Macarpine

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

Top

Internal ID	e6fcf810-9d18-48b7-8b29-6d48caca37b1
Taxonomy	Alkaloids and derivatives > Benzophenanthridine alkaloids > Quaternary benzophenanthridine alkaloids
IUPAC Name	11,15-dimethoxy-24-methyl-5,7,18,20-tetraoxa-24-azoniahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-1(13),2,4(8),9,11,14,16,21,23-nonaene
SMILES (Canonical)	C[N+]1=CC2=C3C(=CC(=C2C4=C1C5=CC6=C(C=C5C(=C4)OC)OCO6)OC)OCO3
SMILES (Isomeric)	C[N+]1=CC2=C3C(=CC(=C2C4=C1C5=CC6=C(C=C5C(=C4)OC)OCO6)OC)OCO3
InChI	InChI=1S/C22H18NO6/c1-23-8-14-20(18(25-3)7-19-22(14)29-10-28-19)13-6-15(24-2)11-4-16-17(27-9-26-16)5-12(11)21(13)23/h4-8H,9-10H2,1-3H3/q+1
InChI Key	SBVRPBAVNZNLKX-UHFFFAOYSA-N
Popularity	14 references in papers

Physical and Chemical Properties

Top

Molecular Formula	C₂₂H₁₈NO₆+
Molecular Weight	392.40 g/mol
Exact Mass	392.11341229 g/mol
Topological Polar Surface Area (TPSA)	59.30 Å²
XlogP	4.40
Atomic LogP (AlogP)	3.45
H-Bond Acceptor	6
H-Bond Donor	0
Rotatable Bonds	2

Synonyms

Top

23594-80-1

5,7-dimethoxy-13-methyl-2H,10H-[1,3]dioxolo[4,5-i][1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridinium

C06165

CHEMBL5205934

CHEBI:17101

DTXSID20946395

Q3841952

[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium, 5,7-dimethoxy-13-methyl-

11,15-dimethoxy-24-methyl-5,7,18,20-tetraoxa-24-azoniahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-1(13),2,4(8),9,11,14,16,21,23-nonaene

5,7-Dimethoxy-13-methyl-2H,10H-[1,3]benzodioxolo[5,6-c][1,3]dioxolo[4,5-i]phenanthridin-13-ium

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

2D Structure

Top

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6479	64.79%
Caco-2	+	0.9142	91.42%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Nucleus	0.4752	47.52%
OATP2B1 inhibitior	-	0.8878	88.78%
OATP1B1 inhibitior	+	0.9412	94.12%
OATP1B3 inhibitior	+	0.9400	94.00%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.8348	83.48%
BSEP inhibitior	+	0.9127	91.27%
P-glycoprotein inhibitior	+	0.7671	76.71%
P-glycoprotein substrate	-	0.7433	74.33%
CYP3A4 substrate	+	0.5290	52.90%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7625	76.25%
CYP3A4 inhibition	-	0.5716	57.16%
CYP2C9 inhibition	-	0.8507	85.07%
CYP2C19 inhibition	+	0.7924	79.24%
CYP2D6 inhibition	+	0.7252	72.52%
CYP1A2 inhibition	+	0.8562	85.62%
CYP2C8 inhibition	-	0.6817	68.17%
CYP inhibitory promiscuity	+	0.8311	83.11%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.3496	34.96%
Eye corrosion	-	0.9864	98.64%
Eye irritation	-	0.8339	83.39%
Skin irritation	-	0.8175	81.75%
Skin corrosion	-	0.9541	95.41%
Ames mutagenesis	+	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7998	79.98%
Micronuclear	+	0.7300	73.00%
Hepatotoxicity	+	0.6500	65.00%
skin sensitisation	-	0.8584	85.84%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.6310	63.10%
Acute Oral Toxicity (c)	III	0.7095	70.95%
Estrogen receptor binding	+	0.8982	89.82%
Androgen receptor binding	+	0.5596	55.96%
Thyroid receptor binding	+	0.7160	71.60%
Glucocorticoid receptor binding	+	0.8966	89.66%
Aromatase binding	+	0.5786	57.86%
PPAR gamma	+	0.7007	70.07%
Honey bee toxicity	-	0.7202	72.02%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.7400	74.00%
Fish aquatic toxicity	-	0.4525	45.25%

Targets

Top

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
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	98.62%	96.77%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	95.14%	94.80%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.28%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.47%	91.11%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	89.98%	92.62%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.35%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.21%	96.09%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	88.62%	89.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.94%	94.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.93%	96.00%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	85.75%	82.67%
CHEMBL3192	Q9BY41	Histone deacetylase 8	85.28%	93.99%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.95%	92.94%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.73%	86.33%
CHEMBL230	P35354	Cyclooxygenase-2	82.31%	89.63%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.46%	97.36%
CHEMBL2581	P07339	Cathepsin D	81.27%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	81.22%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.99%	89.00%

Plants that contains it

Top

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.

Eschscholzia californica

Garcinia xanthochymus

Macleaya cordata

Stylophorum diphyllum

Stylophorum lasiocarpum