methyl (1S,4aS,5S,7aS)-7-(benzoyloxymethyl)-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-carboxylate

Details

• Internal ID: 88315ebf-eb13-4d2d-b170-b93997fdc897
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl (1S,4aS,5S,7aS)-7-(benzoyloxymethyl)-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-carboxylate
• InChI: InChI=1S/C24H28O12/c1-32-22(31)13-10-34-23(36-24-20(29)19(28)18(27)15(8-25)35-24)16-12(7-14(26)17(13)16)9-33-21(30)11-5-3-2-4-6-11/h2-7,10,14-20,23-29H,8-9H2,1H3/t14-,15+,16+,17-,18+,19-,20+,23-,24-/m0/s1
• InChI Key: OVNBCJLEFGLOJC-CKEFBNLZSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₈O₁₂
• Molecular Weight: 508.50 g/mol
• Exact Mass: 508.15807632 g/mol
• Topological Polar Surface Area (TPSA): 181.00 Ų
• XlogP: -1.20
• Atomic LogP (AlogP): -1.39
• H-Bond Acceptor: 12
• H-Bond Donor: 5
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5168	51.68%
Caco-2	-	0.9048	90.48%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.6543	65.43%
OATP2B1 inhibitior	-	0.8473	84.73%
OATP1B1 inhibitior	+	0.7956	79.56%
OATP1B3 inhibitior	+	0.9722	97.22%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.4876	48.76%
P-glycoprotein inhibitior	-	0.6366	63.66%
P-glycoprotein substrate	-	0.7375	73.75%
CYP3A4 substrate	+	0.6052	60.52%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8616	86.16%
CYP3A4 inhibition	-	0.9410	94.10%
CYP2C9 inhibition	-	0.8493	84.93%
CYP2C19 inhibition	-	0.7876	78.76%
CYP2D6 inhibition	-	0.9089	90.89%
CYP1A2 inhibition	-	0.8741	87.41%
CYP2C8 inhibition	+	0.6476	64.76%
CYP inhibitory promiscuity	-	0.7288	72.88%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6312	63.12%
Eye corrosion	-	0.9883	98.83%
Eye irritation	-	0.9418	94.18%
Skin irritation	-	0.8087	80.87%
Skin corrosion	-	0.9549	95.49%
Ames mutagenesis	-	0.6837	68.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.4861	48.61%
Micronuclear	-	0.5541	55.41%
Hepatotoxicity	-	0.7948	79.48%
skin sensitisation	-	0.8609	86.09%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.7529	75.29%
Acute Oral Toxicity (c)	III	0.5412	54.12%
Estrogen receptor binding	+	0.7502	75.02%
Androgen receptor binding	+	0.5745	57.45%
Thyroid receptor binding	-	0.5523	55.23%
Glucocorticoid receptor binding	-	0.5206	52.06%
Aromatase binding	-	0.5716	57.16%
PPAR gamma	+	0.6592	65.92%
Honey bee toxicity	-	0.8093	80.93%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	+	0.6909	69.09%

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	93.66%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.42%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.16%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	91.41%	94.73%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.35%	91.11%
CHEMBL2581	P07339	Cathepsin D	88.14%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.56%	95.56%
CHEMBL5028	O14672	ADAM10	82.57%	97.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.48%	99.23%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.89%	96.00%

Plants that contains it

• Oldenlandia corymbosa

Cross-Links

• PubChem: 15714684
• LOTUS: LTS0173203
• wikiData: Q105200860