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

Details

• Internal ID: 1e1b393d-9644-4378-87d9-8ed92de3d450
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: (1S,4aS,7S,7aR)-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-7-carboxylic acid
• SMILES (Canonical): C1CC(C2C1C=COC2OC3C(C(C(C(O3)CO)O)O)O)C(=O)O
• SMILES (Isomeric): C1C[C@@H]([C@H]2[C@@H]1C=CO[C@H]2O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C(=O)O
• InChI: InChI=1S/C15H22O9/c16-5-8-10(17)11(18)12(19)15(23-8)24-14-9-6(3-4-22-14)1-2-7(9)13(20)21/h3-4,6-12,14-19H,1-2,5H2,(H,20,21)/t6-,7-,8+,9+,10+,11-,12+,14-,15+/m0/s1
• InChI Key: ZUKLFFYDSALIQW-UWQNFANSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₉
• Molecular Weight: 346.33 g/mol
• Exact Mass: 346.12638228 g/mol
• Topological Polar Surface Area (TPSA): 146.00 Ų
• XlogP: -1.10
• Atomic LogP (AlogP): -1.60
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6235	62.35%
Caco-2	-	0.8796	87.96%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.7283	72.83%
OATP2B1 inhibitior	-	0.8558	85.58%
OATP1B1 inhibitior	+	0.8593	85.93%
OATP1B3 inhibitior	+	0.9577	95.77%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9584	95.84%
P-glycoprotein inhibitior	-	0.9219	92.19%
P-glycoprotein substrate	-	0.9320	93.20%
CYP3A4 substrate	+	0.5615	56.15%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8602	86.02%
CYP3A4 inhibition	-	0.9216	92.16%
CYP2C9 inhibition	-	0.9136	91.36%
CYP2C19 inhibition	-	0.8872	88.72%
CYP2D6 inhibition	-	0.8992	89.92%
CYP1A2 inhibition	-	0.8890	88.90%
CYP2C8 inhibition	-	0.7996	79.96%
CYP inhibitory promiscuity	-	0.8619	86.19%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6977	69.77%
Eye corrosion	-	0.9861	98.61%
Eye irritation	-	0.9619	96.19%
Skin irritation	-	0.8096	80.96%
Skin corrosion	-	0.9517	95.17%
Ames mutagenesis	-	0.5770	57.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.5140	51.40%
Micronuclear	-	0.7841	78.41%
Hepatotoxicity	-	0.7199	71.99%
skin sensitisation	-	0.8917	89.17%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	+	0.4749	47.49%
Acute Oral Toxicity (c)	III	0.4439	44.39%
Estrogen receptor binding	-	0.5919	59.19%
Androgen receptor binding	-	0.5523	55.23%
Thyroid receptor binding	-	0.6600	66.00%
Glucocorticoid receptor binding	-	0.7130	71.30%
Aromatase binding	-	0.5701	57.01%
PPAR gamma	+	0.6190	61.90%
Honey bee toxicity	-	0.8195	81.95%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.7455	74.55%
Fish aquatic toxicity	-	0.6531	65.31%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.94%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.26%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.37%	97.09%
CHEMBL5255	O00206	Toll-like receptor 4	86.48%	92.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.81%	99.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.70%	95.89%

Plants that contains it

• Tithonia pedunculata
• Tithonia rotundifolia

Cross-Links

• PubChem: 162997367
• LOTUS: LTS0240306
• wikiData: Q104911461