(4S,6aR)-1,2,3-trimethoxy-7,7-dimethyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-4-ol

Details

• Internal ID: 9af561e4-9656-4bfa-b909-a78812f3cbc2
• Taxonomy: Alkaloids and derivatives > Aporphines
• IUPAC Name: (4S,6aR)-1,2,3-trimethoxy-7,7-dimethyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-4-ol
• SMILES (Canonical): CC1(C2C3=C(C4=CC=CC=C41)C(=C(C(=C3C(CN2)O)OC)OC)OC)C
• SMILES (Isomeric): CC1([C@@H]2C3=C(C4=CC=CC=C41)C(=C(C(=C3[C@@H](CN2)O)OC)OC)OC)C
• InChI: InChI=1S/C21H25NO4/c1-21(2)12-9-7-6-8-11(12)14-16-15(13(23)10-22-20(16)21)18(25-4)19(26-5)17(14)24-3/h6-9,13,20,22-23H,10H2,1-5H3/t13-,20+/m1/s1
• InChI Key: LGQWKWCRVZSCKZ-XCLFUZPHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₅NO₄
• Molecular Weight: 355.40 g/mol
• Exact Mass: 355.17835828 g/mol
• Topological Polar Surface Area (TPSA): 60.00 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 3.35
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9440	94.40%
Caco-2	+	0.8020	80.20%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	+	0.7429	74.29%
Subcellular localzation	Mitochondria	0.4544	45.44%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9089	90.89%
OATP1B3 inhibitior	+	0.9593	95.93%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.5636	56.36%
P-glycoprotein inhibitior	-	0.6673	66.73%
P-glycoprotein substrate	-	0.6557	65.57%
CYP3A4 substrate	+	0.5917	59.17%
CYP2C9 substrate	-	0.8204	82.04%
CYP2D6 substrate	+	0.6616	66.16%
CYP3A4 inhibition	-	0.7690	76.90%
CYP2C9 inhibition	-	0.8639	86.39%
CYP2C19 inhibition	-	0.7852	78.52%
CYP2D6 inhibition	-	0.8693	86.93%
CYP1A2 inhibition	-	0.6926	69.26%
CYP2C8 inhibition	+	0.5269	52.69%
CYP inhibitory promiscuity	-	0.8941	89.41%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.6068	60.68%
Eye corrosion	-	0.9918	99.18%
Eye irritation	-	0.9353	93.53%
Skin irritation	-	0.8040	80.40%
Skin corrosion	-	0.9179	91.79%
Ames mutagenesis	+	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7572	75.72%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.8451	84.51%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.7607	76.07%
Acute Oral Toxicity (c)	III	0.5689	56.89%
Estrogen receptor binding	+	0.7988	79.88%
Androgen receptor binding	+	0.6709	67.09%
Thyroid receptor binding	+	0.8657	86.57%
Glucocorticoid receptor binding	+	0.5987	59.87%
Aromatase binding	+	0.5800	58.00%
PPAR gamma	+	0.7442	74.42%
Honey bee toxicity	-	0.9134	91.34%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	-	0.7987	79.87%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.33%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.91%	96.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	95.81%	82.69%
CHEMBL2581	P07339	Cathepsin D	93.33%	98.95%
CHEMBL2535	P11166	Glucose transporter	92.80%	98.75%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.60%	97.09%
CHEMBL221	P23219	Cyclooxygenase-1	90.60%	90.17%
CHEMBL4208	P20618	Proteasome component C5	89.58%	90.00%
CHEMBL1937	Q92769	Histone deacetylase 2	83.39%	94.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.33%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.23%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.12%	86.33%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.10%	93.03%

Plants that contains it

• Guatteria friesiana
• Trigonostemon reidioides

Cross-Links

• PubChem: 44254607
• LOTUS: LTS0267369
• wikiData: Q105245488