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

Details

• Internal ID: 6bd57e10-cb46-4aaf-8b8d-2d247989d07b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: (3aR,5E,8R,9E,11aS)-8-hydroxy-6,10-dimethyl-3-methylidene-3a,4,7,8,11,11a-hexahydrocyclodeca[b]furan-2-one
• SMILES (Canonical): CC1=CCC2C(CC(=CC(C1)O)C)OC(=O)C2=C
• SMILES (Isomeric): C/C/1=C\C[C@H]2[C@H](C/C(=C/[C@@H](C1)O)/C)OC(=O)C2=C
• InChI: InChI=1S/C15H20O3/c1-9-4-5-13-11(3)15(17)18-14(13)8-10(2)7-12(16)6-9/h4,7,12-14,16H,3,5-6,8H2,1-2H3/b9-4+,10-7+/t12-,13-,14+/m1/s1
• InChI Key: TXXSOUFHWOHCLV-CARDDPLKSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.32 g/mol
• Exact Mass: 248.14124450 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 2.52
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9947	99.47%
Caco-2	+	0.8766	87.66%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.5237	52.37%
OATP2B1 inhibitior	-	0.8559	85.59%
OATP1B1 inhibitior	+	0.9087	90.87%
OATP1B3 inhibitior	+	0.9380	93.80%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.8970	89.70%
P-glycoprotein inhibitior	-	0.8941	89.41%
P-glycoprotein substrate	-	0.9292	92.92%
CYP3A4 substrate	+	0.5182	51.82%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8285	82.85%
CYP3A4 inhibition	-	0.7159	71.59%
CYP2C9 inhibition	-	0.9296	92.96%
CYP2C19 inhibition	-	0.8373	83.73%
CYP2D6 inhibition	-	0.9483	94.83%
CYP1A2 inhibition	-	0.5820	58.20%
CYP2C8 inhibition	-	0.8503	85.03%
CYP inhibitory promiscuity	-	0.9210	92.10%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9417	94.17%
Carcinogenicity (trinary)	Non-required	0.5827	58.27%
Eye corrosion	-	0.9581	95.81%
Eye irritation	-	0.6171	61.71%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9152	91.52%
Ames mutagenesis	-	0.6354	63.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4850	48.50%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	+	0.6750	67.50%
skin sensitisation	-	0.5741	57.41%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.6188	61.88%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.8608	86.08%
Acute Oral Toxicity (c)	III	0.4877	48.77%
Estrogen receptor binding	-	0.6495	64.95%
Androgen receptor binding	-	0.5684	56.84%
Thyroid receptor binding	-	0.6849	68.49%
Glucocorticoid receptor binding	-	0.5407	54.07%
Aromatase binding	-	0.7065	70.65%
PPAR gamma	-	0.6066	60.66%
Honey bee toxicity	-	0.8404	84.04%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9876	98.76%

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	90.03%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.51%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.29%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.14%	99.23%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	85.28%	93.03%
CHEMBL2581	P07339	Cathepsin D	85.16%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	81.32%	94.73%

Plants that contains it

• Geigeria rigida

Cross-Links

• PubChem: 14414341
• LOTUS: LTS0131974
• wikiData: Q105267140