[(1S,12S,14R)-9-methoxy-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraen-14-yl] (3S)-3-acetyloxybutanoate

Details

• Internal ID: 829fc665-1760-4b6c-b5db-b26b3fa3f254
• Taxonomy: Alkaloids and derivatives > Amaryllidaceae alkaloids > Galanthamine-type amaryllidaceae alkaloids
• IUPAC Name: [(1S,12S,14R)-9-methoxy-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraen-14-yl] (3S)-3-acetyloxybutanoate
• SMILES (Canonical): CC(CC(=O)OC1CC2C3(CCNCC4=C3C(=C(C=C4)OC)O2)C=C1)OC(=O)C
• SMILES (Isomeric): C[C@@H](CC(=O)O[C@@H]1C[C@H]2[C@@]3(CCNCC4=C3C(=C(C=C4)OC)O2)C=C1)OC(=O)C
• InChI: InChI=1S/C22H27NO6/c1-13(27-14(2)24)10-19(25)28-16-6-7-22-8-9-23-12-15-4-5-17(26-3)21(20(15)22)29-18(22)11-16/h4-7,13,16,18,23H,8-12H2,1-3H3/t13-,16-,18-,22-/m0/s1
• InChI Key: SAWXNICMRKEZSR-WSEKGTJNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₇NO₆
• Molecular Weight: 401.50 g/mol
• Exact Mass: 401.18383758 g/mol
• Topological Polar Surface Area (TPSA): 83.10 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.40
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9888	98.88%
Caco-2	-	0.5716	57.16%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.4016	40.16%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8856	88.56%
OATP1B3 inhibitior	+	0.9263	92.63%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.9241	92.41%
P-glycoprotein inhibitior	+	0.6159	61.59%
P-glycoprotein substrate	+	0.6897	68.97%
CYP3A4 substrate	+	0.6883	68.83%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.6886	68.86%
CYP3A4 inhibition	+	0.6384	63.84%
CYP2C9 inhibition	-	0.8220	82.20%
CYP2C19 inhibition	-	0.7710	77.10%
CYP2D6 inhibition	-	0.7904	79.04%
CYP1A2 inhibition	-	0.7622	76.22%
CYP2C8 inhibition	+	0.4540	45.40%
CYP inhibitory promiscuity	-	0.8217	82.17%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.5058	50.58%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.9569	95.69%
Skin irritation	-	0.7736	77.36%
Skin corrosion	-	0.9332	93.32%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3667	36.67%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	-	0.5801	58.01%
skin sensitisation	-	0.8010	80.10%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.7876	78.76%
Acute Oral Toxicity (c)	III	0.4863	48.63%
Estrogen receptor binding	+	0.7229	72.29%
Androgen receptor binding	-	0.6036	60.36%
Thyroid receptor binding	+	0.6729	67.29%
Glucocorticoid receptor binding	+	0.7463	74.63%
Aromatase binding	-	0.5655	56.55%
PPAR gamma	+	0.5859	58.59%
Honey bee toxicity	-	0.7046	70.46%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5355	53.55%
Fish aquatic toxicity	+	0.8151	81.51%

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	99.55%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.98%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.57%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.55%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.61%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.61%	86.33%
CHEMBL1907598	P05106	Integrin alpha-V/beta-3	88.34%	95.71%
CHEMBL2413	P32246	C-C chemokine receptor type 1	87.73%	89.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.67%	95.89%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.30%	97.25%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	86.98%	97.21%
CHEMBL3922	P50579	Methionine aminopeptidase 2	86.18%	97.28%
CHEMBL340	P08684	Cytochrome P450 3A4	85.40%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.51%	95.56%
CHEMBL2581	P07339	Cathepsin D	84.35%	98.95%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.32%	92.62%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.93%	96.77%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.59%	94.00%
CHEMBL2535	P11166	Glucose transporter	83.08%	98.75%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.67%	96.00%
CHEMBL255	P29275	Adenosine A2b receptor	82.39%	98.59%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.87%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.52%	89.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.19%	95.71%
CHEMBL5028	O14672	ADAM10	80.18%	97.50%

Plants that contains it

• Leucojum vernum

Cross-Links

• PubChem: 162926437
• LOTUS: LTS0121653
• wikiData: Q105249185