(5Z)-5-[(1S,4S,5R,6S,8S,13R)-9-butyl-4-methyl-2,14-dioxa-10-azapentacyclo[6.5.1.01,5.06,10.09,13]tetradecan-3-ylidene]-4-methoxy-3-methylfuran-2-one

Details

• Internal ID: f90b68ef-5483-49f4-8ded-23e7ad14f123
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Aminosaccharides > Aminoglycosides
• IUPAC Name: (5Z)-5-[(1S,4S,5R,6S,8S,13R)-9-butyl-4-methyl-2,14-dioxa-10-azapentacyclo[6.5.1.01,5.06,10.09,13]tetradecan-3-ylidene]-4-methoxy-3-methylfuran-2-one
• SMILES (Canonical): CCCCC12C3CCN1C4CC2OC35C4C(C(=C6C(=C(C(=O)O6)C)OC)O5)C
• SMILES (Isomeric): CCCCC12[C@H]3CCN1[C@H]4C[C@@H]2O[C@]35[C@@H]4[C@@H](/C(=C/6\C(=C(C(=O)O6)C)OC)/O5)C
• InChI: InChI=1S/C22H29NO5/c1-5-6-8-21-14-7-9-23(21)13-10-15(21)27-22(14)16(13)11(2)18(28-22)19-17(25-4)12(3)20(24)26-19/h11,13-16H,5-10H2,1-4H3/b19-18-/t11-,13-,14+,15-,16+,21?,22+/m0/s1
• InChI Key: DTVYAHOULQCSMS-WFDNSANHSA-N
• Popularity: 23 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₉NO₅
• Molecular Weight: 387.50 g/mol
• Exact Mass: 387.20457303 g/mol
• Topological Polar Surface Area (TPSA): 57.20 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 3.09
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

• Q27104971

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9481	94.81%
Caco-2	+	0.6741	67.41%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5670	56.70%
OATP2B1 inhibitior	-	0.8603	86.03%
OATP1B1 inhibitior	+	0.8728	87.28%
OATP1B3 inhibitior	+	0.9360	93.60%
MATE1 inhibitior	-	0.8609	86.09%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.7922	79.22%
P-glycoprotein inhibitior	-	0.4603	46.03%
P-glycoprotein substrate	+	0.5916	59.16%
CYP3A4 substrate	+	0.6705	67.05%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8026	80.26%
CYP3A4 inhibition	-	0.8918	89.18%
CYP2C9 inhibition	-	0.8907	89.07%
CYP2C19 inhibition	-	0.8884	88.84%
CYP2D6 inhibition	-	0.8897	88.97%
CYP1A2 inhibition	-	0.8034	80.34%
CYP2C8 inhibition	-	0.5734	57.34%
CYP inhibitory promiscuity	-	0.6454	64.54%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4883	48.83%
Eye corrosion	-	0.9875	98.75%
Eye irritation	-	0.9257	92.57%
Skin irritation	-	0.7549	75.49%
Skin corrosion	-	0.9242	92.42%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3629	36.29%
Micronuclear	+	0.5300	53.00%
Hepatotoxicity	-	0.5704	57.04%
skin sensitisation	-	0.8501	85.01%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.6105	61.05%
Acute Oral Toxicity (c)	III	0.6013	60.13%
Estrogen receptor binding	+	0.8583	85.83%
Androgen receptor binding	+	0.7233	72.33%
Thyroid receptor binding	+	0.6969	69.69%
Glucocorticoid receptor binding	+	0.7520	75.20%
Aromatase binding	+	0.6328	63.28%
PPAR gamma	+	0.6650	66.50%
Honey bee toxicity	-	0.8621	86.21%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9228	92.28%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.78%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.61%	96.09%
CHEMBL4588	P22894	Matrix metalloproteinase 8	94.53%	94.66%
CHEMBL218	P21554	Cannabinoid CB1 receptor	93.99%	96.61%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.99%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.02%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.46%	97.09%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	89.69%	82.38%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.46%	86.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.24%	97.14%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	86.89%	95.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.64%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.92%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.42%	99.23%
CHEMBL221	P23219	Cyclooxygenase-1	84.51%	90.17%
CHEMBL1871	P10275	Androgen Receptor	84.50%	96.43%
CHEMBL5255	O00206	Toll-like receptor 4	84.36%	92.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.29%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.44%	94.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	82.93%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.83%	92.94%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.03%	93.00%
CHEMBL332	P03956	Matrix metalloproteinase-1	80.68%	94.50%
CHEMBL299	P17252	Protein kinase C alpha	80.32%	98.03%

Plants that contains it

• Stemona aphylla
• Stemona burkillii
• Stemona cochinchinensis
• Stemona collinsae
• Stemona japonica

Cross-Links

• PubChem: 139031145
• LOTUS: LTS0070371
• wikiData: Q27104971