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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-13 13:18:56 UTC

Update Date

2022-09-22 18:34:18 UTC

HMDB ID

HMDB0004160

Secondary Accession Numbers

HMDB0004159
HMDB0004161
HMDB04159
HMDB04160
HMDB04161

Metabolite Identification

Common Name

Urobilin

Description

Urobilin, 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

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

  Mrv1652304062012592D          

 44 47  0  0  0  0            999 V2000
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   -0.7846   -2.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -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
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    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
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 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

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
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 40 84  1  0
 41 85  1  0
M  END

  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
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   -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
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   -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
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 19 21  2  0  0  0  0
 19 20  1  0  0  0  0
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 22 23  1  0  0  0  0
 23 25  1  0  0  0  0
 25 24  2  0  0  0  0
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 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

$$$$

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
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   -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
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   -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
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    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
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    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
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   -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
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    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
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    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
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  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  3
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 27 12  2  0
 22 16  1  0
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 40 84  1  0
 41 85  1  0
M  END

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

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

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
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 21 62  1  0
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 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

View in JSmol View Stereo Labels

Synonyms

Value	Source
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 acid	ChEBI
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 acid	ChEBI
8,12-Bis(2-carboxyethyl)-3,18-diethyl-2,7,13,17-tetramethylbilene-b-1,19(4H,16H)-dione	ChEBI
I-urobilin	ChEBI
3,18-Diethyl-1,4,5,15,16,19,22,24-octahydro-2,7,13,17-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoate	Generator
3,18-Diethyl-1,4,5,15,16,19,22,24-octahydro-2,7,13,17-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropionate	Generator
(-)-Urobilin	HMDB
3,18-Diethyl-1,4,5,15,16,19,22,24-octahydro-2,7,13,17-tetramethyl-1,19-dioxo-biline-8,12-dipropionic acid	HMDB
Urobilin ixα	HMDB
Urobilin ixalpha	HMDB
Urobilin	HMDB

Chemical Formula

C₃₃H₄₂N₄O₆

Average Molecular Weight

590.721

Monoisotopic Molecular Weight

590.310435088

IUPAC Name

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

Traditional Name

urobilin

CAS Registry Number

1856-98-0

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 Key

KDCCOOGTVSRCHX-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrapyrroles and derivatives

Sub Class

Bilirubins

Direct Parent

Bilirubins

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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

bilenes (CHEBI:36378 )

Ontology

Not Available

Urine (PMID: 24023812)
Feces (PMID: 21458633)

Source

Endogenous

Endogenous (HMDB: HMDB0004160)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	1.363	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.048 g/L	ALOGPS
logP	3.04	ALOGPS
logP	1.23	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	3.88	ChemAxon
pKa (Strongest Basic)	5.98	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	160.95 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	166.26 m³·mol⁻¹	ChemAxon
Polarizability	66.89 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	234.644	30932474
DeepCCS	[M-H]-	232.748	30932474
DeepCCS	[M-2H]-	265.989	30932474
DeepCCS	[M+Na]+	240.33	30932474
AllCCS	[M+H]+	240.2	32859911
AllCCS	[M+H-H2O]+	239.1	32859911
AllCCS	[M+NH4]+	241.3	32859911
AllCCS	[M+Na]+	241.6	32859911
AllCCS	[M-H]-	233.7	32859911
AllCCS	[M+Na-2H]-	236.6	32859911
AllCCS	[M+HCOO]-	239.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
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	7127.2	Standard polar	33892256
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	4318.3	Standard non polar	33892256
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	5395.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Urobilin,1TMS,isomer #1	CCC1=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=O	5165.8	Semi standard non polar	33892256
Urobilin,1TMS,isomer #1	CCC1=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=O	4784.8	Standard non polar	33892256
Urobilin,1TMS,isomer #1	CCC1=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=O	7041.5	Standard polar	33892256
Urobilin,1TMS,isomer #2	CCC1=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=O	5180.6	Semi standard non polar	33892256
Urobilin,1TMS,isomer #2	CCC1=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=O	4771.9	Standard non polar	33892256
Urobilin,1TMS,isomer #2	CCC1=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=O	7053.9	Standard polar	33892256
Urobilin,1TMS,isomer #3	CCC1=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=O	5070.1	Semi standard non polar	33892256
Urobilin,1TMS,isomer #3	CCC1=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=O	4733.6	Standard non polar	33892256
Urobilin,1TMS,isomer #3	CCC1=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=O	6835.3	Standard polar	33892256
Urobilin,1TMS,isomer #4	CCC1=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=O	5236.6	Semi standard non polar	33892256
Urobilin,1TMS,isomer #4	CCC1=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=O	4878.0	Standard non polar	33892256
Urobilin,1TMS,isomer #4	CCC1=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=O	7104.2	Standard polar	33892256
Urobilin,1TMS,isomer #5	CCC1=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=O	5085.7	Semi standard non polar	33892256
Urobilin,1TMS,isomer #5	CCC1=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=O	4736.1	Standard non polar	33892256
Urobilin,1TMS,isomer #5	CCC1=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=O	6881.7	Standard polar	33892256
Urobilin,2TMS,isomer #1	CCC1=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=O	5068.5	Semi standard non polar	33892256
Urobilin,2TMS,isomer #1	CCC1=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=O	4779.5	Standard non polar	33892256
Urobilin,2TMS,isomer #1	CCC1=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=O	6789.6	Standard polar	33892256
Urobilin,2TMS,isomer #10	CCC1=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=O	5058.7	Semi standard non polar	33892256
Urobilin,2TMS,isomer #10	CCC1=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=O	4850.8	Standard non polar	33892256
Urobilin,2TMS,isomer #10	CCC1=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=O	6652.4	Standard polar	33892256
Urobilin,2TMS,isomer #2	CCC1=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=O	5144.8	Semi standard non polar	33892256
Urobilin,2TMS,isomer #2	CCC1=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=O	4876.5	Standard non polar	33892256
Urobilin,2TMS,isomer #2	CCC1=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=O	6809.8	Standard polar	33892256
Urobilin,2TMS,isomer #3	CCC1=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=O	4942.7	Semi standard non polar	33892256
Urobilin,2TMS,isomer #3	CCC1=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=O	4749.0	Standard non polar	33892256
Urobilin,2TMS,isomer #3	CCC1=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=O	6538.1	Standard polar	33892256
Urobilin,2TMS,isomer #4	CCC1=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=O	4955.1	Semi standard non polar	33892256
Urobilin,2TMS,isomer #4	CCC1=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=O	4752.8	Standard non polar	33892256
Urobilin,2TMS,isomer #4	CCC1=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=O	6588.0	Standard polar	33892256
Urobilin,2TMS,isomer #5	CCC1=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=O	5156.9	Semi standard non polar	33892256
Urobilin,2TMS,isomer #5	CCC1=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=O	4866.4	Standard non polar	33892256
Urobilin,2TMS,isomer #5	CCC1=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=O	6829.0	Standard polar	33892256
Urobilin,2TMS,isomer #6	CCC1=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=O	4956.5	Semi standard non polar	33892256
Urobilin,2TMS,isomer #6	CCC1=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=O	4740.3	Standard non polar	33892256
Urobilin,2TMS,isomer #6	CCC1=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=O	6548.8	Standard polar	33892256
Urobilin,2TMS,isomer #7	CCC1=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=O	4966.7	Semi standard non polar	33892256
Urobilin,2TMS,isomer #7	CCC1=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=O	4745.4	Standard non polar	33892256
Urobilin,2TMS,isomer #7	CCC1=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=O	6599.2	Standard polar	33892256
Urobilin,2TMS,isomer #8	CCC1=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=O	5060.7	Semi standard non polar	33892256
Urobilin,2TMS,isomer #8	CCC1=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=O	4837.1	Standard non polar	33892256
Urobilin,2TMS,isomer #8	CCC1=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=O	6605.2	Standard polar	33892256
Urobilin,2TMS,isomer #9	CCC1=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=O	4849.3	Semi standard non polar	33892256
Urobilin,2TMS,isomer #9	CCC1=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=O	4711.9	Standard non polar	33892256
Urobilin,2TMS,isomer #9	CCC1=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=O	6377.5	Standard polar	33892256
Urobilin,3TMS,isomer #1	CCC1=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=O	5033.9	Semi standard non polar	33892256
Urobilin,3TMS,isomer #1	CCC1=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=O	4849.4	Standard non polar	33892256
Urobilin,3TMS,isomer #1	CCC1=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=O	6528.9	Standard polar	33892256
Urobilin,3TMS,isomer #10	CCC1=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=O	4891.3	Semi standard non polar	33892256
Urobilin,3TMS,isomer #10	CCC1=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=O	4811.2	Standard non polar	33892256
Urobilin,3TMS,isomer #10	CCC1=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=O	6150.2	Standard polar	33892256
Urobilin,3TMS,isomer #2	CCC1=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=O	4845.6	Semi standard non polar	33892256
Urobilin,3TMS,isomer #2	CCC1=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=O	4737.8	Standard non polar	33892256
Urobilin,3TMS,isomer #2	CCC1=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=O	6259.2	Standard polar	33892256
Urobilin,3TMS,isomer #3	CCC1=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=O	4858.9	Semi standard non polar	33892256
Urobilin,3TMS,isomer #3	CCC1=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=O	4745.8	Standard non polar	33892256
Urobilin,3TMS,isomer #3	CCC1=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=O	6311.8	Standard polar	33892256
Urobilin,3TMS,isomer #4	CCC1=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=O	4942.5	Semi standard non polar	33892256
Urobilin,3TMS,isomer #4	CCC1=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=O	4827.8	Standard non polar	33892256
Urobilin,3TMS,isomer #4	CCC1=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=O	6291.7	Standard polar	33892256
Urobilin,3TMS,isomer #5	CCC1=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=O	4936.3	Semi standard non polar	33892256
Urobilin,3TMS,isomer #5	CCC1=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=O	4840.4	Standard non polar	33892256
Urobilin,3TMS,isomer #5	CCC1=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=O	6342.4	Standard polar	33892256
Urobilin,3TMS,isomer #6	CCC1=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=O	4720.7	Semi standard non polar	33892256
Urobilin,3TMS,isomer #6	CCC1=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=O	4718.7	Standard non polar	33892256
Urobilin,3TMS,isomer #6	CCC1=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=O	6081.3	Standard polar	33892256
Urobilin,3TMS,isomer #7	CCC1=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=O	4959.8	Semi standard non polar	33892256
Urobilin,3TMS,isomer #7	CCC1=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=O	4820.8	Standard non polar	33892256
Urobilin,3TMS,isomer #7	CCC1=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=O	6309.9	Standard polar	33892256
Urobilin,3TMS,isomer #8	CCC1=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=O	4952.4	Semi standard non polar	33892256
Urobilin,3TMS,isomer #8	CCC1=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=O	4834.8	Standard non polar	33892256
Urobilin,3TMS,isomer #8	CCC1=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=O	6361.2	Standard polar	33892256
Urobilin,3TMS,isomer #9	CCC1=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=O	4735.0	Semi standard non polar	33892256
Urobilin,3TMS,isomer #9	CCC1=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=O	4713.7	Standard non polar	33892256
Urobilin,3TMS,isomer #9	CCC1=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=O	6094.5	Standard polar	33892256
Urobilin,4TMS,isomer #1	CCC1=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=O	4867.1	Semi standard non polar	33892256
Urobilin,4TMS,isomer #1	CCC1=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=O	4811.5	Standard non polar	33892256
Urobilin,4TMS,isomer #1	CCC1=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=O	6019.4	Standard polar	33892256
Urobilin,4TMS,isomer #2	CCC1=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=O	4861.3	Semi standard non polar	33892256
Urobilin,4TMS,isomer #2	CCC1=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=O	4818.1	Standard non polar	33892256
Urobilin,4TMS,isomer #2	CCC1=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=O	6076.0	Standard polar	33892256
Urobilin,4TMS,isomer #3	CCC1=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=O	4662.7	Semi standard non polar	33892256
Urobilin,4TMS,isomer #3	CCC1=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=O	4715.7	Standard non polar	33892256
Urobilin,4TMS,isomer #3	CCC1=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=O	5816.3	Standard polar	33892256
Urobilin,4TMS,isomer #4	CCC1=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=O	4776.0	Semi standard non polar	33892256
Urobilin,4TMS,isomer #4	CCC1=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=O	4805.1	Standard non polar	33892256
Urobilin,4TMS,isomer #4	CCC1=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=O	5872.3	Standard polar	33892256
Urobilin,4TMS,isomer #5	CCC1=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=O	4790.9	Semi standard non polar	33892256
Urobilin,4TMS,isomer #5	CCC1=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=O	4801.0	Standard non polar	33892256
Urobilin,4TMS,isomer #5	CCC1=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=O	5891.2	Standard polar	33892256
Urobilin,1TBDMS,isomer #1	CCC1=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=O	5356.9	Semi standard non polar	33892256
Urobilin,1TBDMS,isomer #1	CCC1=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=O	4981.3	Standard non polar	33892256
Urobilin,1TBDMS,isomer #1	CCC1=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=O	6994.9	Standard polar	33892256
Urobilin,1TBDMS,isomer #2	CCC1=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=O	5370.2	Semi standard non polar	33892256
Urobilin,1TBDMS,isomer #2	CCC1=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=O	4967.5	Standard non polar	33892256
Urobilin,1TBDMS,isomer #2	CCC1=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=O	7005.3	Standard polar	33892256
Urobilin,1TBDMS,isomer #3	CCC1=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=O	5299.6	Semi standard non polar	33892256
Urobilin,1TBDMS,isomer #3	CCC1=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=O	4929.0	Standard non polar	33892256
Urobilin,1TBDMS,isomer #3	CCC1=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=O	6820.5	Standard polar	33892256
Urobilin,1TBDMS,isomer #4	CCC1=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=O	5393.4	Semi standard non polar	33892256
Urobilin,1TBDMS,isomer #4	CCC1=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=O	5060.7	Standard non polar	33892256
Urobilin,1TBDMS,isomer #4	CCC1=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=O	7028.9	Standard polar	33892256
Urobilin,1TBDMS,isomer #5	CCC1=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=O	5309.5	Semi standard non polar	33892256
Urobilin,1TBDMS,isomer #5	CCC1=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=O	4927.9	Standard non polar	33892256
Urobilin,1TBDMS,isomer #5	CCC1=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=O	6863.1	Standard polar	33892256
Urobilin,2TBDMS,isomer #1	CCC1=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=O	5396.9	Semi standard non polar	33892256
Urobilin,2TBDMS,isomer #1	CCC1=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=O	5138.4	Standard non polar	33892256
Urobilin,2TBDMS,isomer #1	CCC1=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=O	6719.8	Standard polar	33892256
Urobilin,2TBDMS,isomer #10	CCC1=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=O	5426.5	Semi standard non polar	33892256
Urobilin,2TBDMS,isomer #10	CCC1=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=O	5196.1	Standard non polar	33892256
Urobilin,2TBDMS,isomer #10	CCC1=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=O	6579.8	Standard polar	33892256
Urobilin,2TBDMS,isomer #2	CCC1=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=O	5443.4	Semi standard non polar	33892256
Urobilin,2TBDMS,isomer #2	CCC1=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=O	5218.6	Standard non polar	33892256
Urobilin,2TBDMS,isomer #2	CCC1=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=O	6711.7	Standard polar	33892256
Urobilin,2TBDMS,isomer #3	CCC1=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=O	5334.4	Semi standard non polar	33892256
Urobilin,2TBDMS,isomer #3	CCC1=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=O	5108.2	Standard non polar	33892256
Urobilin,2TBDMS,isomer #3	CCC1=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=O	6505.4	Standard polar	33892256
Urobilin,2TBDMS,isomer #4	CCC1=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=O	5339.8	Semi standard non polar	33892256
Urobilin,2TBDMS,isomer #4	CCC1=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=O	5103.8	Standard non polar	33892256
Urobilin,2TBDMS,isomer #4	CCC1=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=O	6555.0	Standard polar	33892256
Urobilin,2TBDMS,isomer #5	CCC1=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=O	5449.2	Semi standard non polar	33892256
Urobilin,2TBDMS,isomer #5	CCC1=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=O	5208.2	Standard non polar	33892256
Urobilin,2TBDMS,isomer #5	CCC1=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=O	6729.6	Standard polar	33892256
Urobilin,2TBDMS,isomer #6	CCC1=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=O	5349.4	Semi standard non polar	33892256
Urobilin,2TBDMS,isomer #6	CCC1=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=O	5099.0	Standard non polar	33892256
Urobilin,2TBDMS,isomer #6	CCC1=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=O	6518.1	Standard polar	33892256
Urobilin,2TBDMS,isomer #7	CCC1=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=O	5354.8	Semi standard non polar	33892256
Urobilin,2TBDMS,isomer #7	CCC1=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=O	5096.1	Standard non polar	33892256
Urobilin,2TBDMS,isomer #7	CCC1=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=O	6567.6	Standard polar	33892256
Urobilin,2TBDMS,isomer #8	CCC1=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=O	5439.6	Semi standard non polar	33892256
Urobilin,2TBDMS,isomer #8	CCC1=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=O	5187.3	Standard non polar	33892256
Urobilin,2TBDMS,isomer #8	CCC1=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=O	6532.7	Standard polar	33892256
Urobilin,2TBDMS,isomer #9	CCC1=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=O	5300.2	Semi standard non polar	33892256
Urobilin,2TBDMS,isomer #9	CCC1=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=O	5073.0	Standard non polar	33892256
Urobilin,2TBDMS,isomer #9	CCC1=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=O	6367.3	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Urobilin 10V, Negative-QTOF	splash10-000i-0000090000-d85b5fa954be28328eea	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Urobilin 20V, Negative-QTOF	splash10-059i-1230980000-7aaa425dbac6f050567b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Urobilin 40V, Negative-QTOF	splash10-0079-1590620000-21469cd955bcda852e04	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Urobilin 10V, Positive-QTOF	splash10-00dl-0200390000-89bfa93324aa87bfd8fe	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Urobilin 20V, Positive-QTOF	splash10-00el-1600590000-81d90b579c77efab02b4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Urobilin 40V, Positive-QTOF	splash10-001l-3302950000-7625ffaca4872cd8837e	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	21458633	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	23384618	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	28842642	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25496753	details
Urine	Detected and Quantified	3.36-15.13 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Liver cirrhosis	21458633	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	hepatocellular carcinoma	21458633	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	liver cirrhosis	23384618	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Crohn disease	28842642	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ulcerative colitis	28842642	details

Associated Disorders and Diseases

Disease References

Cirrhosis
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 ] 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
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
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 ] 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
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
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

114550 (Hepatocellular carcinoma)
114500 (Colorectal cancer)
266600 (Crohn's disease)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB111639

KNApSAcK ID

Not Available

Chemspider ID

389650

KEGG Compound ID

C05794

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Urobilin

METLIN ID

Not Available

PubChem Compound

440785

PDB ID

Not Available

ChEBI ID

36378

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Watson, 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

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 ]
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 ]

Showing metabocard for Urobilin (HMDB0004160)

MOL for HMDB0004160 (Urobilin)

3D MOL for HMDB0004160 (Urobilin)

3D SDF for HMDB0004160 (Urobilin)

3D-SDF for HMDB0004160 (Urobilin)

PDB for HMDB0004160 (Urobilin)

3D PDB for HMDB0004160 (Urobilin)

SMILES for HMDB0004160 (Urobilin)

INCHI for HMDB0004160 (Urobilin)

Structure for HMDB0004160 (Urobilin)

3D Structure for HMDB0004160 (Urobilin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

MS/MS Spectra