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

Details

• Internal ID: ce06878d-f2d6-46a3-9845-8401497d853e
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: (1S,4aS,5S,6S,7R,7aR)-6-chloro-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,6,7,7a-tetrahydro-1H-cyclopenta[c]pyran-4a,5,7-triol
• SMILES (Canonical): C1=COC(C2C1(C(C(C2O)Cl)O)O)OC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): C1=CO[C@H]([C@H]2[C@@]1([C@@H]([C@H]([C@@H]2O)Cl)O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• InChI: InChI=1S/C14H21ClO10/c15-6-8(18)5-12(23-2-1-14(5,22)11(6)21)25-13-10(20)9(19)7(17)4(3-16)24-13/h1-2,4-13,16-22H,3H2/t4-,5+,6+,7-,8-,9+,10-,11-,12+,13+,14+/m1/s1
• InChI Key: XPQICTJAJUZIGE-LIHLBRGYSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₂₁ClO₁₀
• Molecular Weight: 384.76 g/mol
• Exact Mass: 384.0823246 g/mol
• Topological Polar Surface Area (TPSA): 169.00 Ų
• XlogP: -3.20
• Atomic LogP (AlogP): -3.64
• 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	-	0.4624	46.24%
Caco-2	-	0.8946	89.46%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.5489	54.89%
OATP2B1 inhibitior	-	0.8592	85.92%
OATP1B1 inhibitior	+	0.8683	86.83%
OATP1B3 inhibitior	+	0.9426	94.26%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9676	96.76%
P-glycoprotein inhibitior	-	0.8697	86.97%
P-glycoprotein substrate	-	0.9370	93.70%
CYP3A4 substrate	+	0.5711	57.11%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8387	83.87%
CYP3A4 inhibition	-	0.8804	88.04%
CYP2C9 inhibition	-	0.8728	87.28%
CYP2C19 inhibition	-	0.7033	70.33%
CYP2D6 inhibition	-	0.8631	86.31%
CYP1A2 inhibition	-	0.8354	83.54%
CYP2C8 inhibition	-	0.7713	77.13%
CYP inhibitory promiscuity	-	0.6956	69.56%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8638	86.38%
Carcinogenicity (trinary)	Non-required	0.5319	53.19%
Eye corrosion	-	0.9871	98.71%
Eye irritation	-	0.9778	97.78%
Skin irritation	-	0.7761	77.61%
Skin corrosion	-	0.9358	93.58%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3808	38.08%
Micronuclear	-	0.7241	72.41%
Hepatotoxicity	-	0.8625	86.25%
skin sensitisation	-	0.8611	86.11%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.4069	40.69%
Estrogen receptor binding	-	0.7562	75.62%
Androgen receptor binding	-	0.5393	53.93%
Thyroid receptor binding	+	0.6103	61.03%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	+	0.6749	67.49%
PPAR gamma	+	0.7275	72.75%
Honey bee toxicity	-	0.6133	61.33%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5450	54.50%
Fish aquatic toxicity	+	0.6539	65.39%

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	97.33%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.91%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	89.85%	95.93%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.00%	86.92%
CHEMBL218	P21554	Cannabinoid CB1 receptor	83.24%	96.61%
CHEMBL3401	O75469	Pregnane X receptor	83.22%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.23%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.09%	94.45%

Plants that contains it

• Retzia capensis
• Thunbergia alata
• Thunbergia fragrans

Cross-Links

• PubChem: 101664500
• LOTUS: LTS0141217
• wikiData: Q104402668