(6aS)-6-[(2S)-2-hydroxypropyl]-1,10-dimethoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-2,11-diol

Details

• Internal ID: 02e60de0-dead-4243-bf54-587f8a1ac9b6
• Taxonomy: Alkaloids and derivatives > Aporphines
• IUPAC Name: (6aS)-6-[(2S)-2-hydroxypropyl]-1,10-dimethoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-2,11-diol
• SMILES (Canonical): CC(CN1CCC2=CC(=C(C3=C2C1CC4=C3C(=C(C=C4)OC)O)OC)O)O
• SMILES (Isomeric): C[C@@H](CN1CCC2=CC(=C(C3=C2[C@@H]1CC4=C3C(=C(C=C4)OC)O)OC)O)O
• InChI: InChI=1S/C21H25NO5/c1-11(23)10-22-7-6-13-9-15(24)21(27-3)19-17(13)14(22)8-12-4-5-16(26-2)20(25)18(12)19/h4-5,9,11,14,23-25H,6-8,10H2,1-3H3/t11-,14-/m0/s1
• InChI Key: CPJQTONOKGWFSY-FZMZJTMJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₅NO₅
• Molecular Weight: 371.40 g/mol
• Exact Mass: 371.17327290 g/mol
• Topological Polar Surface Area (TPSA): 82.40 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.62
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6282	62.82%
Caco-2	+	0.8691	86.91%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6752	67.52%
OATP2B1 inhibitior	-	0.8551	85.51%
OATP1B1 inhibitior	+	0.9227	92.27%
OATP1B3 inhibitior	+	0.9378	93.78%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.5099	50.99%
BSEP inhibitior	+	0.8298	82.98%
P-glycoprotein inhibitior	-	0.6848	68.48%
P-glycoprotein substrate	-	0.5162	51.62%
CYP3A4 substrate	+	0.6014	60.14%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.7827	78.27%
CYP3A4 inhibition	-	0.8564	85.64%
CYP2C9 inhibition	-	0.9038	90.38%
CYP2C19 inhibition	-	0.7048	70.48%
CYP2D6 inhibition	+	0.6896	68.96%
CYP1A2 inhibition	-	0.7298	72.98%
CYP2C8 inhibition	-	0.5847	58.47%
CYP inhibitory promiscuity	-	0.9117	91.17%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6650	66.50%
Eye corrosion	-	0.9920	99.20%
Eye irritation	-	0.9501	95.01%
Skin irritation	-	0.7838	78.38%
Skin corrosion	-	0.9402	94.02%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6445	64.45%
Micronuclear	-	0.5500	55.00%
Hepatotoxicity	-	0.8125	81.25%
skin sensitisation	-	0.8884	88.84%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.9612	96.12%
Acute Oral Toxicity (c)	III	0.6163	61.63%
Estrogen receptor binding	+	0.5637	56.37%
Androgen receptor binding	+	0.6479	64.79%
Thyroid receptor binding	-	0.4891	48.91%
Glucocorticoid receptor binding	+	0.8097	80.97%
Aromatase binding	+	0.5486	54.86%
PPAR gamma	+	0.5837	58.37%
Honey bee toxicity	-	0.8893	88.93%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	-	0.5236	52.36%

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	99.58%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.02%	91.11%
CHEMBL3192	Q9BY41	Histone deacetylase 8	96.68%	93.99%
CHEMBL2581	P07339	Cathepsin D	95.58%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.51%	94.45%
CHEMBL217	P14416	Dopamine D2 receptor	94.81%	95.62%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.57%	85.14%
CHEMBL261	P00915	Carbonic anhydrase I	92.16%	96.76%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	92.02%	89.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.73%	95.89%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.82%	99.15%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.26%	95.89%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	88.15%	91.03%
CHEMBL4208	P20618	Proteasome component C5	87.22%	90.00%
CHEMBL1951	P21397	Monoamine oxidase A	86.55%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.08%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.39%	99.17%
CHEMBL213	P08588	Beta-1 adrenergic receptor	84.73%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.21%	94.00%
CHEMBL1744525	P43490	Nicotinamide phosphoribosyltransferase	82.65%	96.25%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.57%	90.71%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.49%	92.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.26%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.99%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.84%	89.00%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	81.39%	91.79%
CHEMBL4835	P00338	L-lactate dehydrogenase A chain	81.20%	95.34%
CHEMBL3438	Q05513	Protein kinase C zeta	80.31%	88.48%

Plants that contains it

• Actinodaphne pruinosa

Cross-Links

• PubChem: 162940136
• LOTUS: LTS0200329
• wikiData: Q104967605