Nornantenine

Details

• Internal ID: c0661840-ee1b-40b9-8d56-403d64a32608
• Taxonomy: Alkaloids and derivatives > Aporphines
• IUPAC Name: 18,19-dimethoxy-5,7-dioxa-13-azapentacyclo[10.7.1.02,10.04,8.016,20]icosa-1(20),2,4(8),9,16,18-hexaene
• SMILES (Canonical): COC1=C(C2=C3C(CC4=CC5=C(C=C42)OCO5)NCCC3=C1)OC
• SMILES (Isomeric): COC1=C(C2=C3C(CC4=CC5=C(C=C42)OCO5)NCCC3=C1)OC
• InChI: InChI=1S/C19H19NO4/c1-21-16-6-10-3-4-20-13-5-11-7-14-15(24-9-23-14)8-12(11)18(17(10)13)19(16)22-2/h6-8,13,20H,3-5,9H2,1-2H3
• InChI Key: JWXKBCGJLCEZTJ-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₉NO₄
• Molecular Weight: 325.40 g/mol
• Exact Mass: 325.13140809 g/mol
• Topological Polar Surface Area (TPSA): 49.00 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 2.84
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 15401-66-8
• 4H-Benzo(de)(1,3)benzodioxolo(5,6-g)quinoline, 5,6,6a,7-tetrahydro-1,2-dimethoxy-, (S)-
• N-Nornantenine
• (+)-Nornantenine
• SCHEMBL6689417
• CHEMBL1254951
• DTXSID00934896
• CHEBI:175147
• 1,2-Dimethoxy-9,10-methylenedioxynoraporphine
• 1,2-Dimethoxy-5,6,6a,7-tetrahydro-4H,10H-benzo[de][1,3]benzodioxolo[5,6-g]quinoline
• 18,19-dimethoxy-5,7-dioxa-13-azapentacyclo[10.7.1.0^{2,10}.0^{4,8}.0^{16,20}]icosa-1(20),2,4(8),9,16,18-hexaene
• 18,19-dimethoxy-5,7-dioxa-13-azapentacyclo[10.7.1.02,10.04,8.016,20]icosa-1(20),2,4(8),9,16,18-hexaene

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9784	97.84%
Caco-2	+	0.8549	85.49%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.4352	43.52%
OATP2B1 inhibitior	-	0.8663	86.63%
OATP1B1 inhibitior	+	0.9306	93.06%
OATP1B3 inhibitior	+	0.9500	95.00%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.7139	71.39%
P-glycoprotein inhibitior	-	0.5580	55.80%
P-glycoprotein substrate	-	0.7550	75.50%
CYP3A4 substrate	+	0.5792	57.92%
CYP2C9 substrate	-	0.8281	82.81%
CYP2D6 substrate	+	0.6636	66.36%
CYP3A4 inhibition	+	0.6896	68.96%
CYP2C9 inhibition	-	0.7809	78.09%
CYP2C19 inhibition	+	0.5059	50.59%
CYP2D6 inhibition	+	0.7145	71.45%
CYP1A2 inhibition	+	0.8216	82.16%
CYP2C8 inhibition	+	0.4810	48.10%
CYP inhibitory promiscuity	+	0.7855	78.55%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6305	63.05%
Eye corrosion	-	0.9878	98.78%
Eye irritation	-	0.9623	96.23%
Skin irritation	-	0.7153	71.53%
Skin corrosion	-	0.9380	93.80%
Ames mutagenesis	+	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8467	84.67%
Micronuclear	-	0.5100	51.00%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.8340	83.40%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.5709	57.09%
Acute Oral Toxicity (c)	III	0.5045	50.45%
Estrogen receptor binding	+	0.8125	81.25%
Androgen receptor binding	-	0.5504	55.04%
Thyroid receptor binding	+	0.7924	79.24%
Glucocorticoid receptor binding	+	0.8135	81.35%
Aromatase binding	+	0.5537	55.37%
PPAR gamma	+	0.7409	74.09%
Honey bee toxicity	-	0.7956	79.56%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	-	0.3770	37.70%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	96.88%	96.77%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.29%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.78%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.57%	96.09%
CHEMBL3192	Q9BY41	Histone deacetylase 8	92.30%	93.99%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	92.22%	96.21%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	91.01%	92.62%
CHEMBL3231	Q13464	Rho-associated protein kinase 1	90.73%	95.55%
CHEMBL3438	Q05513	Protein kinase C zeta	89.80%	88.48%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	89.77%	80.96%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.64%	86.33%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	89.36%	94.80%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.76%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.03%	94.45%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	87.69%	82.67%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.76%	95.89%
CHEMBL4208	P20618	Proteasome component C5	86.43%	90.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.38%	100.00%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	86.26%	96.86%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.53%	94.00%
CHEMBL2535	P11166	Glucose transporter	84.28%	98.75%
CHEMBL213	P08588	Beta-1 adrenergic receptor	84.14%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.09%	89.00%
CHEMBL5747	Q92793	CREB-binding protein	84.02%	95.12%
CHEMBL2581	P07339	Cathepsin D	83.50%	98.95%
CHEMBL261	P00915	Carbonic anhydrase I	81.71%	96.76%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	81.38%	95.78%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.63%	89.50%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.58%	89.62%

Plants that contains it

• Cyclea atjehensis
• Laureliopsis philippiana
• Ocotea lancifolia
• Siparuna grandiflora
• Xylopia parviflora

Cross-Links

• PubChem: 3084228
• LOTUS: LTS0217012
• wikiData: Q82910882