(1S,4aS,6S,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-6-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid

Details

• Internal ID: 9ecd86ca-5245-42ba-ab06-f99d2fb11d92
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: (1S,4aS,6S,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-6-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid
• SMILES (Canonical): CC1C(CC2C1C(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@@H]1[C@H](C[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/c1-14-21(35)11-18-19(29(40)41)12-44-31(25(14)18)47-32-28(46-30(42)16-4-6-17(33)7-5-16)27(39)26(38)23(45-32)13-43-24(37)9-3-15-2-8-20(34)22(36)10-15/h2-10,12,14,18,21,23,25-28,31-36,38-39H,11,13H2,1H3,(H,40,41)/b9-3+/t14-,18-,21+,23-,25-,26-,27+,28-,31+,32+/m1/s1
• InChI Key: LCVJKCLBUJNLAY-ZLTHKTTISA-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: 1.60
• Atomic LogP (AlogP): 1.01
• 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	+	0.9112	91.12%
Caco-2	-	0.8914	89.14%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7397	73.97%
OATP2B1 inhibitior	-	0.7215	72.15%
OATP1B1 inhibitior	-	0.3332	33.32%
OATP1B3 inhibitior	+	0.9499	94.99%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7640	76.40%
P-glycoprotein inhibitior	+	0.5935	59.35%
P-glycoprotein substrate	+	0.5401	54.01%
CYP3A4 substrate	+	0.6847	68.47%
CYP2C9 substrate	-	0.8102	81.02%
CYP2D6 substrate	-	0.8753	87.53%
CYP3A4 inhibition	-	0.9049	90.49%
CYP2C9 inhibition	-	0.5679	56.79%
CYP2C19 inhibition	-	0.6565	65.65%
CYP2D6 inhibition	-	0.8509	85.09%
CYP1A2 inhibition	-	0.5000	50.00%
CYP2C8 inhibition	+	0.8308	83.08%
CYP inhibitory promiscuity	-	0.7664	76.64%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6390	63.90%
Eye corrosion	-	0.9919	99.19%
Eye irritation	-	0.9159	91.59%
Skin irritation	-	0.7550	75.50%
Skin corrosion	-	0.9408	94.08%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6721	67.21%
Micronuclear	-	0.5141	51.41%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.8087	80.87%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.9664	96.64%
Acute Oral Toxicity (c)	III	0.4222	42.22%
Estrogen receptor binding	+	0.7934	79.34%
Androgen receptor binding	+	0.6698	66.98%
Thyroid receptor binding	+	0.5748	57.48%
Glucocorticoid receptor binding	+	0.6720	67.20%
Aromatase binding	-	0.5189	51.89%
PPAR gamma	+	0.7012	70.12%
Honey bee toxicity	-	0.7580	75.80%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9856	98.56%

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	99.98%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.77%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	98.47%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.15%	89.00%
CHEMBL4208	P20618	Proteasome component C5	96.47%	90.00%
CHEMBL3194	P02766	Transthyretin	96.09%	90.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.78%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.24%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.60%	99.17%
CHEMBL206	P03372	Estrogen receptor alpha	91.09%	97.64%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	90.72%	80.78%
CHEMBL3401	O75469	Pregnane X receptor	90.56%	94.73%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.32%	96.00%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	88.88%	93.10%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	88.88%	95.64%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	88.85%	97.21%
CHEMBL2179	P04062	Beta-glucocerebrosidase	87.70%	85.31%
CHEMBL2581	P07339	Cathepsin D	87.26%	98.95%
CHEMBL5255	O00206	Toll-like receptor 4	86.47%	92.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.96%	95.56%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.90%	96.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.69%	95.89%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	84.90%	83.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.02%	95.83%
CHEMBL226	P30542	Adenosine A1 receptor	83.43%	95.93%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.78%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	80.95%	91.19%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.26%	89.62%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.13%	95.50%

Plants that contains it

• Vitex altissima

Cross-Links

• PubChem: 11365823
• LOTUS: LTS0255907
• wikiData: Q105150020