[(3aR,4S,6Z,10Z,11aR)-6-formyl-10-(hydroxymethyl)-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] 2-methylprop-2-enoate

Details

• Internal ID: b24ed345-a645-4dc5-8ff2-5d25a554dc40
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(3aR,4S,6Z,10Z,11aR)-6-formyl-10-(hydroxymethyl)-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] 2-methylprop-2-enoate
• SMILES (Canonical): CC(=C)C(=O)OC1CC(=CCCC(=CC2C1C(=C)C(=O)O2)CO)C=O
• SMILES (Isomeric): CC(=C)C(=O)O[C@H]1C/C(=C/CC/C(=C/[C@@H]2[C@@H]1C(=C)C(=O)O2)/CO)/C=O
• InChI: InChI=1S/C19H22O6/c1-11(2)18(22)24-15-7-13(9-20)5-4-6-14(10-21)8-16-17(15)12(3)19(23)25-16/h5,8-9,15-17,21H,1,3-4,6-7,10H2,2H3/b13-5-,14-8-/t15-,16+,17+/m0/s1
• InChI Key: MPDLVXQTORTGFB-YINPGZOOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₂O₆
• Molecular Weight: 346.40 g/mol
• Exact Mass: 346.14163842 g/mol
• Topological Polar Surface Area (TPSA): 89.90 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.80
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9722	97.22%
Caco-2	-	0.6521	65.21%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.8169	81.69%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8668	86.68%
OATP1B3 inhibitior	+	0.9568	95.68%
MATE1 inhibitior	-	0.8212	82.12%
OCT2 inhibitior	-	0.6820	68.20%
BSEP inhibitior	-	0.6870	68.70%
P-glycoprotein inhibitior	-	0.6703	67.03%
P-glycoprotein substrate	-	0.6234	62.34%
CYP3A4 substrate	+	0.6183	61.83%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8830	88.30%
CYP3A4 inhibition	-	0.8717	87.17%
CYP2C9 inhibition	-	0.8440	84.40%
CYP2C19 inhibition	-	0.8281	82.81%
CYP2D6 inhibition	-	0.9217	92.17%
CYP1A2 inhibition	-	0.6167	61.67%
CYP2C8 inhibition	-	0.5937	59.37%
CYP inhibitory promiscuity	-	0.8582	85.82%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9543	95.43%
Carcinogenicity (trinary)	Non-required	0.6905	69.05%
Eye corrosion	-	0.9485	94.85%
Eye irritation	-	0.7602	76.02%
Skin irritation	-	0.6967	69.67%
Skin corrosion	-	0.9350	93.50%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4466	44.66%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.5435	54.35%
skin sensitisation	-	0.8422	84.22%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.7627	76.27%
Acute Oral Toxicity (c)	III	0.5264	52.64%
Estrogen receptor binding	-	0.4765	47.65%
Androgen receptor binding	-	0.5283	52.83%
Thyroid receptor binding	-	0.5508	55.08%
Glucocorticoid receptor binding	+	0.6496	64.96%
Aromatase binding	-	0.5309	53.09%
PPAR gamma	+	0.5829	58.29%
Honey bee toxicity	-	0.7476	74.76%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9364	93.64%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	98.48%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.62%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.93%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.65%	94.45%
CHEMBL2581	P07339	Cathepsin D	91.57%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.31%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	84.19%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.05%	86.33%
CHEMBL5028	O14672	ADAM10	81.91%	97.50%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.61%	95.50%

Plants that contains it

• Gymnanthemum pectorale
• Sideritis kuegleriana
• Sideritis leucantha

Cross-Links

• PubChem: 101967046
• LOTUS: LTS0138682
• wikiData: Q105225039