methyl (1S,4aS,5R,7S,7aS)-5-hydroxy-7-[3-(4-hydroxyphenyl)propanoyl]-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate

Details

• Internal ID: 7d813664-be7b-414b-a12e-4cda9ed97ed1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl (1S,4aS,5R,7S,7aS)-5-hydroxy-7-[3-(4-hydroxyphenyl)propanoyl]-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): CC1(CC(C2C1C(OC=C2C(=O)OC)OC3C(C(C(C(O3)CO)O)O)O)O)C(=O)CCC4=CC=C(C=C4)O
• SMILES (Isomeric): C[C@@]1(C[C@H]([C@H]2[C@@H]1[C@@H](OC=C2C(=O)OC)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)C(=O)CCC4=CC=C(C=C4)O
• InChI: InChI=1S/C26H34O12/c1-26(17(30)8-5-12-3-6-13(28)7-4-12)9-15(29)18-14(23(34)35-2)11-36-24(19(18)26)38-25-22(33)21(32)20(31)16(10-27)37-25/h3-4,6-7,11,15-16,18-22,24-25,27-29,31-33H,5,8-10H2,1-2H3/t15-,16-,18+,19-,20-,21+,22-,24+,25+,26-/m1/s1
• InChI Key: HTMGLXYNCJKXJO-SMHATYKFSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₄O₁₂
• Molecular Weight: 538.50 g/mol
• Exact Mass: 538.20502652 g/mol
• Topological Polar Surface Area (TPSA): 192.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -0.87
• H-Bond Acceptor: 12
• H-Bond Donor: 6
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8510	85.10%
Caco-2	-	0.8866	88.66%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7471	74.71%
OATP2B1 inhibitior	-	0.8661	86.61%
OATP1B1 inhibitior	+	0.7456	74.56%
OATP1B3 inhibitior	+	0.9262	92.62%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7875	78.75%
BSEP inhibitior	+	0.6037	60.37%
P-glycoprotein inhibitior	-	0.6250	62.50%
P-glycoprotein substrate	+	0.5491	54.91%
CYP3A4 substrate	+	0.6978	69.78%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8721	87.21%
CYP3A4 inhibition	-	0.7834	78.34%
CYP2C9 inhibition	-	0.8885	88.85%
CYP2C19 inhibition	-	0.8816	88.16%
CYP2D6 inhibition	-	0.9146	91.46%
CYP1A2 inhibition	-	0.8014	80.14%
CYP2C8 inhibition	+	0.7370	73.70%
CYP inhibitory promiscuity	-	0.9206	92.06%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6419	64.19%
Eye corrosion	-	0.9917	99.17%
Eye irritation	-	0.9543	95.43%
Skin irritation	-	0.6243	62.43%
Skin corrosion	-	0.9428	94.28%
Ames mutagenesis	-	0.5737	57.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.4044	40.44%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.8625	86.25%
skin sensitisation	-	0.9048	90.48%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.5332	53.32%
Acute Oral Toxicity (c)	I	0.6351	63.51%
Estrogen receptor binding	+	0.8264	82.64%
Androgen receptor binding	+	0.6659	66.59%
Thyroid receptor binding	+	0.5304	53.04%
Glucocorticoid receptor binding	+	0.7181	71.81%
Aromatase binding	+	0.5336	53.36%
PPAR gamma	+	0.6446	64.46%
Honey bee toxicity	-	0.6812	68.12%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.9754	97.54%

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	98.92%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.51%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.58%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.41%	86.33%
CHEMBL2581	P07339	Cathepsin D	92.10%	98.95%
CHEMBL4208	P20618	Proteasome component C5	90.92%	90.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.83%	85.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.62%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.47%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.99%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	87.16%	94.73%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.61%	96.95%
CHEMBL3437	Q16853	Amine oxidase, copper containing	84.89%	94.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.52%	95.50%
CHEMBL2996	Q05655	Protein kinase C delta	83.93%	97.79%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.61%	95.89%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	82.52%	85.00%
CHEMBL220	P22303	Acetylcholinesterase	82.37%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.04%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.75%	89.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.52%	95.83%

Plants that contains it

• Barleria lupulina

Cross-Links

• PubChem: 102023658
• LOTUS: LTS0225289
• wikiData: Q105033502