Pronuciferine

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

Top

Internal ID	ba8a7712-c13d-408c-9dda-9df33d75badd
Taxonomy	Alkaloids and derivatives > Proaporphines
IUPAC Name	(4R)-10,11-dimethoxy-5-methylspiro[5-azatricyclo[6.3.1.04,12]dodeca-1(12),8,10-triene-2,4'-cyclohexa-2,5-diene]-1'-one
SMILES (Canonical)	CN1CCC2=CC(=C(C3=C2C1CC34C=CC(=O)C=C4)OC)OC
SMILES (Isomeric)	CN1CCC2=CC(=C(C3=C2[C@H]1CC34C=CC(=O)C=C4)OC)OC
InChI	InChI=1S/C19H21NO3/c1-20-9-6-12-10-15(22-2)18(23-3)17-16(12)14(20)11-19(17)7-4-13(21)5-8-19/h4-5,7-8,10,14H,6,9,11H2,1-3H3/t14-/m1/s1
InChI Key	WUYQEGNOQLRQAQ-CQSZACIVSA-N
Popularity	34 references in papers

Physical and Chemical Properties

Top

Molecular Formula	C₁₉H₂₁NO₃
Molecular Weight	311.40 g/mol
Exact Mass	311.15214353 g/mol
Topological Polar Surface Area (TPSA)	38.80 Å²
XlogP	2.50
Atomic LogP (AlogP)	2.57
H-Bond Acceptor	4
H-Bond Donor	0
Rotatable Bonds	2

Synonyms

Top

(+)-Pronuciferine

Milthanthine

N-Methylstepharine

Pronuciferin

N,O-Dimethylcrotonosine

2128-60-1

CHEBI:42

860X46GII1

Spiro(2,5-cyclohexadiene-1,7'-1'H-cyclopent(ij)isoquinolin)-4-one, 2',3',8',8'a-tetrahydro-5',6'-dimethoxy-1'-methyl-, (R)-

(8a'R)-5',6'-dimethoxy-1'-methyl-2',3',8',8a'-tetrahydro-1'H,4H-spiro[cyclohexa-2,5-diene-1,7'-cyclopenta[ij]isoquinolin]-4-one

There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

Top

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9914	99.14%
Caco-2	+	0.8551	85.51%
Blood Brain Barrier	+	1.0000	100.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6425	64.25%
OATP2B1 inhibitior	-	0.8589	85.89%
OATP1B1 inhibitior	+	0.9508	95.08%
OATP1B3 inhibitior	+	0.9529	95.29%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	+	0.6000	60.00%
BSEP inhibitior	+	0.6459	64.59%
P-glycoprotein inhibitior	-	0.7211	72.11%
P-glycoprotein substrate	-	0.5989	59.89%
CYP3A4 substrate	+	0.6836	68.36%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4324	43.24%
CYP3A4 inhibition	-	0.6757	67.57%
CYP2C9 inhibition	-	0.7755	77.55%
CYP2C19 inhibition	-	0.8485	84.85%
CYP2D6 inhibition	+	0.7533	75.33%
CYP1A2 inhibition	-	0.6931	69.31%
CYP2C8 inhibition	-	0.8492	84.92%
CYP inhibitory promiscuity	-	0.7318	73.18%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6375	63.75%
Eye corrosion	-	0.9919	99.19%
Eye irritation	-	0.9835	98.35%
Skin irritation	-	0.7681	76.81%
Skin corrosion	-	0.9384	93.84%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7743	77.43%
Micronuclear	-	0.6300	63.00%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.8591	85.91%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.8632	86.32%
Acute Oral Toxicity (c)	III	0.6760	67.60%
Estrogen receptor binding	-	0.5329	53.29%
Androgen receptor binding	+	0.5560	55.60%
Thyroid receptor binding	-	0.5342	53.42%
Glucocorticoid receptor binding	-	0.5388	53.88%
Aromatase binding	-	0.5452	54.52%
PPAR gamma	-	0.6348	63.48%
Honey bee toxicity	-	0.8251	82.51%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.7100	71.00%
Fish aquatic toxicity	+	0.9480	94.80%

Targets

Top

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
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	98.50%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.21%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.09%	95.56%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	95.01%	93.40%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	92.23%	91.03%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	92.02%	96.77%
CHEMBL217	P14416	Dopamine D2 receptor	91.59%	95.62%
CHEMBL2056	P21728	Dopamine D1 receptor	91.17%	91.00%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	88.87%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.38%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.31%	94.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	85.44%	93.99%
CHEMBL2535	P11166	Glucose transporter	84.91%	98.75%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.74%	95.89%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.20%	95.89%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	82.54%	82.38%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.45%	97.14%
CHEMBL1871	P10275	Androgen Receptor	82.41%	96.43%
CHEMBL4208	P20618	Proteasome component C5	81.73%	90.00%
CHEMBL2581	P07339	Cathepsin D	81.71%	98.95%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	81.54%	92.38%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.41%	90.71%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.04%	100.00%
CHEMBL5203	P33316	dUTP pyrophosphatase	80.42%	99.18%

Plants that contains it

Top

Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.

Achyrocline satureioides

Agathosma bisulca

Annona cherimola

Antizoma angustifolia

Doronicum grandiflorum