Biliverdine IX Alpha

Identification

Name
Biliverdine IX Alpha
Accession Number
DB02073  (EXPT00714)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
O9MIA842K9
CAS number
114-25-0
Weight
Average: 582.657
Monoisotopic: 582.247834831
Chemical Formula
C33H34N4O6
InChI Key
QBUVFDKTZJNUPP-BBROENKCSA-N
InChI
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-
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
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

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UHeme oxygenase 1Not AvailableHuman
UMyoglobinNot AvailableHuman
UFlavin reductase (NADPH)Not AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0001008
KEGG Compound
C00500
PubChem Compound
5280353
PubChem Substance
46505998
ChemSpider
10628548
ChEBI
17033
ChEMBL
CHEMBL455477
HET
BLA

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)>300 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.0129 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity169.36 m3·mol-1ChemAxon
Polarizability65.2 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.8122
Blood Brain Barrier-0.5113
Caco-2 permeable-0.8957
P-glycoprotein substrateSubstrate0.5965
P-glycoprotein inhibitor INon-inhibitor0.7931
P-glycoprotein inhibitor IINon-inhibitor0.8256
Renal organic cation transporterNon-inhibitor0.8736
CYP450 2C9 substrateNon-substrate0.7377
CYP450 2D6 substrateNon-substrate0.8406
CYP450 3A4 substrateSubstrate0.565
CYP450 1A2 substrateInhibitor0.5357
CYP450 2C9 inhibitorInhibitor0.5484
CYP450 2D6 inhibitorNon-inhibitor0.8604
CYP450 2C19 inhibitorNon-inhibitor0.7778
CYP450 3A4 inhibitorNon-inhibitor0.7609
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.827
Ames testNon AMES toxic0.7322
CarcinogenicityNon-carcinogens0.9335
BiodegradationNot ready biodegradable0.9768
Rat acute toxicity2.6091 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9947
hERG inhibition (predictor II)Non-inhibitor0.8978
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound 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
Dipyrrins / Dicarboxylic acids and derivatives / Pyrrolines / Heteroaromatic compounds / Secondary carboxylic acid amides / Lactams / Ketimines / Propargyl-type 1,3-dipolar organic compounds / Carboxylic acids / Azacyclic compounds
show 4 more
Substituents
Bilirubin skeleton / Dipyrrin / Dicarboxylic acid or derivatives / Substituted pyrrole / Pyrrole / Pyrroline / Heteroaromatic compound / Carboxamide group / Ketimine / Lactam
show 16 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
bilins (CHEBI:17033)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Signal transducer 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 a...
Gene Name
HMOX1
Uniprot ID
P09601
Uniprot Name
Heme oxygenase 1
Molecular Weight
32818.345 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Oxygen transporter activity
Specific Function
Serves as a reserve supply of oxygen and facilitates the movement of oxygen within muscles.
Gene Name
MB
Uniprot ID
P02144
Uniprot Name
Myoglobin
Molecular Weight
17183.725 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Riboflavin reductase (nadph) 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)....
Gene Name
BLVRB
Uniprot ID
P30043
Uniprot Name
Flavin reductase (NADPH)
Molecular Weight
22119.215 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on October 01, 2018 13:13