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

Details

• Internal ID: 1e892884-5e3e-4bfe-85fb-615df4ed5a9e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: (3aS,4R,6E,10E,11aR)-4-[(E)-5-hydroxy-3-(hydroxymethyl)-2-oxopent-3-enoxy]-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2-one
• InChI: InChI=1S/C21H28O6/c1-13-5-4-6-14(2)10-19-20(15(3)21(25)27-19)18(9-13)26-12-17(24)16(11-23)7-8-22/h5,7,10,18-20,22-23H,3-4,6,8-9,11-12H2,1-2H3/b13-5+,14-10+,16-7+/t18-,19-,20+/m1/s1
• InChI Key: WZCWQUPNPBJVFL-LOYFWHQGSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₈O₆
• Molecular Weight: 376.40 g/mol
• Exact Mass: 376.18858861 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 2.03
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9066	90.66%
Caco-2	+	0.5247	52.47%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7559	75.59%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9111	91.11%
OATP1B3 inhibitior	+	0.9433	94.33%
MATE1 inhibitior	-	0.8612	86.12%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.4641	46.41%
P-glycoprotein inhibitior	-	0.5187	51.87%
P-glycoprotein substrate	-	0.7813	78.13%
CYP3A4 substrate	+	0.6139	61.39%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9010	90.10%
CYP3A4 inhibition	-	0.6313	63.13%
CYP2C9 inhibition	-	0.8786	87.86%
CYP2C19 inhibition	-	0.8298	82.98%
CYP2D6 inhibition	-	0.9137	91.37%
CYP1A2 inhibition	-	0.5558	55.58%
CYP2C8 inhibition	+	0.4694	46.94%
CYP inhibitory promiscuity	-	0.8901	89.01%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6494	64.94%
Eye corrosion	-	0.9812	98.12%
Eye irritation	-	0.8506	85.06%
Skin irritation	-	0.5624	56.24%
Skin corrosion	-	0.9401	94.01%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4517	45.17%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.9041	90.41%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	+	0.6791	67.91%
Acute Oral Toxicity (c)	III	0.5452	54.52%
Estrogen receptor binding	+	0.6085	60.85%
Androgen receptor binding	+	0.5482	54.82%
Thyroid receptor binding	-	0.5310	53.10%
Glucocorticoid receptor binding	+	0.5900	59.00%
Aromatase binding	-	0.5276	52.76%
PPAR gamma	+	0.5914	59.14%
Honey bee toxicity	-	0.7993	79.93%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9781	97.81%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.88%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.41%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.63%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.27%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.23%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	86.39%	94.73%
CHEMBL2581	P07339	Cathepsin D	85.71%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.80%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.59%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.80%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.35%	99.17%

Plants that contains it

• Picradeniopsis schaffneri

Cross-Links

• PubChem: 162867405
• LOTUS: LTS0200428
• wikiData: Q105322967