(1S,4aS,7S,7aS)-1-[(2S,3R,4S,5S,6R)-6-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxymethyl]-4,5-dihydroxy-3-(4-hydroxybenzoyl)oxyoxan-2-yl]oxy-7-hydroxy-7-methyl-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylic acid

Details

• Internal ID: 9d26e5b5-129e-4be2-acf5-6111ede38bc2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: (1S,4aS,7S,7aS)-1-[(2S,3R,4S,5S,6R)-6-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxymethyl]-4,5-dihydroxy-3-(4-hydroxybenzoyl)oxyoxan-2-yl]oxy-7-hydroxy-7-methyl-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylic acid
• SMILES (Canonical): CC1(CCC2C1C(OC=C2C(=O)O)OC3C(C(C(C(O3)COC(=O)C=CC4=CC(=C(C=C4)O)O)O)O)OC(=O)C5=CC=C(C=C5)O)O
• SMILES (Isomeric): C[C@@]1(CC[C@H]2[C@@H]1[C@@H](OC=C2C(=O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)COC(=O)/C=C/C4=CC(=C(C=C4)O)O)O)O)OC(=O)C5=CC=C(C=C5)O)O
• InChI: InChI=1S/C32H34O15/c1-32(42)11-10-18-19(28(39)40)13-44-30(24(18)32)47-31-27(46-29(41)16-4-6-17(33)7-5-16)26(38)25(37)22(45-31)14-43-23(36)9-3-15-2-8-20(34)21(35)12-15/h2-9,12-13,18,22,24-27,30-31,33-35,37-38,42H,10-11,14H2,1H3,(H,39,40)/b9-3+/t18-,22-,24-,25-,26+,27-,30+,31+,32+/m1/s1
• InChI Key: LZVBQYSONKTXFG-XYYTZZQVSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₃₄O₁₅
• Molecular Weight: 658.60 g/mol
• Exact Mass: 658.18977037 g/mol
• Topological Polar Surface Area (TPSA): 239.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 1.15
• H-Bond Acceptor: 14
• H-Bond Donor: 7
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9174	91.74%
Caco-2	-	0.8889	88.89%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.8171	81.71%
OATP2B1 inhibitior	-	0.7216	72.16%
OATP1B1 inhibitior	+	0.7666	76.66%
OATP1B3 inhibitior	+	0.9156	91.56%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7846	78.46%
BSEP inhibitior	+	0.7737	77.37%
P-glycoprotein inhibitior	+	0.6474	64.74%
P-glycoprotein substrate	-	0.5096	50.96%
CYP3A4 substrate	+	0.7061	70.61%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8773	87.73%
CYP3A4 inhibition	-	0.8753	87.53%
CYP2C9 inhibition	-	0.6759	67.59%
CYP2C19 inhibition	-	0.7232	72.32%
CYP2D6 inhibition	-	0.8710	87.10%
CYP1A2 inhibition	-	0.5393	53.93%
CYP2C8 inhibition	+	0.8597	85.97%
CYP inhibitory promiscuity	-	0.8509	85.09%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5425	54.25%
Eye corrosion	-	0.9918	99.18%
Eye irritation	-	0.9184	91.84%
Skin irritation	-	0.6680	66.80%
Skin corrosion	-	0.9267	92.67%
Ames mutagenesis	-	0.5670	56.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.3699	36.99%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	-	0.7351	73.51%
skin sensitisation	-	0.8516	85.16%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.8878	88.78%
Acute Oral Toxicity (c)	I	0.5025	50.25%
Estrogen receptor binding	+	0.8064	80.64%
Androgen receptor binding	+	0.7059	70.59%
Thyroid receptor binding	+	0.5884	58.84%
Glucocorticoid receptor binding	+	0.7022	70.22%
Aromatase binding	+	0.5362	53.62%
PPAR gamma	+	0.7216	72.16%
Honey bee toxicity	-	0.7667	76.67%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9882	98.82%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.92%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	98.83%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.77%	91.11%
CHEMBL3194	P02766	Transthyretin	96.63%	90.71%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.18%	96.09%
CHEMBL4208	P20618	Proteasome component C5	95.89%	90.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.60%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.00%	97.09%
CHEMBL2179	P04062	Beta-glucocerebrosidase	92.51%	85.31%
CHEMBL206	P03372	Estrogen receptor alpha	92.15%	97.64%
CHEMBL5255	O00206	Toll-like receptor 4	92.07%	92.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.91%	95.89%
CHEMBL226	P30542	Adenosine A1 receptor	91.22%	95.93%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.29%	100.00%
CHEMBL221	P23219	Cyclooxygenase-1	88.86%	90.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.69%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.41%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.67%	99.17%
CHEMBL2581	P07339	Cathepsin D	86.33%	98.95%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.52%	96.95%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	84.38%	83.00%
CHEMBL242	Q92731	Estrogen receptor beta	84.37%	98.35%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.28%	100.00%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	83.22%	80.78%
CHEMBL340	P08684	Cytochrome P450 3A4	82.91%	91.19%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.80%	92.94%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.71%	95.89%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	80.27%	97.21%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	80.21%	95.64%

Plants that contains it

• Vitex altissima

Cross-Links

• PubChem: 11181364
• LOTUS: LTS0195731
• wikiData: Q105160154