[6-(5-acetyloxy-4,9a-dimethyl-2,7-dioxo-3a,5,6,9-tetrahydro-3H-furo[2,3-c]oxocin-4-yl)-5-formyloxy-3-(furan-3-yl)-3a-methyl-7-methylidene-1a,2,3,4,5,6-hexahydroindeno[1,7a-b]oxiren-4-yl] 2-acetyloxy-3-methylpentanoate

Details

• Internal ID: 1b65698b-41df-4f2a-b11c-2c14aaad420d
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Hexacarboxylic acids and derivatives
• IUPAC Name: [6-(5-acetyloxy-4,9a-dimethyl-2,7-dioxo-3a,5,6,9-tetrahydro-3H-furo[2,3-c]oxocin-4-yl)-5-formyloxy-3-(furan-3-yl)-3a-methyl-7-methylidene-1a,2,3,4,5,6-hexahydroindeno[1,7a-b]oxiren-4-yl] 2-acetyloxy-3-methylpentanoate
• SMILES (Canonical): CCC(C)C(C(=O)OC1C(C(C(=C)C23C1(C(CC2O3)C4=COC=C4)C)C5(C6CC(=O)OC6(COC(=O)CC5OC(=O)C)C)C)OC=O)OC(=O)C
• SMILES (Isomeric): CCC(C)C(C(=O)OC1C(C(C(=C)C23C1(C(CC2O3)C4=COC=C4)C)C5(C6CC(=O)OC6(COC(=O)CC5OC(=O)C)C)C)OC=O)OC(=O)C
• InChI: InChI=1S/C37H46O14/c1-9-18(2)30(48-21(5)40)33(43)49-32-31(46-17-38)29(19(3)37-26(50-37)12-23(36(32,37)8)22-10-11-44-15-22)35(7)24-13-28(42)51-34(24,6)16-45-27(41)14-25(35)47-20(4)39/h10-11,15,17-18,23-26,29-32H,3,9,12-14,16H2,1-2,4-8H3
• InChI Key: BILAMKFGAFCWCS-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₄₆O₁₄
• Molecular Weight: 714.80 g/mol
• Exact Mass: 714.28875614 g/mol
• Topological Polar Surface Area (TPSA): 184.00 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.73
• H-Bond Acceptor: 14
• H-Bond Donor: 0
• Rotatable Bonds: 10

Synonyms

• NSC324050
• DREGEANIN
• [6-(5-acetyloxy-4,9a-dimethyl-2,7-dioxo-3a,5,6,9-tetrahydro-3H-furo[2,3-c]oxocin-4-yl)-5-formyloxy-3-(furan-3-yl)-3a-methyl-7-methylidene-1a,2,3,4,5,6-hexahydroindeno[1,7a-b]oxiren-4-yl] 2-acetyloxy-3-methylpentanoate
• DTXSID30330862
• NSC-324050

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9918	99.18%
Caco-2	-	0.8252	82.52%
Blood Brain Barrier	+	0.9000	90.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7300	73.00%
OATP2B1 inhibitior	-	0.8530	85.30%
OATP1B1 inhibitior	-	0.3200	32.00%
OATP1B3 inhibitior	+	0.8566	85.66%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.9839	98.39%
P-glycoprotein inhibitior	+	0.8383	83.83%
P-glycoprotein substrate	+	0.7454	74.54%
CYP3A4 substrate	+	0.7192	71.92%
CYP2C9 substrate	-	0.8051	80.51%
CYP2D6 substrate	-	0.8446	84.46%
CYP3A4 inhibition	+	0.7991	79.91%
CYP2C9 inhibition	-	0.7618	76.18%
CYP2C19 inhibition	-	0.6969	69.69%
CYP2D6 inhibition	-	0.9410	94.10%
CYP1A2 inhibition	-	0.7565	75.65%
CYP2C8 inhibition	+	0.8252	82.52%
CYP inhibitory promiscuity	+	0.5836	58.36%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5987	59.87%
Eye corrosion	-	0.9860	98.60%
Eye irritation	-	0.8992	89.92%
Skin irritation	-	0.6698	66.98%
Skin corrosion	-	0.9384	93.84%
Ames mutagenesis	-	0.5437	54.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.3835	38.35%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	+	0.5474	54.74%
skin sensitisation	-	0.7742	77.42%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	+	0.5300	53.00%
Acute Oral Toxicity (c)	I	0.3981	39.81%
Estrogen receptor binding	+	0.7787	77.87%
Androgen receptor binding	+	0.7603	76.03%
Thyroid receptor binding	+	0.5754	57.54%
Glucocorticoid receptor binding	+	0.8116	81.16%
Aromatase binding	+	0.6759	67.59%
PPAR gamma	+	0.7650	76.50%
Honey bee toxicity	-	0.6546	65.46%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.50%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.37%	96.09%
CHEMBL2581	P07339	Cathepsin D	98.19%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.03%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.28%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.18%	86.33%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	90.10%	95.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.90%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.75%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.59%	97.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	87.57%	82.69%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.92%	96.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	86.53%	91.24%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	86.32%	89.34%
CHEMBL2996	Q05655	Protein kinase C delta	86.14%	97.79%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.08%	92.62%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.53%	97.14%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	84.29%	100.00%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	84.07%	98.75%
CHEMBL340	P08684	Cytochrome P450 3A4	83.84%	91.19%
CHEMBL3922	P50579	Methionine aminopeptidase 2	83.23%	97.28%
CHEMBL221	P23219	Cyclooxygenase-1	83.02%	90.17%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	82.89%	80.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.22%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.10%	97.25%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.52%	99.23%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.42%	89.50%

Plants that contains it

• Trichilia dregeana

Cross-Links

• PubChem: 433157
• LOTUS: LTS0114007
• wikiData: Q82095510