methyl (1R,9R,10S,12R,13E,18S)-13-ethylidene-4-[(1R)-1-[(1S,12S,13R,16S,17R,18R)-16-hydroxy-7-methoxy-3,20-dimethyl-15-oxa-3,20-diazapentacyclo[10.7.1.02,10.04,9.013,18]icosa-2(10),4(9),5,7-tetraen-17-yl]ethyl]-5-methoxy-8-methyl-8,15-diazapentacyclo[10.5.1.01,9.02,7.010,15]octadeca-2(7),3,5-triene-18-carboxylate

Details

• Internal ID: c28c4499-437b-41cb-b106-6d6b859b0b3d
• Taxonomy: Alkaloids and derivatives > Macroline alkaloids
• IUPAC Name: methyl (1R,9R,10S,12R,13E,18S)-13-ethylidene-4-[(1R)-1-[(1S,12S,13R,16S,17R,18R)-16-hydroxy-7-methoxy-3,20-dimethyl-15-oxa-3,20-diazapentacyclo[10.7.1.02,10.04,9.013,18]icosa-2(10),4(9),5,7-tetraen-17-yl]ethyl]-5-methoxy-8-methyl-8,15-diazapentacyclo[10.5.1.01,9.02,7.010,15]octadeca-2(7),3,5-triene-18-carboxylate
• SMILES (Canonical): CC=C1CN2CCC34C(C1CC2C3N(C5=C4C=C(C(=C5)OC)C(C)C6C7CC8C9=C(CC(C7COC6O)N8C)C1=C(N9C)C=CC(=C1)OC)C)C(=O)OC
• SMILES (Isomeric): C/C=C\1/CN2CC[C@]34[C@H]([C@H]1C[C@H]2[C@@H]3N(C5=C4C=C(C(=C5)OC)[C@H](C)[C@H]6[C@@H]7C[C@H]8C9=C(C[C@@H]([C@@H]7CO[C@@H]6O)N8C)C1=C(N9C)C=CC(=C1)OC)C)C(=O)OC
• InChI: InChI=1S/C44H56N4O6/c1-9-23-20-48-13-12-44-31-15-25(37(52-7)19-34(31)47(5)41(44)36(48)16-26(23)39(44)43(50)53-8)22(2)38-28-17-35-40-29(18-33(45(35)3)30(28)21-54-42(38)49)27-14-24(51-6)10-11-32(27)46(40)4/h9-11,14-15,19,22,26,28,30,33,35-36,38-39,41-42,49H,12-13,16-18,20-21H2,1-8H3/b23-9-/t22-,26-,28+,30+,33-,35-,36-,38-,39+,41-,42-,44-/m0/s1
• InChI Key: YFNMZMAFDYJGFF-RKTUJIOLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₄H₅₆N₄O₆
• Molecular Weight: 736.90 g/mol
• Exact Mass: 736.41998552 g/mol
• Topological Polar Surface Area (TPSA): 88.90 Ų
• XlogP: 4.80
• Atomic LogP (AlogP): 5.40
• H-Bond Acceptor: 10
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9393	93.93%
Caco-2	-	0.8012	80.12%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.5675	56.75%
OATP2B1 inhibitior	-	0.7066	70.66%
OATP1B1 inhibitior	+	0.8414	84.14%
OATP1B3 inhibitior	+	0.9150	91.50%
MATE1 inhibitior	-	0.7418	74.18%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.9426	94.26%
P-glycoprotein inhibitior	+	0.8231	82.31%
P-glycoprotein substrate	+	0.8551	85.51%
CYP3A4 substrate	+	0.7422	74.22%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7827	78.27%
CYP3A4 inhibition	+	0.6137	61.37%
CYP2C9 inhibition	-	0.7220	72.20%
CYP2C19 inhibition	-	0.7304	73.04%
CYP2D6 inhibition	-	0.6103	61.03%
CYP1A2 inhibition	-	0.6149	61.49%
CYP2C8 inhibition	+	0.7571	75.71%
CYP inhibitory promiscuity	-	0.5492	54.92%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5793	57.93%
Eye corrosion	-	0.9874	98.74%
Eye irritation	-	0.9246	92.46%
Skin irritation	-	0.7758	77.58%
Skin corrosion	-	0.9430	94.30%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3818	38.18%
Micronuclear	+	0.6200	62.00%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	-	0.8623	86.23%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.8271	82.71%
Acute Oral Toxicity (c)	III	0.6575	65.75%
Estrogen receptor binding	+	0.8507	85.07%
Androgen receptor binding	+	0.7640	76.40%
Thyroid receptor binding	+	0.5578	55.78%
Glucocorticoid receptor binding	+	0.8346	83.46%
Aromatase binding	+	0.6886	68.86%
PPAR gamma	+	0.8117	81.17%
Honey bee toxicity	-	0.6305	63.05%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9819	98.19%

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	99.05%	96.09%
CHEMBL2243	O00519	Anandamide amidohydrolase	98.12%	97.53%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.59%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.98%	91.11%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	94.01%	100.00%
CHEMBL284	P27487	Dipeptidyl peptidase IV	93.01%	95.69%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	92.81%	90.71%
CHEMBL2535	P11166	Glucose transporter	92.35%	98.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.50%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.36%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.93%	94.45%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	90.44%	89.62%
CHEMBL340	P08684	Cytochrome P450 3A4	89.48%	91.19%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	89.34%	97.14%
CHEMBL1744525	P43490	Nicotinamide phosphoribosyltransferase	89.10%	96.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.24%	97.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.41%	96.00%
CHEMBL5747	Q92793	CREB-binding protein	87.19%	95.12%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	86.96%	91.03%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.61%	85.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.38%	99.17%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.89%	92.62%
CHEMBL4208	P20618	Proteasome component C5	85.60%	90.00%
CHEMBL261	P00915	Carbonic anhydrase I	85.46%	96.76%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.21%	86.33%
CHEMBL2581	P07339	Cathepsin D	83.05%	98.95%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	83.04%	92.29%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.82%	95.89%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	81.45%	89.05%
CHEMBL5028	O14672	ADAM10	80.65%	97.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.53%	95.89%

Plants that contains it

• Alstonia angustifolia

Cross-Links

• PubChem: 163195493
• LOTUS: LTS0208388
• wikiData: Q105347696