methyl 3-[(1S,2R,3R,7R,9S,14R)-9-hydroxy-1-methyl-14-propan-2-yl-12-azapentacyclo[8.6.0.02,13.03,7.07,11]hexadecan-2-yl]propanoate

Details

• Internal ID: 5d7eeff7-f264-44c2-8013-dd4f1e7f8ee0
• Taxonomy: Alkaloids and derivatives > Daphniphylline-type alkaloids
• IUPAC Name: methyl 3-[(1S,2R,3R,7R,9S,14R)-9-hydroxy-1-methyl-14-propan-2-yl-12-azapentacyclo[8.6.0.02,13.03,7.07,11]hexadecan-2-yl]propanoate
• SMILES (Canonical): CC(C)C1CCC2(C3C(CC45C3NC1C2(C4CCC5)CCC(=O)OC)O)C
• SMILES (Isomeric): CC(C)[C@H]1CC[C@]2(C3[C@H](C[C@@]45C3NC1[C@@]2([C@@H]4CCC5)CCC(=O)OC)O)C
• InChI: InChI=1S/C23H37NO3/c1-13(2)14-7-10-21(3)18-15(25)12-22-9-5-6-16(22)23(21,11-8-17(26)27-4)19(14)24-20(18)22/h13-16,18-20,24-25H,5-12H2,1-4H3/t14-,15+,16-,18?,19?,20?,21+,22-,23+/m1/s1
• InChI Key: SCMNGYBPXCTRJK-WTYMGFRSSA-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): 58.60 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 3.52
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9471	94.71%
Caco-2	+	0.5157	51.57%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6308	63.08%
OATP2B1 inhibitior	-	0.8623	86.23%
OATP1B1 inhibitior	+	0.8651	86.51%
OATP1B3 inhibitior	+	0.9086	90.86%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.5342	53.42%
P-glycoprotein inhibitior	-	0.7923	79.23%
P-glycoprotein substrate	+	0.5209	52.09%
CYP3A4 substrate	+	0.6606	66.06%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7117	71.17%
CYP3A4 inhibition	-	0.8885	88.85%
CYP2C9 inhibition	-	0.6844	68.44%
CYP2C19 inhibition	-	0.8036	80.36%
CYP2D6 inhibition	-	0.9006	90.06%
CYP1A2 inhibition	-	0.8806	88.06%
CYP2C8 inhibition	-	0.6304	63.04%
CYP inhibitory promiscuity	-	0.7913	79.13%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6902	69.02%
Eye corrosion	-	0.9916	99.16%
Eye irritation	-	0.8971	89.71%
Skin irritation	-	0.6854	68.54%
Skin corrosion	-	0.9077	90.77%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3899	38.99%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	-	0.6826	68.26%
skin sensitisation	-	0.8493	84.93%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.7073	70.73%
Acute Oral Toxicity (c)	III	0.5487	54.87%
Estrogen receptor binding	+	0.8741	87.41%
Androgen receptor binding	+	0.7120	71.20%
Thyroid receptor binding	+	0.5736	57.36%
Glucocorticoid receptor binding	+	0.8071	80.71%
Aromatase binding	+	0.7536	75.36%
PPAR gamma	+	0.5805	58.05%
Honey bee toxicity	-	0.7443	74.43%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.7665	76.65%

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	98.88%	96.09%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	98.22%	96.38%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.91%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.94%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.89%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.40%	97.25%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	94.47%	95.71%
CHEMBL3437	Q16853	Amine oxidase, copper containing	93.12%	94.00%
CHEMBL1937	Q92769	Histone deacetylase 2	92.40%	94.75%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.32%	97.09%
CHEMBL2581	P07339	Cathepsin D	90.96%	98.95%
CHEMBL218	P21554	Cannabinoid CB1 receptor	90.93%	96.61%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	90.42%	93.03%
CHEMBL4227	P25090	Lipoxin A4 receptor	89.79%	100.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	89.06%	96.47%
CHEMBL221	P23219	Cyclooxygenase-1	87.89%	90.17%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	87.69%	94.33%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.69%	91.07%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.54%	95.89%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	87.53%	91.03%
CHEMBL268	P43235	Cathepsin K	87.09%	96.85%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	86.66%	82.69%
CHEMBL220	P22303	Acetylcholinesterase	85.70%	94.45%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.62%	95.50%
CHEMBL2095194	P08709	Coagulation factor VII/tissue factor	84.97%	99.17%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	84.24%	91.24%
CHEMBL213	P08588	Beta-1 adrenergic receptor	83.70%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	83.43%	91.19%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	83.21%	97.50%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	82.93%	92.88%
CHEMBL299	P17252	Protein kinase C alpha	82.84%	98.03%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.83%	92.62%
CHEMBL3837	P07711	Cathepsin L	82.65%	96.61%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.44%	90.71%
CHEMBL1871	P10275	Androgen Receptor	81.11%	96.43%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.43%	89.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.29%	100.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.17%	96.77%
CHEMBL5255	O00206	Toll-like receptor 4	80.12%	92.50%

Plants that contains it

• Daphniphyllum calycinum

Cross-Links

• PubChem: 102282915
• LOTUS: LTS0105807
• wikiData: Q105250278