1-[(1S,4R,5R)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-3-[(1R,2S,3R,7S,10R,11R,13R,14S)-11-hydroxy-1-methyl-14-propan-2-yl-12-azapentacyclo[8.6.0.02,13.03,7.07,12]hexadecan-2-yl]propan-1-one

Details

• Internal ID: a83eacf2-2340-425e-b943-6554a4482b0c
• Taxonomy: Alkaloids and derivatives > Daphniphylline-type alkaloids
• IUPAC Name: 1-[(1S,4R,5R)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-3-[(1R,2S,3R,7S,10R,11R,13R,14S)-11-hydroxy-1-methyl-14-propan-2-yl-12-azapentacyclo[8.6.0.02,13.03,7.07,12]hexadecan-2-yl]propan-1-one
• SMILES (Canonical): CC(C)C1CCC2(C3CCC45CCCC4C2(C1N5C3O)CCC(=O)C6(COC7(CCC6O7)C)C)C
• SMILES (Isomeric): CC(C)[C@@H]1CC[C@@]2([C@H]3CC[C@@]45CCC[C@@H]4[C@@]2([C@@H]1N5[C@@H]3O)CCC(=O)[C@@]6(CO[C@@]7(CC[C@H]6O7)C)C)C
• InChI: InChI=1S/C30H47NO4/c1-18(2)19-8-13-27(4)20-9-15-29-12-6-7-21(29)30(27,24(19)31(29)25(20)33)16-10-22(32)26(3)17-34-28(5)14-11-23(26)35-28/h18-21,23-25,33H,6-17H2,1-5H3/t19-,20-,21-,23+,24+,25+,26-,27+,28-,29-,30+/m0/s1
• InChI Key: AEXQLUFWLSLZKN-RUNTXVDRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₇NO₄
• Molecular Weight: 485.70 g/mol
• Exact Mass: 485.35050898 g/mol
• Topological Polar Surface Area (TPSA): 59.00 Ų
• XlogP: 4.80
• Atomic LogP (AlogP): 5.29
• H-Bond Acceptor: 5
• 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	+	0.9363	93.63%
Caco-2	-	0.6433	64.33%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.5402	54.02%
OATP2B1 inhibitior	-	0.7175	71.75%
OATP1B1 inhibitior	+	0.8619	86.19%
OATP1B3 inhibitior	+	0.9224	92.24%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.4505	45.05%
P-glycoprotein inhibitior	-	0.5584	55.84%
P-glycoprotein substrate	+	0.5434	54.34%
CYP3A4 substrate	+	0.6971	69.71%
CYP2C9 substrate	-	0.8004	80.04%
CYP2D6 substrate	-	0.8041	80.41%
CYP3A4 inhibition	-	0.8929	89.29%
CYP2C9 inhibition	-	0.8980	89.80%
CYP2C19 inhibition	-	0.8850	88.50%
CYP2D6 inhibition	-	0.9500	95.00%
CYP1A2 inhibition	-	0.9091	90.91%
CYP2C8 inhibition	+	0.5382	53.82%
CYP inhibitory promiscuity	-	0.9244	92.44%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6472	64.72%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.8941	89.41%
Skin irritation	-	0.7820	78.20%
Skin corrosion	-	0.8953	89.53%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6186	61.86%
Micronuclear	-	0.5500	55.00%
Hepatotoxicity	-	0.5334	53.34%
skin sensitisation	-	0.8791	87.91%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.7244	72.44%
Acute Oral Toxicity (c)	III	0.6805	68.05%
Estrogen receptor binding	+	0.8241	82.41%
Androgen receptor binding	+	0.7651	76.51%
Thyroid receptor binding	-	0.4944	49.44%
Glucocorticoid receptor binding	+	0.7721	77.21%
Aromatase binding	+	0.7398	73.98%
PPAR gamma	+	0.5831	58.31%
Honey bee toxicity	-	0.7598	75.98%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.8877	88.77%

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	98.73%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.06%	97.25%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	95.26%	89.05%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.19%	94.45%
CHEMBL4072	P07858	Cathepsin B	93.19%	93.67%
CHEMBL2581	P07339	Cathepsin D	91.76%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.95%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.41%	85.14%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	88.73%	82.69%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	88.02%	95.50%
CHEMBL218	P21554	Cannabinoid CB1 receptor	87.89%	96.61%
CHEMBL240	Q12809	HERG	87.55%	89.76%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.54%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.45%	100.00%
CHEMBL221	P23219	Cyclooxygenase-1	86.11%	90.17%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	85.91%	91.24%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	85.46%	91.03%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	85.10%	97.50%
CHEMBL4073	P09237	Matrix metalloproteinase 7	85.07%	97.56%
CHEMBL340	P08684	Cytochrome P450 3A4	85.03%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.91%	95.56%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	82.61%	98.33%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.51%	96.77%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.94%	95.89%
CHEMBL2095194	P08709	Coagulation factor VII/tissue factor	81.42%	99.17%
CHEMBL2413	P32246	C-C chemokine receptor type 1	81.38%	89.50%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.19%	93.04%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.00%	89.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.58%	100.00%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	80.40%	97.47%

Plants that contains it

• Daphniphyllum macropodum

Cross-Links

• PubChem: 163088995
• LOTUS: LTS0117155
• wikiData: Q104910764