methyl 3-[(1S,2R,3S,7S,8S,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]propanoate

Details

• Internal ID: 689af521-7a2f-420c-a148-a4c42b7a086c
• Taxonomy: Alkaloids and derivatives > Daphniphylline-type alkaloids
• IUPAC Name: methyl 3-[(1S,2R,3S,7S,8S,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]propanoate
• SMILES (Canonical): CC(C)C1CCC2(C3CC(C45CCCC4C2(C1N5C3)CCC(=O)OC)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)OC)O)C
• InChI: InChI=1S/C23H37NO3/c1-14(2)16-7-10-21(3)15-12-18(25)23-9-5-6-17(23)22(21,11-8-19(26)27-4)20(16)24(23)13-15/h14-18,20,25H,5-13H2,1-4H3/t15-,16-,17+,18+,20+,21+,22+,23+/m1/s1
• InChI Key: QRPKVUVQWPROMV-ZZCAJEDESA-N
• Popularity: 0 references 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: 3.80
• Atomic LogP (AlogP): 3.62
• 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	+	0.9169	91.69%
Caco-2	+	0.6447	64.47%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6671	66.71%
OATP2B1 inhibitior	-	0.8632	86.32%
OATP1B1 inhibitior	+	0.8794	87.94%
OATP1B3 inhibitior	+	0.9286	92.86%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	-	0.4727	47.27%
P-glycoprotein inhibitior	-	0.8291	82.91%
P-glycoprotein substrate	-	0.5178	51.78%
CYP3A4 substrate	+	0.6861	68.61%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.3549	35.49%
CYP3A4 inhibition	-	0.7582	75.82%
CYP2C9 inhibition	-	0.8035	80.35%
CYP2C19 inhibition	-	0.8808	88.08%
CYP2D6 inhibition	-	0.7189	71.89%
CYP1A2 inhibition	-	0.9015	90.15%
CYP2C8 inhibition	-	0.6857	68.57%
CYP inhibitory promiscuity	-	0.9008	90.08%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6854	68.54%
Eye corrosion	-	0.9914	99.14%
Eye irritation	-	0.8459	84.59%
Skin irritation	-	0.7500	75.00%
Skin corrosion	-	0.9064	90.64%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3893	38.93%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	-	0.6084	60.84%
skin sensitisation	-	0.8777	87.77%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.8315	83.15%
Acute Oral Toxicity (c)	III	0.6335	63.35%
Estrogen receptor binding	+	0.8237	82.37%
Androgen receptor binding	+	0.7306	73.06%
Thyroid receptor binding	+	0.5890	58.90%
Glucocorticoid receptor binding	+	0.8053	80.53%
Aromatase binding	+	0.7458	74.58%
PPAR gamma	-	0.4919	49.19%
Honey bee toxicity	-	0.8301	83.01%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.7203	72.03%

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	98.56%	96.09%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	97.29%	96.38%
CHEMBL4040	P28482	MAP kinase ERK2	96.89%	83.82%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.87%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.23%	97.25%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	92.60%	95.71%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	91.02%	96.47%
CHEMBL3437	Q16853	Amine oxidase, copper containing	90.32%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.21%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.45%	91.11%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	88.23%	82.69%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.09%	97.09%
CHEMBL2581	P07339	Cathepsin D	88.03%	98.95%
CHEMBL218	P21554	Cannabinoid CB1 receptor	87.78%	96.61%
CHEMBL4227	P25090	Lipoxin A4 receptor	87.51%	100.00%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	86.92%	91.03%
CHEMBL4072	P07858	Cathepsin B	86.74%	93.67%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	86.58%	95.58%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	86.46%	91.07%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.93%	96.77%
CHEMBL1871	P10275	Androgen Receptor	85.80%	96.43%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	85.69%	95.17%
CHEMBL3359	P21462	Formyl peptide receptor 1	85.61%	93.56%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	85.58%	93.03%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	85.54%	97.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	85.23%	94.33%
CHEMBL1075317	P61964	WD repeat-containing protein 5	84.47%	96.33%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	84.45%	98.33%
CHEMBL2095194	P08709	Coagulation factor VII/tissue factor	83.24%	99.17%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.08%	95.50%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	82.51%	97.47%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.09%	95.89%
CHEMBL5028	O14672	ADAM10	81.58%	97.50%
CHEMBL2413	P32246	C-C chemokine receptor type 1	81.54%	89.50%
CHEMBL220	P22303	Acetylcholinesterase	81.46%	94.45%
CHEMBL213	P08588	Beta-1 adrenergic receptor	81.36%	95.56%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.31%	100.00%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	80.25%	95.36%

Plants that contains it

• Daphniphyllum calycinum

Cross-Links

• PubChem: 25135569
• LOTUS: LTS0160520
• wikiData: Q105226543