1-[(1S,4aS,7aS)-7-(hydroxymethyl)-1-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-yl]-2-hydroxyethanone

Details

• Internal ID: a99bf127-fbe2-45c3-8246-a0c64897c444
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: 1-[(1S,4aS,7aS)-7-(hydroxymethyl)-1-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-yl]-2-hydroxyethanone
• SMILES (Canonical): C1C=C(C2C1C(=COC2OC3C(C(C(C(O3)CO)O)O)O)C(=O)CO)CO
• SMILES (Isomeric): C1C=C([C@@H]2[C@H]1C(=CO[C@H]2OC3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C(=O)CO)CO
• InChI: InChI=1S/C17H24O10/c18-3-7-1-2-8-9(10(21)4-19)6-25-16(12(7)8)27-17-15(24)14(23)13(22)11(5-20)26-17/h1,6,8,11-20,22-24H,2-5H2/t8-,11-,12-,13-,14+,15-,16+,17?/m1/s1
• InChI Key: KXEWLJDTPOIUSH-AURGCDHCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₄O₁₀
• Molecular Weight: 388.40 g/mol
• Exact Mass: 388.13694696 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: -3.20
• Atomic LogP (AlogP): -2.84
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 6

Synonyms

• AC-20245

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5126	51.26%
Caco-2	-	0.8825	88.25%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7457	74.57%
OATP2B1 inhibitior	-	0.8598	85.98%
OATP1B1 inhibitior	+	0.8233	82.33%
OATP1B3 inhibitior	+	0.9554	95.54%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9062	90.62%
P-glycoprotein inhibitior	-	0.9024	90.24%
P-glycoprotein substrate	-	0.8670	86.70%
CYP3A4 substrate	+	0.5778	57.78%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8532	85.32%
CYP3A4 inhibition	-	0.9424	94.24%
CYP2C9 inhibition	-	0.9368	93.68%
CYP2C19 inhibition	-	0.8280	82.80%
CYP2D6 inhibition	-	0.8957	89.57%
CYP1A2 inhibition	-	0.8766	87.66%
CYP2C8 inhibition	-	0.7491	74.91%
CYP inhibitory promiscuity	-	0.8327	83.27%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7241	72.41%
Eye corrosion	-	0.9872	98.72%
Eye irritation	-	0.9280	92.80%
Skin irritation	-	0.8107	81.07%
Skin corrosion	-	0.9605	96.05%
Ames mutagenesis	-	0.5137	51.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.8375	83.75%
skin sensitisation	-	0.8808	88.08%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.7322	73.22%
Acute Oral Toxicity (c)	IV	0.3602	36.02%
Estrogen receptor binding	-	0.5000	50.00%
Androgen receptor binding	+	0.5337	53.37%
Thyroid receptor binding	-	0.5748	57.48%
Glucocorticoid receptor binding	-	0.5814	58.14%
Aromatase binding	+	0.6381	63.81%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.7811	78.11%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.7305	73.05%
Fish aquatic toxicity	+	0.8288	82.88%

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	95.68%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.82%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.31%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.92%	89.00%

Plants that contains it

• Codonopsis pilosula
• Eucommia ulmoides
• Gardenia jasminoides
• Lantana camara
• Rehmannia glutinosa
• Scrophularia ningpoensis

Cross-Links

• PubChem: 45358128
• NPASS: NPC113219