(2S,3R,4S,5S,6R)-2-[[(1S,4aS,5R,7aR)-5-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: 2876a5c9-5277-463b-bf95-af36731230ff
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[[(1S,4aS,5R,7aR)-5-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): C1=COC(C2C1C(C=C2CO)O)OC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): C1=CO[C@H]([C@@H]2[C@H]1[C@H](C=C2CO)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• InChI: InChI=1S/C15H22O9/c16-4-6-3-8(18)7-1-2-22-14(10(6)7)24-15-13(21)12(20)11(19)9(5-17)23-15/h1-3,7-21H,4-5H2/t7-,8+,9-,10+,11-,12+,13-,14+,15+/m1/s1
• InChI Key: RJWJHRPNHPHBRN-FKGQBLIQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₉
• Molecular Weight: 346.33 g/mol
• Exact Mass: 346.12638228 g/mol
• Topological Polar Surface Area (TPSA): 149.00 Ų
• XlogP: -3.00
• Atomic LogP (AlogP): -2.80
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6717	67.17%
Caco-2	-	0.8583	85.83%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.5905	59.05%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8588	85.88%
OATP1B3 inhibitior	+	0.9631	96.31%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9839	98.39%
P-glycoprotein inhibitior	-	0.8972	89.72%
P-glycoprotein substrate	-	0.8967	89.67%
CYP3A4 substrate	+	0.5175	51.75%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8272	82.72%
CYP3A4 inhibition	-	0.9416	94.16%
CYP2C9 inhibition	-	0.9116	91.16%
CYP2C19 inhibition	-	0.7815	78.15%
CYP2D6 inhibition	-	0.8755	87.55%
CYP1A2 inhibition	-	0.8639	86.39%
CYP2C8 inhibition	-	0.7692	76.92%
CYP inhibitory promiscuity	-	0.6978	69.78%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6579	65.79%
Eye corrosion	-	0.9890	98.90%
Eye irritation	-	0.9388	93.88%
Skin irritation	-	0.8209	82.09%
Skin corrosion	-	0.9609	96.09%
Ames mutagenesis	-	0.5691	56.91%
Human Ether-a-go-go-Related Gene inhibition	-	0.5847	58.47%
Micronuclear	-	0.7441	74.41%
Hepatotoxicity	-	0.9125	91.25%
skin sensitisation	-	0.8878	88.78%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	+	0.5530	55.30%
Acute Oral Toxicity (c)	IV	0.4268	42.68%
Estrogen receptor binding	-	0.7841	78.41%
Androgen receptor binding	-	0.5988	59.88%
Thyroid receptor binding	-	0.5308	53.08%
Glucocorticoid receptor binding	-	0.7675	76.75%
Aromatase binding	+	0.5487	54.87%
PPAR gamma	+	0.5840	58.40%
Honey bee toxicity	-	0.7774	77.74%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.7150	71.50%
Fish aquatic toxicity	-	0.5621	56.21%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1287622	Q9Y468	Lethal(3)malignant brain tumor-like protein 1	63.1 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.14%	91.11%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.59%	86.92%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.72%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	82.41%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.55%	97.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.05%	97.36%

Plants that contains it

• Verbascum georgicum

Cross-Links

• PubChem: 100806018
• LOTUS: LTS0101131
• wikiData: Q105237894