(-)-Bicuculline

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	f18b5804-2043-4e71-9fab-c07c2bf4a7b8
Taxonomy	Alkaloids and derivatives > Phthalide isoquinolines
IUPAC Name	(6S)-6-[(5R)-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6H-furo[3,4-g][1,3]benzodioxol-8-one
SMILES (Canonical)	CN1CCC2=CC3=C(C=C2C1C4C5=C(C6=C(C=C5)OCO6)C(=O)O4)OCO3
SMILES (Isomeric)	CN1CCC2=CC3=C(C=C2[C@@H]1[C@@H]4C5=C(C6=C(C=C5)OCO6)C(=O)O4)OCO3
InChI	InChI=1S/C20H17NO6/c1-21-5-4-10-6-14-15(25-8-24-14)7-12(10)17(21)18-11-2-3-13-19(26-9-23-13)16(11)20(22)27-18/h2-3,6-7,17-18H,4-5,8-9H2,1H3/t17-,18+/m1/s1
InChI Key	IYGYMKDQCDOMRE-MSOLQXFVSA-N
Popularity	41 references in papers

Physical and Chemical Properties

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Molecular Formula	C₂₀H₁₇NO₆
Molecular Weight	367.40 g/mol
Exact Mass	367.10558726 g/mol
Topological Polar Surface Area (TPSA)	66.50 Å²
XlogP	2.60
Atomic LogP (AlogP)	2.58
H-Bond Acceptor	7
H-Bond Donor	0
Rotatable Bonds	1

Synonyms

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dl-Bicuculline

19730-80-4

(+-)-Bicuculline

(6S)-6-[(5R)-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6H-furo[3,4-g][1,3]benzodioxol-8-one

56083-00-2

CHEMBL1316579

SCHEMBL16320040

TNP00219

TNP00335

NCGC00017296-01

There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9731	97.31%
Caco-2	+	0.7738	77.38%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Lysosomes	0.4400	44.00%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9247	92.47%
OATP1B3 inhibitior	+	0.9533	95.33%
MATE1 inhibitior	-	0.9409	94.09%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.8511	85.11%
P-glycoprotein inhibitior	-	0.6282	62.82%
P-glycoprotein substrate	-	0.8209	82.09%
CYP3A4 substrate	+	0.6019	60.19%
CYP2C9 substrate	+	0.8024	80.24%
CYP2D6 substrate	-	0.6799	67.99%
CYP3A4 inhibition	+	0.7959	79.59%
CYP2C9 inhibition	+	0.7664	76.64%
CYP2C19 inhibition	+	0.8993	89.93%
CYP2D6 inhibition	-	0.6229	62.29%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	-	0.9319	93.19%
CYP inhibitory promiscuity	-	0.5366	53.66%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5613	56.13%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.9577	95.77%
Skin irritation	-	0.7658	76.58%
Skin corrosion	-	0.9309	93.09%
Ames mutagenesis	+	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4086	40.86%
Micronuclear	+	0.5474	54.74%
Hepatotoxicity	-	0.6250	62.50%
skin sensitisation	-	0.8574	85.74%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	-	0.6036	60.36%
Acute Oral Toxicity (c)	III	0.7155	71.55%
Estrogen receptor binding	+	0.8442	84.42%
Androgen receptor binding	-	0.5329	53.29%
Thyroid receptor binding	-	0.7445	74.45%
Glucocorticoid receptor binding	+	0.8982	89.82%
Aromatase binding	+	0.5375	53.75%
PPAR gamma	+	0.7847	78.47%
Honey bee toxicity	-	0.8638	86.38%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.7800	78.00%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3622	P33261	Cytochrome P450 2C19	100 nM 15.8 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL3397	P11712	Cytochrome P450 2C9	39810.7 nM 3981.1 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL289	P10635	Cytochrome P450 2D6	15848.9 nM 10000 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	281.8 nM	Potency	via Super-PRED
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	31622.8 nM 31622.8 nM 31622.8 nM 31622.8 nM	Potency Potency Potency Potency	via CMAUP via CMAUP via CMAUP via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	98.56%	96.77%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	98.00%	93.40%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.48%	95.56%
CHEMBL2581	P07339	Cathepsin D	95.51%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.53%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.21%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.39%	94.45%
CHEMBL1841	P06241	Tyrosine-protein kinase FYN	86.21%	81.29%
CHEMBL3192	Q9BY41	Histone deacetylase 8	86.00%	93.99%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.76%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.45%	99.23%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	84.73%	82.67%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.33%	85.14%
CHEMBL2056	P21728	Dopamine D1 receptor	84.27%	91.00%
CHEMBL3384	Q16512	Protein kinase N1	83.70%	80.71%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.54%	100.00%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.62%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.30%	89.00%
CHEMBL2083	P15090	Fatty acid binding protein adipocyte	80.60%	95.71%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	80.57%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.50%	92.62%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.