[(3aS,4S,5S,9R,11aR)-5,9-dihydroxy-6-methyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] 2-methylbut-2-enoate

Details

• Internal ID: 090c72c9-2a4b-482d-b266-64b37846d8bd
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: [(3aS,4S,5S,9R,11aR)-5,9-dihydroxy-6-methyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] 2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1C2C(C=CC(CC=C(C1O)C)O)OC(=O)C2=C
• SMILES (Isomeric): CC=C(C)C(=O)O[C@H]1[C@@H]2[C@@H](C=C[C@@H](CC=C([C@@H]1O)C)O)OC(=O)C2=C
• InChI: InChI=1S/C19H24O6/c1-5-10(2)18(22)25-17-15-12(4)19(23)24-14(15)9-8-13(20)7-6-11(3)16(17)21/h5-6,8-9,13-17,20-21H,4,7H2,1-3H3/t13-,14-,15+,16+,17+/m1/s1
• InChI Key: UYMFHMBJDXOWGB-NRKLIOEPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₄O₆
• Molecular Weight: 348.40 g/mol
• Exact Mass: 348.15728848 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.59
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9681	96.81%
Caco-2	+	0.6008	60.08%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.5541	55.41%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8549	85.49%
OATP1B3 inhibitior	+	0.9265	92.65%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.6290	62.90%
P-glycoprotein inhibitior	-	0.6948	69.48%
P-glycoprotein substrate	-	0.7922	79.22%
CYP3A4 substrate	+	0.5881	58.81%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8820	88.20%
CYP3A4 inhibition	-	0.8237	82.37%
CYP2C9 inhibition	-	0.9052	90.52%
CYP2C19 inhibition	-	0.8397	83.97%
CYP2D6 inhibition	-	0.9219	92.19%
CYP1A2 inhibition	-	0.7612	76.12%
CYP2C8 inhibition	-	0.8078	80.78%
CYP inhibitory promiscuity	-	0.9084	90.84%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5129	51.29%
Eye corrosion	-	0.9602	96.02%
Eye irritation	-	0.9112	91.12%
Skin irritation	-	0.6217	62.17%
Skin corrosion	-	0.9157	91.57%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3682	36.82%
Micronuclear	-	0.5800	58.00%
Hepatotoxicity	+	0.7375	73.75%
skin sensitisation	-	0.7845	78.45%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.6975	69.75%
Acute Oral Toxicity (c)	IV	0.3071	30.71%
Estrogen receptor binding	-	0.5502	55.02%
Androgen receptor binding	-	0.6274	62.74%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6958	69.58%
Aromatase binding	-	0.6175	61.75%
PPAR gamma	-	0.6589	65.89%
Honey bee toxicity	-	0.7351	73.51%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9186	91.86%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.12%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.48%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.59%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	89.28%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.61%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.50%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.29%	86.33%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.84%	91.07%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.26%	99.17%
CHEMBL221	P23219	Cyclooxygenase-1	82.22%	90.17%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.10%	95.50%

Plants that contains it

• Eupatorium rotundifolium

Cross-Links

• PubChem: 162870095
• LOTUS: LTS0050363
• wikiData: Q105281650