1-[(1R,4R,5S)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-3-[(1S,2R,3R,7R,10S,14R)-1-methyl-14-propan-2-yl-12-azapentacyclo[8.6.0.02,13.03,7.07,11]hexadecan-2-yl]propan-1-one

Details

• Internal ID: 58cef5c3-c914-4db1-8aa6-14ead1554418
• Taxonomy: Alkaloids and derivatives > Daphniphylline-type alkaloids
• IUPAC Name: 1-[(1R,4R,5S)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-3-[(1S,2R,3R,7R,10S,14R)-1-methyl-14-propan-2-yl-12-azapentacyclo[8.6.0.02,13.03,7.07,11]hexadecan-2-yl]propan-1-one
• SMILES (Canonical): CC(C)C1CCC2(C3CCC45C3NC1C2(C4CCC5)CCC(=O)C6(COC7(CCC6O7)C)C)C
• SMILES (Isomeric): CC(C)[C@H]1CC[C@]2([C@@H]3CC[C@@]45C3NC1[C@@]2([C@@H]4CCC5)CCC(=O)[C@@]6(CO[C@]7(CC[C@@H]6O7)C)C)C
• InChI: InChI=1S/C30H47NO3/c1-18(2)19-8-13-27(4)20-9-15-29-12-6-7-21(29)30(27,24(19)31-25(20)29)16-10-22(32)26(3)17-33-28(5)14-11-23(26)34-28/h18-21,23-25,31H,6-17H2,1-5H3/t19-,20-,21-,23+,24?,25?,26+,27+,28-,29-,30+/m1/s1
• InChI Key: LYCPGVYCDLJBAA-GACJWEHQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₇NO₃
• Molecular Weight: 469.70 g/mol
• Exact Mass: 469.35559436 g/mol
• Topological Polar Surface Area (TPSA): 47.60 Ų
• XlogP: 5.60
• Atomic LogP (AlogP): 5.88
• H-Bond Acceptor: 4
• 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	+	0.9868	98.68%
Caco-2	-	0.6155	61.55%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6633	66.33%
OATP2B1 inhibitior	-	0.7177	71.77%
OATP1B1 inhibitior	+	0.8569	85.69%
OATP1B3 inhibitior	+	0.9289	92.89%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.5582	55.82%
P-glycoprotein inhibitior	-	0.5058	50.58%
P-glycoprotein substrate	+	0.5483	54.83%
CYP3A4 substrate	+	0.6897	68.97%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7101	71.01%
CYP3A4 inhibition	-	0.8732	87.32%
CYP2C9 inhibition	-	0.7047	70.47%
CYP2C19 inhibition	-	0.7050	70.50%
CYP2D6 inhibition	-	0.8936	89.36%
CYP1A2 inhibition	-	0.8140	81.40%
CYP2C8 inhibition	+	0.6012	60.12%
CYP inhibitory promiscuity	-	0.6686	66.86%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.6555	65.55%
Eye corrosion	-	0.9875	98.75%
Eye irritation	-	0.9227	92.27%
Skin irritation	-	0.7941	79.41%
Skin corrosion	-	0.9107	91.07%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5192	51.92%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	+	0.5291	52.91%
skin sensitisation	-	0.8221	82.21%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.7162	71.62%
Acute Oral Toxicity (c)	III	0.5496	54.96%
Estrogen receptor binding	+	0.7996	79.96%
Androgen receptor binding	+	0.7590	75.90%
Thyroid receptor binding	+	0.5659	56.59%
Glucocorticoid receptor binding	+	0.8148	81.48%
Aromatase binding	+	0.7903	79.03%
PPAR gamma	+	0.6161	61.61%
Honey bee toxicity	-	0.7095	70.95%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9285	92.85%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.39%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.14%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.72%	97.25%
CHEMBL218	P21554	Cannabinoid CB1 receptor	94.94%	96.61%
CHEMBL1937	Q92769	Histone deacetylase 2	93.97%	94.75%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.91%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.91%	97.09%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	91.40%	89.05%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	91.13%	96.47%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	90.72%	82.69%
CHEMBL2581	P07339	Cathepsin D	89.57%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.06%	100.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	88.40%	91.24%
CHEMBL4227	P25090	Lipoxin A4 receptor	88.20%	100.00%
CHEMBL3837	P07711	Cathepsin L	87.65%	96.61%
CHEMBL340	P08684	Cytochrome P450 3A4	87.52%	91.19%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.95%	85.14%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	86.60%	91.03%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	86.43%	98.75%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	85.51%	96.21%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.28%	95.50%
CHEMBL221	P23219	Cyclooxygenase-1	85.20%	90.17%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	84.22%	95.71%
CHEMBL2095194	P08709	Coagulation factor VII/tissue factor	83.76%	99.17%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	83.22%	96.38%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.22%	95.89%
CHEMBL240	Q12809	HERG	82.66%	89.76%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.10%	89.50%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	81.96%	95.71%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.82%	93.03%
CHEMBL259	P32245	Melanocortin receptor 4	81.12%	95.38%
CHEMBL3437	Q16853	Amine oxidase, copper containing	80.86%	94.00%
CHEMBL3310	Q96DB2	Histone deacetylase 11	80.84%	88.56%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	80.69%	97.50%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.43%	93.04%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.32%	92.62%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.04%	99.23%

Plants that contains it

• Daphniphyllum calycinum
• Daphniphyllum pentandrum
• Daphniphyllum subverticillatum

Cross-Links

• PubChem: 102060135
• LOTUS: LTS0261342
• wikiData: Q104398966