(1S,4aS,5R,6S,7R,7aS)-7-methyl-1-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-5,6,7-triol

Details

• Internal ID: bd3fe6d0-c8b6-43e6-9ffe-8b387e5e1e0d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: (1S,4aS,5R,6S,7R,7aS)-7-methyl-1-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-5,6,7-triol
• SMILES (Canonical): CC1(C2C(C=COC2OC3C(C(C(C(O3)CO)O)O)O)C(C1O)O)O
• SMILES (Isomeric): C[C@]1([C@@H]2[C@H](C=CO[C@H]2O[C@@H]3[C@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)[C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C15H24O10/c1-15(22)7-5(8(17)12(15)21)2-3-23-13(7)25-14-11(20)10(19)9(18)6(4-16)24-14/h2-3,5-14,16-22H,4H2,1H3/t5-,6+,7+,8+,9+,10-,11-,12-,13-,14+,15+/m0/s1
• InChI Key: IFPSUYBBTSFRGH-YVSIISQWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₄O₁₀
• Molecular Weight: 364.34 g/mol
• Exact Mass: 364.13694696 g/mol
• Topological Polar Surface Area (TPSA): 169.00 Ų
• XlogP: -3.20
• Atomic LogP (AlogP): -3.61
• H-Bond Acceptor: 10
• H-Bond Donor: 7
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6493	64.93%
Caco-2	-	0.8836	88.36%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6124	61.24%
OATP2B1 inhibitior	-	0.8597	85.97%
OATP1B1 inhibitior	+	0.8305	83.05%
OATP1B3 inhibitior	+	0.9658	96.58%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9587	95.87%
P-glycoprotein inhibitior	-	0.8802	88.02%
P-glycoprotein substrate	-	0.8929	89.29%
CYP3A4 substrate	+	0.5665	56.65%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8472	84.72%
CYP3A4 inhibition	-	0.9429	94.29%
CYP2C9 inhibition	-	0.9393	93.93%
CYP2C19 inhibition	-	0.8656	86.56%
CYP2D6 inhibition	-	0.9368	93.68%
CYP1A2 inhibition	-	0.9079	90.79%
CYP2C8 inhibition	-	0.7731	77.31%
CYP inhibitory promiscuity	-	0.7839	78.39%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5951	59.51%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9850	98.50%
Skin irritation	-	0.8208	82.08%
Skin corrosion	-	0.9525	95.25%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4875	48.75%
Micronuclear	-	0.6941	69.41%
Hepatotoxicity	-	0.8750	87.50%
skin sensitisation	-	0.8920	89.20%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	+	0.4798	47.98%
Acute Oral Toxicity (c)	III	0.4508	45.08%
Estrogen receptor binding	-	0.6972	69.72%
Androgen receptor binding	-	0.6608	66.08%
Thyroid receptor binding	+	0.5280	52.80%
Glucocorticoid receptor binding	-	0.6167	61.67%
Aromatase binding	+	0.5797	57.97%
PPAR gamma	+	0.6807	68.07%
Honey bee toxicity	-	0.8390	83.90%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.6650	66.50%
Fish aquatic toxicity	-	0.6235	62.35%

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	96.51%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.08%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	91.71%	83.82%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.90%	86.92%
CHEMBL3401	O75469	Pregnane X receptor	85.29%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.69%	86.33%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	82.07%	83.57%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.64%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.17%	97.09%

Plants that contains it

• Aronia melanocarpa
• Epacris impressa
• Malus sylvestris
• Oxydendrum arboreum
• Penstemon roseus
• Physostegia virginiana
• Vaccinium angustifolium
• Vaccinium corymbosum
• Vaccinium japonicum
• Vaccinium macrocarpon
• Vaccinium myrtillus
• Vaccinium uliginosum

Cross-Links

• PubChem: 162845885
• LOTUS: LTS0119408
• wikiData: Q104376052