Nigragillin

Details

• Internal ID: a487da40-0161-4157-9854-95d3d460550e
• Taxonomy: Organoheterocyclic compounds > Diazinanes > Piperazines > N-alkylpiperazines > N-methylpiperazines
• IUPAC Name: (2E,4E)-1-[(2R,5S)-2,4,5-trimethylpiperazin-1-yl]hexa-2,4-dien-1-one
• SMILES (Canonical): CC=CC=CC(=O)N1CC(N(CC1C)C)C
• SMILES (Isomeric): C/C=C/C=C/C(=O)N1C[C@@H](N(C[C@H]1C)C)C
• InChI: InChI=1S/C13H22N2O/c1-5-6-7-8-13(16)15-10-11(2)14(4)9-12(15)3/h5-8,11-12H,9-10H2,1-4H3/b6-5+,8-7+/t11-,12+/m0/s1
• InChI Key: DVCNHRTYSUTLOS-OJRXFFSMSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₂₂N₂O
• Molecular Weight: 222.33 g/mol
• Exact Mass: 222.173213330 g/mol
• Topological Polar Surface Area (TPSA): 23.60 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 1.67
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• Nigragilline
• (2E,4E)-1-[(2R,5S)-2,4,5-trimethylpiperazin-1-yl]hexa-2,4-dien-1-one
• 24779-38-2
• MLS004256132
• CHEBI:133753
• DTXSID701141830
• SMR003081017
• N-Methyl-trans-2,5-dimethyl-N'-sorbylpiperazine
• 1-[(2E,4E)-Hexa-2,4-dienoyl]-2,4,5-trimethylpiperazine
• rel-(+)-(2E,4E)-1-[(2R,5S)-2,4,5-Trimethyl-1-piperazinyl]-2,4-hexadien-1-one
• InChI=1/C13H22N2O/c1-5-6-7-8-13(16)15-10-11(2)14(4)9-12(15)3/h5-8,11-12H,9-10H2,1-4H3/b6-5+,8-7+/t11-,12+/m0/s

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9382	93.82%
Caco-2	+	0.9619	96.19%
Blood Brain Barrier	+	0.9750	97.50%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.5277	52.77%
OATP2B1 inhibitior	-	0.8604	86.04%
OATP1B1 inhibitior	+	0.9430	94.30%
OATP1B3 inhibitior	+	0.9446	94.46%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	-	0.7627	76.27%
P-glycoprotein inhibitior	-	0.9730	97.30%
P-glycoprotein substrate	-	0.7778	77.78%
CYP3A4 substrate	-	0.5138	51.38%
CYP2C9 substrate	-	0.6029	60.29%
CYP2D6 substrate	-	0.8165	81.65%
CYP3A4 inhibition	-	0.9317	93.17%
CYP2C9 inhibition	-	0.9497	94.97%
CYP2C19 inhibition	-	0.8651	86.51%
CYP2D6 inhibition	-	0.9394	93.94%
CYP1A2 inhibition	-	0.6850	68.50%
CYP2C8 inhibition	-	0.9841	98.41%
CYP inhibitory promiscuity	-	0.9702	97.02%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.6150	61.50%
Eye corrosion	-	0.9388	93.88%
Eye irritation	-	0.9567	95.67%
Skin irritation	+	0.6653	66.53%
Skin corrosion	-	0.7756	77.56%
Ames mutagenesis	-	0.6037	60.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.7317	73.17%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	+	0.6570	65.70%
skin sensitisation	-	0.8775	87.75%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	-	0.5145	51.45%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.7276	72.76%
Acute Oral Toxicity (c)	III	0.6804	68.04%
Estrogen receptor binding	-	0.8562	85.62%
Androgen receptor binding	-	0.5991	59.91%
Thyroid receptor binding	-	0.6868	68.68%
Glucocorticoid receptor binding	-	0.7893	78.93%
Aromatase binding	-	0.7290	72.90%
PPAR gamma	-	0.8743	87.43%
Honey bee toxicity	-	0.9200	92.00%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	-	0.6911	69.11%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.03%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.57%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.42%	95.56%

Plants that contains it

• Zephyranthes candida

Cross-Links

• PubChem: 15939563
• LOTUS: LTS0074439
• wikiData: Q105104530