Caulophyllumine A

Details

• Internal ID: 92e14e91-5897-47fa-be85-b62854556381
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbonyl compounds > Phenylketones > Alkyl-phenylketones
• IUPAC Name: 1-(4-hydroxy-2,3-dimethoxyphenyl)-2-[(2S)-piperidin-2-yl]ethanone
• SMILES (Canonical): COC1=C(C=CC(=C1OC)O)C(=O)CC2CCCCN2
• SMILES (Isomeric): COC1=C(C=CC(=C1OC)O)C(=O)C[C@@H]2CCCCN2
• InChI: InChI=1S/C15H21NO4/c1-19-14-11(6-7-12(17)15(14)20-2)13(18)9-10-5-3-4-8-16-10/h6-7,10,16-17H,3-5,8-9H2,1-2H3/t10-/m0/s1
• InChI Key: MCMMIRWNWGZONI-JTQLQIEISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₁NO₄
• Molecular Weight: 279.33 g/mol
• Exact Mass: 279.14705815 g/mol
• Topological Polar Surface Area (TPSA): 67.80 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 2.12
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

• 1009318-60-8
• 1-(4-hydroxy-2,3-dimethoxyphenyl)-2-[(2S)-piperidin-2-yl]ethanone
• AKOS040736456

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9590	95.90%
Caco-2	+	0.6030	60.30%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8202	82.02%
OATP2B1 inhibitior	-	0.8574	85.74%
OATP1B1 inhibitior	+	0.9410	94.10%
OATP1B3 inhibitior	+	0.9441	94.41%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.8603	86.03%
P-glycoprotein inhibitior	-	0.9250	92.50%
P-glycoprotein substrate	-	0.7985	79.85%
CYP3A4 substrate	-	0.5430	54.30%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4815	48.15%
CYP3A4 inhibition	-	0.7637	76.37%
CYP2C9 inhibition	-	0.9090	90.90%
CYP2C19 inhibition	-	0.8851	88.51%
CYP2D6 inhibition	+	0.6130	61.30%
CYP1A2 inhibition	-	0.5864	58.64%
CYP2C8 inhibition	-	0.6992	69.92%
CYP inhibitory promiscuity	-	0.9241	92.41%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.7297	72.97%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.8446	84.46%
Skin irritation	-	0.6955	69.55%
Skin corrosion	-	0.9359	93.59%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3930	39.30%
Micronuclear	-	0.5000	50.00%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	-	0.8782	87.82%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.7074	70.74%
Acute Oral Toxicity (c)	III	0.6575	65.75%
Estrogen receptor binding	-	0.5806	58.06%
Androgen receptor binding	-	0.5101	51.01%
Thyroid receptor binding	+	0.6784	67.84%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	-	0.6935	69.35%
PPAR gamma	+	0.5950	59.50%
Honey bee toxicity	-	0.9688	96.88%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.7555	75.55%
Fish aquatic toxicity	-	0.8265	82.65%

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	97.06%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.34%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.93%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.75%	97.09%
CHEMBL2581	P07339	Cathepsin D	92.70%	98.95%
CHEMBL2535	P11166	Glucose transporter	88.20%	98.75%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	83.88%	92.88%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	83.45%	93.03%
CHEMBL4208	P20618	Proteasome component C5	82.27%	90.00%
CHEMBL213	P08588	Beta-1 adrenergic receptor	82.21%	95.56%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.10%	95.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.69%	92.62%

Plants that contains it

• Caulophyllum thalictroides

Cross-Links

• PubChem: 101844612
• LOTUS: LTS0172314
• wikiData: Q105161294