(4R,4aS,6S,7S,7aR)-6-[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-7-hydroxy-4,7-dimethyl-1,4,4a,5,6,7a-hexahydrocyclopenta[c]pyran-3-one

Details

• Internal ID: f433df6e-746e-4d50-970a-eacd7c7fbe2e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: (4R,4aS,6S,7S,7aR)-6-[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-7-hydroxy-4,7-dimethyl-1,4,4a,5,6,7a-hexahydrocyclopenta[c]pyran-3-one
• SMILES (Canonical): CC1C2CC(C(C2COC1=O)(C)O)OC3C(C(C(C(O3)COC4C(C(CO4)(CO)O)O)O)O)O
• SMILES (Isomeric): C[C@@H]1[C@H]2C[C@@H]([C@@]([C@H]2COC1=O)(C)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO[C@H]4[C@@H]([C@](CO4)(CO)O)O)O)O)O
• InChI: InChI=1S/C21H34O13/c1-8-9-3-12(20(2,28)10(9)4-30-17(8)27)34-18-15(25)14(24)13(23)11(33-18)5-31-19-16(26)21(29,6-22)7-32-19/h8-16,18-19,22-26,28-29H,3-7H2,1-2H3/t8-,9-,10+,11-,12+,13-,14+,15-,16+,18+,19-,20+,21-/m1/s1
• InChI Key: ROOBSMJTLSQSCB-XUUQELCVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₄O₁₃
• Molecular Weight: 494.50 g/mol
• Exact Mass: 494.19994113 g/mol
• Topological Polar Surface Area (TPSA): 205.00 Ų
• XlogP: -3.40
• Atomic LogP (AlogP): -3.78
• H-Bond Acceptor: 13
• H-Bond Donor: 7
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4906	49.06%
Caco-2	-	0.8577	85.77%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.6782	67.82%
OATP2B1 inhibitior	-	0.8644	86.44%
OATP1B1 inhibitior	+	0.8834	88.34%
OATP1B3 inhibitior	+	0.9576	95.76%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.8866	88.66%
P-glycoprotein inhibitior	-	0.7174	71.74%
P-glycoprotein substrate	-	0.6028	60.28%
CYP3A4 substrate	+	0.6801	68.01%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8952	89.52%
CYP3A4 inhibition	-	0.9366	93.66%
CYP2C9 inhibition	-	0.9557	95.57%
CYP2C19 inhibition	-	0.9231	92.31%
CYP2D6 inhibition	-	0.9499	94.99%
CYP1A2 inhibition	-	0.9262	92.62%
CYP2C8 inhibition	-	0.6175	61.75%
CYP inhibitory promiscuity	-	0.9583	95.83%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6725	67.25%
Eye corrosion	-	0.9922	99.22%
Eye irritation	-	0.9592	95.92%
Skin irritation	-	0.7550	75.50%
Skin corrosion	-	0.9520	95.20%
Ames mutagenesis	+	0.5346	53.46%
Human Ether-a-go-go-Related Gene inhibition	+	0.7224	72.24%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	-	0.5823	58.23%
skin sensitisation	-	0.9167	91.67%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.5943	59.43%
Acute Oral Toxicity (c)	I	0.5905	59.05%
Estrogen receptor binding	+	0.7627	76.27%
Androgen receptor binding	+	0.5634	56.34%
Thyroid receptor binding	+	0.5147	51.47%
Glucocorticoid receptor binding	+	0.6504	65.04%
Aromatase binding	+	0.7251	72.51%
PPAR gamma	+	0.5285	52.85%
Honey bee toxicity	-	0.6973	69.73%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.7553	75.53%

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	97.10%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	96.52%	95.93%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.09%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.95%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.29%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.93%	100.00%
CHEMBL220	P22303	Acetylcholinesterase	90.67%	94.45%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.46%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.10%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.88%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.79%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.50%	99.23%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.07%	86.92%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.31%	96.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.23%	95.83%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.08%	96.77%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.80%	94.00%
CHEMBL2581	P07339	Cathepsin D	83.39%	98.95%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.84%	92.94%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	80.98%	92.32%
CHEMBL1871	P10275	Androgen Receptor	80.69%	96.43%
CHEMBL218	P21554	Cannabinoid CB1 receptor	80.19%	96.61%

Plants that contains it

• Patrinia scabra

Cross-Links

• PubChem: 101673679
• LOTUS: LTS0122394
• wikiData: Q105242354