(2R,3R,4S,5S,6R)-6-[[(1R,4aS,5R,7aR)-5-hydroxy-4-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxymethyl]oxane-2,3,4,5-tetrol

Details

• Internal ID: cf3e0cd9-fc5c-4b4e-9c06-bfaf23078eb2
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Monosaccharides
• IUPAC Name: (2R,3R,4S,5S,6R)-6-[[(1R,4aS,5R,7aR)-5-hydroxy-4-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxymethyl]oxane-2,3,4,5-tetrol
• SMILES (Canonical): C1=CC(C2C1C(OC=C2CO)OCC3C(C(C(C(O3)O)O)O)O)O
• SMILES (Isomeric): C1=C[C@H]([C@H]2[C@@H]1[C@@H](OC=C2CO)OC[C@@H]3[C@H]([C@@H]([C@H]([C@@H](O3)O)O)O)O)O
• InChI: InChI=1S/C15H22O9/c16-3-6-4-22-15(7-1-2-8(17)10(6)7)23-5-9-11(18)12(19)13(20)14(21)24-9/h1-2,4,7-21H,3,5H2/t7-,8-,9-,10-,11-,12+,13-,14-,15+/m1/s1
• InChI Key: GSXXDXIJOSPEQP-OFUODPKLSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₉
• Molecular Weight: 346.33 g/mol
• Exact Mass: 346.12638228 g/mol
• Topological Polar Surface Area (TPSA): 149.00 Ų
• XlogP: -3.60
• Atomic LogP (AlogP): -2.80
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6717	67.17%
Caco-2	-	0.8604	86.04%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.5905	59.05%
OATP2B1 inhibitior	-	0.8603	86.03%
OATP1B1 inhibitior	+	0.8239	82.39%
OATP1B3 inhibitior	+	0.9631	96.31%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9575	95.75%
P-glycoprotein inhibitior	-	0.8971	89.71%
P-glycoprotein substrate	-	0.8827	88.27%
CYP3A4 substrate	+	0.5159	51.59%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8337	83.37%
CYP3A4 inhibition	-	0.9416	94.16%
CYP2C9 inhibition	-	0.9116	91.16%
CYP2C19 inhibition	-	0.7815	78.15%
CYP2D6 inhibition	-	0.8755	87.55%
CYP1A2 inhibition	-	0.8639	86.39%
CYP2C8 inhibition	-	0.7609	76.09%
CYP inhibitory promiscuity	-	0.6978	69.78%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6579	65.79%
Eye corrosion	-	0.9890	98.90%
Eye irritation	-	0.9559	95.59%
Skin irritation	-	0.8209	82.09%
Skin corrosion	-	0.9609	96.09%
Ames mutagenesis	-	0.5191	51.91%
Human Ether-a-go-go-Related Gene inhibition	-	0.5359	53.59%
Micronuclear	-	0.7441	74.41%
Hepatotoxicity	-	0.7540	75.40%
skin sensitisation	-	0.8878	88.78%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.6039	60.39%
Acute Oral Toxicity (c)	IV	0.4268	42.68%
Estrogen receptor binding	-	0.6143	61.43%
Androgen receptor binding	-	0.6439	64.39%
Thyroid receptor binding	+	0.5349	53.49%
Glucocorticoid receptor binding	-	0.6563	65.63%
Aromatase binding	+	0.6009	60.09%
PPAR gamma	-	0.4923	49.23%
Honey bee toxicity	-	0.7796	77.96%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	-	0.5621	56.21%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL226	P30542	Adenosine A1 receptor	96.96%	95.93%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.93%	91.11%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	92.67%	86.92%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.23%	96.09%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	87.66%	83.57%
CHEMBL3401	O75469	Pregnane X receptor	86.62%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.08%	97.09%
CHEMBL4040	P28482	MAP kinase ERK2	82.83%	83.82%

Plants that contains it

• Mentzelia decapetala

Cross-Links

• PubChem: 163031030
• LOTUS: LTS0188413
• wikiData: Q105018199