Schismoside

Details

• Internal ID: 409a7077-1928-4903-aa6e-9c3524342d86
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl (1S,4aS,5S,6S,7S,7aS)-5,6,7-trihydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): CC1(C2C(C(C1O)O)C(=COC2OC3C(C(C(C(O3)CO)O)O)O)C(=O)OC)O
• SMILES (Isomeric): C[C@@]1([C@@H]2[C@H]([C@@H]([C@@H]1O)O)C(=CO[C@H]2O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C(=O)OC)O
• InChI: InChI=1S/C17H26O12/c1-17(25)8-7(10(20)13(17)23)5(14(24)26-2)4-27-15(8)29-16-12(22)11(21)9(19)6(3-18)28-16/h4,6-13,15-16,18-23,25H,3H2,1-2H3/t6-,7-,8-,9-,10+,11+,12-,13+,15+,16+,17+/m1/s1
• InChI Key: HHDWDLBSGSYIQQ-RHZWLWFHSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₆O₁₂
• Molecular Weight: 422.40 g/mol
• Exact Mass: 422.14242626 g/mol
• Topological Polar Surface Area (TPSA): 196.00 Ų
• XlogP: -3.60
• Atomic LogP (AlogP): -4.07
• H-Bond Acceptor: 12
• H-Bond Donor: 7
• Rotatable Bonds: 4

Synonyms

• CHEMBL2048642

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6019	60.19%
Caco-2	-	0.8649	86.49%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7140	71.40%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7334	73.34%
OATP1B3 inhibitior	+	0.9477	94.77%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9382	93.82%
P-glycoprotein inhibitior	-	0.8493	84.93%
P-glycoprotein substrate	-	0.8009	80.09%
CYP3A4 substrate	+	0.6198	61.98%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8770	87.70%
CYP3A4 inhibition	-	0.9274	92.74%
CYP2C9 inhibition	-	0.9205	92.05%
CYP2C19 inhibition	-	0.8751	87.51%
CYP2D6 inhibition	-	0.9106	91.06%
CYP1A2 inhibition	-	0.9005	90.05%
CYP2C8 inhibition	-	0.6782	67.82%
CYP inhibitory promiscuity	-	0.7532	75.32%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6718	67.18%
Eye corrosion	-	0.9877	98.77%
Eye irritation	-	0.9544	95.44%
Skin irritation	-	0.7532	75.32%
Skin corrosion	-	0.9503	95.03%
Ames mutagenesis	-	0.5237	52.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.5824	58.24%
Micronuclear	-	0.6641	66.41%
Hepatotoxicity	-	0.8348	83.48%
skin sensitisation	-	0.8530	85.30%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	+	0.7601	76.01%
Acute Oral Toxicity (c)	III	0.4425	44.25%
Estrogen receptor binding	+	0.5961	59.61%
Androgen receptor binding	-	0.5503	55.03%
Thyroid receptor binding	-	0.5160	51.60%
Glucocorticoid receptor binding	-	0.5891	58.91%
Aromatase binding	+	0.5313	53.13%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.8302	83.02%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7700	77.00%
Fish aquatic toxicity	-	0.5319	53.19%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.05%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.02%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	88.57%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.95%	86.33%
CHEMBL4208	P20618	Proteasome component C5	84.50%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.99%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.06%	94.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.43%	96.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.15%	86.92%
CHEMBL221	P23219	Cyclooxygenase-1	80.69%	90.17%
CHEMBL5255	O00206	Toll-like receptor 4	80.20%	92.50%

Plants that contains it

• Phlomoides rotata
• Trochocarpa laurina

Cross-Links

• PubChem: 70696679
• NPASS: NPC137210
• LOTUS: LTS0076648
• wikiData: Q104402255