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

Details

• Internal ID: f4309b8c-5a68-4469-96bd-5d94c56c78e5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: [(2R,3S,4S,5R,6R)-6-[[(4S,4aS,7aS)-7-(hydroxymethyl)-3-oxo-4,4a,5,7a-tetrahydro-1H-cyclopenta[c]pyran-4-yl]methoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate
• SMILES (Canonical): COC1=CC(=CC(=C1O)OC)C=CC(=O)OCC2C(C(C(C(O2)OCC3C4CC=C(C4COC3=O)CO)O)O)O
• SMILES (Isomeric): COC1=CC(=CC(=C1O)OC)/C=C/C(=O)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC[C@@H]3[C@H]4CC=C([C@H]4COC3=O)CO)O)O)O
• 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)39-11-17-15-5-4-14(9-28)16(15)10-38-26(17)34/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+/m0/s1
• InChI Key: MRSXXJYRGDMBIT-BFKATWTQSA-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: -0.90
• 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	-	0.8889	88.89%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6590	65.90%
OATP2B1 inhibitior	-	0.8610	86.10%
OATP1B1 inhibitior	+	0.8212	82.12%
OATP1B3 inhibitior	+	0.9672	96.72%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.5590	55.90%
P-glycoprotein inhibitior	-	0.4598	45.98%
P-glycoprotein substrate	+	0.5087	50.87%
CYP3A4 substrate	+	0.6725	67.25%
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	+	0.6625	66.25%
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	-	0.9333	93.33%
Skin irritation	-	0.8130	81.30%
Skin corrosion	-	0.9538	95.38%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6380	63.80%
Micronuclear	-	0.5500	55.00%
Hepatotoxicity	-	0.6819	68.19%
skin sensitisation	-	0.8071	80.71%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.8605	86.05%
Acute Oral Toxicity (c)	III	0.4918	49.18%
Estrogen receptor binding	+	0.8004	80.04%
Androgen receptor binding	+	0.7381	73.81%
Thyroid receptor binding	-	0.5383	53.83%
Glucocorticoid receptor binding	+	0.6129	61.29%
Aromatase binding	+	0.5602	56.02%
PPAR gamma	+	0.6454	64.54%
Honey bee toxicity	-	0.7373	73.73%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
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	99.53%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.52%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	97.17%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.72%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.21%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.27%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.54%	97.09%
CHEMBL2581	P07339	Cathepsin D	90.35%	98.95%
CHEMBL218	P21554	Cannabinoid CB1 receptor	90.02%	96.61%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	89.84%	89.62%
CHEMBL3714130	P46095	G-protein coupled receptor 6	88.01%	97.36%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.95%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.74%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	87.20%	94.73%
CHEMBL5255	O00206	Toll-like receptor 4	86.73%	92.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.52%	92.62%
CHEMBL226	P30542	Adenosine A1 receptor	85.98%	95.93%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.39%	100.00%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	85.05%	89.34%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.22%	94.00%
CHEMBL2002	P12268	Inosine-5'-monophosphate dehydrogenase 2	83.62%	98.21%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.75%	95.89%

Plants that contains it

• Gardenia jasminoides

Cross-Links

• PubChem: 44255333
• NPASS: NPC118851