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

Details

• Internal ID: 8d3122b8-4c75-4a47-850b-4ed26c9a9548
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Pentacarboxylic acids and derivatives
• IUPAC Name: (1aR,3R,3aR,4R,5R,6R,7aS)-4,5-diacetyloxy-6-[(3R,4R)-3-(2-methoxy-2-oxoethyl)-2,2,4-trimethyl-7-oxo-3H-oxepin-4-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)OC(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)OC([C@@H]4CC(=O)OC)(C)C)C
• InChI: InChI=1S/C28H36O11/c1-13-21(26(6)10-9-19(31)39-25(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)11-18-28(13,27)38-18/h9-10,16-18,21-23H,1,11-12H2,2-8H3,(H,33,34)/t16-,17-,18+,21+,22+,23-,26-,27+,28+/m0/s1
• InChI Key: FERCDEWAQLVSBE-LELWZTHMSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₆O₁₁
• Molecular Weight: 548.60 g/mol
• Exact Mass: 548.22576196 g/mol
• Topological Polar Surface Area (TPSA): 155.00 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 2.36
• H-Bond Acceptor: 10
• 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	+	0.9774	97.74%
Caco-2	-	0.7582	75.82%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6770	67.70%
OATP2B1 inhibitior	-	0.8591	85.91%
OATP1B1 inhibitior	+	0.7944	79.44%
OATP1B3 inhibitior	+	0.7966	79.66%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.8950	89.50%
P-glycoprotein inhibitior	+	0.8208	82.08%
P-glycoprotein substrate	+	0.6278	62.78%
CYP3A4 substrate	+	0.6937	69.37%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8960	89.60%
CYP3A4 inhibition	+	0.6427	64.27%
CYP2C9 inhibition	-	0.7745	77.45%
CYP2C19 inhibition	-	0.7595	75.95%
CYP2D6 inhibition	-	0.9319	93.19%
CYP1A2 inhibition	-	0.9129	91.29%
CYP2C8 inhibition	+	0.6417	64.17%
CYP inhibitory promiscuity	-	0.8368	83.68%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6141	61.41%
Eye corrosion	-	0.9837	98.37%
Eye irritation	-	0.8892	88.92%
Skin irritation	-	0.6839	68.39%
Skin corrosion	-	0.9163	91.63%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6082	60.82%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.7375	73.75%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	+	0.5967	59.67%
Acute Oral Toxicity (c)	III	0.3854	38.54%
Estrogen receptor binding	+	0.7173	71.73%
Androgen receptor binding	+	0.7275	72.75%
Thyroid receptor binding	+	0.5529	55.29%
Glucocorticoid receptor binding	+	0.7731	77.31%
Aromatase binding	+	0.6622	66.22%
PPAR gamma	+	0.7308	73.08%
Honey bee toxicity	-	0.7977	79.77%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9564	95.64%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.13%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.54%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.31%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	91.92%	91.19%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.63%	96.09%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	89.31%	95.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.62%	95.56%
CHEMBL4208	P20618	Proteasome component C5	87.22%	90.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.43%	94.00%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	85.89%	81.11%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.72%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.57%	99.23%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.29%	99.17%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	82.97%	94.42%
CHEMBL2581	P07339	Cathepsin D	82.86%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.47%	86.33%
CHEMBL3922	P50579	Methionine aminopeptidase 2	81.88%	97.28%
CHEMBL5028	O14672	ADAM10	81.57%	97.50%

Plants that contains it

• Munronia pinnata

Cross-Links

• PubChem: 122178837
• LOTUS: LTS0228535
• wikiData: Q104994155