Livestock Metabolome Database: Showing metabocard for Biliverdin (LMDB00293)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:46:39 UTC

Update Date

2016-09-23 18:45:05 UTC

Lmdb

LMDB00293

Secondary Accession Numbers

None

Metabolite Identification

Common 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 animal bile or serum.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
8,12-Bis(2-carboxyethyl)-2,7,13,17-tetramethyl-3,18-divinylbilin-1(19)(21H,24H)-dione	ChEBI
Biliverdin IX alpha	ChEBI
Biliverdin ixalpha	ChEBI
Biliverdine	ChEBI
BILIVERDINE IX ALPHA	ChEBI
Biliverdin IX a	Generator
Biliverdin IX α	Generator
BILIVERDINE IX a	Generator
BILIVERDINE IX α	Generator
Biliverdin IX	HMDB
1,3,6,7-Tetramethyl-4,5-dicarboxyethyl-2,8-divinylbilenone	HMDB
Dehydrobilirubin	HMDB
Protobiliverdin IX	HMDB
Uteroverdine	HMDB

Chemical Formula

C₃₃H₃₄N₄O₆

Average Molecular Weight

582.6463

Monoisotopic Molecular Weight

582.24783484

IUPAC Name

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

Traditional Name

biliverdine

CAS Registry Number

114-25-0

SMILES

CC1=C(C=C)\C(NC1=O)=C\C1=C(C)C(CCC(O)=O)=C(N1)\C=C1/N\C(=C\C2=NC(=O)C(C=C)=C2C)C(C)=C1CCC(O)=O

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)/b24-13+,27-14-,28-15-

InChI Key

RCNSAJSGRJSBKK-YKSNQIBWSA-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
Substituted pyrrole
Pyrrole
Pyrroline
Heteroaromatic compound
Carboxamide group
Ketimine
Lactam
Secondary carboxylic acid amide
Azacycle
Organic 1,3-dipolar compound
Carboxylic acid derivative
Carboxylic acid
Propargyl-type 1,3-dipolar organic compound
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

bilins (CHEBI:17033 )

Ontology

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	3.44	ALOGPS
logP	0.57	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	3.87	ChemAxon
pKa (Strongest Basic)	5.86	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	11	ChemAxon
Refractivity	169.36 m³·mol⁻¹	ChemAxon
Polarizability	64.76 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	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("Biliverdin,1TMS,#1" TMS) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 35V, positive	splash10-001i-0020090000-874093fd6fe6d5f0da55	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 25V, positive	splash10-001i-0000090000-242e3cfb1074431707cd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 36V, positive	splash10-001i-0040090000-83f503dd74fa46d0b8c3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 46V, positive	splash10-0002-0090030000-2b21a14ef4c3d9f0fe28	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 58V, positive	splash10-0002-0090000000-48e89a30c017d91911ca	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 68V, positive	splash10-0002-0090000000-23cad1d9dabd8152a37e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 79V, positive	splash10-000b-0190100000-198c1c8608121dc207a2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 89V, positive	splash10-0a4s-0491100000-c2bc552b31380512ee3f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 100V, positive	splash10-0a4j-0691100000-a0bcc22a3e04d7c03a3b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 110V, positive	splash10-0a4j-0982100000-edd8e7ace1f0d2dab0bc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 121V, positive	splash10-0a4j-0962000000-3bbd19a9fb91f72836fd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 131V, positive	splash10-0aos-0962000000-36cc065c1628bd7bddc9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 142V, positive	splash10-0apm-0952000000-67cd6753793276126c5f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 152V, positive	splash10-066v-0952000000-d41423feb72202517842	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 164V, positive	splash10-067l-0952000000-b520e882d402bb5acddf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 174V, positive	splash10-014i-0951000000-3b12ad8a32687e14b0b8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 185V, positive	splash10-014i-0951000000-897becf9303fb0568aa3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 195V, positive	splash10-014l-0951000000-895b6d3b15be956c2630	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 206V, positive	splash10-014l-0951000000-fe8747b84f037f5e5224	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0159-0000090000-ea485acf588e19908463	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00y0-0120390000-06e57745836cc9c214a2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fbi-1512920000-e84010eaf624b552acd4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0000090000-9bc7e68d2e9ed37b5c9b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0540-1000190000-b9e5e8f35aa309a0ed2b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9010230000-260f7a168e7f7d25eb1f	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum