Rhexifoline

Details

• Internal ID: 15285cce-3637-4d6c-8703-a9a2f2d352b4
• Taxonomy: Organoheterocyclic compounds > Pyridines and derivatives > Pyridinecarboxylic acids and derivatives > Pyridinecarboxylic acids
• IUPAC Name: methyl (5R,7R)-5-hydroxy-7-methyl-6,7-dihydro-5H-cyclopenta[c]pyridine-4-carboxylate
• SMILES (Canonical): CC1CC(C2=C(C=NC=C12)C(=O)OC)O
• SMILES (Isomeric): C[C@@H]1C[C@H](C2=C(C=NC=C12)C(=O)OC)O
• InChI: InChI=1S/C11H13NO3/c1-6-3-9(13)10-7(6)4-12-5-8(10)11(14)15-2/h4-6,9,13H,3H2,1-2H3/t6-,9-/m1/s1
• InChI Key: SEQJFRYHSZPDOC-HZGVNTEJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₃NO₃
• Molecular Weight: 207.23 g/mol
• Exact Mass: 207.08954328 g/mol
• Topological Polar Surface Area (TPSA): 59.40 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 1.41
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• 93915-32-3
• C09986
• AC1L4GKH
• CTK5H3886
• methyl (5R,7R)-5-hydroxy-7-methyl-6,7-dihydro-5H-cyclopenta[c]pyridine-4-carboxylate
• CHEBI:8826
• DTXSID60917201
• Q27108155
• methyl 5-hydroxy-7-methyl-6,7-dihydro-5H-cyclopenta[c]pyridine-4-carboxylate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9948	99.48%
Caco-2	+	0.6880	68.80%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7419	74.19%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9509	95.09%
OATP1B3 inhibitior	+	0.9606	96.06%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.7962	79.62%
P-glycoprotein inhibitior	-	0.9601	96.01%
P-glycoprotein substrate	-	0.8144	81.44%
CYP3A4 substrate	+	0.5000	50.00%
CYP2C9 substrate	-	0.8144	81.44%
CYP2D6 substrate	-	0.8507	85.07%
CYP3A4 inhibition	-	0.9085	90.85%
CYP2C9 inhibition	-	0.9126	91.26%
CYP2C19 inhibition	-	0.8753	87.53%
CYP2D6 inhibition	-	0.8667	86.67%
CYP1A2 inhibition	-	0.5801	58.01%
CYP2C8 inhibition	-	0.7132	71.32%
CYP inhibitory promiscuity	-	0.9628	96.28%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.6281	62.81%
Eye corrosion	-	0.9723	97.23%
Eye irritation	-	0.8546	85.46%
Skin irritation	-	0.7247	72.47%
Skin corrosion	-	0.9638	96.38%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4757	47.57%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	+	0.5815	58.15%
skin sensitisation	-	0.8358	83.58%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	+	0.4757	47.57%
Acute Oral Toxicity (c)	III	0.5409	54.09%
Estrogen receptor binding	-	0.9208	92.08%
Androgen receptor binding	-	0.5442	54.42%
Thyroid receptor binding	-	0.6695	66.95%
Glucocorticoid receptor binding	-	0.8346	83.46%
Aromatase binding	-	0.9030	90.30%
PPAR gamma	-	0.8360	83.60%
Honey bee toxicity	-	0.8781	87.81%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	-	0.8876	88.76%

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	97.52%	96.09%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	89.96%	81.11%
CHEMBL2243	O00519	Anandamide amidohydrolase	84.72%	97.53%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.87%	91.07%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.41%	93.03%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.64%	86.33%
CHEMBL2535	P11166	Glucose transporter	80.50%	98.75%

Plants that contains it

• Castilleja rhexifolia
• Castilleja sulphurea
• Kunzea ambigua

Cross-Links

• PubChem: 185301
• LOTUS: LTS0104227
• wikiData: Q105147814