Pyrrolnitrin

Details

• Internal ID: c6b7e583-1f73-4e84-8567-dd2a6d401f3d
• Taxonomy: Organoheterocyclic compounds > Pyrroles > Substituted pyrroles > Phenylpyrroles
• IUPAC Name: 3-chloro-4-(3-chloro-2-nitrophenyl)-1H-pyrrole
• SMILES (Canonical): C1=CC(=C(C(=C1)Cl)[N+](=O)[O-])C2=CNC=C2Cl
• SMILES (Isomeric): C1=CC(=C(C(=C1)Cl)[N+](=O)[O-])C2=CNC=C2Cl
• InChI: InChI=1S/C10H6Cl2N2O2/c11-8-3-1-2-6(10(8)14(15)16)7-4-13-5-9(7)12/h1-5,13H
• InChI Key: QJBZDBLBQWFTPZ-UHFFFAOYSA-N
• Popularity: 1,085 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₆Cl₂N₂O₂
• Molecular Weight: 257.07 g/mol
• Exact Mass: 255.9806328 g/mol
• Topological Polar Surface Area (TPSA): 61.60 Ų
• XlogP: 4.40
• Atomic LogP (AlogP): 3.90
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 1018-71-9
• Pyrrolnitrine
• Pyroace
• 3-Chloro-4-(3-chloro-2-nitrophenyl)pyrrole
• Pirrolnitrina
• Pyrrolnitrinum
• NSC-107654
• FR 005759
• Pyrollnitrin
• 3-Chloro-4-(2'-nitro-3'-chlorophenyl)pyrrole
• 3-chloro-4-(3-chloro-2-nitrophenyl)-1H-pyrrole
• 1H-Pyrrole, 3-chloro-4-(3-chloro-2-nitrophenyl)-
• Pyrrolnitrine [INN-French]
• Pyrrolnitrinum [INN-Latin]
• Pirrolnitrina [INN-Spanish]
• NSC 107654
• Pyrrole, 3-chloro-4-(3-chloro-2-nitrophenyl)-
• Pyrrolnitrin [USAN:INN:JAN]
• EINECS 213-812-7
• NSC107654
• UNII-N0P24B6EDQ
• BRN 1287646
• N0P24B6EDQ
• C10H6Cl2N2O2
• DTXSID9046867
• CHEBI:32079
• 3-Chloro-4-(3-chloro-2-nitro-phenyl)-1H-pyrrole
• NCGC00181136-01
• 5-20-07-00373 (Beilstein Handbook Reference)
• 3-Chloro-4-(3-chloro-2-nitrophenyl)pyrrole;3-Chloro-4-(3-chloro-2-nitrophenyl)pyrrole
• Pirrolnitrin
• 3-chloro-4-(3'-chloro-2'-nitrophenyl)pyrrole
• Pyrrolnitrine;Pyroace
• PYRROLNITRIN [MI]
• PYRROLNITRIN [INN]
• PYRROLNITRIN [JAN]
• PYRROLNITRIN [USAN]
• SCHEMBL73199
• PYRROLNITRIN [MART.]
• CHEMBL97972
• PYRROLNITRIN [WHO-DD]
• DTXCID7026867
• Pyrrolnitrin (JP17/USAN/INN)
• WLN: T5MJ CG DR CG BNW
• QJBZDBLBQWFTPZ-UHFFFAOYSA-N
• BCP33872
• Tox21_112743
• NSC637277
• AKOS040756417
• DB13603
• NSC-637277
• AC-32022
• MS-23618
• CAS-1018-71-9
• HY-133704
• LS-136879
• CS-0129743
• FT-0701269
• FT-0701270
• D01094
• Q371817
• Pyrrolnitrin from Pseudomonas cepacia, >=98% (HPLC), solid
• Pyrrolnitrin;3-Chloro-4-(3-chloro-2-nitrophenyl)pyrrole_HCD40

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9887	98.87%
Caco-2	+	0.9380	93.80%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	+	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7246	72.46%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9073	90.73%
OATP1B3 inhibitior	+	0.9422	94.22%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.5398	53.98%
P-glycoprotein inhibitior	-	0.9605	96.05%
P-glycoprotein substrate	-	0.9459	94.59%
CYP3A4 substrate	+	0.5435	54.35%
CYP2C9 substrate	-	0.8060	80.60%
CYP2D6 substrate	-	0.8399	83.99%
CYP3A4 inhibition	-	0.8558	85.58%
CYP2C9 inhibition	+	0.6719	67.19%
CYP2C19 inhibition	+	0.9382	93.82%
CYP2D6 inhibition	-	0.6851	68.51%
CYP1A2 inhibition	+	0.9504	95.04%
CYP2C8 inhibition	-	0.8830	88.30%
CYP inhibitory promiscuity	+	0.9085	90.85%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.5219	52.19%
Carcinogenicity (trinary)	Non-required	0.7001	70.01%
Eye corrosion	-	0.8657	86.57%
Eye irritation	+	0.8630	86.30%
Skin irritation	-	0.6088	60.88%
Skin corrosion	-	0.9486	94.86%
Ames mutagenesis	+	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7092	70.92%
Micronuclear	+	0.9700	97.00%
Hepatotoxicity	+	0.7875	78.75%
skin sensitisation	-	0.5808	58.08%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	+	0.7678	76.78%
Acute Oral Toxicity (c)	III	0.6793	67.93%
Estrogen receptor binding	+	0.8743	87.43%
Androgen receptor binding	+	0.7111	71.11%
Thyroid receptor binding	+	0.6770	67.70%
Glucocorticoid receptor binding	+	0.8394	83.94%
Aromatase binding	+	0.7215	72.15%
PPAR gamma	+	0.8856	88.56%
Honey bee toxicity	-	0.9637	96.37%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5249	52.49%
Fish aquatic toxicity	+	0.9341	93.41%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2850	P49840	Glycogen synthase kinase-3 alpha	95.48%	88.84%
CHEMBL2581	P07339	Cathepsin D	94.29%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.46%	86.33%
CHEMBL3902	P09211	Glutathione S-transferase Pi	90.45%	93.81%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.80%	95.56%
CHEMBL221	P23219	Cyclooxygenase-1	87.86%	90.17%
CHEMBL3401	O75469	Pregnane X receptor	84.97%	94.73%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.90%	82.69%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	84.13%	91.24%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	82.64%	94.80%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	82.52%	85.94%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.11%	93.03%

Plants that contains it

• Aglaia tomentosa
• Backhousia citriodora
• Capraria biflora
• Centipeda minima
• Mentha suaveolens subsp. timija
• Senecio macrocephalus
• Upuna borneensis

Cross-Links

• PubChem: 13916
• NPASS: NPC115049
• ChEMBL: CHEMBL97972
• LOTUS: LTS0221465
• wikiData: Q371817