methyl 2-[(1S,2R,8R,9S,10R,13R)-2-acetyloxy-13-(furan-3-yl)-4-hydroxy-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.03,8.011,15]hexadeca-5,11-dien-9-yl]acetate

Details

• Internal ID: 5e3d760d-7637-495d-a0d3-8ec7851a70e2
• Taxonomy: Organoheterocyclic compounds > Naphthofurans
• IUPAC Name: methyl 2-[(1S,2R,8R,9S,10R,13R)-2-acetyloxy-13-(furan-3-yl)-4-hydroxy-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.03,8.011,15]hexadeca-5,11-dien-9-yl]acetate
• SMILES (Canonical): CC1=C2C(CC1C3=COC=C3)OC4C2(C(C5(C(C4OC(=O)C)C(C=CC5=O)(C)O)C)CC(=O)OC)C
• SMILES (Isomeric): CC1=C2C(C[C@H]1C3=COC=C3)O[C@H]4[C@@]2([C@@H]([C@@]5(C([C@H]4OC(=O)C)C(C=CC5=O)(C)O)C)CC(=O)OC)C
• InChI: InChI=1S/C28H34O8/c1-14-17(16-8-10-34-13-16)11-18-22(14)28(5)19(12-21(31)33-6)27(4)20(30)7-9-26(3,32)24(27)23(25(28)36-18)35-15(2)29/h7-10,13,17-19,23-25,32H,11-12H2,1-6H3/t17-,18?,19-,23-,24?,25-,26?,27+,28-/m1/s1
• InChI Key: PWFKLZWNGVGKBA-LHRNQYAXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₄O₈
• Molecular Weight: 498.60 g/mol
• Exact Mass: 498.22536804 g/mol
• Topological Polar Surface Area (TPSA): 112.00 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 3.49
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9932	99.32%
Caco-2	-	0.6285	62.85%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7092	70.92%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	-	0.3456	34.56%
OATP1B3 inhibitior	-	0.4810	48.10%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9786	97.86%
P-glycoprotein inhibitior	+	0.8370	83.70%
P-glycoprotein substrate	+	0.6434	64.34%
CYP3A4 substrate	+	0.7073	70.73%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8882	88.82%
CYP3A4 inhibition	+	0.5818	58.18%
CYP2C9 inhibition	-	0.7697	76.97%
CYP2C19 inhibition	-	0.8629	86.29%
CYP2D6 inhibition	-	0.9384	93.84%
CYP1A2 inhibition	-	0.8884	88.84%
CYP2C8 inhibition	+	0.6709	67.09%
CYP inhibitory promiscuity	-	0.5771	57.71%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Danger	0.6037	60.37%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.8986	89.86%
Skin irritation	-	0.6641	66.41%
Skin corrosion	-	0.9323	93.23%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7147	71.47%
Micronuclear	+	0.5059	50.59%
Hepatotoxicity	+	0.6293	62.93%
skin sensitisation	-	0.7896	78.96%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.4889	48.89%
Acute Oral Toxicity (c)	III	0.5678	56.78%
Estrogen receptor binding	+	0.8070	80.70%
Androgen receptor binding	+	0.7158	71.58%
Thyroid receptor binding	+	0.6218	62.18%
Glucocorticoid receptor binding	+	0.8581	85.81%
Aromatase binding	+	0.6424	64.24%
PPAR gamma	+	0.7785	77.85%
Honey bee toxicity	-	0.7203	72.03%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.6200	62.00%
Fish aquatic toxicity	+	0.9748	97.48%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.59%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.20%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.31%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.82%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.62%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.30%	97.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.68%	94.00%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	91.47%	81.11%
CHEMBL4208	P20618	Proteasome component C5	91.18%	90.00%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	88.74%	87.67%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.47%	95.56%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.65%	95.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.32%	89.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.29%	94.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.22%	96.00%
CHEMBL3492	P49721	Proteasome Macropain subunit	83.14%	90.24%
CHEMBL5028	O14672	ADAM10	82.38%	97.50%
CHEMBL3401	O75469	Pregnane X receptor	80.64%	94.73%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.41%	93.00%

Plants that contains it

• Azadirachta indica

Cross-Links

• PubChem: 163193560
• LOTUS: LTS0009831
• wikiData: Q105215816