[5-Hydroxy-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-7-yl]methyl benzoate

Details

• Internal ID: 39290e17-dd11-4088-9280-fe47d7c00e27
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: [5-hydroxy-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-7-yl]methyl benzoate
• SMILES (Canonical): C1=CC=C(C=C1)C(=O)OCC2=CC(C3C2C(OC=C3)OC4C(C(C(C(O4)CO)O)O)O)O
• SMILES (Isomeric): C1=CC=C(C=C1)C(=O)OCC2=CC(C3C2C(OC=C3)OC4C(C(C(C(O4)CO)O)O)O)O
• InChI: InChI=1S/C22H26O10/c23-9-15-17(25)18(26)19(27)22(31-15)32-21-16-12(8-14(24)13(16)6-7-29-21)10-30-20(28)11-4-2-1-3-5-11/h1-8,13-19,21-27H,9-10H2
• InChI Key: LPLWWIHUJXWQSS-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₆O₁₀
• Molecular Weight: 450.40 g/mol
• Exact Mass: 450.15259702 g/mol
• Topological Polar Surface Area (TPSA): 155.00 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): -0.94
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4833	48.33%
Caco-2	-	0.8916	89.16%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.6512	65.12%
OATP2B1 inhibitior	-	0.8489	84.89%
OATP1B1 inhibitior	+	0.8594	85.94%
OATP1B3 inhibitior	+	0.9600	96.00%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.6317	63.17%
P-glycoprotein inhibitior	-	0.7018	70.18%
P-glycoprotein substrate	-	0.8423	84.23%
CYP3A4 substrate	+	0.5858	58.58%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8528	85.28%
CYP3A4 inhibition	-	0.9354	93.54%
CYP2C9 inhibition	-	0.8976	89.76%
CYP2C19 inhibition	-	0.7661	76.61%
CYP2D6 inhibition	-	0.8696	86.96%
CYP1A2 inhibition	-	0.8475	84.75%
CYP2C8 inhibition	+	0.6160	61.60%
CYP inhibitory promiscuity	-	0.6374	63.74%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6811	68.11%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.9418	94.18%
Skin irritation	-	0.8058	80.58%
Skin corrosion	-	0.9628	96.28%
Ames mutagenesis	-	0.6437	64.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.6146	61.46%
Micronuclear	-	0.6241	62.41%
Hepatotoxicity	-	0.8125	81.25%
skin sensitisation	-	0.8456	84.56%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	+	0.5667	56.67%
Acute Oral Toxicity (c)	III	0.3999	39.99%
Estrogen receptor binding	+	0.5968	59.68%
Androgen receptor binding	-	0.4887	48.87%
Thyroid receptor binding	-	0.5306	53.06%
Glucocorticoid receptor binding	-	0.7612	76.12%
Aromatase binding	+	0.5946	59.46%
PPAR gamma	+	0.6315	63.15%
Honey bee toxicity	-	0.7908	79.08%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.6755	67.55%
Fish aquatic toxicity	+	0.7447	74.47%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.80%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.26%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.66%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.41%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.14%	95.56%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	86.01%	94.62%
CHEMBL3401	O75469	Pregnane X receptor	85.37%	94.73%
CHEMBL3891	P07384	Calpain 1	84.13%	93.04%
CHEMBL2581	P07339	Cathepsin D	80.53%	98.95%

Plants that contains it

• Bartsia alpina
• Globularia cordifolia
• Globularia davisiana
• Globularia dumulosa
• Globularia nudicaulis
• Globularia orientalis
• Lathraea squamaria
• Melampyrum arvense
• Melampyrum chlorostachyum
• Parentucellia viscosa
• Penstemon auriberbis

Cross-Links

• PubChem: 73802786
• LOTUS: LTS0195406
• wikiData: Q104252361