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

Details

• Internal ID: be03ccd2-ecf4-4b3a-9079-49fd0c53a23b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: (1S,4aS,5R,7S,7aR)-5-hydroxy-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid
• SMILES (Canonical): C1C(C2C(C1O)C(=COC2OC3C(C(C(C(O3)CO)O)O)O)C(=O)O)CO
• SMILES (Isomeric): C1[C@@H]([C@@H]2[C@H]([C@@H]1O)C(=CO[C@H]2O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C(=O)O)CO
• InChI: InChI=1S/C16H24O11/c17-2-5-1-7(19)10-6(14(23)24)4-25-15(9(5)10)27-16-13(22)12(21)11(20)8(3-18)26-16/h4-5,7-13,15-22H,1-3H2,(H,23,24)/t5-,7-,8-,9-,10+,11-,12+,13-,15+,16+/m1/s1
• InChI Key: SFKKPIKMISYKLY-SQJJMSPMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₄O₁₁
• Molecular Weight: 392.35 g/mol
• Exact Mass: 392.13186158 g/mol
• Topological Polar Surface Area (TPSA): 186.00 Ų
• XlogP: -2.90
• Atomic LogP (AlogP): -3.27
• H-Bond Acceptor: 10
• H-Bond Donor: 7
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5154	51.54%
Caco-2	-	0.9056	90.56%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.6109	61.09%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7076	70.76%
OATP1B3 inhibitior	+	0.9553	95.53%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9617	96.17%
P-glycoprotein inhibitior	-	0.9085	90.85%
P-glycoprotein substrate	-	0.8998	89.98%
CYP3A4 substrate	-	0.5064	50.64%
CYP2C9 substrate	-	0.8078	80.78%
CYP2D6 substrate	-	0.8715	87.15%
CYP3A4 inhibition	-	0.9399	93.99%
CYP2C9 inhibition	-	0.9404	94.04%
CYP2C19 inhibition	-	0.8597	85.97%
CYP2D6 inhibition	-	0.8786	87.86%
CYP1A2 inhibition	-	0.8924	89.24%
CYP2C8 inhibition	-	0.8354	83.54%
CYP inhibitory promiscuity	-	0.8555	85.55%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7127	71.27%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.9380	93.80%
Skin irritation	-	0.7957	79.57%
Skin corrosion	-	0.9537	95.37%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6477	64.77%
Micronuclear	-	0.7141	71.41%
Hepatotoxicity	-	0.7839	78.39%
skin sensitisation	-	0.8787	87.87%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	+	0.5711	57.11%
Acute Oral Toxicity (c)	III	0.3774	37.74%
Estrogen receptor binding	-	0.5696	56.96%
Androgen receptor binding	-	0.4921	49.21%
Thyroid receptor binding	-	0.5155	51.55%
Glucocorticoid receptor binding	-	0.7549	75.49%
Aromatase binding	+	0.5860	58.60%
PPAR gamma	+	0.5620	56.20%
Honey bee toxicity	-	0.8281	82.81%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	-	0.5683	56.83%

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	95.13%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.43%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.27%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.16%	99.17%
CHEMBL5255	O00206	Toll-like receptor 4	82.99%	92.50%
CHEMBL220	P22303	Acetylcholinesterase	82.77%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.71%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.21%	86.33%

Plants that contains it

• Castilleja integra

Cross-Links

• PubChem: 162956006
• LOTUS: LTS0082591
• wikiData: Q105251807