methyl 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]propanoate

Details

• Internal ID: 49db8dfb-2230-4a75-8045-ca9d1558b62b
• Taxonomy: Alkaloids and derivatives > Daphniphylline-type alkaloids
• IUPAC Name: methyl 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]propanoate
• SMILES (Canonical): CC(C)C1CCC2(C3CCC45CCCC4C2(C1N5C3O)CCC(=O)OC)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)OC)C
• InChI: InChI=1S/C23H37NO3/c1-14(2)15-7-11-21(3)16-8-12-22-10-5-6-17(22)23(21,13-9-18(25)27-4)19(15)24(22)20(16)26/h14-17,19-20,26H,5-13H2,1-4H3/t15-,16-,17-,19+,20+,21+,22-,23+/m0/s1
• InChI Key: XKIOJAXKHUEQRM-CEXSRHBFSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₃₇NO₃
• Molecular Weight: 375.50 g/mol
• Exact Mass: 375.27734404 g/mol
• Topological Polar Surface Area (TPSA): 49.80 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 3.96
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9519	95.19%
Caco-2	+	0.5941	59.41%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.6178	61.78%
OATP2B1 inhibitior	-	0.8620	86.20%
OATP1B1 inhibitior	+	0.8718	87.18%
OATP1B3 inhibitior	+	0.9259	92.59%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.5072	50.72%
BSEP inhibitior	-	0.4709	47.09%
P-glycoprotein inhibitior	-	0.8238	82.38%
P-glycoprotein substrate	-	0.5813	58.13%
CYP3A4 substrate	+	0.6701	67.01%
CYP2C9 substrate	-	0.7929	79.29%
CYP2D6 substrate	-	0.8484	84.84%
CYP3A4 inhibition	-	0.8258	82.58%
CYP2C9 inhibition	-	0.6712	67.12%
CYP2C19 inhibition	-	0.7660	76.60%
CYP2D6 inhibition	-	0.8781	87.81%
CYP1A2 inhibition	-	0.8391	83.91%
CYP2C8 inhibition	-	0.6894	68.94%
CYP inhibitory promiscuity	-	0.8481	84.81%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6883	68.83%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.7224	72.24%
Skin irritation	-	0.7568	75.68%
Skin corrosion	-	0.8817	88.17%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4219	42.19%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	-	0.6923	69.23%
skin sensitisation	-	0.8754	87.54%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.8434	84.34%
Acute Oral Toxicity (c)	III	0.5934	59.34%
Estrogen receptor binding	+	0.8653	86.53%
Androgen receptor binding	+	0.7256	72.56%
Thyroid receptor binding	+	0.5641	56.41%
Glucocorticoid receptor binding	+	0.7765	77.65%
Aromatase binding	+	0.7080	70.80%
PPAR gamma	+	0.5319	53.19%
Honey bee toxicity	-	0.8285	82.85%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9019	90.19%

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	98.87%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	98.80%	83.82%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.86%	97.25%
CHEMBL4072	P07858	Cathepsin B	94.86%	93.67%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.91%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.63%	94.45%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	90.17%	91.03%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	90.06%	91.07%
CHEMBL2581	P07339	Cathepsin D	89.91%	98.95%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	88.97%	96.38%
CHEMBL3437	Q16853	Amine oxidase, copper containing	88.92%	94.00%
CHEMBL332	P03956	Matrix metalloproteinase-1	88.66%	94.50%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.31%	91.11%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	88.24%	97.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.21%	97.09%
CHEMBL221	P23219	Cyclooxygenase-1	87.12%	90.17%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	86.48%	89.05%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	86.31%	95.50%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	84.78%	93.03%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.73%	94.33%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.45%	90.71%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.93%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.87%	95.89%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.59%	82.69%
CHEMBL2095194	P08709	Coagulation factor VII/tissue factor	83.31%	99.17%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	83.19%	95.36%
CHEMBL4073	P09237	Matrix metalloproteinase 7	82.67%	97.56%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	82.39%	91.24%
CHEMBL340	P08684	Cytochrome P450 3A4	82.38%	91.19%
CHEMBL5255	O00206	Toll-like receptor 4	81.06%	92.50%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.24%	96.77%

Plants that contains it

• Daphniphyllum calycinum

Cross-Links

• PubChem: 162916245
• LOTUS: LTS0121518
• wikiData: Q105329496