Neferine

Details

• Internal ID: 9f956d3d-1fa2-4adb-a761-709312d4c7b3
• Taxonomy: Organoheterocyclic compounds > Isoquinolines and derivatives > Benzylisoquinolines
• IUPAC Name: 4-[[(1R)-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-1-yl]methyl]-2-[[(1R)-6-methoxy-1-[(4-methoxyphenyl)methyl]-2-methyl-3,4-dihydro-1H-isoquinolin-7-yl]oxy]phenol
• SMILES (Canonical): CN1CCC2=CC(=C(C=C2C1CC3=CC=C(C=C3)OC)OC4=C(C=CC(=C4)CC5C6=CC(=C(C=C6CCN5C)OC)OC)O)OC
• SMILES (Isomeric): CN1CCC2=CC(=C(C=C2[C@H]1CC3=CC=C(C=C3)OC)OC4=C(C=CC(=C4)C[C@@H]5C6=CC(=C(C=C6CCN5C)OC)OC)O)OC
• InChI: InChI=1S/C38H44N2O6/c1-39-15-14-27-21-36(44-5)38(23-30(27)31(39)17-24-7-10-28(42-3)11-8-24)46-34-19-25(9-12-33(34)41)18-32-29-22-37(45-6)35(43-4)20-26(29)13-16-40(32)2/h7-12,19-23,31-32,41H,13-18H2,1-6H3/t31-,32-/m1/s1
• InChI Key: MIBATSHDJRIUJK-ROJLCIKYSA-N
• Popularity: 164 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₄₄N₂O₆
• Molecular Weight: 624.80 g/mol
• Exact Mass: 624.31993713 g/mol
• Topological Polar Surface Area (TPSA): 72.90 Ų
• XlogP: 6.70
• Atomic LogP (AlogP): 6.76
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 10

Synonyms

• 2292-16-2
• Neferin
• 4-[[(1R)-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-1-yl]methyl]-2-[[(1R)-6-methoxy-1-[(4-methoxyphenyl)methyl]-2-methyl-3,4-dihydro-1H-isoquinolin-7-yl]oxy]phenol
• BRN 1523459
• (-)-Neferine
• 4-[(6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-1-yl)methyl]-2-[[6-methoxy-1-[(4-methoxyphenyl)methyl]-2-methyl-3,4-dihydro-1H-isoquinolin-7-yl]oxy]phenol
• Phenol, 4-((1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl)methyl)-2-((1,2,3,4-tetrahydro-6-methoxy-1-((4-methoxyphenyl)methyl)-2-methyl-7-isoquinolinyl)oxy)-
• CHEMBL455560
• SCHEMBL12807595
• DTXSID40177462
• CHEBI:176257
• MIBATSHDJRIUJK-ROJLCIKYSA-N
• AKOS016002114
• LS-105140
• A14743
• A878384
• Q-100292
• 4-{[(1R)-6,7-Dimethoxy-2-methyl-1,2,3,4-tetrahydro-1-isoquinolinyl]methyl}-2-{[(1R)-6-methoxy-1-(4-methoxybenzyl)-2-methyl-1,2,3,4-tetrahydro-7-isoquinolinyl]oxy}phenol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8871	88.71%
Caco-2	-	0.6891	68.91%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6826	68.26%
OATP2B1 inhibitior	-	0.5650	56.50%
OATP1B1 inhibitior	+	0.9329	93.29%
OATP1B3 inhibitior	+	0.9426	94.26%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	+	0.5500	55.00%
BSEP inhibitior	+	0.9927	99.27%
P-glycoprotein inhibitior	+	0.9464	94.64%
P-glycoprotein substrate	-	0.5486	54.86%
CYP3A4 substrate	+	0.6699	66.99%
CYP2C9 substrate	+	0.7865	78.65%
CYP2D6 substrate	+	0.7818	78.18%
CYP3A4 inhibition	-	0.8911	89.11%
CYP2C9 inhibition	-	0.9629	96.29%
CYP2C19 inhibition	-	0.9532	95.32%
CYP2D6 inhibition	-	0.6629	66.29%
CYP1A2 inhibition	-	0.8719	87.19%
CYP2C8 inhibition	+	0.5806	58.06%
CYP inhibitory promiscuity	-	0.9386	93.86%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6884	68.84%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.9329	93.29%
Skin irritation	-	0.7729	77.29%
Skin corrosion	-	0.9491	94.91%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9352	93.52%
Micronuclear	+	0.5100	51.00%
Hepatotoxicity	-	0.8324	83.24%
skin sensitisation	-	0.9042	90.42%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.8939	89.39%
Acute Oral Toxicity (c)	III	0.7974	79.74%
Estrogen receptor binding	+	0.8066	80.66%
Androgen receptor binding	+	0.7485	74.85%
Thyroid receptor binding	+	0.6102	61.02%
Glucocorticoid receptor binding	+	0.8481	84.81%
Aromatase binding	+	0.6076	60.76%
PPAR gamma	+	0.6649	66.49%
Honey bee toxicity	-	0.8899	88.99%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.6700	67.00%
Fish aquatic toxicity	+	0.8123	81.23%

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	99.20%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.86%	85.14%
CHEMBL4208	P20618	Proteasome component C5	94.46%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.08%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.02%	91.11%
CHEMBL5608	Q16288	NT-3 growth factor receptor	93.85%	95.89%
CHEMBL3192	Q9BY41	Histone deacetylase 8	92.75%	93.99%
CHEMBL2581	P07339	Cathepsin D	92.61%	98.95%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	92.27%	95.89%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	91.97%	91.03%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.95%	94.00%
CHEMBL2535	P11166	Glucose transporter	89.85%	98.75%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	88.79%	92.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.75%	99.17%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.96%	92.94%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.01%	86.33%
CHEMBL2056	P21728	Dopamine D1 receptor	86.81%	91.00%
CHEMBL1951	P21397	Monoamine oxidase A	85.78%	91.49%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	85.71%	93.40%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	85.24%	90.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.04%	99.15%
CHEMBL5747	Q92793	CREB-binding protein	84.37%	95.12%
CHEMBL1913	P09619	Platelet-derived growth factor receptor beta	83.40%	95.70%
CHEMBL261	P00915	Carbonic anhydrase I	82.78%	96.76%
CHEMBL3820	P35557	Hexokinase type IV	81.60%	91.96%
CHEMBL3438	Q05513	Protein kinase C zeta	80.30%	88.48%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	80.30%	91.79%

Plants that contains it

• Nelumbo nucifera
• Rubia cordifolia

Cross-Links

• PubChem: 159654
• NPASS: NPC250846
• LOTUS: LTS0084841
• wikiData: Q6039382