[(1S,2R,3R,4S,5R,7S,8R,9R,10R,14R,15R)-2-acetyloxy-4-formyl-14-(furan-3-yl)-5-hydroxy-4,8,10,12-tetramethyl-9-(2-oxoethyl)-16-oxatetracyclo[8.6.0.03,8.011,15]hexadec-11-en-7-yl] (E)-2-methylbut-2-enoate

Details

• Internal ID: cac40f35-8bc5-4589-8ec8-f12e467e77e0
• Taxonomy: Organoheterocyclic compounds > Naphthofurans
• IUPAC Name: [(1S,2R,3R,4S,5R,7S,8R,9R,10R,14R,15R)-2-acetyloxy-4-formyl-14-(furan-3-yl)-5-hydroxy-4,8,10,12-tetramethyl-9-(2-oxoethyl)-16-oxatetracyclo[8.6.0.03,8.011,15]hexadec-11-en-7-yl] (E)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1CC(C(C2C1(C(C3(C(C2OC(=O)C)OC4C3=C(CC4C5=COC=C5)C)C)CC=O)C)(C)C=O)O
• SMILES (Isomeric): C/C=C(\C)/C(=O)O[C@H]1C[C@H]([C@@]([C@H]2[C@]1([C@H]([C@]3([C@@H]([C@@H]2OC(=O)C)O[C@H]4C3=C(C[C@@H]4C5=COC=C5)C)C)CC=O)C)(C)C=O)O
• InChI: InChI=1S/C33H42O9/c1-8-17(2)30(38)41-24-14-23(37)31(5,16-35)28-27(40-19(4)36)29-33(7,22(9-11-34)32(24,28)6)25-18(3)13-21(26(25)42-29)20-10-12-39-15-20/h8,10-12,15-16,21-24,26-29,37H,9,13-14H2,1-7H3/b17-8+/t21-,22-,23-,24+,26-,27-,28+,29-,31-,32+,33-/m1/s1
• InChI Key: ASMYAKGFVUUZKR-OWNWDFMXSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₂O₉
• Molecular Weight: 582.70 g/mol
• Exact Mass: 582.28288291 g/mol
• Topological Polar Surface Area (TPSA): 129.00 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 4.48
• H-Bond Acceptor: 9
• 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	+	0.9956	99.56%
Caco-2	-	0.7607	76.07%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.6680	66.80%
OATP2B1 inhibitior	-	0.7199	71.99%
OATP1B1 inhibitior	+	0.7069	70.69%
OATP1B3 inhibitior	-	0.5820	58.20%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9960	99.60%
P-glycoprotein inhibitior	+	0.8466	84.66%
P-glycoprotein substrate	+	0.6342	63.42%
CYP3A4 substrate	+	0.7232	72.32%
CYP2C9 substrate	-	0.7962	79.62%
CYP2D6 substrate	-	0.8787	87.87%
CYP3A4 inhibition	+	0.6236	62.36%
CYP2C9 inhibition	-	0.7848	78.48%
CYP2C19 inhibition	-	0.8590	85.90%
CYP2D6 inhibition	-	0.9420	94.20%
CYP1A2 inhibition	-	0.8704	87.04%
CYP2C8 inhibition	+	0.7187	71.87%
CYP inhibitory promiscuity	-	0.7594	75.94%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Danger	0.4730	47.30%
Eye corrosion	-	0.9914	99.14%
Eye irritation	-	0.9098	90.98%
Skin irritation	-	0.5511	55.11%
Skin corrosion	-	0.9320	93.20%
Ames mutagenesis	+	0.5082	50.82%
Human Ether-a-go-go-Related Gene inhibition	+	0.7245	72.45%
Micronuclear	-	0.5500	55.00%
Hepatotoxicity	+	0.6168	61.68%
skin sensitisation	-	0.7990	79.90%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.6878	68.78%
Acute Oral Toxicity (c)	I	0.5313	53.13%
Estrogen receptor binding	+	0.8068	80.68%
Androgen receptor binding	+	0.6647	66.47%
Thyroid receptor binding	+	0.5727	57.27%
Glucocorticoid receptor binding	+	0.7907	79.07%
Aromatase binding	+	0.6582	65.82%
PPAR gamma	+	0.7697	76.97%
Honey bee toxicity	-	0.6603	66.03%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.9945	99.45%

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	97.49%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.94%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.35%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.15%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.05%	97.09%
CHEMBL221	P23219	Cyclooxygenase-1	93.91%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.31%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	91.14%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.36%	89.00%
CHEMBL2581	P07339	Cathepsin D	88.12%	98.95%
CHEMBL4208	P20618	Proteasome component C5	87.02%	90.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.48%	94.00%
CHEMBL5028	O14672	ADAM10	85.76%	97.50%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.68%	96.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.99%	95.50%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	81.79%	89.44%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.70%	100.00%
CHEMBL3038469	P24941	CDK2/Cyclin A	81.46%	91.38%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.82%	99.17%

Plants that contains it

• Melia azedarach

Cross-Links

• PubChem: 56950764
• NPASS: NPC41426