Nandinine

Details

• Internal ID: bfefcd38-79c3-431a-976f-70b1e084931a
• Taxonomy: Alkaloids and derivatives > Protoberberine alkaloids and derivatives
• IUPAC Name: (1S)-17-methoxy-5,7-dioxa-13-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-2,4(8),9,15(20),16,18-hexaen-16-ol
• SMILES (Canonical): COC1=C(C2=C(CC3C4=CC5=C(C=C4CCN3C2)OCO5)C=C1)O
• SMILES (Isomeric): COC1=C(C2=C(C[C@H]3C4=CC5=C(C=C4CCN3C2)OCO5)C=C1)O
• InChI: InChI=1S/C19H19NO4/c1-22-16-3-2-11-6-15-13-8-18-17(23-10-24-18)7-12(13)4-5-20(15)9-14(11)19(16)21/h2-3,7-8,15,21H,4-6,9-10H2,1H3/t15-/m0/s1
• InChI Key: PQECCKIOFCWGRJ-HNNXBMFYSA-N
• Popularity: 4 references 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): 51.20 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 2.79
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• (+)-Nandinin
• S-Tetrahydroberberrubine
• Nandinine [MI]
• (+)-Tetrahydroberberrubine
• Nandinine, (+)-
• (S)-nandinine
• 572-76-9
• UNII-7T6VF792DB
• 10-Methoxy-2,3-(methylenedioxy)berbin-9-ol
• 7T6VF792DB
• CHEMBL2314732
• (13aS)-5,8,13,13a-Tetrahydro-10-methoxy-6H-benzo(g)-1,3-benzodioxolo(5,6-a)quinolizin-9-ol
• 6H-Benzo(g)-1,3-benzodioxolo(5,6-a)quinolizin-9-ol, 5,8,13,13a-tetrahydro-10-methoxy-, (13aS)-
• (+)-nandinine
• (13aS)-5,8,13,13a-Tetrahydro-10-methoxy-6H-benzo[g]-1,3-benzodioxolo[5,6-a]quinolizin-9-ol
• SCHEMBL905060
• CHEBI:132749
• DTXSID301024074
• BDBM50424073
• PD119743
• C21370
• Q27225637
• (13aS)-10-methoxy-5,8,13,13a-tetrahydro-2H,6H-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-9-ol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9382	93.82%
Caco-2	+	0.8488	84.88%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.6081	60.81%
OATP2B1 inhibitior	-	0.8627	86.27%
OATP1B1 inhibitior	+	0.9248	92.48%
OATP1B3 inhibitior	+	0.9420	94.20%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.8333	83.33%
P-glycoprotein inhibitior	-	0.6783	67.83%
P-glycoprotein substrate	-	0.6429	64.29%
CYP3A4 substrate	+	0.6026	60.26%
CYP2C9 substrate	-	0.6106	61.06%
CYP2D6 substrate	+	0.6924	69.24%
CYP3A4 inhibition	+	0.6911	69.11%
CYP2C9 inhibition	-	0.8655	86.55%
CYP2C19 inhibition	+	0.8188	81.88%
CYP2D6 inhibition	+	0.8939	89.39%
CYP1A2 inhibition	+	0.9082	90.82%
CYP2C8 inhibition	-	0.6523	65.23%
CYP inhibitory promiscuity	+	0.5348	53.48%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5602	56.02%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9431	94.31%
Skin irritation	-	0.7340	73.40%
Skin corrosion	-	0.9413	94.13%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6452	64.52%
Micronuclear	+	0.6100	61.00%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.8642	86.42%
Respiratory toxicity	+	0.9111	91.11%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	+	0.5374	53.74%
Acute Oral Toxicity (c)	III	0.5210	52.10%
Estrogen receptor binding	+	0.6607	66.07%
Androgen receptor binding	+	0.5510	55.10%
Thyroid receptor binding	+	0.5683	56.83%
Glucocorticoid receptor binding	+	0.6813	68.13%
Aromatase binding	-	0.6553	65.53%
PPAR gamma	+	0.5740	57.40%
Honey bee toxicity	-	0.8695	86.95%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5551	55.51%
Fish aquatic toxicity	+	0.7209	72.09%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4081	P13726	Coagulation factor III	12.17 nM; 36.41 nM; 6.75 nM; 36.41 nM	IC50; IC50; IC50; IC50	via Super-PRED; via Super-PRED; via Super-PRED; PMID: 23199480
CHEMBL2056	P21728	Dopamine D1 receptor	60 nM; 60 nM	Ki; Ki	PMID: 23332346; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.68%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.90%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.77%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.84%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.21%	85.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.88%	95.89%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	90.56%	93.40%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	90.01%	89.62%
CHEMBL2581	P07339	Cathepsin D	88.79%	98.95%
CHEMBL3438	Q05513	Protein kinase C zeta	88.28%	88.48%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.27%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.63%	95.89%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	87.59%	82.38%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	87.50%	90.95%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.25%	90.71%
CHEMBL217	P14416	Dopamine D2 receptor	87.09%	95.62%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	85.47%	89.05%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.45%	92.62%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	84.49%	91.79%
CHEMBL2535	P11166	Glucose transporter	84.46%	98.75%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	84.14%	82.67%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.89%	92.94%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.68%	96.77%
CHEMBL5747	Q92793	CREB-binding protein	83.43%	95.12%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.40%	89.00%
CHEMBL1744525	P43490	Nicotinamide phosphoribosyltransferase	82.32%	96.25%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.62%	99.17%
CHEMBL4208	P20618	Proteasome component C5	81.11%	90.00%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	80.60%	95.78%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	80.58%	96.86%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.11%	94.00%

Plants that contains it

• Argemone mexicana
• Corydalis turtschaninovii
• Eschscholzia californica

Cross-Links

• PubChem: 12313091
• NPASS: NPC238530
• ChEMBL: CHEMBL2314732
• LOTUS: LTS0275873
• wikiData: Q27225637