(3aR,4R,8aS,8bR)-3a,4-dihydroxy-6,8b-dimethyl-4,5,8,8a-tetrahydro-1H-cyclopenta[e][2]benzofuran-3,7-dione

Details

• Internal ID: 7b74a7f5-f237-46ce-894b-5e55aee104f7
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (3aR,4R,8aS,8bR)-3a,4-dihydroxy-6,8b-dimethyl-4,5,8,8a-tetrahydro-1H-cyclopenta[e][2]benzofuran-3,7-dione
• SMILES (Canonical): CC1=C2CC(C3(C(=O)OCC3(C2CC1=O)C)O)O
• SMILES (Isomeric): CC1=C2C[C@H]([C@]3(C(=O)OC[C@]3([C@H]2CC1=O)C)O)O
• InChI: InChI=1S/C13H16O5/c1-6-7-3-10(15)13(17)11(16)18-5-12(13,2)8(7)4-9(6)14/h8,10,15,17H,3-5H2,1-2H3/t8-,10+,12-,13+/m0/s1
• InChI Key: GQOIWZICLSNVJT-YPWHJJHSSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₆O₅
• Molecular Weight: 252.26 g/mol
• Exact Mass: 252.09977361 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): -0.05
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9800	98.00%
Caco-2	+	0.5465	54.65%
Blood Brain Barrier	+	0.5017	50.17%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8370	83.70%
OATP2B1 inhibitior	-	0.8492	84.92%
OATP1B1 inhibitior	+	0.8982	89.82%
OATP1B3 inhibitior	+	0.9716	97.16%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.8524	85.24%
P-glycoprotein inhibitior	-	0.9448	94.48%
P-glycoprotein substrate	-	0.8256	82.56%
CYP3A4 substrate	+	0.5261	52.61%
CYP2C9 substrate	-	0.7907	79.07%
CYP2D6 substrate	-	0.8976	89.76%
CYP3A4 inhibition	-	0.8139	81.39%
CYP2C9 inhibition	-	0.8703	87.03%
CYP2C19 inhibition	-	0.9107	91.07%
CYP2D6 inhibition	-	0.9439	94.39%
CYP1A2 inhibition	-	0.8075	80.75%
CYP2C8 inhibition	-	0.9390	93.90%
CYP inhibitory promiscuity	-	0.9741	97.41%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5012	50.12%
Eye corrosion	-	0.9875	98.75%
Eye irritation	-	0.5323	53.23%
Skin irritation	+	0.5133	51.33%
Skin corrosion	-	0.9223	92.23%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7515	75.15%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	+	0.7177	71.77%
skin sensitisation	-	0.8713	87.13%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.6233	62.33%
Acute Oral Toxicity (c)	III	0.3642	36.42%
Estrogen receptor binding	+	0.7311	73.11%
Androgen receptor binding	+	0.6832	68.32%
Thyroid receptor binding	-	0.5187	51.87%
Glucocorticoid receptor binding	-	0.5473	54.73%
Aromatase binding	-	0.5316	53.16%
PPAR gamma	-	0.5261	52.61%
Honey bee toxicity	-	0.8165	81.65%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9890	98.90%

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	94.18%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.45%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.93%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.79%	91.11%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.05%	96.77%
CHEMBL221	P23219	Cyclooxygenase-1	86.41%	90.17%
CHEMBL2581	P07339	Cathepsin D	85.70%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.45%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.31%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.33%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.75%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.14%	89.00%

Plants that contains it

• Illicium jiadifengpi

Cross-Links

• PubChem: 101792613
• LOTUS: LTS0026113
• wikiData: Q105015487