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

Details

• Internal ID: 3ee804a0-2bb7-4863-a7bc-da828fddb9b7
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(3aS,4R,6E,8R,10E,11aR)-8-hydroxy-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (2S,3S)-2-hydroxy-2-(hydroxymethyl)-3-sulfanylbutanoate
• SMILES (Canonical): CC1=CC2C(C(CC(=CC(C1)O)C)OC(=O)C(CO)(C(C)S)O)C(=C)C(=O)O2
• SMILES (Isomeric): C/C/1=C\[C@@H]2[C@H]([C@@H](C/C(=C/[C@@H](C1)O)/C)OC(=O)[C@@](CO)([C@H](C)S)O)C(=C)C(=O)O2
• InChI: InChI=1S/C20H28O7S/c1-10-5-14(22)6-11(2)8-16(17-12(3)18(23)26-15(17)7-10)27-19(24)20(25,9-21)13(4)28/h6-7,13-17,21-22,25,28H,3,5,8-9H2,1-2,4H3/b10-7+,11-6+/t13-,14+,15+,16+,17+,20+/m0/s1
• InChI Key: VLJMGJBBVNUYSJ-IDIPUOCGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₇S
• Molecular Weight: 412.50 g/mol
• Exact Mass: 412.15557440 g/mol
• Topological Polar Surface Area (TPSA): 114.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 1.08
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8688	86.88%
Caco-2	-	0.6629	66.29%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.5377	53.77%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8304	83.04%
OATP1B3 inhibitior	+	0.9122	91.22%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.7832	78.32%
P-glycoprotein inhibitior	-	0.6465	64.65%
P-glycoprotein substrate	-	0.6056	60.56%
CYP3A4 substrate	+	0.6259	62.59%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8606	86.06%
CYP3A4 inhibition	-	0.6858	68.58%
CYP2C9 inhibition	-	0.8017	80.17%
CYP2C19 inhibition	-	0.7867	78.67%
CYP2D6 inhibition	-	0.9312	93.12%
CYP1A2 inhibition	-	0.7489	74.89%
CYP2C8 inhibition	-	0.7155	71.55%
CYP inhibitory promiscuity	-	0.9224	92.24%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6655	66.55%
Eye corrosion	-	0.9860	98.60%
Eye irritation	-	0.9479	94.79%
Skin irritation	-	0.6166	61.66%
Skin corrosion	-	0.9346	93.46%
Ames mutagenesis	-	0.6454	64.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5568	55.68%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.8507	85.07%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.5380	53.80%
Acute Oral Toxicity (c)	III	0.5004	50.04%
Estrogen receptor binding	+	0.6893	68.93%
Androgen receptor binding	+	0.5395	53.95%
Thyroid receptor binding	+	0.5560	55.60%
Glucocorticoid receptor binding	+	0.7298	72.98%
Aromatase binding	+	0.5897	58.97%
PPAR gamma	+	0.5931	59.31%
Honey bee toxicity	-	0.7871	78.71%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9807	98.07%

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	99.75%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.35%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.07%	98.95%
CHEMBL2996	Q05655	Protein kinase C delta	92.91%	97.79%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.52%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.19%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.12%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.91%	97.25%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	85.80%	97.33%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	84.79%	93.03%
CHEMBL3401	O75469	Pregnane X receptor	83.91%	94.73%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.41%	93.56%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	83.33%	96.37%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	83.16%	93.65%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.02%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.93%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.06%	99.23%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	81.89%	90.93%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.44%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.10%	97.09%

Plants that contains it

• Eupatorium mikanioides

Cross-Links

• PubChem: 162988899
• LOTUS: LTS0048077
• wikiData: Q105288443