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

Details

• Internal ID: e6cfc5c3-bf3d-4ae6-81e9-0bdfdd174c09
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: (3aS,4R,6E,8R,10E,11aR)-4,8-dihydroxy-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2-one
• SMILES (Canonical): CC1=CC2C(C(CC(=CC(C1)O)C)O)C(=C)C(=O)O2
• SMILES (Isomeric): C/C/1=C\[C@@H]2[C@H]([C@@H](C/C(=C/[C@@H](C1)O)/C)O)C(=C)C(=O)O2
• InChI: InChI=1S/C15H20O4/c1-8-4-11(16)5-9(2)7-13-14(12(17)6-8)10(3)15(18)19-13/h4,7,11-14,16-17H,3,5-6H2,1-2H3/b8-4+,9-7+/t11-,12+,13+,14-/m0/s1
• InChI Key: FGJATCOCAOQTBA-WCLYOORWSA-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: 0.70
• 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	+	0.9777	97.77%
Caco-2	+	0.6651	66.51%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.4832	48.32%
OATP2B1 inhibitior	-	0.8582	85.82%
OATP1B1 inhibitior	+	0.9143	91.43%
OATP1B3 inhibitior	+	0.9380	93.80%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9298	92.98%
P-glycoprotein inhibitior	-	0.8619	86.19%
P-glycoprotein substrate	-	0.9072	90.72%
CYP3A4 substrate	-	0.5201	52.01%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8285	82.85%
CYP3A4 inhibition	-	0.7499	74.99%
CYP2C9 inhibition	-	0.8952	89.52%
CYP2C19 inhibition	-	0.8433	84.33%
CYP2D6 inhibition	-	0.9426	94.26%
CYP1A2 inhibition	-	0.7045	70.45%
CYP2C8 inhibition	-	0.9570	95.70%
CYP inhibitory promiscuity	-	0.8854	88.54%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.4987	49.87%
Eye corrosion	-	0.9671	96.71%
Eye irritation	-	0.6610	66.10%
Skin irritation	-	0.5824	58.24%
Skin corrosion	-	0.9084	90.84%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7399	73.99%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	+	0.6774	67.74%
skin sensitisation	-	0.6954	69.54%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.6855	68.55%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.6604	66.04%
Acute Oral Toxicity (c)	II	0.3494	34.94%
Estrogen receptor binding	-	0.6324	63.24%
Androgen receptor binding	-	0.5973	59.73%
Thyroid receptor binding	-	0.5669	56.69%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	-	0.7091	70.91%
PPAR gamma	-	0.5891	58.91%
Honey bee toxicity	-	0.8581	85.81%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9488	94.88%

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	90.14%	95.56%
CHEMBL4040	P28482	MAP kinase ERK2	89.26%	83.82%
CHEMBL3401	O75469	Pregnane X receptor	85.95%	94.73%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.12%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.17%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.96%	99.23%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.43%	93.03%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.14%	85.14%
CHEMBL2581	P07339	Cathepsin D	80.32%	98.95%

Plants that contains it

• Eupatorium mikanioides
• Helianthus pumilus

Cross-Links

• PubChem: 162886775
• LOTUS: LTS0038404
• wikiData: Q104994915