2-(Hydroxymethyl)-6-[[7-(hydroxymethyl)-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-5-yl]oxy]oxane-3,4,5-triol

Details

• Internal ID: 0ec847cf-86d6-4fd4-8cb5-62f5adcfce58
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: 2-(hydroxymethyl)-6-[[7-(hydroxymethyl)-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-5-yl]oxy]oxane-3,4,5-triol
• SMILES (Canonical): C1=COC(C2C1C(C=C2CO)OC3C(C(C(C(O3)CO)O)O)O)OC4C(C(C(C(O4)CO)O)O)O
• SMILES (Isomeric): C1=COC(C2C1C(C=C2CO)OC3C(C(C(C(O3)CO)O)O)O)OC4C(C(C(C(O4)CO)O)O)O
• InChI: InChI=1S/C21H32O14/c22-4-7-3-9(32-20-17(29)15(27)13(25)10(5-23)33-20)8-1-2-31-19(12(7)8)35-21-18(30)16(28)14(26)11(6-24)34-21/h1-3,8-30H,4-6H2
• InChI Key: YJWAGHITGKROID-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₂O₁₄
• Molecular Weight: 508.50 g/mol
• Exact Mass: 508.17920569 g/mol
• Topological Polar Surface Area (TPSA): 228.00 Ų
• XlogP: -4.60
• Atomic LogP (AlogP): -4.98
• H-Bond Acceptor: 14
• H-Bond Donor: 9
• Rotatable Bonds: 7

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	-	0.8901	89.01%
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	+	0.8648	86.48%
OATP1B3 inhibitior	+	0.9631	96.31%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9216	92.16%
P-glycoprotein inhibitior	-	0.7166	71.66%
P-glycoprotein substrate	-	0.8896	88.96%
CYP3A4 substrate	+	0.5306	53.06%
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	-	0.7843	78.43%
CYP inhibitory promiscuity	-	0.6978	69.78%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6579	65.79%
Eye corrosion	-	0.9890	98.90%
Eye irritation	-	0.9129	91.29%
Skin irritation	-	0.8209	82.09%
Skin corrosion	-	0.9609	96.09%
Ames mutagenesis	-	0.5791	57.91%
Human Ether-a-go-go-Related Gene inhibition	+	0.6825	68.25%
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	+	0.5122	51.22%
Acute Oral Toxicity (c)	IV	0.4268	42.68%
Estrogen receptor binding	-	0.5253	52.53%
Androgen receptor binding	+	0.5356	53.56%
Thyroid receptor binding	-	0.4933	49.33%
Glucocorticoid receptor binding	-	0.6518	65.18%
Aromatase binding	+	0.6597	65.97%
PPAR gamma	+	0.5611	56.11%
Honey bee toxicity	-	0.7461	74.61%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6650	66.50%
Fish aquatic toxicity	-	0.5621	56.21%

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	96.69%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.07%	96.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.42%	86.92%
CHEMBL226	P30542	Adenosine A1 receptor	83.17%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.79%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	80.34%	94.73%

Plants that contains it

• Stachys lavandulifolia
• Verbascum salviifolium

Cross-Links

• PubChem: 53462670
• LOTUS: LTS0216014
• wikiData: Q105349507