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

Details

• Internal ID: d4da85b3-f819-4998-a6ff-ce48bb889d48
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: 7-(hydroxymethyl)-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-4a,5,6,7-tetrol
• SMILES (Canonical): C1=COC(C2C1(C(C(C2(CO)O)O)O)O)OC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): C1=COC(C2C1(C(C(C2(CO)O)O)O)O)OC3C(C(C(C(O3)CO)O)O)O
• InChI: InChI=1S/C15H24O12/c16-3-5-6(18)7(19)8(20)12(26-5)27-13-9-14(23,1-2-25-13)10(21)11(22)15(9,24)4-17/h1-2,5-13,16-24H,3-4H2
• InChI Key: GZBWBULYVYCYCC-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₄O₁₂
• Molecular Weight: 396.34 g/mol
• Exact Mass: 396.12677620 g/mol
• Topological Polar Surface Area (TPSA): 210.00 Ų
• XlogP: -4.70
• Atomic LogP (AlogP): -5.52
• H-Bond Acceptor: 12
• H-Bond Donor: 9
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7433	74.33%
Caco-2	-	0.8971	89.71%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.4864	48.64%
OATP2B1 inhibitior	-	0.8597	85.97%
OATP1B1 inhibitior	+	0.8942	89.42%
OATP1B3 inhibitior	+	0.9606	96.06%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9804	98.04%
P-glycoprotein inhibitior	-	0.8607	86.07%
P-glycoprotein substrate	-	0.9217	92.17%
CYP3A4 substrate	+	0.5467	54.67%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8355	83.55%
CYP3A4 inhibition	-	0.9562	95.62%
CYP2C9 inhibition	-	0.9530	95.30%
CYP2C19 inhibition	-	0.8275	82.75%
CYP2D6 inhibition	-	0.9009	90.09%
CYP1A2 inhibition	-	0.9211	92.11%
CYP2C8 inhibition	-	0.8153	81.53%
CYP inhibitory promiscuity	-	0.9008	90.08%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5947	59.47%
Eye corrosion	-	0.9919	99.19%
Eye irritation	-	0.9651	96.51%
Skin irritation	-	0.8217	82.17%
Skin corrosion	-	0.9550	95.50%
Ames mutagenesis	-	0.5937	59.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.7341	73.41%
Hepatotoxicity	-	0.8875	88.75%
skin sensitisation	-	0.8918	89.18%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	+	0.4822	48.22%
Acute Oral Toxicity (c)	IV	0.3764	37.64%
Estrogen receptor binding	-	0.7112	71.12%
Androgen receptor binding	+	0.5265	52.65%
Thyroid receptor binding	+	0.5199	51.99%
Glucocorticoid receptor binding	-	0.6871	68.71%
Aromatase binding	+	0.6906	69.06%
PPAR gamma	+	0.6347	63.47%
Honey bee toxicity	-	0.8311	83.11%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	-	0.7510	75.10%

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	96.25%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.69%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.55%	97.25%
CHEMBL226	P30542	Adenosine A1 receptor	87.45%	95.93%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.40%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.17%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.68%	94.45%

Plants that contains it

• Dolichandra cynanchoides

Cross-Links

• PubChem: 73814157
• LOTUS: LTS0118215
• wikiData: Q105024327