(1S,4aS,5R,7aS)-5-hydroxy-7-(methylsulfanylcarbonyloxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid

Details

• Internal ID: 30a4cd6d-db60-49b8-bd50-85bfdc146d8a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: (1S,4aS,5R,7aS)-5-hydroxy-7-(methylsulfanylcarbonyloxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid
• SMILES (Canonical): CSC(=O)OCC1=CC(C2C1C(OC=C2C(=O)O)OC3C(C(C(C(O3)CO)O)O)O)O
• SMILES (Isomeric): CSC(=O)OCC1=C[C@H]([C@H]2[C@@H]1[C@@H](OC=C2C(=O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O
• InChI: InChI=1S/C18H24O12S/c1-31-18(26)28-4-6-2-8(20)11-7(15(24)25)5-27-16(10(6)11)30-17-14(23)13(22)12(21)9(3-19)29-17/h2,5,8-14,16-17,19-23H,3-4H2,1H3,(H,24,25)/t8-,9-,10-,11+,12-,13+,14-,16+,17+/m1/s1
• InChI Key: ICTKKPLVSHVNDV-LPGRTNKPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₄O₁₂S
• Molecular Weight: 464.40 g/mol
• Exact Mass: 464.09884737 g/mol
• Topological Polar Surface Area (TPSA): 218.00 Ų
• XlogP: -2.30
• Atomic LogP (AlogP): -1.84
• H-Bond Acceptor: 12
• H-Bond Donor: 6
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5064	50.64%
Caco-2	-	0.8918	89.18%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.6663	66.63%
OATP2B1 inhibitior	-	0.8552	85.52%
OATP1B1 inhibitior	+	0.7710	77.10%
OATP1B3 inhibitior	+	0.9490	94.90%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.8575	85.75%
P-glycoprotein inhibitior	-	0.8205	82.05%
P-glycoprotein substrate	-	0.8161	81.61%
CYP3A4 substrate	+	0.5783	57.83%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8739	87.39%
CYP3A4 inhibition	-	0.8761	87.61%
CYP2C9 inhibition	-	0.8078	80.78%
CYP2C19 inhibition	-	0.7131	71.31%
CYP2D6 inhibition	-	0.8899	88.99%
CYP1A2 inhibition	-	0.8125	81.25%
CYP2C8 inhibition	-	0.5944	59.44%
CYP inhibitory promiscuity	-	0.6581	65.81%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6260	62.60%
Eye corrosion	-	0.9849	98.49%
Eye irritation	-	0.9446	94.46%
Skin irritation	-	0.7833	78.33%
Skin corrosion	-	0.9401	94.01%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4430	44.30%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	-	0.8125	81.25%
skin sensitisation	-	0.8527	85.27%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.8672	86.72%
Acute Oral Toxicity (c)	III	0.5129	51.29%
Estrogen receptor binding	+	0.6749	67.49%
Androgen receptor binding	+	0.5352	53.52%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.5541	55.41%
Aromatase binding	+	0.5978	59.78%
PPAR gamma	+	0.5513	55.13%
Honey bee toxicity	-	0.7120	71.20%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7150	71.50%
Fish aquatic toxicity	+	0.7514	75.14%

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	95.67%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.17%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.87%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	87.25%	94.73%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.50%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.25%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.64%	89.00%
CHEMBL2581	P07339	Cathepsin D	81.28%	98.95%

Plants that contains it

• Saprosma scortechinii

Cross-Links

• PubChem: 21672046
• LOTUS: LTS0052106
• wikiData: Q105111156