(3aS,4S,5E,9R,10Z,11aR)-4,9-dihydroxy-6,10-dimethyl-3-methylidene-3a,4,7,8,9,11a-hexahydrocyclodeca[b]furan-2-one

Details

• Internal ID: 0bc82153-70eb-4dbb-b926-8c7627a88dce
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: (3aS,4S,5E,9R,10Z,11aR)-4,9-dihydroxy-6,10-dimethyl-3-methylidene-3a,4,7,8,9,11a-hexahydrocyclodeca[b]furan-2-one
• SMILES (Canonical): CC1=CC(C2C(C=C(C(CC1)O)C)OC(=O)C2=C)O
• SMILES (Isomeric): C/C/1=C\[C@@H]([C@H]2[C@@H](/C=C(\[C@@H](CC1)O)/C)OC(=O)C2=C)O
• InChI: InChI=1S/C15H20O4/c1-8-4-5-11(16)9(2)7-13-14(12(17)6-8)10(3)15(18)19-13/h6-7,11-14,16-17H,3-5H2,1-2H3/b8-6+,9-7-/t11-,12+,13-,14+/m1/s1
• InChI Key: YMNZWKHEJQGPIA-ZPWTYTSQSA-N
• Popularity: 0 references 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: 0.60
• Atomic LogP (AlogP): 1.49
• 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	+	0.9817	98.17%
Caco-2	+	0.7370	73.70%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.5523	55.23%
OATP2B1 inhibitior	-	0.8568	85.68%
OATP1B1 inhibitior	+	0.9398	93.98%
OATP1B3 inhibitior	+	0.9238	92.38%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8071	80.71%
BSEP inhibitior	-	0.9543	95.43%
P-glycoprotein inhibitior	-	0.8962	89.62%
P-glycoprotein substrate	-	0.9350	93.50%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8285	82.85%
CYP3A4 inhibition	-	0.6712	67.12%
CYP2C9 inhibition	-	0.8984	89.84%
CYP2C19 inhibition	-	0.8526	85.26%
CYP2D6 inhibition	-	0.9202	92.02%
CYP1A2 inhibition	+	0.5157	51.57%
CYP2C8 inhibition	-	0.9019	90.19%
CYP inhibitory promiscuity	-	0.9101	91.01%
UGT catelyzed	-	0.5638	56.38%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5430	54.30%
Eye corrosion	-	0.9743	97.43%
Eye irritation	-	0.8406	84.06%
Skin irritation	-	0.5166	51.66%
Skin corrosion	-	0.8202	82.02%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7073	70.73%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	+	0.6500	65.00%
skin sensitisation	-	0.7475	74.75%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7521	75.21%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.5561	55.61%
Acute Oral Toxicity (c)	II	0.3525	35.25%
Estrogen receptor binding	-	0.5252	52.52%
Androgen receptor binding	-	0.7256	72.56%
Thyroid receptor binding	-	0.6586	65.86%
Glucocorticoid receptor binding	-	0.4800	48.00%
Aromatase binding	-	0.7232	72.32%
PPAR gamma	-	0.5611	56.11%
Honey bee toxicity	-	0.8625	86.25%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9329	93.29%

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	92.71%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.73%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.39%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.11%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.13%	89.00%
CHEMBL2581	P07339	Cathepsin D	83.66%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.90%	97.09%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.60%	93.03%

Plants that contains it

• Artemisia arbuscula
• Cota altissima
• Gonospermum gomerae
• Tanacetum vulgare

Cross-Links

• PubChem: 163075601
• LOTUS: LTS0027147
• wikiData: Q105350667