ChemFOnt: Showing chemical card for Stercobilin (CFc000220523)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 01:39:40 UTC

Chemfont ID

CFc000220523

Molecule Identification

Common Name

Stercobilin

Definition

Stercobilin 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(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 acid	ChEBI
(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 acid	ChEBI
Stercobilin IX	ChEBI
(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-dipropanoate	Generator
(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-dipropionate	Generator
(-)-Stercobilin	HMDB
Stercobilin ixalpha	HMDB
Stercobilin ixα	HMDB
Stercobiline	HMDB
Stercobilin	ChEBI

Chemical Formula

C₃₃H₄₆N₄O₆

Average Molecular Weight

594.753

Monoisotopic Molecular Weight

594.341735217

IUPAC Name

3-(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 Number

34217-90-8

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 Key

DEEUSUJLZQQESV-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.

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
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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

stercobilin (CHEBI:29023 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0240259)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.011 g/L	ALOGPS
logP	2.98	ALOGPS
logP	1.42	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	3.87	ChemAxon
pKa (Strongest Basic)	6.02	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	165.2 m³·mol⁻¹	ChemAxon
Polarizability	67.94 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0240259

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

16736732

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Stercobilin

METLIN ID

Not Available

PubChem Compound

44457542

PDB ID

Not Available

ChEBI ID

29023

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Stercobilin (CFc000220523)

MOL for CFc000220523 (Stercobilin)

3D MOL for CFc000220523 (Stercobilin)

3D SDF for CFc000220523 (Stercobilin)

3D-SDF for CFc000220523 (Stercobilin)

PDB for CFc000220523 (Stercobilin)

3D PDB for CFc000220523 (Stercobilin)

SMILES for CFc000220523 (Stercobilin)

INCHI for CFc000220523 (Stercobilin)

Structure for CFc000220523 (Stercobilin)

3D Structure for CFc000220523 (Stercobilin)