Zanthocadinanine A

Details

• Internal ID: 23f2c918-b772-4db4-a65d-7685899e80ff
• Taxonomy: Alkaloids and derivatives > Benzophenanthridine alkaloids > Dihydrobenzophenanthridine alkaloids
• IUPAC Name: (13R)-13-[[(4aR,5S,8S,8aR)-5-methoxy-5-methyl-8-propan-2-yl-4,4a,6,7,8,8a-hexahydro-3H-naphthalen-2-yl]methyl]-1,2-dimethoxy-12-methyl-13H-[1,3]benzodioxolo[5,6-c]phenanthridine
• SMILES (Canonical): CC(C)C1CCC(C2C1C=C(CC2)CC3C4=C(C=CC(=C4OC)OC)C5=C(N3C)C6=CC7=C(C=C6C=C5)OCO7)(C)OC
• SMILES (Isomeric): CC(C)[C@@H]1CC[C@]([C@H]2[C@H]1C=C(CC2)C[C@@H]3C4=C(C=CC(=C4OC)OC)C5=C(N3C)C6=CC7=C(C=C6C=C5)OCO7)(C)OC
• InChI: InChI=1S/C37H45NO5/c1-21(2)24-14-15-37(3,41-7)29-12-8-22(16-28(24)29)17-30-34-25(11-13-31(39-5)36(34)40-6)26-10-9-23-18-32-33(43-20-42-32)19-27(23)35(26)38(30)4/h9-11,13,16,18-19,21,24,28-30H,8,12,14-15,17,20H2,1-7H3/t24-,28-,29+,30+,37-/m0/s1
• InChI Key: RDACIPRKFVDYFL-XXZQSUMOSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₄₅NO₅
• Molecular Weight: 583.80 g/mol
• Exact Mass: 583.32977354 g/mol
• Topological Polar Surface Area (TPSA): 49.40 Ų
• XlogP: 7.80
• Atomic LogP (AlogP): 8.56
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 6

Synonyms

• CHEMBL507355

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9444	94.44%
Caco-2	-	0.5575	55.75%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.5911	59.11%
OATP2B1 inhibitior	-	0.7127	71.27%
OATP1B1 inhibitior	+	0.8583	85.83%
OATP1B3 inhibitior	+	0.9311	93.11%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	+	1.0000	100.00%
P-glycoprotein inhibitior	+	0.9504	95.04%
P-glycoprotein substrate	+	0.7675	76.75%
CYP3A4 substrate	+	0.7042	70.42%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4391	43.91%
CYP3A4 inhibition	+	0.7444	74.44%
CYP2C9 inhibition	-	0.8058	80.58%
CYP2C19 inhibition	-	0.5314	53.14%
CYP2D6 inhibition	+	0.5426	54.26%
CYP1A2 inhibition	-	0.6628	66.28%
CYP2C8 inhibition	+	0.7839	78.39%
CYP inhibitory promiscuity	+	0.7109	71.09%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.5448	54.48%
Eye corrosion	-	0.9878	98.78%
Eye irritation	-	0.9481	94.81%
Skin irritation	-	0.7899	78.99%
Skin corrosion	-	0.9339	93.39%
Ames mutagenesis	-	0.5191	51.91%
Human Ether-a-go-go-Related Gene inhibition	+	0.9308	93.08%
Micronuclear	+	0.5400	54.00%
Hepatotoxicity	+	0.5875	58.75%
skin sensitisation	-	0.8486	84.86%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.9077	90.77%
Acute Oral Toxicity (c)	III	0.6980	69.80%
Estrogen receptor binding	+	0.8361	83.61%
Androgen receptor binding	+	0.7729	77.29%
Thyroid receptor binding	+	0.6497	64.97%
Glucocorticoid receptor binding	+	0.8401	84.01%
Aromatase binding	+	0.5942	59.42%
PPAR gamma	+	0.7383	73.83%
Honey bee toxicity	-	0.7466	74.66%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9921	99.21%

Targets

Proven Targets:

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	98.97%	96.77%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.29%	96.09%
CHEMBL261	P00915	Carbonic anhydrase I	98.10%	96.76%
CHEMBL1937	Q92769	Histone deacetylase 2	98.04%	94.75%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	97.13%	89.62%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	96.74%	92.62%
CHEMBL344	Q99705	Melanin-concentrating hormone receptor 1	96.56%	92.50%
CHEMBL3192	Q9BY41	Histone deacetylase 8	95.13%	93.99%
CHEMBL2581	P07339	Cathepsin D	95.06%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.02%	97.25%
CHEMBL5608	Q16288	NT-3 growth factor receptor	93.35%	95.89%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.22%	91.11%
CHEMBL2730	P21980	Protein-glutamine gamma-glutamyltransferase	92.86%	92.38%
CHEMBL4835	P00338	L-lactate dehydrogenase A chain	92.80%	95.34%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.55%	94.45%
CHEMBL5747	Q92793	CREB-binding protein	92.29%	95.12%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	92.10%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.89%	94.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	89.69%	89.50%
CHEMBL4302	P08183	P-glycoprotein 1	89.13%	92.98%
CHEMBL3837	P07711	Cathepsin L	88.63%	96.61%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.37%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.78%	96.00%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	87.52%	95.78%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.37%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.75%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.73%	95.56%
CHEMBL4040	P28482	MAP kinase ERK2	86.68%	83.82%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	85.47%	97.31%
CHEMBL1871	P10275	Androgen Receptor	84.91%	96.43%
CHEMBL5555	O00767	Acyl-CoA desaturase	84.76%	97.50%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	83.60%	100.00%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	83.22%	96.67%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.11%	89.00%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	82.66%	94.03%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	82.25%	93.40%
CHEMBL2535	P11166	Glucose transporter	82.24%	98.75%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	81.40%	92.88%
CHEMBL4158	P49327	Fatty acid synthase	81.35%	82.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.62%	95.89%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	80.51%	85.49%
CHEMBL4208	P20618	Proteasome component C5	80.31%	90.00%

Plants that contains it

• Toddalia asiatica
• Zanthoxylum nitidum

Cross-Links

• PubChem: 44567550
• NPASS: NPC238008
• LOTUS: LTS0179939
• wikiData: Q105234105