Angoline

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	67487d2e-b234-4d87-84f1-b2bd84508506
Taxonomy	Alkaloids and derivatives > Benzophenanthridine alkaloids > Dihydrobenzophenanthridine alkaloids
IUPAC Name	1,2,13-trimethoxy-12-methyl-13H-[1,3]benzodioxolo[5,6-c]phenanthridine
SMILES (Canonical)	CN1C(C2=C(C=CC(=C2OC)OC)C3=C1C4=CC5=C(C=C4C=C3)OCO5)OC
SMILES (Isomeric)	CN1C(C2=C(C=CC(=C2OC)OC)C3=C1C4=CC5=C(C=C4C=C3)OCO5)OC
InChI	InChI=1S/C22H21NO5/c1-23-20-14(6-5-12-9-17-18(10-15(12)20)28-11-27-17)13-7-8-16(24-2)21(25-3)19(13)22(23)26-4/h5-10,22H,11H2,1-4H3
InChI Key	LVWAKZBZWYHYCJ-UHFFFAOYSA-N
Popularity	3 references in papers

Physical and Chemical Properties

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Molecular Formula	C₂₂H₂₁NO₅
Molecular Weight	379.40 g/mol
Exact Mass	379.14197277 g/mol
Topological Polar Surface Area (TPSA)	49.40 Å²
XlogP	4.20
Atomic LogP (AlogP)	4.35
H-Bond Acceptor	6
H-Bond Donor	0
Rotatable Bonds	3

Synonyms

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21080-31-9

1,2,13-trimethoxy-12-methyl-13H-[1,3]benzodioxolo[5,6-c]phenanthridine

[1,3]Benzodioxolo[5,6-c]phenanthridine, 12,13-dihydro-1,2,13-trimethoxy-12-methyl-

1,2,13-Trimethoxy-12-methyl-12,13-dihydro-[1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridine

AC1L4NZH

AC1Q703U

6-Methoxyldihydrochelerythrine

SureCN13103356

CHEBI:2721

CHEMBL4294195

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	+	0.8956	89.56%
Caco-2	+	0.9302	93.02%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.3510	35.10%
OATP2B1 inhibitior	-	0.8819	88.19%
OATP1B1 inhibitior	+	0.9317	93.17%
OATP1B3 inhibitior	+	0.9475	94.75%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9348	93.48%
BSEP inhibitior	+	0.9446	94.46%
P-glycoprotein inhibitior	+	0.8830	88.30%
P-glycoprotein substrate	+	0.6184	61.84%
CYP3A4 substrate	+	0.5799	57.99%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.3798	37.98%
CYP3A4 inhibition	+	0.6585	65.85%
CYP2C9 inhibition	-	0.7405	74.05%
CYP2C19 inhibition	+	0.7377	73.77%
CYP2D6 inhibition	-	0.6781	67.81%
CYP1A2 inhibition	+	0.6438	64.38%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	+	0.7258	72.58%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.4499	44.99%
Eye corrosion	-	0.9875	98.75%
Eye irritation	-	0.9325	93.25%
Skin irritation	-	0.8157	81.57%
Skin corrosion	-	0.9521	95.21%
Ames mutagenesis	+	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7874	78.74%
Micronuclear	+	0.7900	79.00%
Hepatotoxicity	+	0.5534	55.34%
skin sensitisation	-	0.8735	87.35%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.7231	72.31%
Acute Oral Toxicity (c)	III	0.6994	69.94%
Estrogen receptor binding	+	0.8817	88.17%
Androgen receptor binding	+	0.7722	77.22%
Thyroid receptor binding	+	0.8206	82.06%
Glucocorticoid receptor binding	+	0.8675	86.75%
Aromatase binding	+	0.6112	61.12%
PPAR gamma	+	0.7196	71.96%
Honey bee toxicity	-	0.8646	86.46%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.6500	65.00%
Fish aquatic toxicity	+	0.8071	80.71%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	94.93%	89.62%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	94.59%	96.77%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.86%	96.09%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	93.28%	92.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.57%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.98%	94.00%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	90.51%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.23%	95.56%
CHEMBL2581	P07339	Cathepsin D	89.72%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.43%	96.00%
CHEMBL2535	P11166	Glucose transporter	87.24%	98.75%
CHEMBL2039	P27338	Monoamine oxidase B	86.36%	92.51%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.85%	89.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.52%	91.11%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.77%	95.89%
CHEMBL5747	Q92793	CREB-binding protein	84.76%	95.12%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	84.51%	92.38%
CHEMBL3192	Q9BY41	Histone deacetylase 8	82.56%	93.99%
CHEMBL4208	P20618	Proteasome component C5	82.22%	90.00%
CHEMBL2730	P21980	Protein-glutamine gamma-glutamyltransferase	81.56%	92.38%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	81.36%	82.67%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	80.80%	85.49%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	80.79%	96.00%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	80.54%	100.00%

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.

Zanthoxylum leprieurii

Zanthoxylum thomense

Zanthoxylum zanthoxyloides