[(2R)-1-[(1R,4R,5S)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-3-[(1S,2R,3S,7R,10S,13S,14R)-1-methyl-14-propan-2-yl-12-azapentacyclo[8.6.0.02,13.03,7.07,12]hexadecan-2-yl]-1-oxopropan-2-yl] acetate

Details

• Internal ID: 299a1eef-ec14-47a8-8906-a832843d0664
• Taxonomy: Alkaloids and derivatives > Daphniphylline-type alkaloids
• IUPAC Name: [(2R)-1-[(1R,4R,5S)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-3-[(1S,2R,3S,7R,10S,13S,14R)-1-methyl-14-propan-2-yl-12-azapentacyclo[8.6.0.02,13.03,7.07,12]hexadecan-2-yl]-1-oxopropan-2-yl] acetate
• SMILES (Canonical): CC(C)C1CCC2(C3CCC45CCCC4C2(C1N5C3)CC(C(=O)C6(COC7(CCC6O7)C)C)OC(=O)C)C
• SMILES (Isomeric): CC(C)[C@H]1CC[C@]2([C@@H]3CC[C@]45CCC[C@H]4[C@]2([C@H]1N5C3)C[C@H](C(=O)[C@@]6(CO[C@]7(CC[C@@H]6O7)C)C)OC(=O)C)C
• InChI: InChI=1S/C32H49NO5/c1-19(2)22-10-13-29(5)21-9-15-31-12-7-8-24(31)32(29,26(22)33(31)17-21)16-23(37-20(3)34)27(35)28(4)18-36-30(6)14-11-25(28)38-30/h19,21-26H,7-18H2,1-6H3/t21-,22-,23-,24-,25+,26+,28-,29+,30-,31-,32+/m1/s1
• InChI Key: LFLWRPZTBUUBEQ-IXHADGFVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₄₉NO₅
• Molecular Weight: 527.70 g/mol
• Exact Mass: 527.36107366 g/mol
• Topological Polar Surface Area (TPSA): 65.10 Ų
• XlogP: 5.40
• Atomic LogP (AlogP): 5.51
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8645	86.45%
Caco-2	-	0.6674	66.74%
Blood Brain Barrier	+	0.9250	92.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.5539	55.39%
OATP2B1 inhibitior	-	0.7219	72.19%
OATP1B1 inhibitior	+	0.8744	87.44%
OATP1B3 inhibitior	+	0.9337	93.37%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.6907	69.07%
P-glycoprotein inhibitior	+	0.6597	65.97%
P-glycoprotein substrate	+	0.5705	57.05%
CYP3A4 substrate	+	0.7003	70.03%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7604	76.04%
CYP3A4 inhibition	-	0.7461	74.61%
CYP2C9 inhibition	-	0.8787	87.87%
CYP2C19 inhibition	-	0.7803	78.03%
CYP2D6 inhibition	-	0.8978	89.78%
CYP1A2 inhibition	-	0.8468	84.68%
CYP2C8 inhibition	+	0.5723	57.23%
CYP inhibitory promiscuity	-	0.7966	79.66%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.5598	55.98%
Eye corrosion	-	0.9854	98.54%
Eye irritation	-	0.9024	90.24%
Skin irritation	-	0.8063	80.63%
Skin corrosion	-	0.9155	91.55%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5151	51.51%
Micronuclear	-	0.6300	63.00%
Hepatotoxicity	+	0.5541	55.41%
skin sensitisation	-	0.8557	85.57%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.5374	53.74%
Acute Oral Toxicity (c)	III	0.7103	71.03%
Estrogen receptor binding	+	0.7521	75.21%
Androgen receptor binding	+	0.7792	77.92%
Thyroid receptor binding	-	0.5502	55.02%
Glucocorticoid receptor binding	+	0.7573	75.73%
Aromatase binding	+	0.6858	68.58%
PPAR gamma	+	0.6496	64.96%
Honey bee toxicity	-	0.7291	72.91%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.8936	89.36%

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	98.25%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.27%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.94%	97.25%
CHEMBL240	Q12809	HERG	95.23%	89.76%
CHEMBL204	P00734	Thrombin	93.72%	96.01%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	93.02%	97.47%
CHEMBL218	P21554	Cannabinoid CB1 receptor	91.73%	96.61%
CHEMBL4073	P09237	Matrix metalloproteinase 7	91.50%	97.56%
CHEMBL2581	P07339	Cathepsin D	90.31%	98.95%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	90.23%	95.17%
CHEMBL340	P08684	Cytochrome P450 3A4	88.54%	91.19%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	87.64%	89.05%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	87.14%	95.50%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.93%	85.14%
CHEMBL3837	P07711	Cathepsin L	86.50%	96.61%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.43%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.95%	95.89%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.65%	91.11%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	85.24%	91.03%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.21%	95.56%
CHEMBL2413	P32246	C-C chemokine receptor type 1	85.03%	89.50%
CHEMBL1937	Q92769	Histone deacetylase 2	84.40%	94.75%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	83.60%	97.50%
CHEMBL2095194	P08709	Coagulation factor VII/tissue factor	83.15%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.99%	94.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.81%	93.56%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.78%	100.00%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	81.75%	98.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.58%	99.23%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.51%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.32%	97.14%
CHEMBL4072	P07858	Cathepsin B	81.17%	93.67%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.83%	96.77%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.39%	82.69%

Plants that contains it

• Daphniphyllum himalayense

Cross-Links

• PubChem: 154496438
• LOTUS: LTS0270935
• wikiData: Q105151075