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[5-(5-Amino-1H-pyrrolo[3,2-b]pyridin-2-yl)-6-hydroxy-3'-nitro-3-biphenylyl]acetic acid

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Identification

Generic Name
[5-(5-Amino-1H-pyrrolo[3,2-b]pyridin-2-yl)-6-hydroxy-3'-nitro-3-biphenylyl]acetic acid
DrugBank Accession Number
DB08232
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 404.3755
Monoisotopic: 404.112069642
Chemical Formula
C21H16N4O5
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UCoagulation factor VIINot AvailableHumans
UTissue factorNot AvailableHumans
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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Biphenyls and derivatives
Direct Parent
Biphenyls and derivatives
Alternative Parents
Phenylpyrroles / Pyrrolopyridines / Nitrobenzenes / Nitroaromatic compounds / Aminopyridines and derivatives / Phenols / Imidolactams / Heteroaromatic compounds / Amino acids / Organic oxoazanium compounds
show 10 more
Substituents
2-phenylpyrrole / Allyl-type 1,3-dipolar organic compound / Amine / Amino acid / Amino acid or derivatives / Aminopyridine / Aromatic heteropolycyclic compound / Azacycle / Biphenyl / C-nitro compound
show 27 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
BVBGZXXLVHYBKI-UHFFFAOYSA-N
InChI
InChI=1S/C21H16N4O5/c22-19-5-4-16-18(24-19)10-17(23-16)15-7-11(8-20(26)27)6-14(21(15)28)12-2-1-3-13(9-12)25(29)30/h1-7,9-10,23,28H,8H2,(H2,22,24)(H,26,27)
IUPAC Name
2-(5-{5-amino-1H-pyrrolo[3,2-b]pyridin-2-yl}-6-hydroxy-3'-nitro-[1,1'-biphenyl]-3-yl)acetic acid
SMILES
NC1=CC=C2NC(=CC2=N1)C1=CC(CC(O)=O)=CC(=C1O)C1=CC=CC(=C1)[N+]([O-])=O

References

General References
Not Available
PubChem Compound
10135836
PubChem Substance
99444703
ChemSpider
20136275
BindingDB
13781
ChEMBL
CHEMBL377956
ZINC
ZINC000014953807
PDBe Ligand
N1H
PDB Entries
2f9b

Clinical Trials

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Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0185 mg/mLALOGPS
logP3.59ALOGPS
logP1.66Chemaxon
logS-4.3ALOGPS
pKa (Strongest Acidic)3.88Chemaxon
pKa (Strongest Basic)5.98Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area155.37 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity109.39 m3·mol-1Chemaxon
Polarizability41.35 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.899
Blood Brain Barrier+0.5457
Caco-2 permeable-0.614
P-glycoprotein substrateNon-substrate0.581
P-glycoprotein inhibitor INon-inhibitor0.9074
P-glycoprotein inhibitor IINon-inhibitor0.7435
Renal organic cation transporterNon-inhibitor0.9336
CYP450 2C9 substrateNon-substrate0.8169
CYP450 2D6 substrateNon-substrate0.8431
CYP450 3A4 substrateNon-substrate0.5697
CYP450 1A2 substrateNon-inhibitor0.571
CYP450 2C9 inhibitorNon-inhibitor0.5324
CYP450 2D6 inhibitorNon-inhibitor0.8339
CYP450 2C19 inhibitorNon-inhibitor0.6605
CYP450 3A4 inhibitorNon-inhibitor0.7066
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5775
Ames testAMES toxic0.8014
CarcinogenicityNon-carcinogens0.6764
BiodegradationNot ready biodegradable0.9925
Rat acute toxicity2.3475 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8902
hERG inhibition (predictor II)Non-inhibitor0.8749
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 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-184.72429
predicted
DeepCCS 1.0 (2019)
[M+H]+187.08229
predicted
DeepCCS 1.0 (2019)
[M+Na]+193.48355
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Coagulation factor VII
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Initiates the extrinsic pathway of blood coagulation. Serine protease that circulates in the blood in a zymogen form. Factor VII is converted to factor VIIa by factor Xa, factor XIIa, factor IXa, or thrombin by minor proteolysis. In the presence of tissue factor and calcium ions, factor VIIa then converts factor X to factor Xa by limited proteolysis. Factor VIIa will also convert factor IX to factor IXa in the presence of tissue factor and calcium
Specific Function
Calcium ion binding
Gene Name
F7
Uniprot ID
P08709
Uniprot Name
Coagulation factor VII
Molecular Weight
51593.465 Da
References
  1. 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. [Article]
Details2. Tissue factor
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Initiates blood coagulation by forming a complex with circulating factor VII or VIIa. The [TF:VIIa] complex activates factors IX or X by specific limited proteolysis. TF plays a role in normal hemostasis by initiating the cell-surface assembly and propagation of the coagulation protease cascade
Specific Function
Cytokine receptor activity
Gene Name
F3
Uniprot ID
P13726
Uniprot Name
Tissue factor
Molecular Weight
33067.3 Da
References
  1. 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. [Article]

Drug created at September 15, 2010 21:30 / Updated at June 12, 2020 16:52