Showing Compound Biliverdin (FDB022366)

Record Information

Version

1.0

Creation date

2011-09-21 00:12:50 UTC

Update date

2015-07-21 06:57:10 UTC

Primary ID

FDB022366

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Biliverdin

Description

Biliverdin is a green pigment formed as a byproduct of hemoglobin breakdown. It consists of four linearly connected pyrrole rings (a tetrapyrrole). Biliverdin is formed when the heme group in hemoglobin is cleaved at its alpha-methene bridge. The resulting biliverdin is then reduced to bilirubin, a yellow pigment, by the enzyme biliverdin reductase. The changing color of a bruise from deep purple to yellow over time is a graphical indicator of this reaction. Biosynthesized from hemoglobin as a precursor of bilirubin. Occurs in the bile of amphibia and of birds, but not in normal human bile or serum. [HMDB]

CAS Number

114-25-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Showing 1 to 7 of 7 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.012 g/L	ALOGPS
logP	3.77	ALOGPS
logP	3.17	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	3.96	ChemAxon
pKa (Strongest Basic)	0.44	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	160.95 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	169.16 m³·mol⁻¹	ChemAxon
Polarizability	64.98 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

C33H34N4O6

IUPAC name

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

InChI Identifier

InChI=1S/C33H34N4O6/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/h7-8,13-15,34-35H,1-2,9-12H2,3-6H3,(H,37,42)(H,38,39)(H,40,41)

InChI Key

RCNSAJSGRJSBKK-UHFFFAOYSA-N

Isomeric SMILES

CC1=C(C=C)C(NC1=O)=CC1=C(C)C(CCC(O)=O)=C(N1)C=C1NC(=CC2=NC(=O)C(C=C)=C2C)C(C)=C1CCC(O)=O

Average Molecular Weight

582.6463

Monoisotopic Molecular Weight

582.24783484

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
Dipyrrin
Dicarboxylic acid or derivatives
Substituted pyrrole
Pyrrole
Pyrroline
Heteroaromatic compound
Carboxamide group
Lactam
N-acylimine
Secondary carboxylic acid amide
Azacycle
Organic 1,3-dipolar compound
Carboxylic acid derivative
Carboxylic acid
Propargyl-type 1,3-dipolar organic compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

No ontology term

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

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0159-0000090000-5a17130dc930cdf393d8	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00sa-0000090000-d8f255560e3f3a7b1abd	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0110390000-9fa4e19b0f78c1280cce	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0000090000-cdbb4cd3041e869343ce	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00m3-0000290000-515429de938efffe3341	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-0030930000-46d011da26688aee5f66	2021-10-12	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

4510089

ChEMBL ID

Not Available

KEGG Compound ID

C00500

Pubchem Compound ID

5353439

Pubchem Substance ID

Not Available

ChEBI ID

17033

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB01008

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

35167

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

Biliverdin

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

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 Biliverdin (FDB022366)

Structure for FDB022366 (Biliverdin)