[(3aR,4R,6R,9E,11aR)-6,10-bis(hydroxymethyl)-3-methylidene-2-oxo-3a,4,5,6,7,8,11,11a-octahydrocyclodeca[b]furan-4-yl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: f0fd09fe-abdf-4186-ad34-2799023884a0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(3aR,4R,6R,9E,11aR)-6,10-bis(hydroxymethyl)-3-methylidene-2-oxo-3a,4,5,6,7,8,11,11a-octahydrocyclodeca[b]furan-4-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1CC(CCC=C(CC2C1C(=C)C(=O)O2)CO)CO
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@@H]1C[C@@H](CC/C=C(\C[C@@H]2[C@@H]1C(=C)C(=O)O2)/CO)CO
• InChI: InChI=1S/C20H28O6/c1-4-12(2)19(23)25-16-8-14(10-21)6-5-7-15(11-22)9-17-18(16)13(3)20(24)26-17/h4,7,14,16-18,21-22H,3,5-6,8-11H2,1-2H3/b12-4-,15-7+/t14-,16-,17-,18-/m1/s1
• InChI Key: OOKRHFBXNRLUNX-XBGVIYRFSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₆
• Molecular Weight: 364.40 g/mol
• Exact Mass: 364.18858861 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 2.06
• 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	+	0.9249	92.49%
Caco-2	-	0.5154	51.54%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8365	83.65%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8770	87.70%
OATP1B3 inhibitior	+	0.9550	95.50%
MATE1 inhibitior	-	0.8012	80.12%
OCT2 inhibitior	-	0.7320	73.20%
BSEP inhibitior	-	0.5252	52.52%
P-glycoprotein inhibitior	-	0.6417	64.17%
P-glycoprotein substrate	-	0.6637	66.37%
CYP3A4 substrate	+	0.6156	61.56%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8868	88.68%
CYP3A4 inhibition	-	0.8016	80.16%
CYP2C9 inhibition	-	0.8866	88.66%
CYP2C19 inhibition	-	0.8260	82.60%
CYP2D6 inhibition	-	0.8996	89.96%
CYP1A2 inhibition	-	0.6793	67.93%
CYP2C8 inhibition	+	0.4439	44.39%
CYP inhibitory promiscuity	-	0.8518	85.18%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9543	95.43%
Carcinogenicity (trinary)	Non-required	0.6777	67.77%
Eye corrosion	-	0.9678	96.78%
Eye irritation	-	0.8868	88.68%
Skin irritation	-	0.7451	74.51%
Skin corrosion	-	0.9406	94.06%
Ames mutagenesis	-	0.6870	68.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7114	71.14%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	+	0.6428	64.28%
skin sensitisation	-	0.8535	85.35%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.9039	90.39%
Acute Oral Toxicity (c)	III	0.4822	48.22%
Estrogen receptor binding	-	0.4937	49.37%
Androgen receptor binding	-	0.5668	56.68%
Thyroid receptor binding	-	0.5484	54.84%
Glucocorticoid receptor binding	+	0.6772	67.72%
Aromatase binding	-	0.5592	55.92%
PPAR gamma	-	0.6638	66.38%
Honey bee toxicity	-	0.6700	67.00%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9390	93.90%

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	97.21%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.09%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.18%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.03%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.01%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	89.61%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.84%	95.56%
CHEMBL2581	P07339	Cathepsin D	84.02%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.78%	86.33%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	83.53%	94.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.18%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.18%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.99%	95.89%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	81.42%	96.37%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.95%	99.23%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.79%	99.17%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.04%	95.50%

Plants that contains it

• Anisodus tanguticus
• Cardopatium corymbosum
• Indocypraea montana
• Lonchocarpus yucatanensis
• Sidastrum tehuacanum

Cross-Links

• PubChem: 44421658
• NPASS: NPC305475
• ChEMBL: CHEMBL389917
• LOTUS: LTS0158453
• wikiData: Q105195429