Showing Compound Mesobilirubinogen (FDB022727)

Record Information

Version

1.0

Creation date

2011-09-21 00:18:33 UTC

Update date

2015-07-21 06:57:20 UTC

Primary ID

FDB022727

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Mesobilirubinogen

Description

Urobilinogen is an uribiniloid, the product of bilirubin reduction in multiple sequential reactions. Urobilinogens are colorless chromogens that may in turn be oxidized to respective yellow oxidation products, urobilins. Under normal conditions only small amounts of bilirubin can be found in stools of adults while urobilinoids are predominant bile pigments (50-250 mg/day). Only negligible amounts of fecal urobilinoids are present in the intestinal lumen of infants during the first months of their life, due to undeveloped intestinal microflora capable of reducing bilirubin. This presumably contributes importantly to the pathogenesis of neonatal jaundice. In adults, the urobilinoid production is highly efficient. At times, it is re-excreted in the urine, where it may be later oxidized to urobilin. (PMID: 16504607) [HMDB]

CAS Number

14684-37-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
2,17-Diethyl-1,4,5,10,15,16,19,22,23,24-decahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoate	Generator
2,17-Diethyl-1,4,5,10,15,16,19,22,23,24-decahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoic acid	ChEBI
2,17-Diethyl-1,4,5,10,15,16,19,22,23,24-decahydro-3,7,13,18-tetramethyl-1,19-dioxo-biline-8,12-dipropionic acid	HMDB
2,17-diethyl-1,4,5,10,15,16,19,22,23,24-decahydro-3,7,13,18-tetramethyl-1,19-dioxo-Biline-8,12-dipropionic acid	hmdb
8,12-Bis(2-carboxyethyl)-3,18-diethyl-2,7,13,17-tetramethylbilane-1,19(4H,16H)-dione	ChEBI
I-urobilinogen	ChEBI
i-Urobilinogen	hmdb
Mesobilirubinogen	ChEBI
Mesobilirubinogen ixalpha	ChEBI
Mesobilirubinogen IXα	HMDB

Showing 1 to 10 of 13 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.017 g/L	ALOGPS
logP	3.11	ALOGPS
logP	3.77	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	4.06	ChemAxon
pKa (Strongest Basic)	-0.018	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	166.04 m³·mol⁻¹	ChemAxon
Polarizability	67.38 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

Chemical Formula

C33H44N4O6

IUPAC name

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

InChI Identifier

InChI=1S/C33H44N4O6/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/h26-27,34-35H,7-15H2,1-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)

InChI Key

OBHRVMZSZIDDEK-UHFFFAOYSA-N

Isomeric SMILES

CCC1=C(C)C(=O)NC1CC1=C(C)C(CCC(O)=O)=C(CC2=C(CCC(O)=O)C(C)=C(CC3NC(=O)C(CC)=C3C)N2)N1

Average Molecular Weight

592.7257

Monoisotopic Molecular Weight

592.32608516

Classification

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
Pyrrole
Pyrroline
Heteroaromatic compound
Secondary carboxylic acid amide
Lactam
Carboxamide group
Azacycle
Carboxylic acid
Carboxylic acid derivative
Organopnictogen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

bilanes (CHEBI:29026 )

Ontology

Endogenous

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Mesobilirubinogen, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-6500190000-673e8c4460e3cdbdd8e2	Spectrum
Predicted GC-MS	Mesobilirubinogen, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00dj-7500019000-dc792020abb23fbb3064	Spectrum
Predicted GC-MS	Mesobilirubinogen, "Mesobilirubinogen,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Mesobilirubinogen, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Mesobilirubinogen, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Mesobilirubinogen, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Mesobilirubinogen, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Mesobilirubinogen, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Mesobilirubinogen, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Mesobilirubinogen, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Mesobilirubinogen, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Mesobilirubinogen, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Mesobilirubinogen, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Mesobilirubinogen, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Mesobilirubinogen, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Mesobilirubinogen, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Mesobilirubinogen, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Mesobilirubinogen, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Mesobilirubinogen, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Mesobilirubinogen, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Mesobilirubinogen, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Mesobilirubinogen, TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Mesobilirubinogen, TMS_2_15, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Mesobilirubinogen, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Mesobilirubinogen, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-014i-0060900000-67682461aceaa81b9cc2	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-006x-0000090000-a65bbba494a7e099f9c4	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00dm-1100190000-7cf7854534fedc5bbfc1	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9010240000-d75cd70ca41532190bfc	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0000290000-a18b99b2b4373146a032	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-2200890000-cf0c2e6ff644591038b0	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000f-4970330000-d515de7fece55949f271	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0000090000-181b914f66e7110dfe7d	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00bj-0100290000-875b38ee4fed5fc0ecd8	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05n0-1010940000-9f8c080267aa82fc0b96	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ufr-0011960000-50b1dbb2c2c4f704b5c8	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0w4i-0210940000-17857bfc32a5c7d5f66c	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-008a-4642920000-dd8a11d07863f98ea6f2	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

24980

ChEMBL ID

Not Available

KEGG Compound ID

C05790

Pubchem Compound ID

26818

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB01898

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

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Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound Mesobilirubinogen (FDB022727)

Structure for FDB022727 (Mesobilirubinogen)