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

Details

• Internal ID: 4d1b383f-079c-484a-999a-060d2be41423
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: (4S,4aS,6S,7S,7aR)-7-hydroxy-4,7-dimethyl-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4,4a,5,6,7a-hexahydrocyclopenta[c]pyran-3-one
• SMILES (Canonical): CC1C2CC(C(C2COC1=O)(C)O)OC3C(C(C(C(O3)CO)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)O)O)O
• InChI: InChI=1S/C16H26O9/c1-6-7-3-10(16(2,22)8(7)5-23-14(6)21)25-15-13(20)12(19)11(18)9(4-17)24-15/h6-13,15,17-20,22H,3-5H2,1-2H3/t6-,7+,8-,9+,10-,11+,12-,13+,15-,16-/m0/s1
• InChI Key: ZHEBCILICLSWEG-RJYBRNOOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₆O₉
• Molecular Weight: 362.37 g/mol
• Exact Mass: 362.15768240 g/mol
• Topological Polar Surface Area (TPSA): 146.00 Ų
• XlogP: -1.60
• Atomic LogP (AlogP): -2.25
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6119	61.19%
Caco-2	-	0.8674	86.74%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7231	72.31%
OATP2B1 inhibitior	-	0.8564	85.64%
OATP1B1 inhibitior	+	0.8852	88.52%
OATP1B3 inhibitior	+	0.9461	94.61%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8783	87.83%
P-glycoprotein inhibitior	-	0.8953	89.53%
P-glycoprotein substrate	-	0.8297	82.97%
CYP3A4 substrate	+	0.6276	62.76%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8952	89.52%
CYP3A4 inhibition	-	0.9589	95.89%
CYP2C9 inhibition	-	0.9521	95.21%
CYP2C19 inhibition	-	0.9100	91.00%
CYP2D6 inhibition	-	0.9578	95.78%
CYP1A2 inhibition	-	0.9174	91.74%
CYP2C8 inhibition	-	0.8517	85.17%
CYP inhibitory promiscuity	-	0.9464	94.64%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7115	71.15%
Eye corrosion	-	0.9917	99.17%
Eye irritation	-	0.9817	98.17%
Skin irritation	-	0.7955	79.55%
Skin corrosion	-	0.9587	95.87%
Ames mutagenesis	-	0.6154	61.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5779	57.79%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.7073	70.73%
skin sensitisation	-	0.9246	92.46%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.6396	63.96%
Acute Oral Toxicity (c)	I	0.4368	43.68%
Estrogen receptor binding	+	0.6575	65.75%
Androgen receptor binding	-	0.5089	50.89%
Thyroid receptor binding	+	0.6127	61.27%
Glucocorticoid receptor binding	-	0.4789	47.89%
Aromatase binding	+	0.6463	64.63%
PPAR gamma	+	0.5184	51.84%
Honey bee toxicity	-	0.7049	70.49%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	0.7903	79.03%

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	96.83%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.61%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.06%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.29%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.82%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.22%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.96%	100.00%
CHEMBL220	P22303	Acetylcholinesterase	88.27%	94.45%
CHEMBL218	P21554	Cannabinoid CB1 receptor	86.74%	96.61%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.57%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.54%	89.00%
CHEMBL2581	P07339	Cathepsin D	85.24%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.44%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.34%	96.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	82.64%	91.24%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.63%	95.83%
CHEMBL2996	Q05655	Protein kinase C delta	82.47%	97.79%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.48%	86.92%
CHEMBL226	P30542	Adenosine A1 receptor	80.32%	95.93%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.31%	96.77%

Plants that contains it

• Patrinia scabra
• Trinia scabra

Cross-Links

• PubChem: 101673676
• LOTUS: LTS0127715
• wikiData: Q105375654