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

Details

• Internal ID: b30849aa-1ee0-4124-99b5-3bb8a5b3dc23
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: 6-chloro-7-methyl-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-4a,5,7-triol
• SMILES (Canonical): CC1(C2C(OC=CC2(C(C1Cl)O)O)OC3C(C(C(C(O3)CO)O)O)O)O
• SMILES (Isomeric): CC1(C2C(OC=CC2(C(C1Cl)O)O)OC3C(C(C(C(O3)CO)O)O)O)O
• InChI: InChI=1S/C15H23ClO10/c1-14(22)9-13(24-3-2-15(9,23)11(21)10(14)16)26-12-8(20)7(19)6(18)5(4-17)25-12/h2-3,5-13,17-23H,4H2,1H3
• InChI Key: DRWIVSAUXCDFQK-UHFFFAOYSA-N
• Popularity: 0 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: -3.00
• Atomic LogP (AlogP): -3.25
• H-Bond Acceptor: 10
• H-Bond Donor: 7
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5764	57.64%
Caco-2	-	0.8841	88.41%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.5617	56.17%
OATP2B1 inhibitior	-	0.8595	85.95%
OATP1B1 inhibitior	+	0.8405	84.05%
OATP1B3 inhibitior	+	0.9460	94.60%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9551	95.51%
P-glycoprotein inhibitior	-	0.8563	85.63%
P-glycoprotein substrate	-	0.8967	89.67%
CYP3A4 substrate	+	0.6186	61.86%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8488	84.88%
CYP3A4 inhibition	-	0.9159	91.59%
CYP2C9 inhibition	-	0.8684	86.84%
CYP2C19 inhibition	-	0.7391	73.91%
CYP2D6 inhibition	-	0.8886	88.86%
CYP1A2 inhibition	-	0.8411	84.11%
CYP2C8 inhibition	-	0.7742	77.42%
CYP inhibitory promiscuity	-	0.6482	64.82%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8638	86.38%
Carcinogenicity (trinary)	Non-required	0.5092	50.92%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.9806	98.06%
Skin irritation	-	0.7791	77.91%
Skin corrosion	-	0.9334	93.34%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6741	67.41%
Micronuclear	-	0.7241	72.41%
Hepatotoxicity	-	0.8322	83.22%
skin sensitisation	-	0.8672	86.72%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	+	0.5206	52.06%
Acute Oral Toxicity (c)	III	0.4524	45.24%
Estrogen receptor binding	-	0.6584	65.84%
Androgen receptor binding	-	0.4826	48.26%
Thyroid receptor binding	+	0.6397	63.97%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	+	0.6261	62.61%
PPAR gamma	+	0.6991	69.91%
Honey bee toxicity	-	0.7502	75.02%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6050	60.50%
Fish aquatic toxicity	+	0.6647	66.47%

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	96.12%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.06%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.42%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	86.46%	94.73%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.63%	97.25%
CHEMBL226	P30542	Adenosine A1 receptor	83.59%	95.93%
CHEMBL221	P23219	Cyclooxygenase-1	82.51%	90.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.02%	86.92%

Plants that contains it

• Antirrhinum majus
• Cymbalaria muralis
• Kickxia elatine
• Linaria flava
• Linaria genistifolia
• Linaria japonica
• Linaria simplex
• Linaria vulgaris

Cross-Links

• PubChem: 12311243
• LOTUS: LTS0026701
• wikiData: Q104389239