(1S,4aS,5R,7aS)-7-(methylsulfanylcarbonyloxymethyl)-1,5-bis[[(2R,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: c9f1d8e3-8769-4829-8b49-f6913c85c4d7
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: (1S,4aS,5R,7aS)-7-(methylsulfanylcarbonyloxymethyl)-1,5-bis[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid
• InChI: InChI=1S/C24H34O17S/c1-42-24(35)37-5-7-2-9(38-22-18(31)16(29)14(27)10(3-25)39-22)13-8(20(33)34)6-36-21(12(7)13)41-23-19(32)17(30)15(28)11(4-26)40-23/h2,6,9-19,21-23,25-32H,3-5H2,1H3,(H,33,34)/t9-,10-,11-,12-,13+,14-,15-,16+,17+,18-,19-,21+,22-,23+/m1/s1
• InChI Key: CNPALDDVGYFARC-OXIQENOPSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₄O₁₇S
• Molecular Weight: 626.60 g/mol
• Exact Mass: 626.15167079 g/mol
• Topological Polar Surface Area (TPSA): 297.00 Ų
• XlogP: -3.90
• Atomic LogP (AlogP): -4.02
• H-Bond Acceptor: 17
• H-Bond Donor: 9
• Rotatable Bonds: 9

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	-	0.9006	90.06%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.6663	66.63%
OATP2B1 inhibitior	-	0.8603	86.03%
OATP1B1 inhibitior	+	0.7954	79.54%
OATP1B3 inhibitior	+	0.9490	94.90%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.6608	66.08%
P-glycoprotein inhibitior	-	0.5705	57.05%
P-glycoprotein substrate	-	0.7711	77.11%
CYP3A4 substrate	+	0.6027	60.27%
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	-	0.5847	58.47%
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	-	0.9202	92.02%
Skin irritation	-	0.7833	78.33%
Skin corrosion	-	0.9401	94.01%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6794	67.94%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.8527	85.27%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.8482	84.82%
Acute Oral Toxicity (c)	III	0.5129	51.29%
Estrogen receptor binding	+	0.7336	73.36%
Androgen receptor binding	+	0.6284	62.84%
Thyroid receptor binding	-	0.5695	56.95%
Glucocorticoid receptor binding	-	0.5083	50.83%
Aromatase binding	+	0.5726	57.26%
PPAR gamma	+	0.5646	56.46%
Honey bee toxicity	-	0.7341	73.41%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6950	69.50%
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	95.81%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.33%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.38%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.90%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	85.42%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.80%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.56%	95.56%
CHEMBL2581	P07339	Cathepsin D	83.42%	98.95%

Plants that contains it

• Paederia foetida

Cross-Links

• PubChem: 162845142
• LOTUS: LTS0058209
• wikiData: Q104966202