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

Details

• Internal ID: 6304d05e-f6ab-49db-8106-ff4eba6d269a
• Taxonomy: Alkaloids and derivatives > Amaryllidaceae alkaloids > Galanthamine-type amaryllidaceae alkaloids
• IUPAC Name: (1S,3S,12S,14R)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraene-3,14-diol
• InChI: InChI=1S/C17H21NO4/c1-18-9-10-3-4-12(21-2)16-15(10)17(8-14(18)20)6-5-11(19)7-13(17)22-16/h3-6,11,13-14,19-20H,7-9H2,1-2H3/t11-,13-,14-,17-/m0/s1
• InChI Key: NJAONUQFLGTYPU-MJFSBKNWSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₁NO₄
• Molecular Weight: 303.35 g/mol
• Exact Mass: 303.14705815 g/mol
• Topological Polar Surface Area (TPSA): 62.20 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 1.17
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9945	99.45%
Caco-2	+	0.6734	67.34%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Lysosomes	0.3845	38.45%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9402	94.02%
OATP1B3 inhibitior	+	0.9430	94.30%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.7721	77.21%
P-glycoprotein inhibitior	-	0.9247	92.47%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.7101	71.01%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.3945	39.45%
CYP3A4 inhibition	-	0.8688	86.88%
CYP2C9 inhibition	-	0.8383	83.83%
CYP2C19 inhibition	-	0.7528	75.28%
CYP2D6 inhibition	-	0.8227	82.27%
CYP1A2 inhibition	-	0.8639	86.39%
CYP2C8 inhibition	-	0.7821	78.21%
CYP inhibitory promiscuity	-	0.9143	91.43%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5666	56.66%
Eye corrosion	-	0.9878	98.78%
Eye irritation	-	0.9870	98.70%
Skin irritation	-	0.7815	78.15%
Skin corrosion	-	0.9349	93.49%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5127	51.27%
Micronuclear	+	0.5800	58.00%
Hepatotoxicity	-	0.7699	76.99%
skin sensitisation	-	0.8350	83.50%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.8176	81.76%
Acute Oral Toxicity (c)	III	0.5358	53.58%
Estrogen receptor binding	-	0.5788	57.88%
Androgen receptor binding	-	0.7803	78.03%
Thyroid receptor binding	+	0.5391	53.91%
Glucocorticoid receptor binding	-	0.6715	67.15%
Aromatase binding	-	0.8308	83.08%
PPAR gamma	-	0.5738	57.38%
Honey bee toxicity	-	0.8237	82.37%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.9208	92.08%

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	99.41%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.85%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.54%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.59%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.24%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.61%	97.25%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.08%	95.89%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	86.72%	89.62%
CHEMBL1951	P21397	Monoamine oxidase A	85.16%	91.49%
CHEMBL3192	Q9BY41	Histone deacetylase 8	84.52%	93.99%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.29%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.49%	94.45%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.52%	97.14%

Plants that contains it

• Cyrtanthus obliquus

Cross-Links

• PubChem: 20846211
• LOTUS: LTS0125671
• wikiData: Q105180069