[(3S)-3-[(3aR,6S,7R,8aR)-5,7-dimethyl-3-methylidene-2-oxo-6,7,8,8a-tetrahydro-3aH-cyclohepta[b]furan-6-yl]-3-hydroxypropyl] acetate

Details

• Internal ID: 00f8f0bb-2860-4f7a-9146-6fd01a388227
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: [(3S)-3-[(3aR,6S,7R,8aR)-5,7-dimethyl-3-methylidene-2-oxo-6,7,8,8a-tetrahydro-3aH-cyclohepta[b]furan-6-yl]-3-hydroxypropyl] acetate
• SMILES (Canonical): CC1CC2C(C=C(C1C(CCOC(=O)C)O)C)C(=C)C(=O)O2
• SMILES (Isomeric): C[C@@H]1C[C@@H]2[C@H](C=C([C@H]1[C@H](CCOC(=O)C)O)C)C(=C)C(=O)O2
• InChI: InChI=1S/C17H24O5/c1-9-7-13-11(3)17(20)22-15(13)8-10(2)16(9)14(19)5-6-21-12(4)18/h7,10,13-16,19H,3,5-6,8H2,1-2,4H3/t10-,13-,14+,15-,16-/m1/s1
• InChI Key: UBTXDGQQIJWQJQ-LMXXTMHSSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₄O₅
• Molecular Weight: 308.40 g/mol
• Exact Mass: 308.16237386 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.00
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9828	98.28%
Caco-2	-	0.6106	61.06%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6592	65.92%
OATP2B1 inhibitior	-	0.8562	85.62%
OATP1B1 inhibitior	+	0.9048	90.48%
OATP1B3 inhibitior	+	0.9077	90.77%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.8935	89.35%
P-glycoprotein inhibitior	-	0.7391	73.91%
P-glycoprotein substrate	-	0.7225	72.25%
CYP3A4 substrate	+	0.6192	61.92%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8823	88.23%
CYP3A4 inhibition	-	0.5757	57.57%
CYP2C9 inhibition	-	0.7446	74.46%
CYP2C19 inhibition	-	0.8156	81.56%
CYP2D6 inhibition	-	0.9342	93.42%
CYP1A2 inhibition	+	0.5539	55.39%
CYP2C8 inhibition	-	0.7725	77.25%
CYP inhibitory promiscuity	-	0.9254	92.54%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6945	69.45%
Eye corrosion	-	0.9806	98.06%
Eye irritation	-	0.7390	73.90%
Skin irritation	-	0.5801	58.01%
Skin corrosion	-	0.9292	92.92%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5109	51.09%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	+	0.7306	73.06%
skin sensitisation	-	0.8587	85.87%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.5691	56.91%
Acute Oral Toxicity (c)	III	0.3833	38.33%
Estrogen receptor binding	+	0.6267	62.67%
Androgen receptor binding	+	0.5473	54.73%
Thyroid receptor binding	-	0.5718	57.18%
Glucocorticoid receptor binding	-	0.4727	47.27%
Aromatase binding	-	0.6325	63.25%
PPAR gamma	-	0.7521	75.21%
Honey bee toxicity	-	0.8280	82.80%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.9781	97.81%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.63%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.34%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.31%	91.11%
CHEMBL2581	P07339	Cathepsin D	88.56%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.32%	85.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.13%	99.17%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	84.68%	94.80%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.92%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	83.26%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.06%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.12%	94.45%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.65%	95.50%

Plants that contains it

• Gaillardia pulchella

Cross-Links

• PubChem: 162946681
• LOTUS: LTS0224338
• wikiData: Q105269659