(2S)-1-[(1R,4R,5S)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-2-hydroxy-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]propan-1-one

Details

• Internal ID: 781b8c4f-bd2d-4d04-89c0-b13e35b3e666
• Taxonomy: Alkaloids and derivatives > Daphniphylline-type alkaloids
• IUPAC Name: (2S)-1-[(1R,4R,5S)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-2-hydroxy-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]propan-1-one
• SMILES (Canonical): CC(C)C1CCC2(C3CCC45CCCC4C2(C1N5C3)CC(C(=O)C6(COC7(CCC6O7)C)C)O)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)O)C
• InChI: InChI=1S/C30H47NO4/c1-18(2)20-9-12-27(4)19-8-14-29-11-6-7-22(29)30(27,24(20)31(29)16-19)15-21(32)25(33)26(3)17-34-28(5)13-10-23(26)35-28/h18-24,32H,6-17H2,1-5H3/t19-,20-,21+,22-,23+,24+,26-,27+,28-,29-,30+/m1/s1
• InChI Key: MZFIJLHWABOTEH-ZTABVLHMSA-N
• Popularity: 5 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): 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	+	0.8285	82.85%
Caco-2	-	0.5901	59.01%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Lysosomes	0.4199	41.99%
OATP2B1 inhibitior	-	0.7197	71.97%
OATP1B1 inhibitior	+	0.8717	87.17%
OATP1B3 inhibitior	+	0.9365	93.65%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	-	0.5263	52.63%
P-glycoprotein inhibitior	-	0.5726	57.26%
P-glycoprotein substrate	+	0.5723	57.23%
CYP3A4 substrate	+	0.6817	68.17%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.6577	65.77%
CYP3A4 inhibition	-	0.9059	90.59%
CYP2C9 inhibition	-	0.9166	91.66%
CYP2C19 inhibition	-	0.8412	84.12%
CYP2D6 inhibition	-	0.8978	89.78%
CYP1A2 inhibition	-	0.9044	90.44%
CYP2C8 inhibition	+	0.4922	49.22%
CYP inhibitory promiscuity	-	0.9582	95.82%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.5855	58.55%
Eye corrosion	-	0.9862	98.62%
Eye irritation	-	0.9131	91.31%
Skin irritation	-	0.7813	78.13%
Skin corrosion	-	0.9098	90.98%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5363	53.63%
Micronuclear	-	0.6300	63.00%
Hepatotoxicity	-	0.5459	54.59%
skin sensitisation	-	0.8467	84.67%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.5780	57.80%
Acute Oral Toxicity (c)	III	0.6680	66.80%
Estrogen receptor binding	+	0.7597	75.97%
Androgen receptor binding	+	0.7767	77.67%
Thyroid receptor binding	-	0.4948	49.48%
Glucocorticoid receptor binding	+	0.7986	79.86%
Aromatase binding	+	0.7312	73.12%
PPAR gamma	+	0.5500	55.00%
Honey bee toxicity	-	0.8069	80.69%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.7368	73.68%

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	97.67%	96.09%
CHEMBL240	Q12809	HERG	97.63%	89.76%
CHEMBL218	P21554	Cannabinoid CB1 receptor	97.06%	96.61%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.06%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.56%	94.45%
CHEMBL2581	P07339	Cathepsin D	92.10%	98.95%
CHEMBL4073	P09237	Matrix metalloproteinase 7	91.54%	97.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.29%	85.14%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	88.64%	89.05%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.74%	97.09%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	87.37%	97.47%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.98%	95.50%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	85.19%	96.47%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	84.92%	98.33%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	84.19%	97.50%
CHEMBL2413	P32246	C-C chemokine receptor type 1	83.88%	89.50%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.66%	91.11%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.41%	100.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	83.39%	91.24%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.19%	93.56%
CHEMBL340	P08684	Cytochrome P450 3A4	83.16%	91.19%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	83.11%	91.03%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.93%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.59%	95.89%
CHEMBL4816	Q9Y243	Serine/threonine-protein kinase AKT3	82.19%	96.28%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	81.95%	98.75%
CHEMBL2095194	P08709	Coagulation factor VII/tissue factor	81.89%	99.17%
CHEMBL1944495	P28065	Proteasome subunit beta type-9	81.42%	97.50%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.35%	82.69%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.20%	89.00%
CHEMBL4835	P00338	L-lactate dehydrogenase A chain	80.59%	95.34%
CHEMBL204	P00734	Thrombin	80.43%	96.01%

Plants that contains it

• Daphniphyllum calycinum
• Daphniphyllum pentandrum
• Daphniphyllum subverticillatum

Cross-Links

• PubChem: 101391555
• LOTUS: LTS0037511
• wikiData: Q104399771