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

Details

• Internal ID: 5c86a279-c9c5-4c4a-ad76-ac12af946344
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: 2-[(6-chloro-4a,7-dihydroxy-7-methyl-1,5,6,7a-tetrahydrocyclopenta[c]pyran-1-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC1(C(CC2(C1C(OC=C2)OC3C(C(C(C(O3)CO)O)O)O)O)Cl)O
• SMILES (Isomeric): CC1(C(CC2(C1C(OC=C2)OC3C(C(C(C(O3)CO)O)O)O)O)Cl)O
• InChI: InChI=1S/C15H23ClO9/c1-14(21)7(16)4-15(22)2-3-23-13(11(14)15)25-12-10(20)9(19)8(18)6(5-17)24-12/h2-3,6-13,17-22H,4-5H2,1H3
• InChI Key: AVDZNEHHIWOSGQ-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₃ClO₉
• Molecular Weight: 382.79 g/mol
• Exact Mass: 382.1030600 g/mol
• Topological Polar Surface Area (TPSA): 149.00 Ų
• XlogP: -2.00
• Atomic LogP (AlogP): -2.22
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7162	71.62%
Caco-2	-	0.8742	87.42%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Lysosomes	0.5066	50.66%
OATP2B1 inhibitior	-	0.8583	85.83%
OATP1B1 inhibitior	+	0.8653	86.53%
OATP1B3 inhibitior	+	0.9312	93.12%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.9581	95.81%
P-glycoprotein inhibitior	-	0.8741	87.41%
P-glycoprotein substrate	-	0.8360	83.60%
CYP3A4 substrate	+	0.6219	62.19%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8403	84.03%
CYP3A4 inhibition	-	0.9352	93.52%
CYP2C9 inhibition	-	0.8946	89.46%
CYP2C19 inhibition	-	0.8197	81.97%
CYP2D6 inhibition	-	0.9027	90.27%
CYP1A2 inhibition	-	0.8260	82.60%
CYP2C8 inhibition	-	0.7077	70.77%
CYP inhibitory promiscuity	-	0.7963	79.63%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8638	86.38%
Carcinogenicity (trinary)	Non-required	0.5572	55.72%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9880	98.80%
Skin irritation	-	0.7267	72.67%
Skin corrosion	-	0.9253	92.53%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6848	68.48%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.8052	80.52%
skin sensitisation	-	0.8692	86.92%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	+	0.5261	52.61%
Acute Oral Toxicity (c)	III	0.4702	47.02%
Estrogen receptor binding	-	0.6057	60.57%
Androgen receptor binding	-	0.5364	53.64%
Thyroid receptor binding	+	0.6130	61.30%
Glucocorticoid receptor binding	-	0.5252	52.52%
Aromatase binding	+	0.6380	63.80%
PPAR gamma	+	0.7241	72.41%
Honey bee toxicity	-	0.6940	69.40%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.7418	74.18%

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	97.14%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.06%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.88%	97.25%
CHEMBL218	P21554	Cannabinoid CB1 receptor	92.50%	96.61%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.11%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.87%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	88.13%	95.93%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	86.84%	96.21%
CHEMBL1951	P21397	Monoamine oxidase A	84.06%	91.49%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.59%	95.89%
CHEMBL221	P23219	Cyclooxygenase-1	83.48%	90.17%
CHEMBL4208	P20618	Proteasome component C5	81.51%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.66%	86.33%

Plants that contains it

• Physostegia virginiana

Cross-Links

• PubChem: 162901241
• LOTUS: LTS0275125
• wikiData: Q104919392