(-)-Sivasinolide

Details

• Internal ID: 1d7eb641-09a4-4555-9fbd-9b05c482fc43
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3aS,4R,4aS,8R,8aR,9aS)-4,8-dihydroxy-5,8a-dimethyl-3-methylidene-4,4a,7,8,9,9a-hexahydro-3aH-benzo[f][1]benzofuran-2-one
• SMILES (Canonical): CC1=CCC(C2(C1C(C3C(C2)OC(=O)C3=C)O)C)O
• SMILES (Isomeric): CC1=CC[C@H]([C@]2([C@H]1[C@H]([C@H]3[C@H](C2)OC(=O)C3=C)O)C)O
• InChI: InChI=1S/C15H20O4/c1-7-4-5-10(16)15(3)6-9-11(13(17)12(7)15)8(2)14(18)19-9/h4,9-13,16-17H,2,5-6H2,1,3H3/t9-,10+,11+,12+,13-,15-/m0/s1
• InChI Key: BICYHGOZXYLJIO-XFKURJONSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.32 g/mol
• Exact Mass: 264.13615911 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 1.18
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• CHEMBL512455

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9916	99.16%
Caco-2	+	0.5635	56.35%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6035	60.35%
OATP2B1 inhibitior	-	0.8581	85.81%
OATP1B1 inhibitior	+	0.9370	93.70%
OATP1B3 inhibitior	+	0.9066	90.66%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9646	96.46%
P-glycoprotein inhibitior	-	0.9090	90.90%
P-glycoprotein substrate	-	0.8845	88.45%
CYP3A4 substrate	+	0.5943	59.43%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8379	83.79%
CYP3A4 inhibition	-	0.5315	53.15%
CYP2C9 inhibition	-	0.8999	89.99%
CYP2C19 inhibition	-	0.8721	87.21%
CYP2D6 inhibition	-	0.9489	94.89%
CYP1A2 inhibition	-	0.7694	76.94%
CYP2C8 inhibition	-	0.8032	80.32%
CYP inhibitory promiscuity	-	0.8359	83.59%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4299	42.99%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.9308	93.08%
Skin irritation	+	0.5427	54.27%
Skin corrosion	-	0.8823	88.23%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6777	67.77%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	+	0.7744	77.44%
skin sensitisation	-	0.7021	70.21%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	+	0.5180	51.80%
Acute Oral Toxicity (c)	I	0.4738	47.38%
Estrogen receptor binding	-	0.4834	48.34%
Androgen receptor binding	+	0.5825	58.25%
Thyroid receptor binding	-	0.5445	54.45%
Glucocorticoid receptor binding	-	0.6275	62.75%
Aromatase binding	-	0.7989	79.89%
PPAR gamma	-	0.4903	49.03%
Honey bee toxicity	-	0.7675	76.75%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9941	99.41%

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	94.24%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.62%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.55%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.46%	94.00%
CHEMBL4530	P00488	Coagulation factor XIII	86.55%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	86.39%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.23%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.46%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.45%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.34%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.13%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.63%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.20%	97.25%

Plants that contains it

• Cota altissima
• Gonospermum canariense
• Tanacetum argenteum
• Tanacetum densum

Cross-Links

• PubChem: 10333024
• LOTUS: LTS0054606
• wikiData: Q104936390