5-[(E)-3-hydroxy-3-methylbut-1-enyl]-6-propan-2-yl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclohepta-2,4,6-trien-1-one

Details

• Internal ID: 9b0b3f7c-2336-4f5e-9f40-41f14935a009
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: 5-[(E)-3-hydroxy-3-methylbut-1-enyl]-6-propan-2-yl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclohepta-2,4,6-trien-1-one
• SMILES (Canonical): CC(C)C1=CC(=O)C(=CC=C1C=CC(C)(C)O)OC2C(C(C(C(O2)CO)O)O)O
• SMILES (Isomeric): CC(C)C1=CC(=O)C(=CC=C1/C=C/C(C)(C)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
• InChI: InChI=1S/C21H30O8/c1-11(2)13-9-14(23)15(6-5-12(13)7-8-21(3,4)27)28-20-19(26)18(25)17(24)16(10-22)29-20/h5-9,11,16-20,22,24-27H,10H2,1-4H3/b8-7+/t16-,17-,18+,19-,20-/m1/s1
• InChI Key: YKWRJWQJGXOUMW-DJLJYXLHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₀O₈
• Molecular Weight: 410.50 g/mol
• Exact Mass: 410.19406791 g/mol
• Topological Polar Surface Area (TPSA): 137.00 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 0.13
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4585	45.85%
Caco-2	-	0.7925	79.25%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.7706	77.06%
OATP2B1 inhibitior	-	0.8590	85.90%
OATP1B1 inhibitior	+	0.9037	90.37%
OATP1B3 inhibitior	+	0.9494	94.94%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.5616	56.16%
P-glycoprotein inhibitior	-	0.6702	67.02%
P-glycoprotein substrate	-	0.8309	83.09%
CYP3A4 substrate	+	0.5931	59.31%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8636	86.36%
CYP3A4 inhibition	-	0.7967	79.67%
CYP2C9 inhibition	-	0.8138	81.38%
CYP2C19 inhibition	-	0.8050	80.50%
CYP2D6 inhibition	-	0.9208	92.08%
CYP1A2 inhibition	-	0.6608	66.08%
CYP2C8 inhibition	-	0.6776	67.76%
CYP inhibitory promiscuity	-	0.8295	82.95%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6771	67.71%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.9545	95.45%
Skin irritation	-	0.8041	80.41%
Skin corrosion	-	0.9296	92.96%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3692	36.92%
Micronuclear	-	0.6486	64.86%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.7623	76.23%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	-	0.5726	57.26%
Acute Oral Toxicity (c)	III	0.6553	65.53%
Estrogen receptor binding	+	0.7206	72.06%
Androgen receptor binding	-	0.6102	61.02%
Thyroid receptor binding	+	0.5776	57.76%
Glucocorticoid receptor binding	+	0.5683	56.83%
Aromatase binding	+	0.5657	56.57%
PPAR gamma	+	0.5871	58.71%
Honey bee toxicity	-	0.7480	74.80%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.8362	83.62%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.71%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.90%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	95.28%	94.73%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.57%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.48%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.21%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.49%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.51%	99.17%
CHEMBL3714130	P46095	G-protein coupled receptor 6	87.23%	97.36%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.99%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.98%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.86%	94.45%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.56%	90.71%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.06%	95.89%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.60%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.19%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.05%	95.89%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	81.94%	89.34%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	81.56%	100.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.56%	93.56%

Plants that contains it

• Cupressus sempervirens

Cross-Links

• PubChem: 10001595
• LOTUS: LTS0143980
• wikiData: Q105349932