2-[7-methyl-5-oxo-1-[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4,4a,6,7,7a-hexahydro-1H-cyclopenta[c]pyran-4-yl]acetic acid

Details

• Internal ID: d6c6d21e-3a5d-485d-bc94-51e5f88d6919
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: 2-[7-methyl-5-oxo-1-[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4,4a,6,7,7a-hexahydro-1H-cyclopenta[c]pyran-4-yl]acetic acid
• InChI: InChI=1S/C17H26O10/c1-6-2-8(19)12-7(3-10(20)21)5-25-16(11(6)12)27-17-15(24)14(23)13(22)9(4-18)26-17/h6-7,9,11-18,22-24H,2-5H2,1H3,(H,20,21)/t6?,7?,9-,11?,12?,13+,14-,15+,16?,17-/m0/s1
• InChI Key: GOUKNTWZECJCMH-BXMCUSTPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₆O₁₀
• Molecular Weight: 390.40 g/mol
• Exact Mass: 390.15259702 g/mol
• Topological Polar Surface Area (TPSA): 163.00 Ų
• XlogP: -2.00
• Atomic LogP (AlogP): -1.91
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7281	72.81%
Caco-2	-	0.8231	82.31%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.6246	62.46%
OATP2B1 inhibitior	-	0.8593	85.93%
OATP1B1 inhibitior	+	0.8515	85.15%
OATP1B3 inhibitior	+	0.9611	96.11%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.6317	63.17%
P-glycoprotein inhibitior	-	0.8918	89.18%
P-glycoprotein substrate	-	0.8099	80.99%
CYP3A4 substrate	+	0.5673	56.73%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8837	88.37%
CYP3A4 inhibition	-	0.9267	92.67%
CYP2C9 inhibition	-	0.9579	95.79%
CYP2C19 inhibition	-	0.9184	91.84%
CYP2D6 inhibition	-	0.9453	94.53%
CYP1A2 inhibition	-	0.9128	91.28%
CYP2C8 inhibition	-	0.8739	87.39%
CYP inhibitory promiscuity	-	0.9728	97.28%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7036	70.36%
Eye corrosion	-	0.9918	99.18%
Eye irritation	-	0.9573	95.73%
Skin irritation	-	0.8444	84.44%
Skin corrosion	-	0.9624	96.24%
Ames mutagenesis	-	0.5445	54.45%
Human Ether-a-go-go-Related Gene inhibition	-	0.6682	66.82%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.9402	94.02%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.6885	68.85%
Acute Oral Toxicity (c)	III	0.4986	49.86%
Estrogen receptor binding	-	0.5191	51.91%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	-	0.5344	53.44%
Glucocorticoid receptor binding	-	0.6102	61.02%
Aromatase binding	-	0.4913	49.13%
PPAR gamma	+	0.5296	52.96%
Honey bee toxicity	-	0.8263	82.63%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.7053	70.53%
Fish aquatic toxicity	-	0.4510	45.10%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	95.52%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.41%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.63%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	91.50%	83.82%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.31%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.66%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.14%	99.17%
CHEMBL5255	O00206	Toll-like receptor 4	86.73%	92.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.66%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.67%	89.00%

Plants that contains it

• Verbena officinalis

Cross-Links

• PubChem: 5316746
• NPASS: NPC273373