(3aR,4R,5aR,6R,9bS)-4,6-dihydroxy-5a,9-dimethyl-3-methylidene-3a,4,5,6,7,9b-hexahydrobenzo[g][1]benzofuran-2,8-dione

Details

• Internal ID: 0fc2d4fa-5ddd-442e-8f06-af226689d758
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3aR,4R,5aR,6R,9bS)-4,6-dihydroxy-5a,9-dimethyl-3-methylidene-3a,4,5,6,7,9b-hexahydrobenzo[g][1]benzofuran-2,8-dione
• SMILES (Canonical): CC1=C2C3C(C(CC2(C(CC1=O)O)C)O)C(=C)C(=O)O3
• SMILES (Isomeric): CC1=C2[C@@H]3[C@@H]([C@@H](C[C@]2([C@@H](CC1=O)O)C)O)C(=C)C(=O)O3
• InChI: InChI=1S/C15H18O5/c1-6-8(16)4-10(18)15(3)5-9(17)11-7(2)14(19)20-13(11)12(6)15/h9-11,13,17-18H,2,4-5H2,1,3H3/t9-,10-,11-,13+,15+/m1/s1
• InChI Key: DQHMFGYAZPJNTJ-FHEMJXCISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₅
• Molecular Weight: 278.30 g/mol
• Exact Mass: 278.11542367 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): 0.51
• 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	+	0.9943	99.43%
Caco-2	+	0.6409	64.09%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6949	69.49%
OATP2B1 inhibitior	-	0.8574	85.74%
OATP1B1 inhibitior	+	0.8806	88.06%
OATP1B3 inhibitior	+	0.9105	91.05%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.9381	93.81%
P-glycoprotein inhibitior	-	0.8370	83.70%
P-glycoprotein substrate	-	0.8266	82.66%
CYP3A4 substrate	+	0.5782	57.82%
CYP2C9 substrate	-	0.7735	77.35%
CYP2D6 substrate	-	0.8955	89.55%
CYP3A4 inhibition	-	0.6015	60.15%
CYP2C9 inhibition	-	0.8934	89.34%
CYP2C19 inhibition	-	0.9485	94.85%
CYP2D6 inhibition	-	0.9539	95.39%
CYP1A2 inhibition	-	0.8121	81.21%
CYP2C8 inhibition	-	0.9216	92.16%
CYP inhibitory promiscuity	-	0.9237	92.37%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4115	41.15%
Eye corrosion	-	0.9861	98.61%
Eye irritation	-	0.6811	68.11%
Skin irritation	+	0.5348	53.48%
Skin corrosion	-	0.8670	86.70%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5702	57.02%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	+	0.6908	69.08%
skin sensitisation	-	0.7205	72.05%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	+	0.7683	76.83%
Acute Oral Toxicity (c)	I	0.3976	39.76%
Estrogen receptor binding	-	0.4851	48.51%
Androgen receptor binding	-	0.4830	48.30%
Thyroid receptor binding	-	0.5223	52.23%
Glucocorticoid receptor binding	-	0.4680	46.80%
Aromatase binding	-	0.7956	79.56%
PPAR gamma	-	0.5465	54.65%
Honey bee toxicity	-	0.6515	65.15%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9959	99.59%

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	97.53%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.29%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.32%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.20%	99.23%
CHEMBL221	P23219	Cyclooxygenase-1	87.27%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.87%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.55%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.17%	100.00%
CHEMBL1902	P62942	FK506-binding protein 1A	81.63%	97.05%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.68%	96.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.66%	97.14%

Plants that contains it

• Cassinia subtropica

Cross-Links

• PubChem: 14191313
• LOTUS: LTS0054947
• wikiData: Q104986942