(2S,3S,4S,5R,6R)-2-[[(1S,4aS,5S,6R,7S,7aS)-6-chloro-5,7-dihydroxy-7-(hydroxymethyl)-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: 8c2b26c6-80ac-4180-9abc-6eedfd9a46b6
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: (2S,3S,4S,5R,6R)-2-[[(1S,4aS,5S,6R,7S,7aS)-6-chloro-5,7-dihydroxy-7-(hydroxymethyl)-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• InChI: InChI=1S/C15H23ClO10/c16-12-8(19)5-1-2-24-13(7(5)15(12,23)4-18)26-14-11(22)10(21)9(20)6(3-17)25-14/h1-2,5-14,17-23H,3-4H2/t5-,6+,7+,8-,9-,10-,11-,12+,13-,14-,15+/m0/s1
• InChI Key: MQVBIZWHELLSAW-UQCJWKSRSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₃ClO₁₀
• Molecular Weight: 398.79 g/mol
• Exact Mass: 398.0979746 g/mol
• Topological Polar Surface Area (TPSA): 169.00 Ų
• XlogP: -2.90
• Atomic LogP (AlogP): -3.39
• H-Bond Acceptor: 10
• H-Bond Donor: 7
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5521	55.21%
Caco-2	-	0.8997	89.97%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.4587	45.87%
OATP2B1 inhibitior	-	0.8591	85.91%
OATP1B1 inhibitior	+	0.8562	85.62%
OATP1B3 inhibitior	+	0.9430	94.30%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9711	97.11%
P-glycoprotein inhibitior	-	0.8503	85.03%
P-glycoprotein substrate	-	0.8994	89.94%
CYP3A4 substrate	+	0.5862	58.62%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8387	83.87%
CYP3A4 inhibition	-	0.9110	91.10%
CYP2C9 inhibition	-	0.8853	88.53%
CYP2C19 inhibition	-	0.7252	72.52%
CYP2D6 inhibition	-	0.8411	84.11%
CYP1A2 inhibition	-	0.8362	83.62%
CYP2C8 inhibition	-	0.6936	69.36%
CYP inhibitory promiscuity	-	0.7859	78.59%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8438	84.38%
Carcinogenicity (trinary)	Non-required	0.5139	51.39%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9800	98.00%
Skin irritation	-	0.7778	77.78%
Skin corrosion	-	0.9368	93.68%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4852	48.52%
Micronuclear	-	0.7641	76.41%
Hepatotoxicity	-	0.8072	80.72%
skin sensitisation	-	0.8699	86.99%
Respiratory toxicity	-	0.6444	64.44%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	-	0.6375	63.75%
Nephrotoxicity	+	0.5510	55.10%
Acute Oral Toxicity (c)	III	0.4088	40.88%
Estrogen receptor binding	-	0.6879	68.79%
Androgen receptor binding	-	0.5732	57.32%
Thyroid receptor binding	+	0.5596	55.96%
Glucocorticoid receptor binding	-	0.6143	61.43%
Aromatase binding	+	0.6805	68.05%
PPAR gamma	+	0.7216	72.16%
Honey bee toxicity	-	0.5703	57.03%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	-	0.4751	47.51%

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	96.11%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.49%	96.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	88.41%	86.92%
CHEMBL218	P21554	Cannabinoid CB1 receptor	84.71%	96.61%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.04%	97.25%
CHEMBL226	P30542	Adenosine A1 receptor	83.10%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.63%	97.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.30%	96.95%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	81.16%	92.32%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.02%	94.00%

Plants that contains it

• Mackaya bella

Cross-Links

• PubChem: 163038589
• LOTUS: LTS0030907
• wikiData: Q105170292