[(1S,13R,15R,16S,18R,19R)-9,15-dimethoxy-5,7,17-trioxa-12-azahexacyclo[10.6.2.01,13.02,10.04,8.016,18]icosa-2,4(8),9-trien-19-yl] acetate

Details

• Internal ID: 95b4eff6-3e33-406d-a754-e81648072e90
• Taxonomy: Alkaloids and derivatives > Amaryllidaceae alkaloids > Crinine- and Haemanthamine-type amaryllidaceae alkaloids
• IUPAC Name: [(1S,13R,15R,16S,18R,19R)-9,15-dimethoxy-5,7,17-trioxa-12-azahexacyclo[10.6.2.01,13.02,10.04,8.016,18]icosa-2,4(8),9-trien-19-yl] acetate
• SMILES (Canonical): CC(=O)OC1CN2CC3=C(C4=C(C=C3C15C2CC(C6C5O6)OC)OCO4)OC
• SMILES (Isomeric): CC(=O)O[C@H]1CN2CC3=C(C4=C(C=C3[C@]15[C@H]2C[C@H]([C@H]6[C@@H]5O6)OC)OCO4)OC
• InChI: InChI=1S/C20H23NO7/c1-9(22)27-15-7-21-6-10-11(4-13-17(16(10)24-3)26-8-25-13)20(15)14(21)5-12(23-2)18-19(20)28-18/h4,12,14-15,18-19H,5-8H2,1-3H3/t12-,14-,15+,18+,19+,20+/m1/s1
• InChI Key: HUKHZLUIPVCSIS-KKDMEDJGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₃NO₇
• Molecular Weight: 389.40 g/mol
• Exact Mass: 389.14745207 g/mol
• Topological Polar Surface Area (TPSA): 79.00 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 0.98
• H-Bond Acceptor: 8
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9233	92.33%
Caco-2	+	0.8080	80.80%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Lysosomes	0.6789	67.89%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9148	91.48%
OATP1B3 inhibitior	+	0.9295	92.95%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.8748	87.48%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	-	0.5246	52.46%
CYP3A4 substrate	+	0.6571	65.71%
CYP2C9 substrate	-	0.8042	80.42%
CYP2D6 substrate	-	0.7027	70.27%
CYP3A4 inhibition	+	0.5391	53.91%
CYP2C9 inhibition	-	0.8738	87.38%
CYP2C19 inhibition	-	0.6563	65.63%
CYP2D6 inhibition	-	0.6732	67.32%
CYP1A2 inhibition	-	0.7718	77.18%
CYP2C8 inhibition	-	0.6506	65.06%
CYP inhibitory promiscuity	-	0.6657	66.57%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5616	56.16%
Eye corrosion	-	0.9861	98.61%
Eye irritation	-	0.9290	92.90%
Skin irritation	-	0.8093	80.93%
Skin corrosion	-	0.9403	94.03%
Ames mutagenesis	+	0.6046	60.46%
Human Ether-a-go-go-Related Gene inhibition	-	0.3772	37.72%
Micronuclear	+	0.5800	58.00%
Hepatotoxicity	+	0.5907	59.07%
skin sensitisation	-	0.8090	80.90%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	+	0.6703	67.03%
Acute Oral Toxicity (c)	III	0.5757	57.57%
Estrogen receptor binding	+	0.8381	83.81%
Androgen receptor binding	+	0.5936	59.36%
Thyroid receptor binding	+	0.5897	58.97%
Glucocorticoid receptor binding	+	0.8361	83.61%
Aromatase binding	-	0.5069	50.69%
PPAR gamma	+	0.7649	76.49%
Honey bee toxicity	-	0.7116	71.16%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5155	51.55%
Fish aquatic toxicity	+	0.6891	68.91%

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	98.91%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.54%	94.45%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	97.78%	96.77%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.94%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.78%	85.14%
CHEMBL4040	P28482	MAP kinase ERK2	91.72%	83.82%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.22%	86.33%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	90.61%	80.96%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.33%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.25%	95.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.47%	92.62%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	84.21%	82.38%
CHEMBL2413	P32246	C-C chemokine receptor type 1	83.72%	89.50%
CHEMBL3922	P50579	Methionine aminopeptidase 2	83.70%	97.28%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.52%	92.94%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.91%	94.00%
CHEMBL340	P08684	Cytochrome P450 3A4	81.80%	91.19%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.78%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.17%	97.14%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	80.52%	93.40%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.39%	96.00%

Plants that contains it

• Ammocharis tinneana

Cross-Links

• PubChem: 162845168
• LOTUS: LTS0261698
• wikiData: Q105033825