4,9-Dihydroxy-5-methoxy-16-oxa-24-azapentacyclo[15.7.1.18,12.02,7.019,24]hexacosa-2,4,6,8,10,12(26),13-heptaen-15-one

Details

• Internal ID: e1f37917-9b60-41f5-8877-14f8423a2ed0
• Taxonomy: Organoheterocyclic compounds > Quinolizidines
• IUPAC Name: 4,9-dihydroxy-5-methoxy-16-oxa-24-azapentacyclo[15.7.1.18,12.02,7.019,24]hexacosa-2,4,6,8,10,12(26),13-heptaen-15-one
• SMILES (Canonical): COC1=C(C=C2C3CC(CC4N3CCCC4)OC(=O)C=CC5=CC(=C(C=C5)O)C2=C1)O
• SMILES (Isomeric): COC1=C(C=C2C3CC(CC4N3CCCC4)OC(=O)C=CC5=CC(=C(C=C5)O)C2=C1)O
• InChI: InChI=1S/C25H27NO5/c1-30-24-14-18-19(13-23(24)28)21-12-17(11-16-4-2-3-9-26(16)21)31-25(29)8-6-15-5-7-22(27)20(18)10-15/h5-8,10,13-14,16-17,21,27-28H,2-4,9,11-12H2,1H3
• InChI Key: CDTGNBVPXHNHGE-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₇NO₅
• Molecular Weight: 421.50 g/mol
• Exact Mass: 421.18892296 g/mol
• Topological Polar Surface Area (TPSA): 79.20 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 4.40
• H-Bond Acceptor: 6
• 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	+	0.8792	87.92%
Caco-2	+	0.5058	50.58%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7986	79.86%
OATP2B1 inhibitior	-	0.8589	85.89%
OATP1B1 inhibitior	+	0.8795	87.95%
OATP1B3 inhibitior	+	0.9431	94.31%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.9777	97.77%
P-glycoprotein inhibitior	+	0.8206	82.06%
P-glycoprotein substrate	+	0.6113	61.13%
CYP3A4 substrate	+	0.6795	67.95%
CYP2C9 substrate	-	0.6189	61.89%
CYP2D6 substrate	-	0.6690	66.90%
CYP3A4 inhibition	-	0.8330	83.30%
CYP2C9 inhibition	-	0.8629	86.29%
CYP2C19 inhibition	-	0.5154	51.54%
CYP2D6 inhibition	-	0.5420	54.20%
CYP1A2 inhibition	+	0.6070	60.70%
CYP2C8 inhibition	-	0.5936	59.36%
CYP inhibitory promiscuity	-	0.7620	76.20%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5352	53.52%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9593	95.93%
Skin irritation	-	0.7879	78.79%
Skin corrosion	-	0.9609	96.09%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6869	68.69%
Micronuclear	+	0.6900	69.00%
Hepatotoxicity	+	0.5627	56.27%
skin sensitisation	-	0.8620	86.20%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.5409	54.09%
Acute Oral Toxicity (c)	III	0.7403	74.03%
Estrogen receptor binding	+	0.6292	62.92%
Androgen receptor binding	+	0.8303	83.03%
Thyroid receptor binding	-	0.5226	52.26%
Glucocorticoid receptor binding	+	0.7946	79.46%
Aromatase binding	+	0.6375	63.75%
PPAR gamma	-	0.5186	51.86%
Honey bee toxicity	-	0.8378	83.78%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5951	59.51%
Fish aquatic toxicity	+	0.8317	83.17%

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	96.34%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.96%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.02%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.19%	91.11%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.19%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	91.02%	92.94%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.77%	86.33%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	89.46%	89.62%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.31%	85.14%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	88.22%	82.69%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	87.93%	93.03%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.80%	90.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.54%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.33%	97.25%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.20%	99.23%
CHEMBL2535	P11166	Glucose transporter	86.03%	98.75%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	85.46%	82.67%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	84.03%	93.04%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.78%	97.14%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.59%	99.15%
CHEMBL1873	P00750	Tissue-type plasminogen activator	83.27%	93.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.84%	94.00%
CHEMBL4208	P20618	Proteasome component C5	82.72%	90.00%
CHEMBL3438	Q05513	Protein kinase C zeta	82.69%	88.48%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	82.36%	90.24%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	81.24%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.17%	89.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.97%	100.00%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	80.65%	92.88%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.57%	92.62%
CHEMBL1978	P11511	Cytochrome P450 19A1	80.22%	91.76%

Plants that contains it

• Heimia montana
• Heimia salicifolia

Cross-Links

• PubChem: 321494
• LOTUS: LTS0210958
• wikiData: Q104955164