(3S,3aR,4S,6E,9R,10E,11aR)-4,9-dihydroxy-3,6,10-trimethyl-3a,4,5,8,9,11a-hexahydro-3H-cyclodeca[b]furan-2-one

Details

• Internal ID: f3338970-34d9-4d71-87ce-28e9dbc09a6a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: (3S,3aR,4S,6E,9R,10E,11aR)-4,9-dihydroxy-3,6,10-trimethyl-3a,4,5,8,9,11a-hexahydro-3H-cyclodeca[b]furan-2-one
• SMILES (Canonical): CC1C2C(CC(=CCC(C(=CC2OC1=O)C)O)C)O
• SMILES (Isomeric): C[C@H]1[C@@H]2[C@H](C/C(=C/C[C@H](/C(=C/[C@H]2OC1=O)/C)O)/C)O
• InChI: InChI=1S/C15H22O4/c1-8-4-5-11(16)9(2)7-13-14(12(17)6-8)10(3)15(18)19-13/h4,7,10-14,16-17H,5-6H2,1-3H3/b8-4+,9-7+/t10-,11+,12-,13+,14+/m0/s1
• InChI Key: GOKGKERIBQYAOC-GABXNWTDSA-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: 0.90
• Atomic LogP (AlogP): 1.57
• 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	+	0.9922	99.22%
Caco-2	+	0.6425	64.25%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.4753	47.53%
OATP2B1 inhibitior	-	0.8582	85.82%
OATP1B1 inhibitior	+	0.9233	92.33%
OATP1B3 inhibitior	+	0.9556	95.56%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8985	89.85%
P-glycoprotein inhibitior	-	0.9108	91.08%
P-glycoprotein substrate	-	0.7870	78.70%
CYP3A4 substrate	+	0.5272	52.72%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8313	83.13%
CYP3A4 inhibition	-	0.7524	75.24%
CYP2C9 inhibition	-	0.9330	93.30%
CYP2C19 inhibition	-	0.9077	90.77%
CYP2D6 inhibition	-	0.9561	95.61%
CYP1A2 inhibition	-	0.6002	60.02%
CYP2C8 inhibition	-	0.9515	95.15%
CYP inhibitory promiscuity	-	0.9272	92.72%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.4405	44.05%
Eye corrosion	-	0.9693	96.93%
Eye irritation	-	0.9536	95.36%
Skin irritation	+	0.5126	51.26%
Skin corrosion	-	0.9228	92.28%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8125	81.25%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	+	0.6087	60.87%
skin sensitisation	-	0.7341	73.41%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.6279	62.79%
Acute Oral Toxicity (c)	III	0.3680	36.80%
Estrogen receptor binding	-	0.6813	68.13%
Androgen receptor binding	-	0.7377	73.77%
Thyroid receptor binding	-	0.6232	62.32%
Glucocorticoid receptor binding	-	0.5746	57.46%
Aromatase binding	-	0.8405	84.05%
PPAR gamma	-	0.7729	77.29%
Honey bee toxicity	-	0.8555	85.55%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9507	95.07%

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	90.54%	95.56%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	89.17%	86.00%
CHEMBL2581	P07339	Cathepsin D	87.73%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.99%	97.25%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.31%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.90%	96.09%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.55%	93.03%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.83%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.75%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.70%	100.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	80.19%	91.11%

Plants that contains it

• Helminthotheca echioides

Cross-Links

• PubChem: 162912326
• LOTUS: LTS0014871
• wikiData: Q105014109