(R)-nantenine

Details

• Internal ID: e1b911f6-a9ac-4bce-80ee-d35963e13c15
• Taxonomy: Alkaloids and derivatives > Aporphines
• IUPAC Name: 1-[(12R)-19-acetyl-13-methyl-5,7-dioxa-13-azapentacyclo[10.7.1.02,10.04,8.016,20]icosa-1(20),2,4(8),9,16,18-hexaen-18-yl]ethanone
• SMILES (Canonical): CC(=O)C1=C(C2=C3C(CC4=CC5=C(C=C42)OCO5)N(CCC3=C1)C)C(=O)C
• SMILES (Isomeric): CC(=O)C1=C(C2=C3[C@@H](CC4=CC5=C(C=C42)OCO5)N(CCC3=C1)C)C(=O)C
• InChI: InChI=1S/C22H21NO4/c1-11(24)15-6-13-4-5-23(3)17-7-14-8-18-19(27-10-26-18)9-16(14)22(21(13)17)20(15)12(2)25/h6,8-9,17H,4-5,7,10H2,1-3H3/t17-/m1/s1
• InChI Key: QBCMSGDOKGQABG-QGZVFWFLSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₁NO₄
• Molecular Weight: 363.40 g/mol
• Exact Mass: 363.14705815 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 3.57
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• CHEMBL605626

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9222	92.22%
Caco-2	+	0.7222	72.22%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.4691	46.91%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9134	91.34%
OATP1B3 inhibitior	+	0.9418	94.18%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.7861	78.61%
P-glycoprotein inhibitior	-	0.5296	52.96%
P-glycoprotein substrate	-	0.7042	70.42%
CYP3A4 substrate	+	0.5884	58.84%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4483	44.83%
CYP3A4 inhibition	+	0.6285	62.85%
CYP2C9 inhibition	-	0.8134	81.34%
CYP2C19 inhibition	+	0.5855	58.55%
CYP2D6 inhibition	-	0.5811	58.11%
CYP1A2 inhibition	-	0.5358	53.58%
CYP2C8 inhibition	-	0.8684	86.84%
CYP inhibitory promiscuity	-	0.7412	74.12%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5926	59.26%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9868	98.68%
Skin irritation	-	0.7945	79.45%
Skin corrosion	-	0.9395	93.95%
Ames mutagenesis	+	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6581	65.81%
Micronuclear	-	0.5800	58.00%
Hepatotoxicity	-	0.5781	57.81%
skin sensitisation	-	0.8663	86.63%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.7778	77.78%
Estrogen receptor binding	-	0.5000	50.00%
Androgen receptor binding	-	0.5516	55.16%
Thyroid receptor binding	-	0.6337	63.37%
Glucocorticoid receptor binding	+	0.8037	80.37%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.7460	74.60%
Honey bee toxicity	-	0.8752	87.52%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6534	65.34%
Fish aquatic toxicity	+	0.9683	96.83%

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	98.45%	96.77%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.23%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.52%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.63%	85.14%
CHEMBL217	P14416	Dopamine D2 receptor	90.58%	95.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.17%	89.00%
CHEMBL2056	P21728	Dopamine D1 receptor	88.98%	91.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.61%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.16%	91.11%
CHEMBL4208	P20618	Proteasome component C5	87.07%	90.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.88%	90.71%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.12%	100.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	81.02%	93.40%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	80.65%	82.38%

Plants that contains it

• Corydalis ternata
• Corydalis turtschaninovii
• Corydalis yanhusuo

Cross-Links

• PubChem: 46225255
• NPASS: NPC245942