Scandoside methyl ester

Details

• Internal ID: c4d09379-389e-48ea-be26-b6ebe9e34c7e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl (1S,4aS,5R,7aS)-5-hydroxy-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): COC(=O)C1=COC(C2C1C(C=C2CO)O)OC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): COC(=O)C1=CO[C@H]([C@H]2[C@@H]1[C@@H](C=C2CO)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• InChI: InChI=1S/C17H24O11/c1-25-15(24)7-5-26-16(10-6(3-18)2-8(20)11(7)10)28-17-14(23)13(22)12(21)9(4-19)27-17/h2,5,8-14,16-23H,3-4H2,1H3/t8-,9-,10-,11+,12-,13+,14-,16+,17+/m1/s1
• InChI Key: WSGPLSDARZNMCW-LPGRTNKPSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₄O₁₁
• Molecular Weight: 404.40 g/mol
• Exact Mass: 404.13186158 g/mol
• Topological Polar Surface Area (TPSA): 175.00 Ų
• XlogP: -3.50
• Atomic LogP (AlogP): -3.26
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

• Scandoside methyl ester
• 27530-67-2
• Scandioside methyl ester
• CHEBI:9046
• methyl (1S,4aS,5R,7aS)-5-hydroxy-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
• 6beta-hydroxygeniposide
• Cyclopenta(c)pyran-4-carboxylic acid, 1-(beta-D-glucopyranosyloxy)-1,4aalpha,5,7aalpha-tetrahydro-5beta-hydroxy-7-(hydroxymethyl)-, hexaacetate
• CHEMBL516850
• AKOS015896743
• Scandiosidemethylester
• C09798
• SCHEMBL20572206
• DTXSID80950211
• HY-N6249
• CS-0032784
• Q27108249
• Methyl 1-(hexopyranosyloxy)-5-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5197	51.97%
Caco-2	-	0.8746	87.46%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.6687	66.87%
OATP2B1 inhibitior	-	0.8573	85.73%
OATP1B1 inhibitior	+	0.7494	74.94%
OATP1B3 inhibitior	+	0.9687	96.87%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9489	94.89%
P-glycoprotein inhibitior	-	0.8902	89.02%
P-glycoprotein substrate	-	0.8185	81.85%
CYP3A4 substrate	+	0.5683	56.83%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8649	86.49%
CYP3A4 inhibition	-	0.9584	95.84%
CYP2C9 inhibition	-	0.9103	91.03%
CYP2C19 inhibition	-	0.8324	83.24%
CYP2D6 inhibition	-	0.9035	90.35%
CYP1A2 inhibition	-	0.8940	89.40%
CYP2C8 inhibition	-	0.7317	73.17%
CYP inhibitory promiscuity	-	0.7100	71.00%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6732	67.32%
Eye corrosion	-	0.9865	98.65%
Eye irritation	-	0.9504	95.04%
Skin irritation	-	0.8055	80.55%
Skin corrosion	-	0.9549	95.49%
Ames mutagenesis	-	0.5237	52.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.6302	63.02%
Micronuclear	-	0.7241	72.41%
Hepatotoxicity	-	0.8125	81.25%
skin sensitisation	-	0.8843	88.43%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	+	0.7335	73.35%
Acute Oral Toxicity (c)	III	0.4889	48.89%
Estrogen receptor binding	+	0.5555	55.55%
Androgen receptor binding	-	0.5405	54.05%
Thyroid receptor binding	-	0.6067	60.67%
Glucocorticoid receptor binding	-	0.6413	64.13%
Aromatase binding	+	0.5610	56.10%
PPAR gamma	-	0.5581	55.81%
Honey bee toxicity	-	0.8283	82.83%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.8200	82.00%
Fish aquatic toxicity	-	0.6246	62.46%

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	95.77%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.69%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	90.21%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.99%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.67%	86.92%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.27%	96.00%
CHEMBL2581	P07339	Cathepsin D	81.39%	98.95%

Plants that contains it

• Catunaregam spinosa
• Cordiera macrophylla
• Eucommia ulmoides
• Feretia apodanthera
• Galium mollugo
• Gardenia jasminoides
• Genipa americana
• Oldenlandia corymbosa
• Oldenlandia herbacea var. herbacea
• Paederia foetida
• Rhododendron latoucheae
• Rosenbergiodendron formosum
• Spermacoce verticillata

Cross-Links

• PubChem: 442433
• NPASS: NPC298255
• LOTUS: LTS0129231
• wikiData: Q27108249