(1S,4aS,5R,7aS)-7-(acetyloxymethyl)-5-hydroxy-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: 091f849e-fc65-4676-8856-2d049afb970f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: (1S,4aS,5R,7aS)-7-(acetyloxymethyl)-5-hydroxy-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): CC(=O)OCC1=CC(C2C1C(OC=C2C(=O)O)OC3C(C(C(C(O3)CO)O)O)O)O
• SMILES (Isomeric): CC(=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/C18H24O12/c1-6(20)27-4-7-2-9(21)12-8(16(25)26)5-28-17(11(7)12)30-18-15(24)14(23)13(22)10(3-19)29-18/h2,5,9-15,17-19,21-24H,3-4H2,1H3,(H,25,26)/t9-,10-,11-,12+,13-,14+,15-,17+,18+/m1/s1
• InChI Key: DGDWCRWJRNMRKX-FUIAOSIISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₄O₁₂
• Molecular Weight: 432.40 g/mol
• Exact Mass: 432.12677620 g/mol
• Topological Polar Surface Area (TPSA): 192.00 Ų
• XlogP: -3.20
• Atomic LogP (AlogP): -2.78
• H-Bond Acceptor: 11
• 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	-	0.4586	45.86%
Caco-2	-	0.9121	91.21%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.7191	71.91%
OATP2B1 inhibitior	-	0.8542	85.42%
OATP1B1 inhibitior	+	0.7367	73.67%
OATP1B3 inhibitior	+	0.9642	96.42%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.7857	78.57%
P-glycoprotein inhibitior	-	0.8502	85.02%
P-glycoprotein substrate	-	0.8606	86.06%
CYP3A4 substrate	+	0.5493	54.93%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8902	89.02%
CYP3A4 inhibition	-	0.9647	96.47%
CYP2C9 inhibition	-	0.8985	89.85%
CYP2C19 inhibition	-	0.8758	87.58%
CYP2D6 inhibition	-	0.9205	92.05%
CYP1A2 inhibition	-	0.8741	87.41%
CYP2C8 inhibition	-	0.7065	70.65%
CYP inhibitory promiscuity	-	0.8171	81.71%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7161	71.61%
Eye corrosion	-	0.9883	98.83%
Eye irritation	-	0.9347	93.47%
Skin irritation	-	0.7686	76.86%
Skin corrosion	-	0.9438	94.38%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5558	55.58%
Micronuclear	-	0.6941	69.41%
Hepatotoxicity	-	0.8750	87.50%
skin sensitisation	-	0.8918	89.18%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	+	0.8624	86.24%
Acute Oral Toxicity (c)	III	0.4467	44.67%
Estrogen receptor binding	+	0.6410	64.10%
Androgen receptor binding	+	0.5285	52.85%
Thyroid receptor binding	-	0.5967	59.67%
Glucocorticoid receptor binding	-	0.5512	55.12%
Aromatase binding	+	0.5582	55.82%
PPAR gamma	+	0.5448	54.48%
Honey bee toxicity	-	0.7875	78.75%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7950	79.50%
Fish aquatic toxicity	+	0.7696	76.96%

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	96.28%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.02%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	89.22%	94.73%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.00%	91.11%
CHEMBL2581	P07339	Cathepsin D	86.58%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.54%	86.33%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	85.07%	94.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.08%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.89%	95.56%

Plants that contains it

• Eucommia ulmoides
• Galium rivale
• Globularia trichosantha
• Lasianthus acuminatissimus
• Morinda citrifolia
• Morinda coreia
• Paederia foetida
• Saprosma scortechinii
• Spermacoce remota

Cross-Links

• PubChem: 101714788
• LOTUS: LTS0246382
• wikiData: Q104978627