC1=O6789.6Standard polar33892256
Urobilin,2TMS,isomer #10CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4NC(=O)C(C)=C4CC)N3[Si](C)(C)C)C(CCC(=O)O)=C2C)N([Si](C)(C)C)C1=O5058.7Semi standard non polar33892256
Urobilin,2TMS,isomer #10CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4NC(=O)C(C)=C4CC)N3[Si](C)(C)C)C(CCC(=O)O)=C2C)N([Si](C)(C)C)C1=O4850.8Standard non polar33892256
Urobilin,2TMS,isomer #10CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4NC(=O)C(C)=C4CC)N3[Si](C)(C)C)C(CCC(=O)O)=C2C)N([Si](C)(C)C)C1=O6652.4Standard polar33892256
Urobilin,2TMS,isomer #2CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC4NC(=O)C(C)=C4CC)N3[Si](C)(C)C)C(CCC(=O)O)=C2C)NC1=O5144.8Semi standard non polar33892256
Urobilin,2TMS,isomer #2CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC4NC(=O)C(C)=C4CC)N3[Si](C)(C)C)C(CCC(=O)O)=C2C)NC1=O4876.5Standard non polar33892256
Urobilin,2TMS,isomer #2CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC4NC(=O)C(C)=C4CC)N3[Si](C)(C)C)C(CCC(=O)O)=C2C)NC1=O6809.8Standard polar33892256
Urobilin,2TMS,isomer #3CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)C(CCC(=O)O)=C2C)NC1=O4942.7Semi standard non polar33892256
Urobilin,2TMS,isomer #3CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)C(CCC(=O)O)=C2C)NC1=O4749.0Standard non polar33892256
Urobilin,2TMS,isomer #3CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)C(CCC(=O)O)=C2C)NC1=O6538.1Standard polar33892256
Urobilin,2TMS,isomer #4CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC4NC(=O)C(C)=C4CC)[NH]3)C(CCC(=O)O)=C2C)N([Si](C)(C)C)C1=O4955.1Semi standard non polar33892256
Urobilin,2TMS,isomer #4CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC4NC(=O)C(C)=C4CC)[NH]3)C(CCC(=O)O)=C2C)N([Si](C)(C)C)C1=O4752.8Standard non polar33892256
Urobilin,2TMS,isomer #4CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC4NC(=O)C(C)=C4CC)[NH]3)C(CCC(=O)O)=C2C)N([Si](C)(C)C)C1=O6588.0Standard polar33892256
Urobilin,2TMS,isomer #5CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4NC(=O)C(C)=C4CC)N3[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C2C)NC1=O5156.9Semi standard non polar33892256
Urobilin,2TMS,isomer #5CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4NC(=O)C(C)=C4CC)N3[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C2C)NC1=O4866.4Standard non polar33892256
Urobilin,2TMS,isomer #5CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4NC(=O)C(C)=C4CC)N3[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C2C)NC1=O6829.0Standard polar33892256
Urobilin,2TMS,isomer #6CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)C(CCC(=O)O[Si](C)(C)C)=C2C)NC1=O4956.5Semi standard non polar33892256
Urobilin,2TMS,isomer #6CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)C(CCC(=O)O[Si](C)(C)C)=C2C)NC1=O4740.3Standard non polar33892256
Urobilin,2TMS,isomer #6CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)C(CCC(=O)O[Si](C)(C)C)=C2C)NC1=O6548.8Standard polar33892256
Urobilin,2TMS,isomer #7CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4NC(=O)C(C)=C4CC)[NH]3)C(CCC(=O)O[Si](C)(C)C)=C2C)N([Si](C)(C)C)C1=O4966.7Semi standard non polar33892256
Urobilin,2TMS,isomer #7CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4NC(=O)C(C)=C4CC)[NH]3)C(CCC(=O)O[Si](C)(C)C)=C2C)N([Si](C)(C)C)C1=O4745.4Standard non polar33892256
Urobilin,2TMS,isomer #7CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4NC(=O)C(C)=C4CC)[NH]3)C(CCC(=O)O[Si](C)(C)C)=C2C)N([Si](C)(C)C)C1=O6599.2Standard polar33892256
Urobilin,2TMS,isomer #8CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)C(CCC(=O)O)=C2C)NC1=O5060.7Semi standard non polar33892256
Urobilin,2TMS,isomer #8CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)C(CCC(=O)O)=C2C)NC1=O4837.1Standard non polar33892256
Urobilin,2TMS,isomer #8CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)C(CCC(=O)O)=C2C)NC1=O6605.2Standard polar33892256
Urobilin,2TMS,isomer #9CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)C(CCC(=O)O)=C2C)N([Si](C)(C)C)C1=O4849.3Semi standard non polar33892256
Urobilin,2TMS,isomer #9CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)C(CCC(=O)O)=C2C)N([Si](C)(C)C)C1=O4711.9Standard non polar33892256
Urobilin,2TMS,isomer #9CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)C(CCC(=O)O)=C2C)N([Si](C)(C)C)C1=O6377.5Standard polar33892256
Urobilin,3TMS,isomer #1CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC4NC(=O)C(C)=C4CC)N3[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C2C)NC1=O5033.9Semi standard non polar33892256
Urobilin,3TMS,isomer #1CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC4NC(=O)C(C)=C4CC)N3[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C2C)NC1=O4849.4Standard non polar33892256
Urobilin,3TMS,isomer #1CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC4NC(=O)C(C)=C4CC)N3[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C2C)NC1=O6528.9Standard polar33892256
Urobilin,3TMS,isomer #10CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)C(CCC(=O)O)=C2C)N([Si](C)(C)C)C1=O4891.3Semi standard non polar33892256
Urobilin,3TMS,isomer #10CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)C(CCC(=O)O)=C2C)N([Si](C)(C)C)C1=O4811.2Standard non polar33892256
Urobilin,3TMS,isomer #10CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)C(CCC(=O)O)=C2C)N([Si](C)(C)C)C1=O6150.2Standard polar33892256
Urobilin,3TMS,isomer #2CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)C(CCC(=O)O[Si](C)(C)C)=C2C)NC1=O4845.6Semi standard non polar33892256
Urobilin,3TMS,isomer #2CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)C(CCC(=O)O[Si](C)(C)C)=C2C)NC1=O4737.8Standard non polar33892256
Urobilin,3TMS,isomer #2CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)C(CCC(=O)O[Si](C)(C)C)=C2C)NC1=O6259.2Standard polar33892256
Urobilin,3TMS,isomer #3CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC4NC(=O)C(C)=C4CC)[NH]3)C(CCC(=O)O[Si](C)(C)C)=C2C)N([Si](C)(C)C)C1=O4858.9Semi standard non polar33892256
Urobilin,3TMS,isomer #3CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC4NC(=O)C(C)=C4CC)[NH]3)C(CCC(=O)O[Si](C)(C)C)=C2C)N([Si](C)(C)C)C1=O4745.8Standard non polar33892256
Urobilin,3TMS,isomer #3CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC4NC(=O)C(C)=C4CC)[NH]3)C(CCC(=O)O[Si](C)(C)C)=C2C)N([Si](C)(C)C)C1=O6311.8Standard polar33892256
Urobilin,3TMS,isomer #4CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)C(CCC(=O)O)=C2C)NC1=O4942.5Semi standard non polar33892256
Urobilin,3TMS,isomer #4CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)C(CCC(=O)O)=C2C)NC1=O4827.8Standard non polar33892256
Urobilin,3TMS,isomer #4CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)C(CCC(=O)O)=C2C)NC1=O6291.7Standard polar33892256
Urobilin,3TMS,isomer #5CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC4NC(=O)C(C)=C4CC)N3[Si](C)(C)C)C(CCC(=O)O)=C2C)N([Si](C)(C)C)C1=O4936.3Semi standard non polar33892256
Urobilin,3TMS,isomer #5CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC4NC(=O)C(C)=C4CC)N3[Si](C)(C)C)C(CCC(=O)O)=C2C)N([Si](C)(C)C)C1=O4840.4Standard non polar33892256
Urobilin,3TMS,isomer #5CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC4NC(=O)C(C)=C4CC)N3[Si](C)(C)C)C(CCC(=O)O)=C2C)N([Si](C)(C)C)C1=O6342.4Standard polar33892256
Urobilin,3TMS,isomer #6CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)C(CCC(=O)O)=C2C)N([Si](C)(C)C)C1=O4720.7Semi standard non polar33892256
Urobilin,3TMS,isomer #6CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)C(CCC(=O)O)=C2C)N([Si](C)(C)C)C1=O4718.7Standard non polar33892256
Urobilin,3TMS,isomer #6CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)C(CCC(=O)O)=C2C)N([Si](C)(C)C)C1=O6081.3Standard polar33892256
Urobilin,3TMS,isomer #7CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C2C)NC1=O4959.8Semi standard non polar33892256
Urobilin,3TMS,isomer #7CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C2C)NC1=O4820.8Standard non polar33892256
Urobilin,3TMS,isomer #7CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C2C)NC1=O6309.9Standard polar33892256
Urobilin,3TMS,isomer #8CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4NC(=O)C(C)=C4CC)N3[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C2C)N([Si](C)(C)C)C1=O4952.4Semi standard non polar33892256
Urobilin,3TMS,isomer #8CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4NC(=O)C(C)=C4CC)N3[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C2C)N([Si](C)(C)C)C1=O4834.8Standard non polar33892256
Urobilin,3TMS,isomer #8CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4NC(=O)C(C)=C4CC)N3[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C2C)N([Si](C)(C)C)C1=O6361.2Standard polar33892256
Urobilin,3TMS,isomer #9CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)C(CCC(=O)O[Si](C)(C)C)=C2C)N([Si](C)(C)C)C1=O4735.0Semi standard non polar33892256
Urobilin,3TMS,isomer #9CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)C(CCC(=O)O[Si](C)(C)C)=C2C)N([Si](C)(C)C)C1=O4713.7Standard non polar33892256
Urobilin,3TMS,isomer #9CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)C(CCC(=O)O[Si](C)(C)C)=C2C)N([Si](C)(C)C)C1=O6094.5Standard polar33892256
Urobilin,4TMS,isomer #1CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C2C)NC1=O4867.1Semi standard non polar33892256
Urobilin,4TMS,isomer #1CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C2C)NC1=O4811.5Standard non polar33892256
Urobilin,4TMS,isomer #1CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C2C)NC1=O6019.4Standard polar33892256
Urobilin,4TMS,isomer #2CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC4NC(=O)C(C)=C4CC)N3[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C2C)N([Si](C)(C)C)C1=O4861.3Semi standard non polar33892256
Urobilin,4TMS,isomer #2CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC4NC(=O)C(C)=C4CC)N3[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C2C)N([Si](C)(C)C)C1=O4818.1Standard non polar33892256
Urobilin,4TMS,isomer #2CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC4NC(=O)C(C)=C4CC)N3[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C2C)N([Si](C)(C)C)C1=O6076.0Standard polar33892256
Urobilin,4TMS,isomer #3CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)C(CCC(=O)O[Si](C)(C)C)=C2C)N([Si](C)(C)C)C1=O4662.7Semi standard non polar33892256
Urobilin,4TMS,isomer #3CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)C(CCC(=O)O[Si](C)(C)C)=C2C)N([Si](C)(C)C)C1=O4715.7Standard non polar33892256
Urobilin,4TMS,isomer #3CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C)[NH]3)C(CCC(=O)O[Si](C)(C)C)=C2C)N([Si](C)(C)C)C1=O5816.3Standard polar33892256
Urobilin,4TMS,isomer #4CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)C(CCC(=O)O)=C2C)N([Si](C)(C)C)C1=O4776.0Semi standard non polar33892256
Urobilin,4TMS,isomer #4CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)C(CCC(=O)O)=C2C)N([Si](C)(C)C)C1=O4805.1Standard non polar33892256
Urobilin,4TMS,isomer #4CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)C(CCC(=O)O)=C2C)N([Si](C)(C)C)C1=O5872.3Standard polar33892256
Urobilin,4TMS,isomer #5CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C2C)N([Si](C)(C)C)C1=O4790.9Semi standard non polar33892256
Urobilin,4TMS,isomer #5CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C2C)N([Si](C)(C)C)C1=O4801.0Standard non polar33892256
Urobilin,4TMS,isomer #5CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C2C)N([Si](C)(C)C)C1=O5891.2Standard polar33892256
Urobilin,1TBDMS,isomer #1CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C(C)(C)C)C(C)=C(CC4NC(=O)C(C)=C4CC)[NH]3)C(CCC(=O)O)=C2C)NC1=O5356.9Semi standard non polar33892256
Urobilin,1TBDMS,isomer #1CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C(C)(C)C)C(C)=C(CC4NC(=O)C(C)=C4CC)[NH]3)C(CCC(=O)O)=C2C)NC1=O4981.3Standard non polar33892256
Urobilin,1TBDMS,isomer #1CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C(C)(C)C)C(C)=C(CC4NC(=O)C(C)=C4CC)[NH]3)C(CCC(=O)O)=C2C)NC1=O6994.9Standard polar33892256
Urobilin,1TBDMS,isomer #2CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4NC(=O)C(C)=C4CC)[NH]3)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C2C)NC1=O5370.2Semi standard non polar33892256
Urobilin,1TBDMS,isomer #2CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4NC(=O)C(C)=C4CC)[NH]3)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C2C)NC1=O4967.5Standard non polar33892256
Urobilin,1TBDMS,isomer #2CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4NC(=O)C(C)=C4CC)[NH]3)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C2C)NC1=O7005.3Standard polar33892256
Urobilin,1TBDMS,isomer #3CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C(C)(C)C)[NH]3)C(CCC(=O)O)=C2C)NC1=O5299.6Semi standard non polar33892256
Urobilin,1TBDMS,isomer #3CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C(C)(C)C)[NH]3)C(CCC(=O)O)=C2C)NC1=O4929.0Standard non polar33892256
Urobilin,1TBDMS,isomer #3CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C(C)(C)C)[NH]3)C(CCC(=O)O)=C2C)NC1=O6820.5Standard polar33892256
Urobilin,1TBDMS,isomer #4CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4NC(=O)C(C)=C4CC)N3[Si](C)(C)C(C)(C)C)C(CCC(=O)O)=C2C)NC1=O5393.4Semi standard non polar33892256
Urobilin,1TBDMS,isomer #4CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4NC(=O)C(C)=C4CC)N3[Si](C)(C)C(C)(C)C)C(CCC(=O)O)=C2C)NC1=O5060.7Standard non polar33892256
Urobilin,1TBDMS,isomer #4CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4NC(=O)C(C)=C4CC)N3[Si](C)(C)C(C)(C)C)C(CCC(=O)O)=C2C)NC1=O7028.9Standard polar33892256
Urobilin,1TBDMS,isomer #5CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4NC(=O)C(C)=C4CC)[NH]3)C(CCC(=O)O)=C2C)N([Si](C)(C)C(C)(C)C)C1=O5309.5Semi standard non polar33892256
Urobilin,1TBDMS,isomer #5CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4NC(=O)C(C)=C4CC)[NH]3)C(CCC(=O)O)=C2C)N([Si](C)(C)C(C)(C)C)C1=O4927.9Standard non polar33892256
Urobilin,1TBDMS,isomer #5CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4NC(=O)C(C)=C4CC)[NH]3)C(CCC(=O)O)=C2C)N([Si](C)(C)C(C)(C)C)C1=O6863.1Standard polar33892256
Urobilin,2TBDMS,isomer #1CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C(C)(C)C)C(C)=C(CC4NC(=O)C(C)=C4CC)[NH]3)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C2C)NC1=O5396.9Semi standard non polar33892256
Urobilin,2TBDMS,isomer #1CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C(C)(C)C)C(C)=C(CC4NC(=O)C(C)=C4CC)[NH]3)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C2C)NC1=O5138.4Standard non polar33892256
Urobilin,2TBDMS,isomer #1CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C(C)(C)C)C(C)=C(CC4NC(=O)C(C)=C4CC)[NH]3)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C2C)NC1=O6719.8Standard polar33892256
Urobilin,2TBDMS,isomer #10CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4NC(=O)C(C)=C4CC)N3[Si](C)(C)C(C)(C)C)C(CCC(=O)O)=C2C)N([Si](C)(C)C(C)(C)C)C1=O5426.5Semi standard non polar33892256
Urobilin,2TBDMS,isomer #10CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4NC(=O)C(C)=C4CC)N3[Si](C)(C)C(C)(C)C)C(CCC(=O)O)=C2C)N([Si](C)(C)C(C)(C)C)C1=O5196.1Standard non polar33892256
Urobilin,2TBDMS,isomer #10CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4NC(=O)C(C)=C4CC)N3[Si](C)(C)C(C)(C)C)C(CCC(=O)O)=C2C)N([Si](C)(C)C(C)(C)C)C1=O6579.8Standard polar33892256
Urobilin,2TBDMS,isomer #2CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C(C)(C)C)C(C)=C(CC4NC(=O)C(C)=C4CC)N3[Si](C)(C)C(C)(C)C)C(CCC(=O)O)=C2C)NC1=O5443.4Semi standard non polar33892256
Urobilin,2TBDMS,isomer #2CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C(C)(C)C)C(C)=C(CC4NC(=O)C(C)=C4CC)N3[Si](C)(C)C(C)(C)C)C(CCC(=O)O)=C2C)NC1=O5218.6Standard non polar33892256
Urobilin,2TBDMS,isomer #2CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C(C)(C)C)C(C)=C(CC4NC(=O)C(C)=C4CC)N3[Si](C)(C)C(C)(C)C)C(CCC(=O)O)=C2C)NC1=O6711.7Standard polar33892256
Urobilin,2TBDMS,isomer #3CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C(C)(C)C)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C(C)(C)C)[NH]3)C(CCC(=O)O)=C2C)NC1=O5334.4Semi standard non polar33892256
Urobilin,2TBDMS,isomer #3CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C(C)(C)C)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C(C)(C)C)[NH]3)C(CCC(=O)O)=C2C)NC1=O5108.2Standard non polar33892256
Urobilin,2TBDMS,isomer #3CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C(C)(C)C)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C(C)(C)C)[NH]3)C(CCC(=O)O)=C2C)NC1=O6505.4Standard polar33892256
Urobilin,2TBDMS,isomer #4CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C(C)(C)C)C(C)=C(CC4NC(=O)C(C)=C4CC)[NH]3)C(CCC(=O)O)=C2C)N([Si](C)(C)C(C)(C)C)C1=O5339.8Semi standard non polar33892256
Urobilin,2TBDMS,isomer #4CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C(C)(C)C)C(C)=C(CC4NC(=O)C(C)=C4CC)[NH]3)C(CCC(=O)O)=C2C)N([Si](C)(C)C(C)(C)C)C1=O5103.8Standard non polar33892256
Urobilin,2TBDMS,isomer #4CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O[Si](C)(C)C(C)(C)C)C(C)=C(CC4NC(=O)C(C)=C4CC)[NH]3)C(CCC(=O)O)=C2C)N([Si](C)(C)C(C)(C)C)C1=O6555.0Standard polar33892256
Urobilin,2TBDMS,isomer #5CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4NC(=O)C(C)=C4CC)N3[Si](C)(C)C(C)(C)C)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C2C)NC1=O5449.2Semi standard non polar33892256
Urobilin,2TBDMS,isomer #5CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4NC(=O)C(C)=C4CC)N3[Si](C)(C)C(C)(C)C)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C2C)NC1=O5208.2Standard non polar33892256
Urobilin,2TBDMS,isomer #5CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4NC(=O)C(C)=C4CC)N3[Si](C)(C)C(C)(C)C)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C2C)NC1=O6729.6Standard polar33892256
Urobilin,2TBDMS,isomer #6CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C(C)(C)C)[NH]3)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C2C)NC1=O5349.4Semi standard non polar33892256
Urobilin,2TBDMS,isomer #6CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C(C)(C)C)[NH]3)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C2C)NC1=O5099.0Standard non polar33892256
Urobilin,2TBDMS,isomer #6CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C(C)(C)C)[NH]3)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C2C)NC1=O6518.1Standard polar33892256
Urobilin,2TBDMS,isomer #7CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4NC(=O)C(C)=C4CC)[NH]3)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C2C)N([Si](C)(C)C(C)(C)C)C1=O5354.8Semi standard non polar33892256
Urobilin,2TBDMS,isomer #7CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4NC(=O)C(C)=C4CC)[NH]3)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C2C)N([Si](C)(C)C(C)(C)C)C1=O5096.1Standard non polar33892256
Urobilin,2TBDMS,isomer #7CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4NC(=O)C(C)=C4CC)[NH]3)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C2C)N([Si](C)(C)C(C)(C)C)C1=O6567.6Standard polar33892256
Urobilin,2TBDMS,isomer #8CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C(C)(C)C)N3[Si](C)(C)C(C)(C)C)C(CCC(=O)O)=C2C)NC1=O5439.6Semi standard non polar33892256
Urobilin,2TBDMS,isomer #8CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C(C)(C)C)N3[Si](C)(C)C(C)(C)C)C(CCC(=O)O)=C2C)NC1=O5187.3Standard non polar33892256
Urobilin,2TBDMS,isomer #8CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C(C)(C)C)N3[Si](C)(C)C(C)(C)C)C(CCC(=O)O)=C2C)NC1=O6532.7Standard polar33892256
Urobilin,2TBDMS,isomer #9CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C(C)(C)C)[NH]3)C(CCC(=O)O)=C2C)N([Si](C)(C)C(C)(C)C)C1=O5300.2Semi standard non polar33892256
Urobilin,2TBDMS,isomer #9CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C(C)(C)C)[NH]3)C(CCC(=O)O)=C2C)N([Si](C)(C)C(C)(C)C)C1=O5073.0Standard non polar33892256
Urobilin,2TBDMS,isomer #9CCC1=C(C)C(CC2=NC(=CC3=C(CCC(=O)O)C(C)=C(CC4C(CC)=C(C)C(=O)N4[Si](C)(C)C(C)(C)C)[NH]3)C(CCC(=O)O)=C2C)N([Si](C)(C)C(C)(C)C)C1=O6367.3Standard polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Urobilin 10V, Negative-QTOFsplash10-000i-0000090000-d85b5fa954be28328eea2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Urobilin 20V, Negative-QTOFsplash10-059i-1230980000-7aaa425dbac6f050567b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Urobilin 40V, Negative-QTOFsplash10-0079-1590620000-21469cd955bcda852e042021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Urobilin 10V, Positive-QTOFsplash10-00dl-0200390000-89bfa93324aa87bfd8fe2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Urobilin 20V, Positive-QTOFsplash10-00el-1600590000-81d90b579c77efab02b42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Urobilin 40V, Positive-QTOFsplash10-001l-3302950000-7625ffaca4872cd8837e2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified3.36-15.13 umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedLiver cirrhosis details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not Specifiedhepatocellular carcinoma details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Bothliver cirrhosis details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Crohn disease		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative colitis		 details
Associated Disorders and Diseases
Disease References
Cirrhosis
  1. Cao H, Huang H, Xu W, Chen D, Yu J, Li J, Li L: Fecal metabolome profiling of liver cirrhosis and hepatocellular carcinoma patients by ultra performance liquid chromatography-mass spectrometry. Anal Chim Acta. 2011 Apr 8;691(1-2):68-75. doi: 10.1016/j.aca.2011.02.038. Epub 2011 Feb 23. [PubMed:21458633 ]
  2. Huang HJ, Zhang AY, Cao HC, Lu HF, Wang BH, Xie Q, Xu W, Li LJ: Metabolomic analyses of faeces reveals malabsorption in cirrhotic patients. Dig Liver Dis. 2013 Aug;45(8):677-82. doi: 10.1016/j.dld.2013.01.001. Epub 2013 Feb 4. [PubMed:23384618 ]
Hepatocellular carcinoma
  1. Cao H, Huang H, Xu W, Chen D, Yu J, Li J, Li L: Fecal metabolome profiling of liver cirrhosis and hepatocellular carcinoma patients by ultra performance liquid chromatography-mass spectrometry. Anal Chim Acta. 2011 Apr 8;691(1-2):68-75. doi: 10.1016/j.aca.2011.02.038. Epub 2011 Feb 23. [PubMed:21458633 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Crohn's disease
  1. Azario I, Pievani A, Del Priore F, Antolini L, Santi L, Corsi A, Cardinale L, Sawamoto K, Kubaski F, Gentner B, Bernardo ME, Valsecchi MG, Riminucci M, Tomatsu S, Aiuti A, Biondi A, Serafini M: Neonatal umbilical cord blood transplantation halts skeletal disease progression in the murine model of MPS-I. Sci Rep. 2017 Aug 25;7(1):9473. doi: 10.1038/s41598-017-09958-9. [PubMed:28842642 ]
Ulcerative colitis
  1. Azario I, Pievani A, Del Priore F, Antolini L, Santi L, Corsi A, Cardinale L, Sawamoto K, Kubaski F, Gentner B, Bernardo ME, Valsecchi MG, Riminucci M, Tomatsu S, Aiuti A, Biondi A, Serafini M: Neonatal umbilical cord blood transplantation halts skeletal disease progression in the murine model of MPS-I. Sci Rep. 2017 Aug 25;7(1):9473. doi: 10.1038/s41598-017-09958-9. [PubMed:28842642 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB111639
KNApSAcK IDNot Available
Chemspider ID389650
KEGG Compound IDC05794
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkUrobilin
METLIN IDNot Available
PubChem Compound440785
PDB IDNot Available
ChEBI ID36378
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceWatson, C. J.; Weimer, Mary; Hawkinson, Violet E. Differences in the formation of mesobiliviolin and glaucobilin from d- and i-urobilins. Journal of Biological Chemistry (1960), 235 787-94.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Treem WR, Malet PF, Gourley GR, Hyams JS: Bile and stone analysis in two infants with brown pigment gallstones and infected bile. Gastroenterology. 1989 Feb;96(2 Pt 1):519-23. [PubMed:2642880 ]
  2. Jones-Lepp TL: Chemical markers of human waste contamination: analysis of urobilin and pharmaceuticals in source waters. J Environ Monit. 2006 Apr;8(4):472-8. Epub 2006 Mar 10. [PubMed:16604237 ]