(1aR,3R,3aR,4R,5R,6R,7aS)-4,5-diacetyloxy-6-[(1S,6R)-6-(2-methoxy-2-oxoethyl)-1,5,5-trimethyl-4-oxocyclohex-2-en-1-yl]-3a-methyl-7-methylidene-1a,2,3,4,5,6-hexahydroindeno[3,3a-b]oxirene-3-carboxylic acid

Details

• Internal ID: 22163860-fc53-4f14-8992-bcaba3ae1d7e
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Tetracarboxylic acids and derivatives
• IUPAC Name: (1aR,3R,3aR,4R,5R,6R,7aS)-4,5-diacetyloxy-6-[(1S,6R)-6-(2-methoxy-2-oxoethyl)-1,5,5-trimethyl-4-oxocyclohex-2-en-1-yl]-3a-methyl-7-methylidene-1a,2,3,4,5,6-hexahydroindeno[3,3a-b]oxirene-3-carboxylic acid
• SMILES (Canonical): CC(=O)OC1C(C(=C)C23C(O2)CC(C3(C1OC(=O)C)C)C(=O)O)C4(C=CC(=O)C(C4CC(=O)OC)(C)C)C
• SMILES (Isomeric): CC(=O)O[C@@H]1[C@@H](C(=C)[C@]23[C@H](O2)C[C@H]([C@@]3([C@H]1OC(=O)C)C)C(=O)O)[C@]4(C=CC(=O)C([C@@H]4CC(=O)OC)(C)C)C
• InChI: InChI=1S/C28H36O10/c1-13-21(26(6)10-9-18(31)25(4,5)17(26)12-20(32)35-8)22(36-14(2)29)23(37-15(3)30)27(7)16(24(33)34)11-19-28(13,27)38-19/h9-10,16-17,19,21-23H,1,11-12H2,2-8H3,(H,33,34)/t16-,17-,19+,21+,22+,23-,26-,27+,28+/m0/s1
• InChI Key: OZDJONMGTDYJGH-GFTJKIDQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₆O₁₀
• Molecular Weight: 532.60 g/mol
• Exact Mass: 532.23084734 g/mol
• Topological Polar Surface Area (TPSA): 146.00 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 2.63
• H-Bond Acceptor: 9
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9806	98.06%
Caco-2	-	0.7317	73.17%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6986	69.86%
OATP2B1 inhibitior	-	0.8589	85.89%
OATP1B1 inhibitior	+	0.7858	78.58%
OATP1B3 inhibitior	+	0.8062	80.62%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.8189	81.89%
P-glycoprotein inhibitior	+	0.8012	80.12%
P-glycoprotein substrate	+	0.6052	60.52%
CYP3A4 substrate	+	0.6845	68.45%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8938	89.38%
CYP3A4 inhibition	+	0.5557	55.57%
CYP2C9 inhibition	-	0.7321	73.21%
CYP2C19 inhibition	-	0.7163	71.63%
CYP2D6 inhibition	-	0.9326	93.26%
CYP1A2 inhibition	-	0.8718	87.18%
CYP2C8 inhibition	+	0.5792	57.92%
CYP inhibitory promiscuity	-	0.7949	79.49%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6271	62.71%
Eye corrosion	-	0.9835	98.35%
Eye irritation	-	0.8934	89.34%
Skin irritation	-	0.6718	67.18%
Skin corrosion	-	0.9228	92.28%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6107	61.07%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	+	0.5158	51.58%
skin sensitisation	-	0.7219	72.19%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.5574	55.74%
Acute Oral Toxicity (c)	III	0.4583	45.83%
Estrogen receptor binding	+	0.7127	71.27%
Androgen receptor binding	+	0.7238	72.38%
Thyroid receptor binding	+	0.5565	55.65%
Glucocorticoid receptor binding	+	0.7854	78.54%
Aromatase binding	+	0.6452	64.52%
PPAR gamma	+	0.7268	72.68%
Honey bee toxicity	-	0.8036	80.36%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9597	95.97%

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	98.11%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.93%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.63%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.26%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	91.38%	91.19%
CHEMBL2581	P07339	Cathepsin D	87.96%	98.95%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.73%	95.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.73%	95.56%
CHEMBL4208	P20618	Proteasome component C5	86.57%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.57%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.52%	94.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.74%	93.00%
CHEMBL2996	Q05655	Protein kinase C delta	82.70%	97.79%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.38%	99.17%
CHEMBL5028	O14672	ADAM10	82.31%	97.50%
CHEMBL3922	P50579	Methionine aminopeptidase 2	81.19%	97.28%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.04%	95.89%

Plants that contains it

• Turraea pubescens

Cross-Links

• PubChem: 24764409
• LOTUS: LTS0051903
• wikiData: Q105203700