Bovine Metabolome Database: Showing metabocard for L-Urobilinogen (BMDB0004157)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:08:15 UTC

Update Date

2020-04-22 15:13:25 UTC

BMDB ID

BMDB0004157

Secondary Accession Numbers

BMDB04157

Metabolite Identification

Common Name

L-Urobilinogen

Description

Stercobilinogen belongs to the class of organic compounds known as bilirubins. These are organic compounds containing a dicarboxylic acyclic tetrapyrrole derivative. Based on a literature review a small amount of articles have been published on Stercobilinogen.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

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

Chemical Formula

C₃₃H₄₈N₄O₆

Average Molecular Weight

596.769

Monoisotopic Molecular Weight

596.357385282

IUPAC Name

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

Traditional Name

(-)-stercobilinogen

CAS Registry Number

17095-63-5

SMILES

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

InChI Identifier

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

InChI Key

VKGRRZVYCXLHII-OLFWPHQKSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrapyrroles and derivatives

Sub Class

Bilirubins

Direct Parent

Bilirubins

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

stercobilinogen (CHEBI:6320 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Membrane

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	2.917	Not Available

Predicted Properties

Property	Value	Source
logP	2.96	ALOGPS
logP	4	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	4.05	ChemAxon
pKa (Strongest Basic)	-0.89	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	164.38 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	164.98 m³·mol⁻¹	ChemAxon
Polarizability	68.4 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_15) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002b-0010090000-8d4700b90de37cd6cfed	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002b-0130390000-9ce1b8f9b676e551d59a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-0190320000-f2ca1940eca5f528b86b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004j-0022090000-2e6bfc17a2d9bae5658e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002g-0460190000-14bec3765de9829daa22	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00l6-0931310000-b62b58a03fed0e7db5ae	View in MoNA

Biological Properties

Cellular Locations

Cell membrane
Membrane

Biospecimen Locations

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0004157

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB112384

KNApSAcK ID

Not Available

Chemspider ID

7827641

KEGG Compound ID

C05789

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Stercobilinogen

METLIN ID

Not Available

PubChem Compound

9548718

PDB ID

Not Available

ChEBI ID

6320

References

Synthesis Reference

Birch, A. J. The structure of stercobilin. Chemistry & Industry (London, United Kingdom) (1955), 652. CODEN: CHINAG ISSN:0009-3068. CAN 50:36041 AN 1956:36041

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for L-Urobilinogen (BMDB0004157)

Structure for BMDB0004157 (L-Urobilinogen)