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

Details

• Internal ID: d1b11112-858d-42ab-a992-4d8a415ff1cb
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: 2-(hydroxymethyl)-6-[[7-(hydroxymethyl)-5-methoxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxy]oxane-3,4,5-triol
• SMILES (Canonical): COC1C=C(C2C1C=COC2OC3C(C(C(C(O3)CO)O)O)O)CO
• SMILES (Isomeric): COC1C=C(C2C1C=COC2OC3C(C(C(C(O3)CO)O)O)O)CO
• InChI: InChI=1S/C16H24O9/c1-22-9-4-7(5-17)11-8(9)2-3-23-15(11)25-16-14(21)13(20)12(19)10(6-18)24-16/h2-4,8-21H,5-6H2,1H3
• InChI Key: CJQZGOSZRGOGDQ-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₄O₉
• Molecular Weight: 360.36 g/mol
• Exact Mass: 360.14203234 g/mol
• Topological Polar Surface Area (TPSA): 138.00 Ų
• XlogP: -2.50
• Atomic LogP (AlogP): -2.15
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6428	64.28%
Caco-2	-	0.8496	84.96%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.5827	58.27%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8138	81.38%
OATP1B3 inhibitior	+	0.9707	97.07%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9401	94.01%
P-glycoprotein inhibitior	-	0.8630	86.30%
P-glycoprotein substrate	-	0.8475	84.75%
CYP3A4 substrate	+	0.5623	56.23%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8328	83.28%
CYP3A4 inhibition	-	0.9508	95.08%
CYP2C9 inhibition	-	0.9008	90.08%
CYP2C19 inhibition	-	0.7895	78.95%
CYP2D6 inhibition	-	0.8880	88.80%
CYP1A2 inhibition	-	0.8713	87.13%
CYP2C8 inhibition	-	0.8050	80.50%
CYP inhibitory promiscuity	-	0.6653	66.53%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6323	63.23%
Eye corrosion	-	0.9879	98.79%
Eye irritation	-	0.9626	96.26%
Skin irritation	-	0.8194	81.94%
Skin corrosion	-	0.9582	95.82%
Ames mutagenesis	-	0.6191	61.91%
Human Ether-a-go-go-Related Gene inhibition	-	0.4523	45.23%
Micronuclear	-	0.7341	73.41%
Hepatotoxicity	-	0.8250	82.50%
skin sensitisation	-	0.8906	89.06%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	+	0.6043	60.43%
Acute Oral Toxicity (c)	III	0.4731	47.31%
Estrogen receptor binding	-	0.5998	59.98%
Androgen receptor binding	-	0.5840	58.40%
Thyroid receptor binding	+	0.5490	54.90%
Glucocorticoid receptor binding	-	0.6485	64.85%
Aromatase binding	+	0.5503	55.03%
PPAR gamma	+	0.5350	53.50%
Honey bee toxicity	-	0.7711	77.11%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6955	69.55%
Fish aquatic toxicity	-	0.7118	71.18%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.68%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.82%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	89.87%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.78%	86.92%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.10%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.31%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.21%	96.00%
CHEMBL2581	P07339	Cathepsin D	80.18%	98.95%

Plants that contains it

• Pedicularis artselaeri

Cross-Links

• PubChem: 162997828
• LOTUS: LTS0159910
• wikiData: Q104961550