1-[(1R,4R,5S)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-3-[(1S,2R,3S,7S,8R,10S,13S,14R)-8-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: 82fd5d1c-704a-4b89-9589-04941176b93d
• 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,3S,7S,8R,10S,13S,14R)-8-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(C3CC(C45CCCC4C2(C1N5C3)CCC(=O)C6(COC7(CCC6O7)C)C)O)C
• SMILES (Isomeric): CC(C)[C@H]1CC[C@]2([C@@H]3C[C@H]([C@]45CCC[C@H]4[C@]2([C@H]1N5C3)CCC(=O)[C@@]6(CO[C@]7(CC[C@@H]6O7)C)C)O)C
• InChI: InChI=1S/C30H47NO4/c1-18(2)20-8-12-27(4)19-15-23(33)30-11-6-7-21(30)29(27,25(20)31(30)16-19)14-9-22(32)26(3)17-34-28(5)13-10-24(26)35-28/h18-21,23-25,33H,6-17H2,1-5H3/t19-,20-,21+,23-,24+,25+,26+,27+,28-,29+,30+/m1/s1
• InChI Key: JENRSDUHJGGCGW-BMOHLVNYSA-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: 4.40
• Atomic LogP (AlogP): 4.94
• 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	+	0.8622	86.22%
Caco-2	-	0.6209	62.09%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Lysosomes	0.5307	53.07%
OATP2B1 inhibitior	-	0.7155	71.55%
OATP1B1 inhibitior	+	0.8678	86.78%
OATP1B3 inhibitior	+	0.9261	92.61%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	+	0.5634	56.34%
P-glycoprotein inhibitior	-	0.5647	56.47%
P-glycoprotein substrate	+	0.5923	59.23%
CYP3A4 substrate	+	0.7074	70.74%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.6789	67.89%
CYP3A4 inhibition	-	0.8961	89.61%
CYP2C9 inhibition	-	0.9407	94.07%
CYP2C19 inhibition	-	0.8933	89.33%
CYP2D6 inhibition	-	0.9121	91.21%
CYP1A2 inhibition	-	0.9384	93.84%
CYP2C8 inhibition	+	0.5428	54.28%
CYP inhibitory promiscuity	-	0.9673	96.73%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5834	58.34%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9207	92.07%
Skin irritation	-	0.7750	77.50%
Skin corrosion	-	0.9151	91.51%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6133	61.33%
Micronuclear	-	0.5600	56.00%
Hepatotoxicity	+	0.5291	52.91%
skin sensitisation	-	0.8604	86.04%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.7066	70.66%
Acute Oral Toxicity (c)	III	0.6037	60.37%
Estrogen receptor binding	+	0.7889	78.89%
Androgen receptor binding	+	0.7684	76.84%
Thyroid receptor binding	+	0.5298	52.98%
Glucocorticoid receptor binding	+	0.7770	77.70%
Aromatase binding	+	0.7471	74.71%
PPAR gamma	+	0.5877	58.77%
Honey bee toxicity	-	0.7645	76.45%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.7398	73.98%

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	98.38%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.78%	94.45%
CHEMBL218	P21554	Cannabinoid CB1 receptor	95.57%	96.61%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.16%	97.25%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	93.39%	96.47%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	93.19%	96.38%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	92.05%	82.69%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.60%	97.09%
CHEMBL2581	P07339	Cathepsin D	90.19%	98.95%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	89.33%	98.33%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	88.29%	98.75%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.68%	91.11%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.65%	96.77%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	86.29%	95.71%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	85.76%	89.05%
CHEMBL1871	P10275	Androgen Receptor	85.74%	96.43%
CHEMBL2413	P32246	C-C chemokine receptor type 1	85.69%	89.50%
CHEMBL3359	P21462	Formyl peptide receptor 1	85.47%	93.56%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.13%	95.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.77%	100.00%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	84.56%	97.47%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.48%	85.14%
CHEMBL4072	P07858	Cathepsin B	82.91%	93.67%
CHEMBL3837	P07711	Cathepsin L	82.79%	96.61%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.66%	100.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.55%	96.21%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	82.33%	90.24%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	81.84%	97.50%
CHEMBL340	P08684	Cytochrome P450 3A4	81.64%	91.19%
CHEMBL4073	P09237	Matrix metalloproteinase 7	81.63%	97.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.57%	89.00%
CHEMBL2095194	P08709	Coagulation factor VII/tissue factor	81.35%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.28%	99.23%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.19%	100.00%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	80.99%	91.03%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.28%	95.56%
CHEMBL2514	O95665	Neurotensin receptor 2	80.20%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.00%	95.89%

Plants that contains it

• Daphniphyllum subverticillatum

Cross-Links

• PubChem: 102418716
• LOTUS: LTS0237755
• wikiData: Q105126239