NAV

3,4-bis(7-chloro-1H-indol-3-yl)-1H-pyrrole-2,5-dicarboxylic acid

Identification

Generic Name
3,4-bis(7-chloro-1H-indol-3-yl)-1H-pyrrole-2,5-dicarboxylic acid
DrugBank Accession Number
DB06955
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 454.262
Monoisotopic: 453.028311333
Chemical Formula
C22H13Cl2N3O4
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UCytochrome P450Not AvailableStreptomyces sp. TP-A0274
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 indoles. These are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
Indoles
Direct Parent
Indoles
Alternative Parents
Pyrrole 2-carboxylic acids / Substituted pyrroles / Dicarboxylic acids and derivatives / Benzenoids / Aryl chlorides / Heteroaromatic compounds / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds
show 4 more
Substituents
Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzenoid / Carboxylic acid / Carboxylic acid derivative / Dicarboxylic acid or derivatives / Heteroaromatic compound / Hydrocarbon derivative
show 13 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organochlorine compound, indoles, pyrroledicarboxylic acid (CHEBI:59196)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
OAMCCJASDLMTOO-UHFFFAOYSA-N
InChI
InChI=1S/C22H13Cl2N3O4/c23-13-5-1-3-9-11(7-25-17(9)13)15-16(20(22(30)31)27-19(15)21(28)29)12-8-26-18-10(12)4-2-6-14(18)24/h1-8,25-27H,(H,28,29)(H,30,31)
IUPAC Name
3,4-bis(7-chloro-1H-indol-3-yl)-1H-pyrrole-2,5-dicarboxylic acid
SMILES
OC(=O)C1=C(C2=CNC3=C(Cl)C=CC=C23)C(=C(N1)C(O)=O)C1=CNC2=C(Cl)C=CC=C12

References

General References
Not Available
PubChem Compound
25246329
PubChem Substance
99443426
ChemSpider
25057663
ChEBI
59196
PDBe Ligand
2CC
PDB Entries
3a1l

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility0.000674 mg/mLALOGPS
logP4.66ALOGPS
logP4.91Chemaxon
logS-5.8ALOGPS
pKa (Strongest Acidic)3.21Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area121.97 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity117.14 m3·mol-1Chemaxon
Polarizability43.13 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9868
Blood Brain Barrier+0.8403
Caco-2 permeable-0.6166
P-glycoprotein substrateNon-substrate0.636
P-glycoprotein inhibitor INon-inhibitor0.9753
P-glycoprotein inhibitor IINon-inhibitor0.9612
Renal organic cation transporterNon-inhibitor0.9394
CYP450 2C9 substrateNon-substrate0.7987
CYP450 2D6 substrateNon-substrate0.8565
CYP450 3A4 substrateNon-substrate0.7044
CYP450 1A2 substrateInhibitor0.7553
CYP450 2C9 inhibitorNon-inhibitor0.7119
CYP450 2D6 inhibitorNon-inhibitor0.9128
CYP450 2C19 inhibitorNon-inhibitor0.8462
CYP450 3A4 inhibitorNon-inhibitor0.8969
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8425
Ames testNon AMES toxic0.9299
CarcinogenicityNon-carcinogens0.8519
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5326 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9922
hERG inhibition (predictor II)Non-inhibitor0.867
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 GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0pb9-1001900000-a4772dccda5bf071b300
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0000900000-2e7abc0939606273533a
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0009000000-a2f5b223a4f29f4b1c66
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0000900000-f3bcd22c3c82ef851062
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9002300000-1888033907bdbae78880
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-000f-0009200000-33fc5bb2f5bfbc06581a
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9003000000-e073417ceae7fbef1f15
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]-199.8553265
predicted
DarkChem Lite v0.1.0
[M-H]-190.99628
predicted
DeepCCS 1.0 (2019)
[M+H]+193.39183
predicted
DeepCCS 1.0 (2019)
[M+Na]+199.37344
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Cytochrome P450
Kind
Protein
Organism
Streptomyces sp. TP-A0274
Pharmacological action
Unknown
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen
Specific Function
Not Available
Gene Name
staP
Uniprot ID
Q83WG3
Uniprot Name
Cytochrome P450
Molecular Weight
46125.6 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 21:17 / Updated at June 12, 2020 16:52