11-Hydroxygalantamine

Details

• Internal ID: d2f2fd01-6434-4764-ba4c-f4c172f06853
• Taxonomy: Alkaloids and derivatives > Amaryllidaceae alkaloids > Galanthamine-type amaryllidaceae alkaloids
• IUPAC Name: (1S,2S,12S,14R)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraene-2,14-diol
• SMILES (Canonical): CN1CC(C23C=CC(CC2OC4=C(C=CC(=C34)C1)OC)O)O
• SMILES (Isomeric): CN1C[C@H]([C@@]23C=C[C@@H](C[C@@H]2OC4=C(C=CC(=C34)C1)OC)O)O
• InChI: InChI=1S/C17H21NO4/c1-18-8-10-3-4-12(21-2)16-15(10)17(13(20)9-18)6-5-11(19)7-14(17)22-16/h3-6,11,13-14,19-20H,7-9H2,1-2H3/t11-,13+,14-,17-/m0/s1
• InChI Key: YLFKDWVECRVHGB-SYEQVDHESA-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: 0.90
• Atomic LogP (AlogP): 0.82
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• CHEMBL409610
• BDBM50221068

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9374	93.74%
Caco-2	+	0.7461	74.61%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Lysosomes	0.5605	56.05%
OATP2B1 inhibitior	-	0.8598	85.98%
OATP1B1 inhibitior	+	0.9443	94.43%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.7176	71.76%
P-glycoprotein inhibitior	-	0.9265	92.65%
P-glycoprotein substrate	+	0.6175	61.75%
CYP3A4 substrate	+	0.6962	69.62%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.6839	68.39%
CYP3A4 inhibition	-	0.8708	87.08%
CYP2C9 inhibition	-	0.8235	82.35%
CYP2C19 inhibition	-	0.5911	59.11%
CYP2D6 inhibition	-	0.6921	69.21%
CYP1A2 inhibition	-	0.8104	81.04%
CYP2C8 inhibition	-	0.8118	81.18%
CYP inhibitory promiscuity	-	0.7216	72.16%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9208	92.08%
Carcinogenicity (trinary)	Non-required	0.4840	48.40%
Eye corrosion	-	0.9865	98.65%
Eye irritation	-	0.9900	99.00%
Skin irritation	-	0.7987	79.87%
Skin corrosion	-	0.9257	92.57%
Ames mutagenesis	-	0.5837	58.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.5256	52.56%
Micronuclear	+	0.5200	52.00%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.7916	79.16%
Respiratory toxicity	+	0.9000	90.00%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.7414	74.14%
Acute Oral Toxicity (c)	III	0.5649	56.49%
Estrogen receptor binding	-	0.6292	62.92%
Androgen receptor binding	-	0.6638	66.38%
Thyroid receptor binding	+	0.6177	61.77%
Glucocorticoid receptor binding	-	0.6224	62.24%
Aromatase binding	-	0.6846	68.46%
PPAR gamma	-	0.6064	60.64%
Honey bee toxicity	-	0.8231	82.31%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	-	0.3913	39.13%

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	98.85%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.61%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.71%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.79%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.30%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.73%	94.00%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	84.86%	91.03%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.63%	86.33%
CHEMBL2337	P48067	Glycine transporter 1	82.14%	95.45%
CHEMBL340	P08684	Cytochrome P450 3A4	82.00%	91.19%
CHEMBL3192	Q9BY41	Histone deacetylase 8	81.45%	93.99%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.33%	97.09%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	80.05%	90.95%

Plants that contains it

• Hippeastrum papilio

Cross-Links

• PubChem: 10402718
• LOTUS: LTS0211867
• wikiData: Q105350105