(3aR)-3abeta,4,5,5a,6,7,8,9balpha-Octahydro-4beta,6alpha-dihydroxy-3beta,5aalpha,9-trimethylnaphtho[1,2-b]furan-2(3H)-one

Details

• Internal ID: 8498a632-e4f4-4202-b3dd-e60fbc1621a4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3S,3aR,4S,5aR,6R,9bS)-4,6-dihydroxy-3,5a,9-trimethyl-3,3a,4,5,6,7,8,9b-octahydrobenzo[g][1]benzofuran-2-one
• SMILES (Canonical): CC1C2C(CC3(C(CCC(=C3C2OC1=O)C)O)C)O
• SMILES (Isomeric): C[C@H]1[C@@H]2[C@H](C[C@]3([C@@H](CCC(=C3[C@H]2OC1=O)C)O)C)O
• InChI: InChI=1S/C15H22O4/c1-7-4-5-10(17)15(3)6-9(16)11-8(2)14(18)19-13(11)12(7)15/h8-11,13,16-17H,4-6H2,1-3H3/t8-,9-,10+,11+,13-,15-/m0/s1
• InChI Key: PFMLUPKGJXFNCW-CEMRCVNMSA-N
• Popularity: 0 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: 0.70
• Atomic LogP (AlogP): 1.41
• 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	+	0.9959	99.59%
Caco-2	+	0.5517	55.17%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7077	70.77%
OATP2B1 inhibitior	-	0.8548	85.48%
OATP1B1 inhibitior	+	0.9149	91.49%
OATP1B3 inhibitior	+	0.9401	94.01%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	-	0.9070	90.70%
P-glycoprotein inhibitior	-	0.9190	91.90%
P-glycoprotein substrate	-	0.8551	85.51%
CYP3A4 substrate	+	0.6100	61.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8383	83.83%
CYP3A4 inhibition	-	0.6321	63.21%
CYP2C9 inhibition	-	0.9181	91.81%
CYP2C19 inhibition	-	0.9530	95.30%
CYP2D6 inhibition	-	0.9626	96.26%
CYP1A2 inhibition	-	0.7206	72.06%
CYP2C8 inhibition	-	0.9122	91.22%
CYP inhibitory promiscuity	-	0.9394	93.94%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4567	45.67%
Eye corrosion	-	0.9921	99.21%
Eye irritation	-	0.9492	94.92%
Skin irritation	+	0.6641	66.41%
Skin corrosion	-	0.9185	91.85%
Ames mutagenesis	-	0.6770	67.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.8061	80.61%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	+	0.5533	55.33%
skin sensitisation	-	0.7855	78.55%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	+	0.6395	63.95%
Acute Oral Toxicity (c)	I	0.4469	44.69%
Estrogen receptor binding	-	0.5867	58.67%
Androgen receptor binding	-	0.6059	60.59%
Thyroid receptor binding	+	0.5970	59.70%
Glucocorticoid receptor binding	+	0.5558	55.58%
Aromatase binding	-	0.7977	79.77%
PPAR gamma	-	0.7236	72.36%
Honey bee toxicity	-	0.8634	86.34%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9899	98.99%

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	96.41%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.25%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.98%	100.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.16%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.51%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.43%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.08%	89.00%
CHEMBL2581	P07339	Cathepsin D	83.50%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	83.12%	91.49%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.15%	97.09%

Plants that contains it

• Artemisia herba-alba

Cross-Links

• PubChem: 14413710
• LOTUS: LTS0019978
• wikiData: Q105207838