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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2018-03-01 20:56:52 UTC
Update Date2021-09-14 15:44:26 UTC
HMDB IDHMDB0240259
Secondary Accession NumbersNone
Metabolite Identification
Common NameStercobilin
DescriptionStercobilin is the tetrapyrrole chemical compound that is primarily responsible for the brown color of feces. It was originally isolated from feces in 1932. Stercobilin is formed through the reduction of its parent compound stercblinogen. Urobilinogen 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. Urobilinogen that remains in the colon can either be reduced to stercobilinogen and finally oxidized to stercobilin, or it can be directly reduced to stercobilin. Stercobilin is responsible for the brown color of human feces. Stercobilin is then excreted in the feces. It is a microbial metabolite.
Structure
Data?1563892738
Synonyms
ValueSource
(2R,3R,4S,16S,17R,18R)-3,18-Diethyl-1,2,3,4,5,15,16,17,18,19,22,24-dodecahydro-2,7,13,17-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoic acidChEBI
(2R,3R,4S,16S,17R,18R)-3,18-Diethyl-1,2,3,4,5,15,16,17,18,19,22,24-dodecahydro-2,7,13,17-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropionic acidChEBI
StercobilinChEBI
Stercobilin IXChEBI
(2R,3R,4S,16S,17R,18R)-3,18-Diethyl-1,2,3,4,5,15,16,17,18,19,22,24-dodecahydro-2,7,13,17-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoateGenerator
(2R,3R,4S,16S,17R,18R)-3,18-Diethyl-1,2,3,4,5,15,16,17,18,19,22,24-dodecahydro-2,7,13,17-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropionateGenerator
(-)-StercobilinHMDB
Stercobilin IXalphaHMDB
Stercobilin IXαHMDB
StercobilineHMDB
Chemical FormulaC33H46N4O6
Average Molecular Weight594.753
Monoisotopic Molecular Weight594.341735217
IUPAC Name3-(2-{[(2Z)-3-(2-carboxyethyl)-5-{[(2S,3R,4R)-4-ethyl-3-methyl-5-oxopyrrolidin-2-yl]methyl}-4-methyl-2H-pyrrol-2-ylidene]methyl}-5-{[(2S,3R,4R)-3-ethyl-4-methyl-5-oxopyrrolidin-2-yl]methyl}-4-methyl-1H-pyrrol-3-yl)propanoic acid
Traditional Name(-)-stercobilin
CAS Registry Number34217-90-8
SMILES
CC[C@H]1[C@H](CC2=C(C)C(CCC(O)=O)=C(N2)\C=C2/N=C(C[C@@H]3NC(=O)[C@H](CC)[C@H]3C)C(C)=C2CCC(O)=O)NC(=O)[C@@H]1C
InChI Identifier
InChI=1S/C33H46N4O6/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/h15-16,19-21,26-27,35H,7-14H2,1-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/b28-15-/t16-,19-,20-,21-,26+,27+/m1/s1
InChI KeyDEEUSUJLZQQESV-BQUSTMGCSA-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
  • Pyrrolidone
  • 2-pyrrolidone
  • Substituted pyrrole
  • Pyrrole
  • Pyrrolidine
  • Heteroaromatic compound
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Ketimine
  • Lactam
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • 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
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP2.98ALOGPS
logP1.42ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)3.87ChemAxon
pKa (Strongest Basic)6.02ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area160.95 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity165.2 m³·mol⁻¹ChemAxon
Polarizability67.94 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
AllCCS[M+H]+240.77731661259
AllCCS[M-H]-240.35431661259
DeepCCS[M+H]+230.17730932474
DeepCCS[M-H]-228.35230932474
DeepCCS[M-2H]-261.98630932474
DeepCCS[M+Na]+235.78330932474
AllCCS[M+H]+240.832859911
AllCCS[M+H-H2O]+239.432859911
AllCCS[M+NH4]+242.032859911
AllCCS[M+Na]+242.332859911
AllCCS[M-H]-240.432859911
AllCCS[M+Na-2H]-244.332859911
AllCCS[M+HCOO]-248.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
StercobilinCC[C@H]1[C@H](CC2=C(C)C(CCC(O)=O)=C(N2)\C=C2/N=C(C[C@@H]3NC(=O)[C@H](CC)[C@H]3C)C(C)=C2CCC(O)=O)NC(=O)[C@@H]1C6831.2Standard polar33892256
StercobilinCC[C@H]1[C@H](CC2=C(C)C(CCC(O)=O)=C(N2)\C=C2/N=C(C[C@@H]3NC(=O)[C@H](CC)[C@H]3C)C(C)=C2CCC(O)=O)NC(=O)[C@@H]1C4726.0Standard non polar33892256
StercobilinCC[C@H]1[C@H](CC2=C(C)C(CCC(O)=O)=C(N2)\C=C2/N=C(C[C@@H]3NC(=O)[C@H](CC)[C@H]3C)C(C)=C2CCC(O)=O)NC(=O)[C@@H]1C5371.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Stercobilin,1TMS,isomer #1CC[C@H]1C(=O)N[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(C[C@@H]4NC(=O)[C@H](C)[C@H]4CC)[NH]3)C(CCC(=O)O)=C2C)[C@@H]1C4846.1Semi standard non polar33892256
Stercobilin,1TMS,isomer #2CC[C@H]1C(=O)N[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O)C(C)=C(C[C@@H]4NC(=O)[C@H](C)[C@H]4CC)[NH]3)C(CCC(=O)O[Si](C)(C)C)=C2C)[C@@H]1C4857.3Semi standard non polar33892256
Stercobilin,1TMS,isomer #3CC[C@H]1C(=O)N[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O)C(C)=C(C[C@@H]4NC(=O)[C@H](C)[C@H]4CC)N3[Si](C)(C)C)C(CCC(=O)O)=C2C)[C@@H]1C4879.9Semi standard non polar33892256
Stercobilin,1TMS,isomer #4CC[C@H]1C(=O)N([Si](C)(C)C)[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O)C(C)=C(C[C@@H]4NC(=O)[C@H](C)[C@H]4CC)[NH]3)C(CCC(=O)O)=C2C)[C@@H]1C4707.9Semi standard non polar33892256
Stercobilin,1TMS,isomer #5CC[C@H]1C(=O)N[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O)C(C)=C(C[C@H]4[C@H](CC)[C@@H](C)C(=O)N4[Si](C)(C)C)[NH]3)C(CCC(=O)O)=C2C)[C@@H]1C4693.9Semi standard non polar33892256
Stercobilin,2TMS,isomer #1CC[C@H]1C(=O)N[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(C[C@@H]4NC(=O)[C@H](C)[C@H]4CC)[NH]3)C(CCC(=O)O[Si](C)(C)C)=C2C)[C@@H]1C4766.6Semi standard non polar33892256
Stercobilin,2TMS,isomer #10CC[C@H]1C(=O)N([Si](C)(C)C)[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O)C(C)=C(C[C@H]4[C@H](CC)[C@@H](C)C(=O)N4[Si](C)(C)C)[NH]3)C(CCC(=O)O)=C2C)[C@@H]1C4444.3Semi standard non polar33892256
Stercobilin,2TMS,isomer #2CC[C@H]1C(=O)N([Si](C)(C)C)[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(C[C@@H]4NC(=O)[C@H](C)[C@H]4CC)[NH]3)C(CCC(=O)O)=C2C)[C@@H]1C4604.3Semi standard non polar33892256
Stercobilin,2TMS,isomer #3CC[C@H]1C(=O)N[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(C[C@@H]4NC(=O)[C@H](C)[C@H]4CC)N3[Si](C)(C)C)C(CCC(=O)O)=C2C)[C@@H]1C4805.6Semi standard non polar33892256
Stercobilin,2TMS,isomer #4CC[C@H]1C(=O)N[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(C[C@H]4[C@H](CC)[C@@H](C)C(=O)N4[Si](C)(C)C)[NH]3)C(CCC(=O)O)=C2C)[C@@H]1C4582.7Semi standard non polar33892256
Stercobilin,2TMS,isomer #5CC[C@H]1C(=O)N([Si](C)(C)C)[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O)C(C)=C(C[C@@H]4NC(=O)[C@H](C)[C@H]4CC)[NH]3)C(CCC(=O)O[Si](C)(C)C)=C2C)[C@@H]1C4621.3Semi standard non polar33892256
Stercobilin,2TMS,isomer #6CC[C@H]1C(=O)N[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O)C(C)=C(C[C@@H]4NC(=O)[C@H](C)[C@H]4CC)N3[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C2C)[C@@H]1C4811.4Semi standard non polar33892256
Stercobilin,2TMS,isomer #7CC[C@H]1C(=O)N[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O)C(C)=C(C[C@H]4[C@H](CC)[C@@H](C)C(=O)N4[Si](C)(C)C)[NH]3)C(CCC(=O)O[Si](C)(C)C)=C2C)[C@@H]1C4601.5Semi standard non polar33892256
Stercobilin,2TMS,isomer #8CC[C@H]1C(=O)N([Si](C)(C)C)[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O)C(C)=C(C[C@@H]4NC(=O)[C@H](C)[C@H]4CC)N3[Si](C)(C)C)C(CCC(=O)O)=C2C)[C@@H]1C4694.1Semi standard non polar33892256
Stercobilin,2TMS,isomer #9CC[C@H]1C(=O)N[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O)C(C)=C(C[C@H]4[C@H](CC)[C@@H](C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)C(CCC(=O)O)=C2C)[C@@H]1C4675.8Semi standard non polar33892256
Stercobilin,3TMS,isomer #1CC[C@H]1C(=O)N([Si](C)(C)C)[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(C[C@@H]4NC(=O)[C@H](C)[C@H]4CC)[NH]3)C(CCC(=O)O[Si](C)(C)C)=C2C)[C@@H]1C4552.1Semi standard non polar33892256
Stercobilin,3TMS,isomer #1CC[C@H]1C(=O)N([Si](C)(C)C)[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(C[C@@H]4NC(=O)[C@H](C)[C@H]4CC)[NH]3)C(CCC(=O)O[Si](C)(C)C)=C2C)[C@@H]1C4590.9Standard non polar33892256
Stercobilin,3TMS,isomer #1CC[C@H]1C(=O)N([Si](C)(C)C)[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(C[C@@H]4NC(=O)[C@H](C)[C@H]4CC)[NH]3)C(CCC(=O)O[Si](C)(C)C)=C2C)[C@@H]1C6285.1Standard polar33892256
Stercobilin,3TMS,isomer #10CC[C@H]1C(=O)N([Si](C)(C)C)[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O)C(C)=C(C[C@H]4[C@H](CC)[C@@H](C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)C(CCC(=O)O)=C2C)[C@@H]1C4515.2Semi standard non polar33892256
Stercobilin,3TMS,isomer #10CC[C@H]1C(=O)N([Si](C)(C)C)[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O)C(C)=C(C[C@H]4[C@H](CC)[C@@H](C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)C(CCC(=O)O)=C2C)[C@@H]1C4677.7Standard non polar33892256
Stercobilin,3TMS,isomer #10CC[C@H]1C(=O)N([Si](C)(C)C)[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O)C(C)=C(C[C@H]4[C@H](CC)[C@@H](C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)C(CCC(=O)O)=C2C)[C@@H]1C6097.6Standard polar33892256
Stercobilin,3TMS,isomer #2CC[C@H]1C(=O)N[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(C[C@@H]4NC(=O)[C@H](C)[C@H]4CC)N3[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C2C)[C@@H]1C4729.4Semi standard non polar33892256
Stercobilin,3TMS,isomer #2CC[C@H]1C(=O)N[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(C[C@@H]4NC(=O)[C@H](C)[C@H]4CC)N3[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C2C)[C@@H]1C4661.5Standard non polar33892256
Stercobilin,3TMS,isomer #2CC[C@H]1C(=O)N[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(C[C@@H]4NC(=O)[C@H](C)[C@H]4CC)N3[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C2C)[C@@H]1C6491.6Standard polar33892256
Stercobilin,3TMS,isomer #3CC[C@H]1C(=O)N[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(C[C@H]4[C@H](CC)[C@@H](C)C(=O)N4[Si](C)(C)C)[NH]3)C(CCC(=O)O[Si](C)(C)C)=C2C)[C@@H]1C4523.6Semi standard non polar33892256
Stercobilin,3TMS,isomer #3CC[C@H]1C(=O)N[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(C[C@H]4[C@H](CC)[C@@H](C)C(=O)N4[Si](C)(C)C)[NH]3)C(CCC(=O)O[Si](C)(C)C)=C2C)[C@@H]1C4603.7Standard non polar33892256
Stercobilin,3TMS,isomer #3CC[C@H]1C(=O)N[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(C[C@H]4[C@H](CC)[C@@H](C)C(=O)N4[Si](C)(C)C)[NH]3)C(CCC(=O)O[Si](C)(C)C)=C2C)[C@@H]1C6251.6Standard polar33892256
Stercobilin,3TMS,isomer #4CC[C@H]1C(=O)N([Si](C)(C)C)[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(C[C@@H]4NC(=O)[C@H](C)[C@H]4CC)N3[Si](C)(C)C)C(CCC(=O)O)=C2C)[C@@H]1C4609.8Semi standard non polar33892256
Stercobilin,3TMS,isomer #4CC[C@H]1C(=O)N([Si](C)(C)C)[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(C[C@@H]4NC(=O)[C@H](C)[C@H]4CC)N3[Si](C)(C)C)C(CCC(=O)O)=C2C)[C@@H]1C4671.2Standard non polar33892256
Stercobilin,3TMS,isomer #4CC[C@H]1C(=O)N([Si](C)(C)C)[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(C[C@@H]4NC(=O)[C@H](C)[C@H]4CC)N3[Si](C)(C)C)C(CCC(=O)O)=C2C)[C@@H]1C6276.5Standard polar33892256
Stercobilin,3TMS,isomer #5CC[C@H]1C(=O)N([Si](C)(C)C)[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(C[C@H]4[C@H](CC)[C@@H](C)C(=O)N4[Si](C)(C)C)[NH]3)C(CCC(=O)O)=C2C)[C@@H]1C4399.9Semi standard non polar33892256
Stercobilin,3TMS,isomer #5CC[C@H]1C(=O)N([Si](C)(C)C)[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(C[C@H]4[C@H](CC)[C@@H](C)C(=O)N4[Si](C)(C)C)[NH]3)C(CCC(=O)O)=C2C)[C@@H]1C4607.3Standard non polar33892256
Stercobilin,3TMS,isomer #5CC[C@H]1C(=O)N([Si](C)(C)C)[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(C[C@H]4[C@H](CC)[C@@H](C)C(=O)N4[Si](C)(C)C)[NH]3)C(CCC(=O)O)=C2C)[C@@H]1C6039.4Standard polar33892256
Stercobilin,3TMS,isomer #6CC[C@H]1C(=O)N[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(C[C@H]4[C@H](CC)[C@@H](C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)C(CCC(=O)O)=C2C)[C@@H]1C4592.7Semi standard non polar33892256
Stercobilin,3TMS,isomer #6CC[C@H]1C(=O)N[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(C[C@H]4[C@H](CC)[C@@H](C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)C(CCC(=O)O)=C2C)[C@@H]1C4690.2Standard non polar33892256
Stercobilin,3TMS,isomer #6CC[C@H]1C(=O)N[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(C[C@H]4[C@H](CC)[C@@H](C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)C(CCC(=O)O)=C2C)[C@@H]1C6240.9Standard polar33892256
Stercobilin,3TMS,isomer #7CC[C@H]1C(=O)N([Si](C)(C)C)[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O)C(C)=C(C[C@@H]4NC(=O)[C@H](C)[C@H]4CC)N3[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C2C)[C@@H]1C4627.0Semi standard non polar33892256
Stercobilin,3TMS,isomer #7CC[C@H]1C(=O)N([Si](C)(C)C)[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O)C(C)=C(C[C@@H]4NC(=O)[C@H](C)[C@H]4CC)N3[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C2C)[C@@H]1C4662.8Standard non polar33892256
Stercobilin,3TMS,isomer #7CC[C@H]1C(=O)N([Si](C)(C)C)[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O)C(C)=C(C[C@@H]4NC(=O)[C@H](C)[C@H]4CC)N3[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C2C)[C@@H]1C6296.2Standard polar33892256
Stercobilin,3TMS,isomer #8CC[C@H]1C(=O)N([Si](C)(C)C)[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O)C(C)=C(C[C@H]4[C@H](CC)[C@@H](C)C(=O)N4[Si](C)(C)C)[NH]3)C(CCC(=O)O[Si](C)(C)C)=C2C)[C@@H]1C4418.4Semi standard non polar33892256
Stercobilin,3TMS,isomer #8CC[C@H]1C(=O)N([Si](C)(C)C)[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O)C(C)=C(C[C@H]4[C@H](CC)[C@@H](C)C(=O)N4[Si](C)(C)C)[NH]3)C(CCC(=O)O[Si](C)(C)C)=C2C)[C@@H]1C4600.5Standard non polar33892256
Stercobilin,3TMS,isomer #8CC[C@H]1C(=O)N([Si](C)(C)C)[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O)C(C)=C(C[C@H]4[C@H](CC)[C@@H](C)C(=O)N4[Si](C)(C)C)[NH]3)C(CCC(=O)O[Si](C)(C)C)=C2C)[C@@H]1C6054.9Standard polar33892256
Stercobilin,3TMS,isomer #9CC[C@H]1C(=O)N[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O)C(C)=C(C[C@H]4[C@H](CC)[C@@H](C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C2C)[C@@H]1C4608.2Semi standard non polar33892256
Stercobilin,3TMS,isomer #9CC[C@H]1C(=O)N[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O)C(C)=C(C[C@H]4[C@H](CC)[C@@H](C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C2C)[C@@H]1C4682.5Standard non polar33892256
Stercobilin,3TMS,isomer #9CC[C@H]1C(=O)N[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O)C(C)=C(C[C@H]4[C@H](CC)[C@@H](C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C2C)[C@@H]1C6260.5Standard polar33892256
Stercobilin,4TMS,isomer #1CC[C@H]1C(=O)N([Si](C)(C)C)[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(C[C@@H]4NC(=O)[C@H](C)[C@H]4CC)N3[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C2C)[C@@H]1C4561.2Semi standard non polar33892256
Stercobilin,4TMS,isomer #1CC[C@H]1C(=O)N([Si](C)(C)C)[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(C[C@@H]4NC(=O)[C@H](C)[C@H]4CC)N3[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C2C)[C@@H]1C4642.8Standard non polar33892256
Stercobilin,4TMS,isomer #1CC[C@H]1C(=O)N([Si](C)(C)C)[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(C[C@@H]4NC(=O)[C@H](C)[C@H]4CC)N3[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C2C)[C@@H]1C5991.1Standard polar33892256
Stercobilin,4TMS,isomer #2CC[C@H]1C(=O)N([Si](C)(C)C)[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(C[C@H]4[C@H](CC)[C@@H](C)C(=O)N4[Si](C)(C)C)[NH]3)C(CCC(=O)O[Si](C)(C)C)=C2C)[C@@H]1C4395.8Semi standard non polar33892256
Stercobilin,4TMS,isomer #2CC[C@H]1C(=O)N([Si](C)(C)C)[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(C[C@H]4[C@H](CC)[C@@H](C)C(=O)N4[Si](C)(C)C)[NH]3)C(CCC(=O)O[Si](C)(C)C)=C2C)[C@@H]1C4602.4Standard non polar33892256
Stercobilin,4TMS,isomer #2CC[C@H]1C(=O)N([Si](C)(C)C)[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(C[C@H]4[C@H](CC)[C@@H](C)C(=O)N4[Si](C)(C)C)[NH]3)C(CCC(=O)O[Si](C)(C)C)=C2C)[C@@H]1C5738.4Standard polar33892256
Stercobilin,4TMS,isomer #3CC[C@H]1C(=O)N[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(C[C@H]4[C@H](CC)[C@@H](C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C2C)[C@@H]1C4541.1Semi standard non polar33892256
Stercobilin,4TMS,isomer #3CC[C@H]1C(=O)N[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(C[C@H]4[C@H](CC)[C@@H](C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C2C)[C@@H]1C4659.0Standard non polar33892256
Stercobilin,4TMS,isomer #3CC[C@H]1C(=O)N[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(C[C@H]4[C@H](CC)[C@@H](C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C2C)[C@@H]1C5957.5Standard polar33892256
Stercobilin,4TMS,isomer #4CC[C@H]1C(=O)N([Si](C)(C)C)[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(C[C@H]4[C@H](CC)[C@@H](C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)C(CCC(=O)O)=C2C)[C@@H]1C4465.3Semi standard non polar33892256
Stercobilin,4TMS,isomer #4CC[C@H]1C(=O)N([Si](C)(C)C)[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(C[C@H]4[C@H](CC)[C@@H](C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)C(CCC(=O)O)=C2C)[C@@H]1C4670.9Standard non polar33892256
Stercobilin,4TMS,isomer #4CC[C@H]1C(=O)N([Si](C)(C)C)[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O[Si](C)(C)C)C(C)=C(C[C@H]4[C@H](CC)[C@@H](C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)C(CCC(=O)O)=C2C)[C@@H]1C5781.8Standard polar33892256
Stercobilin,4TMS,isomer #5CC[C@H]1C(=O)N([Si](C)(C)C)[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O)C(C)=C(C[C@H]4[C@H](CC)[C@@H](C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C2C)[C@@H]1C4481.2Semi standard non polar33892256
Stercobilin,4TMS,isomer #5CC[C@H]1C(=O)N([Si](C)(C)C)[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O)C(C)=C(C[C@H]4[C@H](CC)[C@@H](C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C2C)[C@@H]1C4664.7Standard non polar33892256
Stercobilin,4TMS,isomer #5CC[C@H]1C(=O)N([Si](C)(C)C)[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O)C(C)=C(C[C@H]4[C@H](CC)[C@@H](C)C(=O)N4[Si](C)(C)C)N3[Si](C)(C)C)C(CCC(=O)O[Si](C)(C)C)=C2C)[C@@H]1C5803.2Standard polar33892256
Stercobilin,1TBDMS,isomer #1CC[C@H]1C(=O)N[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O[Si](C)(C)C(C)(C)C)C(C)=C(C[C@@H]4NC(=O)[C@H](C)[C@H]4CC)[NH]3)C(CCC(=O)O)=C2C)[C@@H]1C5028.7Semi standard non polar33892256
Stercobilin,1TBDMS,isomer #2CC[C@H]1C(=O)N[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O)C(C)=C(C[C@@H]4NC(=O)[C@H](C)[C@H]4CC)[NH]3)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C2C)[C@@H]1C5039.4Semi standard non polar33892256
Stercobilin,1TBDMS,isomer #3CC[C@H]1C(=O)N[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O)C(C)=C(C[C@@H]4NC(=O)[C@H](C)[C@H]4CC)N3[Si](C)(C)C(C)(C)C)C(CCC(=O)O)=C2C)[C@@H]1C5035.4Semi standard non polar33892256
Stercobilin,1TBDMS,isomer #4CC[C@H]1C(=O)N([Si](C)(C)C(C)(C)C)[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O)C(C)=C(C[C@@H]4NC(=O)[C@H](C)[C@H]4CC)[NH]3)C(CCC(=O)O)=C2C)[C@@H]1C4924.7Semi standard non polar33892256
Stercobilin,1TBDMS,isomer #5CC[C@H]1C(=O)N[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O)C(C)=C(C[C@H]4[C@H](CC)[C@@H](C)C(=O)N4[Si](C)(C)C(C)(C)C)[NH]3)C(CCC(=O)O)=C2C)[C@@H]1C4894.1Semi standard non polar33892256
Stercobilin,2TBDMS,isomer #1CC[C@H]1C(=O)N[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O[Si](C)(C)C(C)(C)C)C(C)=C(C[C@@H]4NC(=O)[C@H](C)[C@H]4CC)[NH]3)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C2C)[C@@H]1C5078.9Semi standard non polar33892256
Stercobilin,2TBDMS,isomer #10CC[C@H]1C(=O)N([Si](C)(C)C(C)(C)C)[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O)C(C)=C(C[C@H]4[C@H](CC)[C@@H](C)C(=O)N4[Si](C)(C)C(C)(C)C)[NH]3)C(CCC(=O)O)=C2C)[C@@H]1C4844.8Semi standard non polar33892256
Stercobilin,2TBDMS,isomer #2CC[C@H]1C(=O)N([Si](C)(C)C(C)(C)C)[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O[Si](C)(C)C(C)(C)C)C(C)=C(C[C@@H]4NC(=O)[C@H](C)[C@H]4CC)[NH]3)C(CCC(=O)O)=C2C)[C@@H]1C4973.1Semi standard non polar33892256
Stercobilin,2TBDMS,isomer #3CC[C@H]1C(=O)N[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O[Si](C)(C)C(C)(C)C)C(C)=C(C[C@@H]4NC(=O)[C@H](C)[C@H]4CC)N3[Si](C)(C)C(C)(C)C)C(CCC(=O)O)=C2C)[C@@H]1C5107.3Semi standard non polar33892256
Stercobilin,2TBDMS,isomer #4CC[C@H]1C(=O)N[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O[Si](C)(C)C(C)(C)C)C(C)=C(C[C@H]4[C@H](CC)[C@@H](C)C(=O)N4[Si](C)(C)C(C)(C)C)[NH]3)C(CCC(=O)O)=C2C)[C@@H]1C4940.5Semi standard non polar33892256
Stercobilin,2TBDMS,isomer #5CC[C@H]1C(=O)N([Si](C)(C)C(C)(C)C)[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O)C(C)=C(C[C@@H]4NC(=O)[C@H](C)[C@H]4CC)[NH]3)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C2C)[C@@H]1C4986.5Semi standard non polar33892256
Stercobilin,2TBDMS,isomer #6CC[C@H]1C(=O)N[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O)C(C)=C(C[C@@H]4NC(=O)[C@H](C)[C@H]4CC)N3[Si](C)(C)C(C)(C)C)C(CCC(=O)O[Si](C)(C)C(C)(C)C)=C2C)[C@@H]1C5110.3Semi standard non polar33892256
Stercobilin,2TBDMS,isomer #7CC[C@H]1C(=O)N[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O)C(C)=C(C[C@H]4[C@H](CC)[C@@H](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)[C@@H]1C4955.9Semi standard non polar33892256
Stercobilin,2TBDMS,isomer #8CC[C@H]1C(=O)N([Si](C)(C)C(C)(C)C)[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O)C(C)=C(C[C@@H]4NC(=O)[C@H](C)[C@H]4CC)N3[Si](C)(C)C(C)(C)C)C(CCC(=O)O)=C2C)[C@@H]1C5031.7Semi standard non polar33892256
Stercobilin,2TBDMS,isomer #9CC[C@H]1C(=O)N[C@@H](CC2=N/C(=C\C3=C(CCC(=O)O)C(C)=C(C[C@H]4[C@H](CC)[C@@H](C)C(=O)N4[Si](C)(C)C(C)(C)C)N3[Si](C)(C)C(C)(C)C)C(CCC(=O)O)=C2C)[C@@H]1C5007.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Stercobilin GC-MS ("Stercobilin,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-10-14Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Stercobilin GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Stercobilin GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Stercobilin GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Stercobilin GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Stercobilin GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Stercobilin GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Stercobilin GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Stercobilin GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Stercobilin GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Stercobilin GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Stercobilin GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Stercobilin GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Stercobilin GC-MS (TMS_2_8) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Stercobilin GC-MS (TMS_2_9) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Stercobilin GC-MS (TMS_2_10) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Stercobilin GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Stercobilin GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Stercobilin GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Stercobilin GC-MS (TBDMS_1_4) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Stercobilin GC-MS (TBDMS_1_5) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Stercobilin GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Stercobilin GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Stercobilin GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Stercobilin GC-MS (TBDMS_2_4) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stercobilin 10V, Positive-QTOFsplash10-004i-0000090000-80abce3e1b5b633de45c2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stercobilin 20V, Positive-QTOFsplash10-002k-0110290000-74155d790c51cb5f4f642019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stercobilin 40V, Positive-QTOFsplash10-00kk-2250970000-ca8deae27a6888e1c0d92019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stercobilin 10V, Negative-QTOFsplash10-002f-0000090000-bea486462a6e82c61e6a2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stercobilin 20V, Negative-QTOFsplash10-004m-1000190000-0cfa4abfbc03ce47cce82019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stercobilin 40V, Negative-QTOFsplash10-0006-9010350000-6e1d6331d86917b843f02019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stercobilin 10V, Negative-QTOFsplash10-0006-0000090000-567dfbe6efb0fc293caa2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stercobilin 20V, Negative-QTOFsplash10-06rx-0100970000-34b0639e34a29d36b0a22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stercobilin 40V, Negative-QTOFsplash10-006x-2720960000-913bff59f1ce6be922152021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stercobilin 10V, Positive-QTOFsplash10-0udi-0000940000-e911f2a7c65201a17cd12021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stercobilin 20V, Positive-QTOFsplash10-0fba-0200960000-112789f3b6500034d7c32021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stercobilin 40V, Positive-QTOFsplash10-001i-2200930000-f1e79c43c389134cf5e82021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID16736732
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID29023
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
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. Jimenez-Giron A, Ibanez C, Cifuentes A, Simo C, Munoz-Gonzalez I, Martin-Alvarez PJ, Bartolome B, Moreno-Arribas MV: Faecal metabolomic fingerprint after moderate consumption of red wine by healthy subjects. J Proteome Res. 2015 Feb 6;14(2):897-905. doi: 10.1021/pr500960g. Epub 2014 Dec 31. [PubMed:25496753 ]
  3. Seyfried H, Klicpera M, Leithner C, Penner E: [Bilirubin metabolism (author's transl)]. Wien Klin Wochenschr. 1976 Aug 13;88(15):477-82. [PubMed:793184 ]