Record Information
Version1.0
Created at2020-04-17 18:45:55 UTC
Updated at2020-11-18 16:38:55 UTC
CannabisDB IDCDB004876
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameBiliverdin
DescriptionBiliverdin, also known as biliverdin IX α or dehydrobilirubin, belongs to the class of organic compounds known as bilirubins. These are organic compounds containing a dicarboxylic acyclic tetrapyrrole derivative. Biliverdin is a very strong basic compound (based on its pKa). Biliverdin exists in all living organisms, ranging from bacteria to humans. In humans, biliverdin is involved in the metabolic disorder called congenital erythropoietic porphyria (cep) or gunther disease pathway. A linear tetrapyrrole produced in the reticuloendothelial system by the first step of heme degradation, catalysed by heme oxygenase. Biliverdin is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
Synonyms
ValueSource
8,12-Bis(2-carboxyethyl)-2,7,13,17-tetramethyl-3,18-divinylbilin-1(19)(21H,24H)-dioneChEBI
Biliverdin IX alphaChEBI
Biliverdin ixalphaChEBI
BiliverdineChEBI
BILIVERDINE IX ALPHAChEBI
Biliverdin IX aGenerator
Biliverdin IX αGenerator
BILIVERDINE IX aGenerator
BILIVERDINE IX αGenerator
Biliverdin IXHMDB
1,3,6,7-Tetramethyl-4,5-dicarboxyethyl-2,8-divinylbilenoneHMDB
DehydrobilirubinHMDB
Protobiliverdin IXHMDB
UteroverdineHMDB
Chemical FormulaC33H34N4O6
Average Molecular Weight582.66
Monoisotopic Molecular Weight582.2478
IUPAC Name3-(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 Namebiliverdine
CAS Registry Number114-25-0
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/h7-8,13-15,35H,1-2,9-12H2,3-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/b26-13-,27-14-,28-15-
InChI KeyQBUVFDKTZJNUPP-BBROENKCSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as bilirubins. These are organic compounds containing a dicarboxylic acyclic tetrapyrrole derivative.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTetrapyrroles and derivatives
Sub ClassBilirubins
Direct ParentBilirubins
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 FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point> 300 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.44ALOGPS
logP0.57ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)3.87ChemAxon
pKa (Strongest Basic)5.86ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area160.95 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity169.36 m³·mol⁻¹ChemAxon
Polarizability64.76 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSBiliverdin, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBiliverdin, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBiliverdin, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBiliverdin, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBiliverdin, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBiliverdin, "Biliverdin,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBiliverdin, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBiliverdin, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBiliverdin, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBiliverdin, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBiliverdin, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBiliverdin, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBiliverdin, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBiliverdin, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBiliverdin, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBiliverdin, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBiliverdin, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBiliverdin, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBiliverdin, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBiliverdin, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBiliverdin, TBDMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBiliverdin, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBiliverdin, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBiliverdin, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBiliverdin, TBDMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, positivesplash10-001i-0020090000-874093fd6fe6d5f0da552020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 25V, positivesplash10-001i-0000090000-242e3cfb1074431707cd2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 36V, positivesplash10-001i-0040090000-83f503dd74fa46d0b8c32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 46V, positivesplash10-0002-0090030000-2b21a14ef4c3d9f0fe282020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 58V, positivesplash10-0002-0090000000-48e89a30c017d91911ca2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 68V, positivesplash10-0002-0090000000-23cad1d9dabd8152a37e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 79V, positivesplash10-000b-0190100000-198c1c8608121dc207a22020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 89V, positivesplash10-0a4s-0491100000-c2bc552b31380512ee3f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 100V, positivesplash10-0a4j-0691100000-a0bcc22a3e04d7c03a3b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 110V, positivesplash10-0a4j-0982100000-edd8e7ace1f0d2dab0bc2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 121V, positivesplash10-0a4j-0962000000-3bbd19a9fb91f72836fd2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 131V, positivesplash10-0aos-0962000000-36cc065c1628bd7bddc92020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 142V, positivesplash10-0apm-0952000000-67cd6753793276126c5f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 152V, positivesplash10-066v-0952000000-d41423feb722025178422020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 164V, positivesplash10-067l-0952000000-b520e882d402bb5acddf2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 174V, positivesplash10-014i-0951000000-3b12ad8a32687e14b0b82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 185V, positivesplash10-014i-0951000000-897becf9303fb0568aa32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 195V, positivesplash10-014l-0951000000-895b6d3b15be956c26302020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 206V, positivesplash10-014l-0951000000-fe8747b84f037f5e52242020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-0000090000-ea485acf588e199084632017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00y0-0120390000-06e57745836cc9c214a22017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fbi-1512920000-e84010eaf624b552acd42017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000090000-9bc7e68d2e9ed37b5c9b2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0540-1000190000-b9e5e8f35aa309a0ed2b2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9010230000-260f7a168e7f7d25eb1f2017-07-26View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Heme oxygenase 2HMOX216p13.3P30519 details
Heme oxygenase 1HMOX122q13.1P09601 details
Biliverdin reductase ABLVRA7p13P53004 details
Flavin reductase (NADPH)BLVRB19q13.1-q13.2P30043 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Heme oxygenase 2HMOX216p13.3P30519 details
Heme oxygenase 1HMOX122q13.1P09601 details
Biliverdin reductase ABLVRA7p13P53004 details
ReceptorsNot Available
Transcriptional Factors
Protein NameGene NameLocusUniprot IDDetails
Heme oxygenase 1HMOX122q13.1P09601 details
Concentrations Data
Not Available
HMDB IDHMDB0001008
DrugBank IDDB02073
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022366
KNApSAcK IDNot Available
Chemspider ID10628548
KEGG Compound IDC00500
BioCyc IDBILIVERDINE
BiGG ID35167
Wikipedia LinkBiliverdin
METLIN ID5938
PubChem Compound5353439
PDB IDNot Available
ChEBI ID17033
References
General ReferencesNot Available

Enzymes

General function:
Involved in heme oxygenase (decyclizing) activity
Specific function:
Heme oxygenase cleaves the heme ring at the alpha methene bridge to form biliverdin. Biliverdin is subsequently converted to bilirubin by biliverdin reductase. Under physiological conditions, the activity of heme oxygenase is highest in the spleen, where senescent erythrocytes are sequestrated and destroyed. Heme oxygenase 2 could be implicated in the production of carbon monoxide in brain where it could act as a neurotransmitter.
Gene Name:
HMOX2
Uniprot ID:
P30519
Molecular weight:
36032.615
General function:
Involved in heme oxygenase (decyclizing) activity
Specific function:
Heme oxygenase cleaves the heme ring at the alpha methene bridge to form biliverdin. Biliverdin is subsequently converted to bilirubin by biliverdin reductase. Under physiological conditions, the activity of heme oxygenase is highest in the spleen, where senescent erythrocytes are sequestrated and destroyed.
Gene Name:
HMOX1
Uniprot ID:
P09601
Molecular weight:
32818.345
General function:
Involved in biliverdin reductase activity
Specific function:
Reduces the gamma-methene bridge of the open tetrapyrrole, biliverdin IX alpha, to bilirubin with the concomitant oxidation of a NADH or NADPH cofactor.
Gene Name:
BLVRA
Uniprot ID:
P53004
Molecular weight:
33428.225
General function:
Involved in catalytic activity
Specific function:
Broad specificity oxidoreductase that catalyzes the NADPH-dependent reduction of a variety of flavins, such as riboflavin, FAD or FMN, biliverdins, methemoglobin and PQQ (pyrroloquinoline quinone). Contributes to heme catabolism and metabolizes linear tetrapyrroles. Can also reduce the complexed Fe(3+) iron to Fe(2+) in the presence of FMN and NADPH. In the liver, converts biliverdin to bilirubin.
Gene Name:
BLVRB
Uniprot ID:
P30043
Molecular weight:
22119.215