[(2S)-1-(1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl)-3-[(3S,7S,11S,14R)-11-hydroxy-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: 1f594deb-c6e1-40d1-920b-a1299e29bbb2
• Taxonomy: Alkaloids and derivatives > Daphniphylline-type alkaloids
• IUPAC Name: [(2S)-1-(1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl)-3-[(3S,7S,11S,14R)-11-hydroxy-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(C1N5C3O)CC(C(=O)C6(COC7(CCC6O7)C)C)OC(=O)C)C
• SMILES (Isomeric): CC(C)[C@H]1CCC2(C3CC[C@@]45CCC[C@H]4C2(C1N5[C@H]3O)C[C@@H](C(=O)C6(COC7(CCC6O7)C)C)OC(=O)C)C
• InChI: InChI=1S/C32H49NO6/c1-18(2)20-9-13-29(5)21-10-15-31-12-7-8-23(31)32(29,25(20)33(31)27(21)36)16-22(38-19(3)34)26(35)28(4)17-37-30(6)14-11-24(28)39-30/h18,20-25,27,36H,7-17H2,1-6H3/t20-,21?,22+,23-,24?,25?,27+,28?,29?,30?,31+,32?/m1/s1
• InChI Key: ZPVWRZNKODIESD-KHXFDDTNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₄₉NO₆
• Molecular Weight: 543.70 g/mol
• Exact Mass: 543.35598828 g/mol
• Topological Polar Surface Area (TPSA): 85.30 Ų
• XlogP: 4.90
• Atomic LogP (AlogP): 4.83
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9000	90.00%
Caco-2	-	0.7363	73.63%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.5745	57.45%
OATP2B1 inhibitior	-	0.7161	71.61%
OATP1B1 inhibitior	+	0.8626	86.26%
OATP1B3 inhibitior	+	0.9042	90.42%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.6614	66.14%
BSEP inhibitior	+	0.6637	66.37%
P-glycoprotein inhibitior	+	0.6176	61.76%
P-glycoprotein substrate	+	0.5682	56.82%
CYP3A4 substrate	+	0.7143	71.43%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8550	85.50%
CYP3A4 inhibition	-	0.8422	84.22%
CYP2C9 inhibition	-	0.8700	87.00%
CYP2C19 inhibition	-	0.8839	88.39%
CYP2D6 inhibition	-	0.9646	96.46%
CYP1A2 inhibition	-	0.9243	92.43%
CYP2C8 inhibition	+	0.6149	61.49%
CYP inhibitory promiscuity	-	0.8803	88.03%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6040	60.40%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9099	90.99%
Skin irritation	-	0.7742	77.42%
Skin corrosion	-	0.9133	91.33%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5934	59.34%
Micronuclear	-	0.5100	51.00%
Hepatotoxicity	-	0.5709	57.09%
skin sensitisation	-	0.9011	90.11%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	+	0.5103	51.03%
Acute Oral Toxicity (c)	III	0.6588	65.88%
Estrogen receptor binding	+	0.7660	76.60%
Androgen receptor binding	+	0.7760	77.60%
Thyroid receptor binding	-	0.5787	57.87%
Glucocorticoid receptor binding	+	0.7416	74.16%
Aromatase binding	+	0.7268	72.68%
PPAR gamma	+	0.6145	61.45%
Honey bee toxicity	-	0.6968	69.68%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9152	91.52%

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	99.04%	96.09%
CHEMBL240	Q12809	HERG	98.56%	89.76%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.37%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.81%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.43%	94.45%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	92.41%	89.05%
CHEMBL2581	P07339	Cathepsin D	91.93%	98.95%
CHEMBL3837	P07711	Cathepsin L	89.46%	96.61%
CHEMBL340	P08684	Cytochrome P450 3A4	89.42%	91.19%
CHEMBL4073	P09237	Matrix metalloproteinase 7	89.31%	97.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.21%	91.11%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	88.59%	91.03%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.49%	97.09%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	87.82%	95.50%
CHEMBL4072	P07858	Cathepsin B	87.29%	93.67%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.05%	96.77%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.88%	95.89%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	86.47%	97.47%
CHEMBL204	P00734	Thrombin	85.78%	96.01%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.19%	95.56%
CHEMBL2413	P32246	C-C chemokine receptor type 1	84.58%	89.50%
CHEMBL218	P21554	Cannabinoid CB1 receptor	84.40%	96.61%
CHEMBL2095194	P08709	Coagulation factor VII/tissue factor	83.99%	99.17%
CHEMBL3922	P50579	Methionine aminopeptidase 2	83.93%	97.28%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.61%	100.00%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	83.41%	97.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.72%	91.07%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.88%	95.71%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.79%	92.62%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	81.32%	95.36%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.51%	94.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.28%	93.04%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.17%	97.14%

Plants that contains it

• Daphniphyllum pentandrum

Cross-Links

• PubChem: 101864270
• LOTUS: LTS0253979
• wikiData: Q105381263