Pronuciferine, (-)-

Details

• Internal ID: 39244b49-3de8-467a-bd67-5b15602be3b9
• Taxonomy: Alkaloids and derivatives > Proaporphines
• IUPAC Name: (4S)-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-/m0/s1
• InChI Key: WUYQEGNOQLRQAQ-AWEZNQCLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

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

Synonyms

• N,O-Dimethylcrotsparine
• Pronuciferine, (-)-
• 6aalpha-Pronuciferine
• UNII-RPT0IU7P8P
• RPT0IU7P8P
• 16654-37-8
• CROTSPARINE, N,O-DIMETHYL-
• SPIRO(2,5-CYCLOHEXADIENE-1,7'(1'H)-CYCLOPENT(IJ)ISOQUINOLIN)-4-ONE, 2',3',8',8'A-TETRAHYDRO-5',6'-DIMETHOXY-1'-METHYL-, (8'AS)-
• SPIRO(2,5-CYCLOHEXADIENE-1,7'(1'H)-CYCLOPENT(IJ)ISOQUINOLIN)-4-ONE, 2',3',8',8'A-TETRAHYDRO-5',6'-DIMETHOXY-1'-METHYL-, (S)-
• 6A.ALPHA.-PRONUCIFERINE
• DTXCID6090611
• WUYQEGNOQLRQAQ-AWEZNQCLSA-N
• Q27288236

2D Structure

ADMET Properties (via admetSAR 2)

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

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	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

• Alstonia angustiloba
• Amphiachyris dracunculoides
• Annona cherimola
• Baccharis grandicapitulata
• Beesia calthifolia
• Boschniakia rossica
• Botrychium ternatum
• Bursera kerberi
• Clerodendrum trichotomum
• Clinacanthus nutans
• Crotalaria stolzii
• Croton bonplandianus
• Curcuma aeruginosa
• Delphinium giraldii
• Eucalyptus albens
• Euonymus fortunei
• Euploca racemosa
• Hedysarum gmelinii
• Helenium integrifolium
• Juniperus scopulorum
• Lasianthaea podocephala
• Lupinus cosentinii
• Melampodium leucanthum
• Myrica pensylvanica
• Nelumbo nucifera
• Neopallasia pectinata
• Papaver pseudocanescens
• Pellacalyx axillaris
• Peperomia filiformis
• Phlomis crinita
• Psidium acutangulum
• Pyrolirion flavum
• Renealmia alpinia
• Rhododendron mucronulatum
• Seseli libanotis
• Sideritis dasygnaphala
• Stellaria media
• Stephania rotunda
• Tephroseris kirilowii
• Tephroseris palustris

Cross-Links

• PubChem: 793841
• NPASS: NPC218652
• LOTUS: LTS0250003
• wikiData: Q27288236