methyl (1R,9R,10S,11R,12S,13R,19R)-11-acetyloxy-12-ethyl-5-methoxy-8-methyl-20-oxa-8,16-diazahexacyclo[10.6.1.110,13.01,9.02,7.016,19]icosa-2(7),3,5-triene-10-carboxylate

Details

• Internal ID: 469e90c0-0664-4b4d-ac93-4b9a48089b20
• Taxonomy: Alkaloids and derivatives > Aspidospermatan-type alkaloids
• IUPAC Name: methyl (1R,9R,10S,11R,12S,13R,19R)-11-acetyloxy-12-ethyl-5-methoxy-8-methyl-20-oxa-8,16-diazahexacyclo[10.6.1.110,13.01,9.02,7.016,19]icosa-2(7),3,5-triene-10-carboxylate
• SMILES (Canonical): CCC12C3CCN4C1C5(CC4)C(C(C2OC(=O)C)(O3)C(=O)OC)N(C6=C5C=CC(=C6)OC)C
• SMILES (Isomeric): CC[C@@]12[C@H]3CCN4[C@@H]1[C@]5(CC4)[C@H]([C@@]([C@@H]2OC(=O)C)(O3)C(=O)OC)N(C6=C5C=CC(=C6)OC)C
• InChI: InChI=1S/C25H32N2O6/c1-6-23-18-9-11-27-12-10-24(19(23)27)16-8-7-15(30-4)13-17(16)26(3)20(24)25(33-18,22(29)31-5)21(23)32-14(2)28/h7-8,13,18-21H,6,9-12H2,1-5H3/t18-,19+,20-,21-,23-,24-,25+/m1/s1
• InChI Key: HYEXIINDBCFMOM-KJHPTJMASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₂N₂O₆
• Molecular Weight: 456.50 g/mol
• Exact Mass: 456.22603674 g/mol
• Topological Polar Surface Area (TPSA): 77.50 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 1.88
• H-Bond Acceptor: 8
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8263	82.63%
Caco-2	+	0.6246	62.46%
Blood Brain Barrier	+	0.9500	95.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.5354	53.54%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8779	87.79%
OATP1B3 inhibitior	+	0.9226	92.26%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	+	0.8765	87.65%
P-glycoprotein inhibitior	+	0.8725	87.25%
P-glycoprotein substrate	+	0.8018	80.18%
CYP3A4 substrate	+	0.6854	68.54%
CYP2C9 substrate	-	0.8047	80.47%
CYP2D6 substrate	+	0.3516	35.16%
CYP3A4 inhibition	+	0.5299	52.99%
CYP2C9 inhibition	-	0.8209	82.09%
CYP2C19 inhibition	-	0.6870	68.70%
CYP2D6 inhibition	-	0.7522	75.22%
CYP1A2 inhibition	-	0.8839	88.39%
CYP2C8 inhibition	-	0.7510	75.10%
CYP inhibitory promiscuity	-	0.7520	75.20%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5663	56.63%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9588	95.88%
Skin irritation	-	0.8359	83.59%
Skin corrosion	-	0.9512	95.12%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8401	84.01%
Micronuclear	+	0.6000	60.00%
Hepatotoxicity	+	0.5324	53.24%
skin sensitisation	-	0.8732	87.32%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.8003	80.03%
Acute Oral Toxicity (c)	III	0.6235	62.35%
Estrogen receptor binding	+	0.8053	80.53%
Androgen receptor binding	+	0.7736	77.36%
Thyroid receptor binding	+	0.5903	59.03%
Glucocorticoid receptor binding	+	0.6838	68.38%
Aromatase binding	+	0.6084	60.84%
PPAR gamma	+	0.6422	64.22%
Honey bee toxicity	-	0.8312	83.12%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.8674	86.74%

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	99.75%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.57%	91.11%
CHEMBL4208	P20618	Proteasome component C5	94.27%	90.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.92%	85.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.50%	95.89%
CHEMBL2581	P07339	Cathepsin D	91.55%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.75%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.81%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.82%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.20%	97.09%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.10%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.03%	94.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.27%	96.77%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.43%	92.62%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	85.25%	91.03%
CHEMBL3492	P49721	Proteasome Macropain subunit	85.00%	90.24%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	82.74%	90.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.79%	96.00%
CHEMBL4588	P22894	Matrix metalloproteinase 8	80.64%	94.66%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.23%	91.07%

Plants that contains it

• Aglaia spectabilis
• Clibadium pentaneuron
• Coespeletia thyrsiformis f. marcanoi
• Croton bonplandianus
• Croton californicus
• Culcitium canescens
• Cymbopogon nardus
• Dendrobium rotundatum
• Malva verticillata
• Nolina erumpens
• Petasites paradoxus
• Philotheca fitzgeraldii
• Piptolepis leptospermoides
• Ratibida latipalearis
• Toxicodendron succedaneum
• Weddellina squamulosa

Cross-Links

• PubChem: 21586687
• NPASS: NPC58799