methyl (1S,2R,5S,12S,15E,24R,25R,26R,28S,40S)-15-ethylidene-34-methoxy-24,30,39-trimethyl-4,6-dioxa-10,17,30,39-tetrazaundecacyclo[26.10.1.114,20.02,26.05,25.07,23.09,21.011,20.012,17.029,37.031,36]tetraconta-7,9(21),10,22,29(37),31(36),32,34-octaene-40-carboxylate

Details

• Internal ID: dc39cfc5-fbaa-480a-afd8-bbf27144fac1
• Taxonomy: Alkaloids and derivatives > Macroline alkaloids
• IUPAC Name: methyl (1S,2R,5S,12S,15E,24R,25R,26R,28S,40S)-15-ethylidene-34-methoxy-24,30,39-trimethyl-4,6-dioxa-10,17,30,39-tetrazaundecacyclo[26.10.1.114,20.02,26.05,25.07,23.09,21.011,20.012,17.029,37.031,36]tetraconta-7,9(21),10,22,29(37),31(36),32,34-octaene-40-carboxylate
• SMILES (Canonical): CC=C1CN2CCC34C(C1CC2C3=NC5=C4C=C6C(C7C8CC9C1=C(CC(C8COC7OC6=C5)N9C)C2=C(N1C)C=CC(=C2)OC)C)C(=O)OC
• SMILES (Isomeric): C/C=C\1/CN2CCC34[C@H](C1C[C@H]2C3=NC5=C4C=C6[C@@H]([C@H]7[C@@H]8C[C@H]9C1=C(C[C@@H]([C@@H]8CO[C@H]7OC6=C5)N9C)C2=C(N1C)C=CC(=C2)OC)C)C(=O)OC
• InChI: InChI=1S/C42H48N4O5/c1-7-21-18-46-11-10-42-29-13-23-20(2)36-26-15-33-38-27(25-12-22(48-5)8-9-31(25)45(38)4)16-32(44(33)3)28(26)19-50-41(36)51-35(23)17-30(29)43-39(42)34(46)14-24(21)37(42)40(47)49-6/h7-9,12-13,17,20,24,26,28,32-34,36-37,41H,10-11,14-16,18-19H2,1-6H3/b21-7-/t20-,24?,26+,28+,32-,33-,34-,36-,37+,41-,42?/m0/s1
• InChI Key: VCBZKBQWCJFXPT-PEORXQDSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₄₈N₄O₅
• Molecular Weight: 688.90 g/mol
• Exact Mass: 688.36247064 g/mol
• Topological Polar Surface Area (TPSA): 77.80 Ų
• XlogP: 4.50
• Atomic LogP (AlogP): 6.06
• H-Bond Acceptor: 9
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9386	93.86%
Caco-2	-	0.7892	78.92%
Blood Brain Barrier	+	0.9000	90.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.4685	46.85%
OATP2B1 inhibitior	+	0.5799	57.99%
OATP1B1 inhibitior	+	0.8283	82.83%
OATP1B3 inhibitior	+	0.9256	92.56%
MATE1 inhibitior	-	0.7618	76.18%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.9707	97.07%
P-glycoprotein inhibitior	+	0.8527	85.27%
P-glycoprotein substrate	+	0.8598	85.98%
CYP3A4 substrate	+	0.7542	75.42%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7834	78.34%
CYP3A4 inhibition	+	0.7612	76.12%
CYP2C9 inhibition	-	0.7641	76.41%
CYP2C19 inhibition	-	0.7777	77.77%
CYP2D6 inhibition	-	0.6379	63.79%
CYP1A2 inhibition	-	0.6299	62.99%
CYP2C8 inhibition	+	0.8066	80.66%
CYP inhibitory promiscuity	-	0.5065	50.65%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.6021	60.21%
Eye corrosion	-	0.9856	98.56%
Eye irritation	-	0.9289	92.89%
Skin irritation	-	0.7786	77.86%
Skin corrosion	-	0.9391	93.91%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7463	74.63%
Micronuclear	+	0.6000	60.00%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.8427	84.27%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.6691	66.91%
Acute Oral Toxicity (c)	III	0.6628	66.28%
Estrogen receptor binding	+	0.8592	85.92%
Androgen receptor binding	+	0.7699	76.99%
Thyroid receptor binding	+	0.5854	58.54%
Glucocorticoid receptor binding	+	0.8187	81.87%
Aromatase binding	+	0.7274	72.74%
PPAR gamma	+	0.7549	75.49%
Honey bee toxicity	-	0.6279	62.79%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9784	97.84%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.04%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.37%	91.11%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	96.72%	89.05%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	95.28%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.30%	95.56%
CHEMBL2243	O00519	Anandamide amidohydrolase	92.85%	97.53%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.23%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.01%	94.45%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	90.12%	90.71%
CHEMBL204	P00734	Thrombin	89.00%	96.01%
CHEMBL5747	Q92793	CREB-binding protein	88.39%	95.12%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.30%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.15%	94.00%
CHEMBL255	P29275	Adenosine A2b receptor	87.94%	98.59%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.76%	92.62%
CHEMBL2581	P07339	Cathepsin D	87.72%	98.95%
CHEMBL2535	P11166	Glucose transporter	87.52%	98.75%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	86.57%	82.38%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.61%	86.33%
CHEMBL4208	P20618	Proteasome component C5	84.30%	90.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.08%	99.23%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.74%	86.92%
CHEMBL284	P27487	Dipeptidyl peptidase IV	82.58%	95.69%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	80.93%	85.00%
CHEMBL2782	P35610	Acyl coenzyme A:cholesterol acyltransferase 1	80.21%	91.65%
CHEMBL1744525	P43490	Nicotinamide phosphoribosyltransferase	80.15%	96.25%

Plants that contains it

• Alstonia angustifolia

Cross-Links

• PubChem: 102075144
• LOTUS: LTS0055764
• wikiData: Q105283606