methyl (1S,4aS,6S,7R,7aS)-6-hydroxy-7-methyl-1-[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate

Details

• Internal ID: 6a7ed58b-9ab2-47b0-ba7d-95add3562821
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Iridoids and derivatives
• IUPAC Name: methyl (1S,4aS,6S,7R,7aS)-6-hydroxy-7-methyl-1-[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
• InChI: InChI=1S/C17H26O10/c1-6-9(18)4-7-8(14(22)23-2)5-25-15(10(6)7)26-17-13(21)11(19)12(20)16(24-3)27-17/h5-7,9-13,15-21H,4H2,1-3H3/t6-,7+,9-,10+,11-,12-,13+,15-,16-,17+/m0/s1
• InChI Key: FRZVJDGMNCUSFA-OAJSKLDCSA-N
• Popularity: 2 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): 144.00 Ų
• XlogP: -1.30
• Atomic LogP (AlogP): -1.54
• H-Bond Acceptor: 10
• H-Bond Donor: 4
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9006	90.06%
Caco-2	-	0.7598	75.98%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.4768	47.68%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.6904	69.04%
OATP1B3 inhibitior	+	0.9319	93.19%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.8994	89.94%
P-glycoprotein inhibitior	-	0.8438	84.38%
P-glycoprotein substrate	-	0.7277	72.77%
CYP3A4 substrate	+	0.6213	62.13%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8668	86.68%
CYP3A4 inhibition	-	0.7791	77.91%
CYP2C9 inhibition	-	0.9566	95.66%
CYP2C19 inhibition	-	0.8937	89.37%
CYP2D6 inhibition	-	0.8892	88.92%
CYP1A2 inhibition	-	0.8902	89.02%
CYP2C8 inhibition	-	0.6229	62.29%
CYP inhibitory promiscuity	-	0.8729	87.29%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4704	47.04%
Eye corrosion	-	0.9856	98.56%
Eye irritation	-	0.9552	95.52%
Skin irritation	-	0.6225	62.25%
Skin corrosion	-	0.9411	94.11%
Ames mutagenesis	-	0.5154	51.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5994	59.94%
Micronuclear	-	0.5800	58.00%
Hepatotoxicity	-	0.5822	58.22%
skin sensitisation	-	0.8238	82.38%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.6852	68.52%
Acute Oral Toxicity (c)	III	0.4327	43.27%
Estrogen receptor binding	+	0.5634	56.34%
Androgen receptor binding	-	0.5701	57.01%
Thyroid receptor binding	+	0.5875	58.75%
Glucocorticoid receptor binding	-	0.5561	55.61%
Aromatase binding	-	0.6293	62.93%
PPAR gamma	-	0.5528	55.28%
Honey bee toxicity	-	0.8697	86.97%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.6718	67.18%

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	96.66%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.44%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.97%	85.14%
CHEMBL4208	P20618	Proteasome component C5	89.12%	90.00%
CHEMBL3401	O75469	Pregnane X receptor	88.72%	94.73%
CHEMBL4040	P28482	MAP kinase ERK2	87.22%	83.82%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.65%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.45%	89.00%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	81.36%	97.21%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.26%	99.17%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.01%	90.71%

Plants that contains it

• Alstonia scholaris

Cross-Links

• PubChem: 163027793
• LOTUS: LTS0256969
• wikiData: Q105000519