[(3S,4S,6E,10Z,11aR)-10-(hydroxymethyl)-3,6-dimethyl-2-oxo-3a,4,5,8,9,11a-hexahydro-3H-cyclodeca[b]furan-4-yl] 2-(hydroxymethyl)prop-2-enoate

Details

• Internal ID: fed383eb-14bc-4ca4-a803-c5cf616ba7d2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(3S,4S,6E,10Z,11aR)-10-(hydroxymethyl)-3,6-dimethyl-2-oxo-3a,4,5,8,9,11a-hexahydro-3H-cyclodeca[b]furan-4-yl] 2-(hydroxymethyl)prop-2-enoate
• SMILES (Canonical): CC1C2C(CC(=CCCC(=CC2OC1=O)CO)C)OC(=O)C(=C)CO
• SMILES (Isomeric): C[C@H]1C2[C@H](C/C(=C/CC/C(=C/[C@H]2OC1=O)/CO)/C)OC(=O)C(=C)CO
• InChI: InChI=1S/C19H26O6/c1-11-5-4-6-14(10-21)8-16-17(13(3)19(23)25-16)15(7-11)24-18(22)12(2)9-20/h5,8,13,15-17,20-21H,2,4,6-7,9-10H2,1,3H3/b11-5+,14-8-/t13-,15-,16+,17?/m0/s1
• InChI Key: WSRGRZRMKSTDQJ-QOSNCYJHSA-N
• Popularity: 0 references 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: 1.00
• 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	+	0.9474	94.74%
Caco-2	+	0.6355	63.55%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7795	77.95%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9088	90.88%
OATP1B3 inhibitior	+	0.9411	94.11%
MATE1 inhibitior	-	0.8812	88.12%
OCT2 inhibitior	-	0.6820	68.20%
BSEP inhibitior	-	0.7221	72.21%
P-glycoprotein inhibitior	-	0.7694	76.94%
P-glycoprotein substrate	-	0.6253	62.53%
CYP3A4 substrate	+	0.6234	62.34%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8889	88.89%
CYP3A4 inhibition	-	0.5332	53.32%
CYP2C9 inhibition	-	0.8771	87.71%
CYP2C19 inhibition	-	0.8544	85.44%
CYP2D6 inhibition	-	0.9134	91.34%
CYP1A2 inhibition	-	0.5364	53.64%
CYP2C8 inhibition	-	0.7654	76.54%
CYP inhibitory promiscuity	-	0.8843	88.43%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6773	67.73%
Eye corrosion	-	0.9824	98.24%
Eye irritation	-	0.8755	87.55%
Skin irritation	-	0.6568	65.68%
Skin corrosion	-	0.9426	94.26%
Ames mutagenesis	+	0.5018	50.18%
Human Ether-a-go-go-Related Gene inhibition	-	0.6032	60.32%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	+	0.5425	54.25%
skin sensitisation	-	0.9001	90.01%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	+	0.6250	62.50%
Acute Oral Toxicity (c)	III	0.4623	46.23%
Estrogen receptor binding	-	0.5632	56.32%
Androgen receptor binding	-	0.5480	54.80%
Thyroid receptor binding	-	0.5454	54.54%
Glucocorticoid receptor binding	+	0.6522	65.22%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.5217	52.17%
Honey bee toxicity	-	0.8174	81.74%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9864	98.64%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.08%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.79%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.82%	97.25%
CHEMBL2581	P07339	Cathepsin D	90.81%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.41%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.64%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.11%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.97%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.15%	97.09%

Plants that contains it

• Centaurea glomerata

Cross-Links

• PubChem: 162899323
• LOTUS: LTS0013297
• wikiData: Q105119278