15-Hydroxy-9,16-dimethoxy-3-methyl-7,11-dioxa-3-azapentacyclo[8.8.0.02,6.06,8.013,18]octadeca-13,15,17-trien-12-one

Details

• Internal ID: a8994b96-afb8-4f03-83d2-0408c1ca1316
• Taxonomy: Alkaloids and derivatives > Amaryllidaceae alkaloids > Homolycorine-type amaryllidaceae alkaloids
• IUPAC Name: 15-hydroxy-9,16-dimethoxy-3-methyl-7,11-dioxa-3-azapentacyclo[8.8.0.02,6.06,8.013,18]octadeca-13,15,17-trien-12-one
• SMILES (Canonical): CN1CCC23C1C4C(C(C2O3)OC)OC(=O)C5=CC(=C(C=C45)OC)O
• SMILES (Isomeric): CN1CCC23C1C4C(C(C2O3)OC)OC(=O)C5=CC(=C(C=C45)OC)O
• InChI: InChI=1S/C18H21NO6/c1-19-5-4-18-15(19)12-8-7-11(22-2)10(20)6-9(8)17(21)24-13(12)14(23-3)16(18)25-18/h6-7,12-16,20H,4-5H2,1-3H3
• InChI Key: OUFUQEVNHDMFTL-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₁NO₆
• Molecular Weight: 347.40 g/mol
• Exact Mass: 347.13688739 g/mol
• Topological Polar Surface Area (TPSA): 80.80 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 0.89
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7570	75.70%
Caco-2	+	0.7925	79.25%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Lysosomes	0.5334	53.34%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8957	89.57%
OATP1B3 inhibitior	+	0.9291	92.91%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.8609	86.09%
P-glycoprotein inhibitior	-	0.6304	63.04%
P-glycoprotein substrate	-	0.5113	51.13%
CYP3A4 substrate	+	0.6786	67.86%
CYP2C9 substrate	-	0.7917	79.17%
CYP2D6 substrate	+	0.3681	36.81%
CYP3A4 inhibition	-	0.7412	74.12%
CYP2C9 inhibition	-	0.8229	82.29%
CYP2C19 inhibition	-	0.7379	73.79%
CYP2D6 inhibition	-	0.7529	75.29%
CYP1A2 inhibition	-	0.8280	82.80%
CYP2C8 inhibition	-	0.8056	80.56%
CYP inhibitory promiscuity	-	0.9424	94.24%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5548	55.48%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.9439	94.39%
Skin irritation	-	0.8000	80.00%
Skin corrosion	-	0.9370	93.70%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6648	66.48%
Micronuclear	-	0.5000	50.00%
Hepatotoxicity	-	0.6469	64.69%
skin sensitisation	-	0.8481	84.81%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	+	0.5426	54.26%
Acute Oral Toxicity (c)	III	0.5673	56.73%
Estrogen receptor binding	+	0.6454	64.54%
Androgen receptor binding	+	0.6359	63.59%
Thyroid receptor binding	+	0.5772	57.72%
Glucocorticoid receptor binding	+	0.7704	77.04%
Aromatase binding	+	0.6149	61.49%
PPAR gamma	+	0.5861	58.61%
Honey bee toxicity	-	0.7706	77.06%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	-	0.4266	42.66%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.08%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.57%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.34%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.33%	95.56%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	94.77%	93.40%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.23%	97.25%
CHEMBL2581	P07339	Cathepsin D	92.15%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.40%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.67%	94.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	90.08%	91.07%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.93%	95.89%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	88.45%	93.03%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.12%	89.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.89%	97.14%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	86.03%	93.04%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	84.99%	90.24%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.86%	99.23%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	84.65%	94.42%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	83.56%	82.38%
CHEMBL1951	P21397	Monoamine oxidase A	83.14%	91.49%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.63%	92.62%
CHEMBL4829	O00763	Acetyl-CoA carboxylase 2	81.37%	98.00%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	81.34%	80.78%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.27%	89.50%

Plants that contains it

• Galanthus elwesii

Cross-Links

• PubChem: 163042807
• LOTUS: LTS0075051
• wikiData: Q105200040