[(1S,8S,10S,11R,12S,13S)-3-hydroxy-4,11,12-trimethoxy-17-methyl-18-oxa-17-azapentacyclo[8.4.3.18,11.01,10.02,7]octadeca-2(7),3,5-trien-13-yl] 3,4-dimethoxybenzoate

Details

• Internal ID: 9afbbad1-fe75-471d-8e18-b8e88872721f
• Taxonomy: Alkaloids and derivatives > Hasubanan alkaloids
• IUPAC Name: [(1S,8S,10S,11R,12S,13S)-3-hydroxy-4,11,12-trimethoxy-17-methyl-18-oxa-17-azapentacyclo[8.4.3.18,11.01,10.02,7]octadeca-2(7),3,5-trien-13-yl] 3,4-dimethoxybenzoate
• SMILES (Canonical): CN1CCC23C14CC(C5=C2C(=C(C=C5)OC)O)OC4(C(C(C3)OC(=O)C6=CC(=C(C=C6)OC)OC)OC)OC
• SMILES (Isomeric): CN1CC[C@@]23[C@]14C[C@@H](C5=C2C(=C(C=C5)OC)O)O[C@]4([C@H]([C@H](C3)OC(=O)C6=CC(=C(C=C6)OC)OC)OC)OC
• InChI: InChI=1S/C29H35NO9/c1-30-12-11-27-14-22(38-26(32)16-7-9-18(33-2)20(13-16)35-4)25(36-5)29(37-6)28(27,30)15-21(39-29)17-8-10-19(34-3)24(31)23(17)27/h7-10,13,21-22,25,31H,11-12,14-15H2,1-6H3/t21-,22-,25-,27-,28-,29-/m0/s1
• InChI Key: DOEAEUPFHPHWIJ-YSNGJTRGSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₅NO₉
• Molecular Weight: 541.60 g/mol
• Exact Mass: 541.23118169 g/mol
• Topological Polar Surface Area (TPSA): 105.00 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 3.19
• H-Bond Acceptor: 10
• H-Bond Donor: 1
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7790	77.90%
Caco-2	-	0.6190	61.90%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Lysosomes	0.4836	48.36%
OATP2B1 inhibitior	-	0.8544	85.44%
OATP1B1 inhibitior	+	0.9037	90.37%
OATP1B3 inhibitior	+	0.9216	92.16%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	+	0.9540	95.40%
P-glycoprotein inhibitior	+	0.8800	88.00%
P-glycoprotein substrate	+	0.7314	73.14%
CYP3A4 substrate	+	0.7042	70.42%
CYP2C9 substrate	-	0.7905	79.05%
CYP2D6 substrate	-	0.6844	68.44%
CYP3A4 inhibition	-	0.7271	72.71%
CYP2C9 inhibition	-	0.8958	89.58%
CYP2C19 inhibition	-	0.7877	78.77%
CYP2D6 inhibition	-	0.7762	77.62%
CYP1A2 inhibition	-	0.8936	89.36%
CYP2C8 inhibition	+	0.7435	74.35%
CYP inhibitory promiscuity	-	0.9147	91.47%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5606	56.06%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.9369	93.69%
Skin irritation	-	0.8180	81.80%
Skin corrosion	-	0.9501	95.01%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8270	82.70%
Micronuclear	-	0.5000	50.00%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	-	0.8757	87.57%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.9129	91.29%
Acute Oral Toxicity (c)	III	0.5331	53.31%
Estrogen receptor binding	+	0.8375	83.75%
Androgen receptor binding	+	0.7771	77.71%
Thyroid receptor binding	+	0.6957	69.57%
Glucocorticoid receptor binding	+	0.8335	83.35%
Aromatase binding	+	0.6803	68.03%
PPAR gamma	+	0.6694	66.94%
Honey bee toxicity	-	0.8477	84.77%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9519	95.19%

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	97.21%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	96.76%	95.89%
CHEMBL2581	P07339	Cathepsin D	95.70%	98.95%
CHEMBL2535	P11166	Glucose transporter	95.24%	98.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.46%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.38%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.11%	91.11%
CHEMBL241	Q14432	Phosphodiesterase 3A	91.08%	92.94%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	90.54%	94.42%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	88.26%	90.71%
CHEMBL2096618	P11274	Bcr/Abl fusion protein	87.66%	85.83%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.66%	91.07%
CHEMBL4302	P08183	P-glycoprotein 1	86.31%	92.98%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	85.32%	96.00%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	84.97%	85.49%
CHEMBL4208	P20618	Proteasome component C5	84.95%	90.00%
CHEMBL340	P08684	Cytochrome P450 3A4	84.83%	91.19%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	83.96%	97.33%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.73%	89.62%
CHEMBL1255126	O15151	Protein Mdm4	83.71%	90.20%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.65%	99.17%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	83.00%	93.03%
CHEMBL2056	P21728	Dopamine D1 receptor	82.84%	91.00%
CHEMBL1873	P00750	Tissue-type plasminogen activator	81.76%	93.33%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	81.54%	91.03%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.41%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.17%	89.00%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	80.61%	90.24%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.42%	97.14%
CHEMBL3192	Q9BY41	Histone deacetylase 8	80.02%	93.99%

Plants that contains it

• Stephania longa

Cross-Links

• PubChem: 11599133
• LOTUS: LTS0240539
• wikiData: Q104985937