(3R,3aR,5aS,7S,9bS)-3a,7-dihydroxy-3,5a,9-trimethyl-4,5,6,7,8,9b-hexahydro-3H-benzo[g][1]benzofuran-2-one

Details

• Internal ID: 0d956e7c-da68-486f-b072-4e3b006eeea5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3R,3aR,5aS,7S,9bS)-3a,7-dihydroxy-3,5a,9-trimethyl-4,5,6,7,8,9b-hexahydro-3H-benzo[g][1]benzofuran-2-one
• SMILES (Canonical): CC1C(=O)OC2C1(CCC3(C2=C(CC(C3)O)C)C)O
• SMILES (Isomeric): C[C@H]1C(=O)O[C@@H]2[C@]1(CC[C@@]3(C2=C(C[C@@H](C3)O)C)C)O
• InChI: InChI=1S/C15H22O4/c1-8-6-10(16)7-14(3)4-5-15(18)9(2)13(17)19-12(15)11(8)14/h9-10,12,16,18H,4-7H2,1-3H3/t9-,10-,12-,14-,15+/m0/s1
• InChI Key: GGJMSNYGRXMJNL-YLHIVMMESA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.33 g/mol
• Exact Mass: 266.15180918 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 1.55
• H-Bond Acceptor: 4
• 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	+	0.9919	99.19%
Caco-2	+	0.8166	81.66%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7348	73.48%
OATP2B1 inhibitior	-	0.8505	85.05%
OATP1B1 inhibitior	+	0.8983	89.83%
OATP1B3 inhibitior	+	0.9299	92.99%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	+	0.5179	51.79%
BSEP inhibitior	-	0.8503	85.03%
P-glycoprotein inhibitior	-	0.9111	91.11%
P-glycoprotein substrate	-	0.7498	74.98%
CYP3A4 substrate	+	0.6121	61.21%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8595	85.95%
CYP3A4 inhibition	-	0.6698	66.98%
CYP2C9 inhibition	-	0.8918	89.18%
CYP2C19 inhibition	-	0.8450	84.50%
CYP2D6 inhibition	-	0.9524	95.24%
CYP1A2 inhibition	-	0.6256	62.56%
CYP2C8 inhibition	-	0.9371	93.71%
CYP inhibitory promiscuity	-	0.9274	92.74%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4124	41.24%
Eye corrosion	-	0.9926	99.26%
Eye irritation	-	0.6218	62.18%
Skin irritation	+	0.7340	73.40%
Skin corrosion	-	0.9138	91.38%
Ames mutagenesis	-	0.6237	62.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.6623	66.23%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.5132	51.32%
skin sensitisation	-	0.8413	84.13%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	+	0.6603	66.03%
Acute Oral Toxicity (c)	I	0.3769	37.69%
Estrogen receptor binding	-	0.4912	49.12%
Androgen receptor binding	-	0.5098	50.98%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.5686	56.86%
Aromatase binding	-	0.5612	56.12%
PPAR gamma	-	0.7068	70.68%
Honey bee toxicity	-	0.7631	76.31%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9880	98.80%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.94%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.98%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.98%	95.56%
CHEMBL2581	P07339	Cathepsin D	83.56%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.56%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.61%	99.23%
CHEMBL1937	Q92769	Histone deacetylase 2	81.30%	94.75%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.13%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.91%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.80%	86.33%

Plants that contains it

• Sphaeranthus indicus
• Sphaeranthus suaveolens

Cross-Links

• PubChem: 14589100
• LOTUS: LTS0272587
• wikiData: Q105008144