(1S,13Z,17S,19S)-6,9-dihydroxy-5-methoxy-16-oxa-24-azapentacyclo[15.7.1.18,12.02,7.019,24]hexacosa-2(7),3,5,8,10,12(26),13-heptaen-15-one

Details

• Internal ID: 04c67c81-e7f3-4204-8e18-8504be282953
• Taxonomy: Organoheterocyclic compounds > Quinolizidines
• IUPAC Name: (1S,13Z,17S,19S)-6,9-dihydroxy-5-methoxy-16-oxa-24-azapentacyclo[15.7.1.18,12.02,7.019,24]hexacosa-2(7),3,5,8,10,12(26),13-heptaen-15-one
• SMILES (Canonical): COC1=C(C2=C(C=C1)C3CC(CC4N3CCCC4)OC(=O)C=CC5=CC2=C(C=C5)O)O
• SMILES (Isomeric): COC1=C(C2=C(C=C1)[C@@H]3C[C@H](C[C@H]4N3CCCC4)OC(=O)/C=C\C5=CC2=C(C=C5)O)O
• InChI: InChI=1S/C25H27NO5/c1-30-22-9-7-18-20-14-17(13-16-4-2-3-11-26(16)20)31-23(28)10-6-15-5-8-21(27)19(12-15)24(18)25(22)29/h5-10,12,16-17,20,27,29H,2-4,11,13-14H2,1H3/b10-6-/t16-,17-,20-/m0/s1
• InChI Key: WBNJBVAHRALIOS-NVEYBWRZSA-N
• Popularity: 1 reference 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	+	0.5000	50.00%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7986	79.86%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8926	89.26%
OATP1B3 inhibitior	+	0.9431	94.31%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.9712	97.12%
P-glycoprotein inhibitior	+	0.8577	85.77%
P-glycoprotein substrate	+	0.5810	58.10%
CYP3A4 substrate	+	0.6983	69.83%
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	+	0.5437	54.37%
CYP inhibitory promiscuity	-	0.7620	76.20%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5352	53.52%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9675	96.75%
Skin irritation	-	0.7879	78.79%
Skin corrosion	-	0.9609	96.09%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7019	70.19%
Micronuclear	+	0.6900	69.00%
Hepatotoxicity	+	0.5949	59.49%
skin sensitisation	-	0.8620	86.20%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.5564	55.64%
Acute Oral Toxicity (c)	III	0.7403	74.03%
Estrogen receptor binding	+	0.6021	60.21%
Androgen receptor binding	+	0.8531	85.31%
Thyroid receptor binding	-	0.5399	53.99%
Glucocorticoid receptor binding	+	0.7894	78.94%
Aromatase binding	+	0.6003	60.03%
PPAR gamma	-	0.5840	58.40%
Honey bee toxicity	-	0.8776	87.76%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5451	54.51%
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
CHEMBL2581	P07339	Cathepsin D	96.87%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.69%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	94.96%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.04%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.48%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.27%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.30%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.12%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.93%	99.23%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	88.49%	90.71%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	88.46%	93.03%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.93%	99.15%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	87.84%	92.88%
CHEMBL1873	P00750	Tissue-type plasminogen activator	86.95%	93.33%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	86.41%	96.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	86.40%	82.69%
CHEMBL2535	P11166	Glucose transporter	86.19%	98.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.91%	94.00%
CHEMBL5203	P33316	dUTP pyrophosphatase	85.65%	99.18%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.07%	85.14%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	84.67%	96.38%
CHEMBL3438	Q05513	Protein kinase C zeta	84.39%	88.48%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.78%	92.94%
CHEMBL340	P08684	Cytochrome P450 3A4	83.59%	91.19%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.11%	97.14%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	81.43%	91.03%
CHEMBL1951	P21397	Monoamine oxidase A	81.25%	91.49%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.32%	96.21%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.03%	92.62%

Plants that contains it

• Heimia salicifolia

Cross-Links

• PubChem: 101863381
• LOTUS: LTS0095552
• wikiData: Q105300858