Bartsioside

Details

• Internal ID: b188ca42-24a9-4d04-bd1c-83f4ef0ec731
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[[(1S,4aS,7aR)-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): C1C=C(C2C1C=COC2OC3C(C(C(C(O3)CO)O)O)O)CO
• SMILES (Isomeric): C1C=C([C@H]2[C@@H]1C=CO[C@H]2O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)CO
• InChI: InChI=1S/C15H22O8/c16-5-8-2-1-7-3-4-21-14(10(7)8)23-15-13(20)12(19)11(18)9(6-17)22-15/h2-4,7,9-20H,1,5-6H2/t7-,9+,10+,11+,12-,13+,14-,15-/m0/s1
• InChI Key: FCHJZJFIDNMNBS-DNRYLMBSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₈
• Molecular Weight: 330.33 g/mol
• Exact Mass: 330.13146766 g/mol
• Topological Polar Surface Area (TPSA): 129.00 Ų
• XlogP: -1.90
• Atomic LogP (AlogP): -1.77
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

• 62133-72-6
• (2S,3R,4S,5S,6R)-2-[[(1S,4aS,7aR)-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6376	63.76%
Caco-2	-	0.8428	84.28%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.6702	67.02%
OATP2B1 inhibitior	-	0.8611	86.11%
OATP1B1 inhibitior	+	0.8919	89.19%
OATP1B3 inhibitior	+	0.9594	95.94%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9721	97.21%
P-glycoprotein inhibitior	-	0.9137	91.37%
P-glycoprotein substrate	-	0.9040	90.40%
CYP3A4 substrate	+	0.5200	52.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8125	81.25%
CYP3A4 inhibition	-	0.9396	93.96%
CYP2C9 inhibition	-	0.9275	92.75%
CYP2C19 inhibition	-	0.7872	78.72%
CYP2D6 inhibition	-	0.8799	87.99%
CYP1A2 inhibition	-	0.8588	85.88%
CYP2C8 inhibition	-	0.7937	79.37%
CYP inhibitory promiscuity	-	0.7974	79.74%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6855	68.55%
Eye corrosion	-	0.9879	98.79%
Eye irritation	-	0.9334	93.34%
Skin irritation	-	0.8188	81.88%
Skin corrosion	-	0.9620	96.20%
Ames mutagenesis	-	0.5191	51.91%
Human Ether-a-go-go-Related Gene inhibition	-	0.5434	54.34%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.8177	81.77%
skin sensitisation	-	0.8884	88.84%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	+	0.5520	55.20%
Acute Oral Toxicity (c)	IV	0.3838	38.38%
Estrogen receptor binding	-	0.7608	76.08%
Androgen receptor binding	-	0.5473	54.73%
Thyroid receptor binding	-	0.6124	61.24%
Glucocorticoid receptor binding	-	0.7367	73.67%
Aromatase binding	+	0.5347	53.47%
PPAR gamma	+	0.5988	59.88%
Honey bee toxicity	-	0.8084	80.84%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6850	68.50%
Fish aquatic toxicity	+	0.7677	76.77%

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	97.06%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.54%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.64%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	80.12%	94.73%

Plants that contains it

• Castilleja miniata
• Castilleja tenuiflora
• Cistanche salsa
• Monochasma savateri
• Pedicularis chinensis
• Penstemon whippleanus
• Plantago subulata
• Scrophularia scorodonia

Cross-Links

• PubChem: 14081907
• LOTUS: LTS0199070
• wikiData: Q104403592