methyl (1R,3S,4S,6S,17S,18S,21R,23R,24S,27E,28S,29R)-27-ethylidene-8,21,40-trimethyl-20,22-dioxa-8,25,30,40-tetrazaundecacyclo[23.11.2.16,17.124,28.01,23.03,21.04,18.07,15.09,14.023,30.031,36]tetraconta-7(15),9,11,13,31,33,35-heptaene-29-carboxylate

Details

• Internal ID: 7974dfd1-7b0c-4a91-9924-448128eaf318
• Taxonomy: Alkaloids and derivatives > Pleiocarpaman alkaloids
• IUPAC Name: methyl (1R,3S,4S,6S,17S,18S,21R,23R,24S,27E,28S,29R)-27-ethylidene-8,21,40-trimethyl-20,22-dioxa-8,25,30,40-tetrazaundecacyclo[23.11.2.16,17.124,28.01,23.03,21.04,18.07,15.09,14.023,30.031,36]tetraconta-7(15),9,11,13,31,33,35-heptaene-29-carboxylate
• SMILES (Canonical): CC=C1CN2CCC34CC5C6CC7C8=C(CC(C6COC5(OC39C2CC1C(N9C1=CC=CC=C41)C(=O)OC)C)N7C)C1=CC=CC=C1N8C
• SMILES (Isomeric): C/C=C\1/CN2CC[C@@]34C[C@H]5[C@H]6C[C@H]7C8=C(C[C@@H]([C@H]6CO[C@@]5(O[C@@]39[C@@H]2C[C@@H]1[C@@H](N9C1=CC=CC=C41)C(=O)OC)C)N7C)C1=CC=CC=C1N8C
• InChI: InChI=1S/C41H48N4O4/c1-6-23-21-44-16-15-40-20-30-26-17-34-36-27(24-11-7-9-13-31(24)43(36)4)18-33(42(34)3)28(26)22-48-39(30,2)49-41(40)35(44)19-25(23)37(38(46)47-5)45(41)32-14-10-8-12-29(32)40/h6-14,25-26,28,30,33-35,37H,15-22H2,1-5H3/b23-6-/t25-,26-,28-,30-,33-,34-,35-,37+,39+,40-,41-/m0/s1
• InChI Key: XXNYZYBYNFRERU-DIUDGSACSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₁H₄₈N₄O₄
• Molecular Weight: 660.80 g/mol
• Exact Mass: 660.36755603 g/mol
• Topological Polar Surface Area (TPSA): 59.40 Ų
• XlogP: 5.20
• Atomic LogP (AlogP): 5.54
• H-Bond Acceptor: 8
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9263	92.63%
Caco-2	-	0.7589	75.89%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.5240	52.40%
OATP2B1 inhibitior	-	0.7122	71.22%
OATP1B1 inhibitior	+	0.8375	83.75%
OATP1B3 inhibitior	+	0.9367	93.67%
MATE1 inhibitior	-	0.7018	70.18%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	+	0.9933	99.33%
P-glycoprotein inhibitior	+	0.8825	88.25%
P-glycoprotein substrate	+	0.8316	83.16%
CYP3A4 substrate	+	0.7709	77.09%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7571	75.71%
CYP3A4 inhibition	+	0.6800	68.00%
CYP2C9 inhibition	-	0.5269	52.69%
CYP2C19 inhibition	+	0.5491	54.91%
CYP2D6 inhibition	-	0.7692	76.92%
CYP1A2 inhibition	-	0.6057	60.57%
CYP2C8 inhibition	+	0.8293	82.93%
CYP inhibitory promiscuity	+	0.6883	68.83%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.6292	62.92%
Eye corrosion	-	0.9873	98.73%
Eye irritation	-	0.9353	93.53%
Skin irritation	-	0.7959	79.59%
Skin corrosion	-	0.9392	93.92%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8125	81.25%
Micronuclear	+	0.6300	63.00%
Hepatotoxicity	-	0.6058	60.58%
skin sensitisation	-	0.8740	87.40%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.5922	59.22%
Acute Oral Toxicity (c)	III	0.6813	68.13%
Estrogen receptor binding	+	0.8539	85.39%
Androgen receptor binding	+	0.7675	76.75%
Thyroid receptor binding	+	0.6236	62.36%
Glucocorticoid receptor binding	+	0.8039	80.39%
Aromatase binding	+	0.6339	63.39%
PPAR gamma	+	0.7879	78.79%
Honey bee toxicity	-	0.6462	64.62%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9541	95.41%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL240	Q12809	HERG	99.65%	89.76%
CHEMBL1914	P06276	Butyrylcholinesterase	99.09%	95.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.94%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.44%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.90%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.62%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.07%	96.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	91.27%	82.69%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.26%	99.23%
CHEMBL2535	P11166	Glucose transporter	91.08%	98.75%
CHEMBL2581	P07339	Cathepsin D	89.93%	98.95%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	89.53%	100.00%
CHEMBL284	P27487	Dipeptidyl peptidase IV	89.50%	95.69%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	88.63%	97.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.12%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.98%	97.25%
CHEMBL217	P14416	Dopamine D2 receptor	86.81%	95.62%
CHEMBL5805	Q9NR97	Toll-like receptor 8	85.51%	96.25%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	85.21%	92.67%
CHEMBL340	P08684	Cytochrome P450 3A4	85.12%	91.19%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	83.74%	93.65%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.45%	97.09%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	83.02%	94.08%
CHEMBL5028	O14672	ADAM10	82.65%	97.50%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	82.25%	96.39%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	82.06%	94.62%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.09%	95.83%
CHEMBL4208	P20618	Proteasome component C5	80.82%	90.00%
CHEMBL4073	P09237	Matrix metalloproteinase 7	80.55%	97.56%

Plants that contains it

• Alstonia angustifolia
• Alstonia macrophylla
• Alstonia muelleriana

Cross-Links

• PubChem: 163053122
• LOTUS: LTS0164234
• wikiData: Q105344123