3,4,7,8-Tetramethoxy-17-methyl-7,8-didehydrohasubanan-6-one

Details

• Internal ID: 7c676de5-6abd-44c9-b609-f349c80282f4
• Taxonomy: Alkaloids and derivatives > Hasubanan alkaloids
• IUPAC Name: 3,4,11,12-tetramethoxy-17-methyl-17-azatetracyclo[8.4.3.01,10.02,7]heptadeca-2(7),3,5,11-tetraen-13-one
• SMILES (Canonical): CN1CCC23C1(CCC4=C2C(=C(C=C4)OC)OC)C(=C(C(=O)C3)OC)OC
• SMILES (Isomeric): CN1CCC23C1(CCC4=C2C(=C(C=C4)OC)OC)C(=C(C(=O)C3)OC)OC
• InChI: InChI=1S/C21H27NO5/c1-22-11-10-20-12-14(23)17(25-3)19(27-5)21(20,22)9-8-13-6-7-15(24-2)18(26-4)16(13)20/h6-7H,8-12H2,1-5H3
• InChI Key: DXUSNRCTWFHYFS-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₇NO₅
• Molecular Weight: 373.40 g/mol
• Exact Mass: 373.18892296 g/mol
• Topological Polar Surface Area (TPSA): 57.20 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.44
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

• 3,4,7,8-Tetramethoxy-17-methyl-7,8-didehydrohasubanan-6-one #

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9880	98.80%
Caco-2	+	0.9271	92.71%
Blood Brain Barrier	+	0.9250	92.50%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6309	63.09%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9373	93.73%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	-	0.6830	68.30%
P-glycoprotein inhibitior	-	0.6287	62.87%
P-glycoprotein substrate	-	0.6048	60.48%
CYP3A4 substrate	+	0.6406	64.06%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4327	43.27%
CYP3A4 inhibition	-	0.7326	73.26%
CYP2C9 inhibition	-	0.9261	92.61%
CYP2C19 inhibition	-	0.8593	85.93%
CYP2D6 inhibition	-	0.6001	60.01%
CYP1A2 inhibition	-	0.8313	83.13%
CYP2C8 inhibition	-	0.8825	88.25%
CYP inhibitory promiscuity	-	0.8243	82.43%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5280	52.80%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.9406	94.06%
Skin irritation	-	0.7944	79.44%
Skin corrosion	-	0.9402	94.02%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3848	38.48%
Micronuclear	-	0.5800	58.00%
Hepatotoxicity	-	0.6250	62.50%
skin sensitisation	-	0.8534	85.34%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.5079	50.79%
Acute Oral Toxicity (c)	III	0.6126	61.26%
Estrogen receptor binding	+	0.7326	73.26%
Androgen receptor binding	+	0.7588	75.88%
Thyroid receptor binding	+	0.5966	59.66%
Glucocorticoid receptor binding	+	0.7080	70.80%
Aromatase binding	+	0.5574	55.74%
PPAR gamma	+	0.5546	55.46%
Honey bee toxicity	-	0.8671	86.71%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.9523	95.23%

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	97.20%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.67%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.09%	86.33%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	93.10%	93.40%
CHEMBL2581	P07339	Cathepsin D	91.81%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.67%	94.00%
CHEMBL1937	Q92769	Histone deacetylase 2	88.41%	94.75%
CHEMBL2535	P11166	Glucose transporter	86.44%	98.75%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.37%	95.89%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	84.01%	82.38%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.43%	99.23%
CHEMBL2056	P21728	Dopamine D1 receptor	83.07%	91.00%

Plants that contains it

• Cephalotaxus fortunei
• Cephalotaxus hainanensis
• Stephania elegans
• Stephania japonica

Cross-Links

• PubChem: 628879
• NPASS: NPC38749
• LOTUS: LTS0264959
• wikiData: Q104991200