Huangshanine

Details

• Internal ID: 6a893752-a5e3-4127-887b-d8d88ecb9d72
• Taxonomy: Alkaloids and derivatives > Aporphines
• IUPAC Name: (6aS)-9-[6-[[(1S)-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-1-yl]methyl]-2,3-dimethoxyphenoxy]-1,2,3,10-tetramethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline
• SMILES (Canonical): CN1CCC2=C3C1CC4=CC(=C(C=C4C3=C(C(=C2OC)OC)OC)OC)OC5=C(C=CC(=C5OC)OC)CC6C7=CC(=C(C=C7CCN6C)OC)OC
• SMILES (Isomeric): CN1CCC2=C3[C@@H]1CC4=CC(=C(C=C4C3=C(C(=C2OC)OC)OC)OC)OC5=C(C=CC(=C5OC)OC)C[C@H]6C7=CC(=C(C=C7CCN6C)OC)OC
• InChI: InChI=1S/C42H50N2O9/c1-43-15-13-23-19-32(46-4)33(47-5)21-27(23)29(43)17-24-11-12-31(45-3)40(50-8)38(24)53-35-20-25-18-30-36-26(14-16-44(30)2)39(49-7)42(52-10)41(51-9)37(36)28(25)22-34(35)48-6/h11-12,19-22,29-30H,13-18H2,1-10H3/t29-,30-/m0/s1
• InChI Key: AAMOLTQKZFTOCO-KYJUHHDHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₅₀N₂O₉
• Molecular Weight: 726.90 g/mol
• Exact Mass: 726.35163118 g/mol
• Topological Polar Surface Area (TPSA): 89.60 Ų
• XlogP: 6.60
• Atomic LogP (AlogP): 7.07
• H-Bond Acceptor: 11
• H-Bond Donor: 0
• Rotatable Bonds: 12

Synonyms

• 88313-35-3
• (+)-Huangshanine
• DTXSID10236954
• 4H-Dibenzo(de,g)quinoline, 9-(2,3-dimethoxy-6-(((1S)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl)methyl)phenoxy)-5,6,6a,7-tetrahydro-1,2,3,10-tetramethoxy-6-methyl-, (6aS)-
• 4H-Dibenzo(de,g)quinoline, 9-(2,3-dimethoxy-6-((1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl)methyl)phenoxy)-5,6,6a,7-tetrahydro-1,2,3,10-tetramethoxy-6-methyl-, (S-(R*,R*))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9128	91.28%
Caco-2	-	0.6861	68.61%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.5564	55.64%
OATP2B1 inhibitior	-	0.7032	70.32%
OATP1B1 inhibitior	+	0.8616	86.16%
OATP1B3 inhibitior	+	0.9361	93.61%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	+	0.9956	99.56%
P-glycoprotein inhibitior	+	0.9272	92.72%
P-glycoprotein substrate	-	0.5605	56.05%
CYP3A4 substrate	+	0.7206	72.06%
CYP2C9 substrate	+	0.7825	78.25%
CYP2D6 substrate	+	0.8198	81.98%
CYP3A4 inhibition	-	0.8890	88.90%
CYP2C9 inhibition	-	0.9775	97.75%
CYP2C19 inhibition	-	0.9685	96.85%
CYP2D6 inhibition	-	0.8439	84.39%
CYP1A2 inhibition	-	0.9220	92.20%
CYP2C8 inhibition	+	0.7171	71.71%
CYP inhibitory promiscuity	-	0.9188	91.88%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6456	64.56%
Eye corrosion	-	0.9924	99.24%
Eye irritation	-	0.9230	92.30%
Skin irritation	-	0.7975	79.75%
Skin corrosion	-	0.9493	94.93%
Ames mutagenesis	+	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9411	94.11%
Micronuclear	-	0.5600	56.00%
Hepatotoxicity	-	0.6699	66.99%
skin sensitisation	-	0.9041	90.41%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.7174	71.74%
Acute Oral Toxicity (c)	III	0.7763	77.63%
Estrogen receptor binding	+	0.7891	78.91%
Androgen receptor binding	+	0.7412	74.12%
Thyroid receptor binding	+	0.6147	61.47%
Glucocorticoid receptor binding	+	0.8291	82.91%
Aromatase binding	+	0.6880	68.80%
PPAR gamma	+	0.7069	70.69%
Honey bee toxicity	-	0.7841	78.41%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.6700	67.00%
Fish aquatic toxicity	+	0.8538	85.38%

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	99.35%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.16%	98.95%
CHEMBL2056	P21728	Dopamine D1 receptor	95.76%	91.00%
CHEMBL217	P14416	Dopamine D2 receptor	95.59%	95.62%
CHEMBL5747	Q92793	CREB-binding protein	94.97%	95.12%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.85%	85.14%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	93.50%	89.62%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	93.17%	95.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.70%	86.33%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	91.75%	91.79%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	91.32%	95.89%
CHEMBL4208	P20618	Proteasome component C5	91.03%	90.00%
CHEMBL2535	P11166	Glucose transporter	90.15%	98.75%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.38%	97.25%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.58%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.87%	92.62%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	86.06%	92.38%
CHEMBL2073	P07947	Tyrosine-protein kinase YES	85.92%	83.14%
CHEMBL2413	P32246	C-C chemokine receptor type 1	85.44%	89.50%
CHEMBL3192	Q9BY41	Histone deacetylase 8	84.83%	93.99%
CHEMBL4302	P08183	P-glycoprotein 1	84.45%	92.98%
CHEMBL3438	Q05513	Protein kinase C zeta	82.44%	88.48%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.34%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.31%	95.56%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	82.16%	91.03%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	81.98%	93.40%
CHEMBL2096618	P11274	Bcr/Abl fusion protein	81.17%	85.83%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	81.17%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.77%	94.00%
CHEMBL264	Q9Y5N1	Histamine H3 receptor	80.56%	91.43%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	80.54%	95.78%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	80.40%	95.53%

Plants that contains it

• Thalictrum faberi

Cross-Links

• PubChem: 181916
• LOTUS: LTS0006528
• wikiData: Q83119037