[(2R,3S,4S,5R,6R)-6-[[(4S,4aS,7aS)-4-(hydroxymethyl)-3-oxo-4,4a,5,7a-tetrahydro-1H-cyclopenta[c]pyran-7-yl]methoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate

Details

• Internal ID: f5d93b5d-f2b6-4c4d-9061-240406aeb4e0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: [(2R,3S,4S,5R,6R)-6-[[(4S,4aS,7aS)-4-(hydroxymethyl)-3-oxo-4,4a,5,7a-tetrahydro-1H-cyclopenta[c]pyran-7-yl]methoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate
• InChI: InChI=1S/C27H34O13/c1-35-18-7-13(8-19(36-2)22(18)30)3-6-21(29)37-12-20-23(31)24(32)25(33)27(40-20)39-10-14-4-5-15-16(9-28)26(34)38-11-17(14)15/h3-4,6-8,15-17,20,23-25,27-28,30-33H,5,9-12H2,1-2H3/b6-3+/t15-,16-,17-,20-,23-,24+,25-,27-/m1/s1
• InChI Key: YHULFFXHTFMKEF-VXLHLEPLSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₄O₁₃
• Molecular Weight: 566.50 g/mol
• Exact Mass: 566.19994113 g/mol
• Topological Polar Surface Area (TPSA): 191.00 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): -0.48
• H-Bond Acceptor: 13
• H-Bond Donor: 5
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6581	65.81%
Caco-2	-	0.8806	88.06%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.6590	65.90%
OATP2B1 inhibitior	-	0.8639	86.39%
OATP1B1 inhibitior	+	0.8274	82.74%
OATP1B3 inhibitior	+	0.9672	96.72%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7710	77.10%
P-glycoprotein inhibitior	-	0.4321	43.21%
P-glycoprotein substrate	+	0.5341	53.41%
CYP3A4 substrate	+	0.6767	67.67%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8660	86.60%
CYP3A4 inhibition	-	0.8065	80.65%
CYP2C9 inhibition	-	0.8659	86.59%
CYP2C19 inhibition	-	0.6837	68.37%
CYP2D6 inhibition	-	0.8878	88.78%
CYP1A2 inhibition	-	0.8139	81.39%
CYP2C8 inhibition	+	0.6944	69.44%
CYP inhibitory promiscuity	-	0.7334	73.34%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7084	70.84%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9385	93.85%
Skin irritation	-	0.8130	81.30%
Skin corrosion	-	0.9538	95.38%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5733	57.33%
Micronuclear	-	0.5500	55.00%
Hepatotoxicity	-	0.6694	66.94%
skin sensitisation	-	0.8071	80.71%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.7660	76.60%
Acute Oral Toxicity (c)	III	0.4918	49.18%
Estrogen receptor binding	+	0.7454	74.54%
Androgen receptor binding	+	0.7427	74.27%
Thyroid receptor binding	-	0.5481	54.81%
Glucocorticoid receptor binding	+	0.6941	69.41%
Aromatase binding	+	0.5956	59.56%
PPAR gamma	+	0.6639	66.39%
Honey bee toxicity	-	0.7282	72.82%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9579	95.79%

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	99.50%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.41%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.03%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.03%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.39%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.60%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.88%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.70%	85.14%
CHEMBL218	P21554	Cannabinoid CB1 receptor	92.85%	96.61%
CHEMBL5255	O00206	Toll-like receptor 4	91.05%	92.50%
CHEMBL2581	P07339	Cathepsin D	89.72%	98.95%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	89.30%	89.62%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.43%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	87.38%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.28%	99.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.48%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.22%	94.45%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.36%	92.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.73%	94.00%
CHEMBL340	P08684	Cytochrome P450 3A4	80.12%	91.19%

Plants that contains it

• Gardenia jasminoides

Cross-Links

• PubChem: 44253992
• NPASS: NPC37167