[(3aR,4S,11S,11aR)-6,10-dimethyl-3-methylidene-11-oxidanyl-2,8-bis(oxidanylidene)-4,5,11,11a-tetrahydro-3aH-cyclodeca[b]furan-4-yl] 2-methylprop-2-enoate

Details

• Internal ID: d6dfda31-3e08-4830-a643-f26dc5d403b6
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(3aR,4S,6Z,9E,11S,11aR)-11-hydroxy-6,10-dimethyl-3-methylidene-2,8-dioxo-4,5,11,11a-tetrahydro-3aH-cyclodeca[b]furan-4-yl] 2-methylprop-2-enoate
• SMILES (Canonical): CC1=CC(=O)C=C(C(C2C(C(C1)OC(=O)C(=C)C)C(=C)C(=O)O2)O)C
• SMILES (Isomeric): C/C/1=C/C(=O)/C=C(/[C@@H]([C@H]2[C@@H]([C@H](C1)OC(=O)C(=C)C)C(=C)C(=O)O2)O)\C
• InChI: InChI=1S/C19H22O6/c1-9(2)18(22)24-14-7-10(3)6-13(20)8-11(4)16(21)17-15(14)12(5)19(23)25-17/h6,8,14-17,21H,1,5,7H2,2-4H3/b10-6-,11-8+/t14-,15+,16-,17+/m0/s1
• InChI Key: LXINRHXYVUTAMQ-VZTPXQGASA-N
• Popularity: 3 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: 2

Synonyms

• MLS000728553
• SMR000445666
• CHEMBL2002162
• BDBM63865
• cid_16745522
• [(3aR,4S,11S,11aR)-11-hydroxy-6,10-dimethyl-3-methylidene-2,8-dioxo-4,5,11,11a-tetrahydro-3aH-cyclodeca[b]furan-4-yl] 2-methylprop-2-enoate
• [(3aR,4S,11S,11aR)-6,10-dimethyl-3-methylidene-11-oxidanyl-2,8-bis(oxidanylidene)-4,5,11,11a-tetrahydro-3aH-cyclodeca[b]furan-4-yl] 2-methylprop-2-enoate
• 2-methyl-2-propenoic acid [(3aR,4S,11S,11aR)-11-hydroxy-6,10-dimethyl-3-methylene-2,8-dioxo-4,5,11,11a-tetrahydro-3aH-cyclodeca[b]furan-4-yl] ester
• 2-methylacrylic acid [(3aR,4S,11S,11aR)-11-hydroxy-2,8-diketo-6,10-dimethyl-3-methylene-4,5,11,11a-tetrahydro-3aH-cyclodeca[b]furan-4-yl] ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9802	98.02%
Caco-2	+	0.6710	67.10%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.5631	56.31%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9154	91.54%
OATP1B3 inhibitior	+	0.8946	89.46%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8364	83.64%
P-glycoprotein inhibitior	-	0.6160	61.60%
P-glycoprotein substrate	-	0.6498	64.98%
CYP3A4 substrate	+	0.6096	60.96%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9005	90.05%
CYP3A4 inhibition	-	0.7806	78.06%
CYP2C9 inhibition	-	0.9326	93.26%
CYP2C19 inhibition	-	0.8588	85.88%
CYP2D6 inhibition	-	0.9555	95.55%
CYP1A2 inhibition	-	0.7457	74.57%
CYP2C8 inhibition	-	0.7396	73.96%
CYP inhibitory promiscuity	-	0.9266	92.66%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9143	91.43%
Carcinogenicity (trinary)	Non-required	0.4473	44.73%
Eye corrosion	-	0.9301	93.01%
Eye irritation	-	0.8141	81.41%
Skin irritation	-	0.6686	66.86%
Skin corrosion	-	0.9407	94.07%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4805	48.05%
Micronuclear	-	0.5300	53.00%
Hepatotoxicity	+	0.5834	58.34%
skin sensitisation	-	0.6612	66.12%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.7580	75.80%
Acute Oral Toxicity (c)	IV	0.4326	43.26%
Estrogen receptor binding	+	0.5270	52.70%
Androgen receptor binding	+	0.5978	59.78%
Thyroid receptor binding	-	0.5225	52.25%
Glucocorticoid receptor binding	+	0.5839	58.39%
Aromatase binding	-	0.6882	68.82%
PPAR gamma	+	0.5992	59.92%
Honey bee toxicity	-	0.6873	68.73%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5350	53.50%
Fish aquatic toxicity	+	0.9401	94.01%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	25118.9 nM	Potency	via CMAUP
CHEMBL5514	P42858	Huntingtin	3548.1 nM	Potency	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	39810.7 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	7943.3 nM; 3981.1 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293277	O15118	Niemann-Pick C1 protein	3162.3 nM	Potency	via CMAUP
CHEMBL1075189	P14618	Pyruvate kinase isozymes M1/M2	11220.2 nM; 11220.2 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293294	P51151	Ras-related protein Rab-9A	5623.4 nM	Potency	via CMAUP
CHEMBL3797	Q13315	Serine-protein kinase ATM	39810.7 nM	Potency	via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	39810.7 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.54%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.08%	99.23%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.20%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.20%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.01%	94.45%
CHEMBL2581	P07339	Cathepsin D	87.60%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	85.28%	83.82%
CHEMBL221	P23219	Cyclooxygenase-1	84.57%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.94%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.01%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	80.37%	94.73%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.33%	95.50%

Plants that contains it

• Elephantopus mollis

Cross-Links

• PubChem: 56642958
• NPASS: NPC288240
• ChEMBL: CHEMBL2002162