[(3aS,5R,6E,10Z,11aR)-5-hydroxy-6-(hydroxymethyl)-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-10-yl]methyl 2-methylpropanoate

Details

• Internal ID: 9790bc3f-a2e9-4294-91f8-94295aac31c8
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(3aS,5R,6E,10Z,11aR)-5-hydroxy-6-(hydroxymethyl)-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-10-yl]methyl 2-methylpropanoate
• SMILES (Canonical): CC(C)C(=O)OCC1=CC2C(CC(C(=CCC1)CO)O)C(=C)C(=O)O2
• SMILES (Isomeric): CC(C)C(=O)OC/C/1=C\[C@@H]2[C@@H](C[C@H](/C(=C/CC1)/CO)O)C(=C)C(=O)O2
• InChI: InChI=1S/C19H26O6/c1-11(2)18(22)24-10-13-5-4-6-14(9-20)16(21)8-15-12(3)19(23)25-17(15)7-13/h6-7,11,15-17,20-21H,3-5,8-10H2,1-2H3/b13-7-,14-6+/t15-,16+,17+/m0/s1
• InChI Key: RVKFWBVDFTVESX-NZKDXQKASA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₆O₆
• Molecular Weight: 350.40 g/mol
• Exact Mass: 350.17293854 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.67
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8762	87.62%
Caco-2	-	0.5914	59.14%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7838	78.38%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8765	87.65%
OATP1B3 inhibitior	+	0.9470	94.70%
MATE1 inhibitior	-	0.9212	92.12%
OCT2 inhibitior	-	0.6820	68.20%
BSEP inhibitior	+	0.6430	64.30%
P-glycoprotein inhibitior	-	0.7254	72.54%
P-glycoprotein substrate	-	0.7797	77.97%
CYP3A4 substrate	+	0.6081	60.81%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8838	88.38%
CYP3A4 inhibition	-	0.7777	77.77%
CYP2C9 inhibition	-	0.8440	84.40%
CYP2C19 inhibition	-	0.8320	83.20%
CYP2D6 inhibition	-	0.8820	88.20%
CYP1A2 inhibition	-	0.7342	73.42%
CYP2C8 inhibition	-	0.6088	60.88%
CYP inhibitory promiscuity	-	0.8633	86.33%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6918	69.18%
Eye corrosion	-	0.9795	97.95%
Eye irritation	-	0.8635	86.35%
Skin irritation	-	0.7204	72.04%
Skin corrosion	-	0.9398	93.98%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7193	71.93%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	+	0.6000	60.00%
skin sensitisation	-	0.8422	84.22%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.6300	63.00%
Acute Oral Toxicity (c)	III	0.5328	53.28%
Estrogen receptor binding	+	0.6318	63.18%
Androgen receptor binding	+	0.5495	54.95%
Thyroid receptor binding	+	0.5537	55.37%
Glucocorticoid receptor binding	+	0.7639	76.39%
Aromatase binding	-	0.6282	62.82%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.7673	76.73%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9250	92.50%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.40%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.59%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.40%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.19%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.33%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.77%	95.56%
CHEMBL2581	P07339	Cathepsin D	89.51%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.80%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.67%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.92%	86.33%

Plants that contains it

• Mikania guaco

Cross-Links

• PubChem: 12039269
• LOTUS: LTS0031697
• wikiData: Q105246081