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methyl (1S,4aR,6S,7R,7aS)-4a,7-dihydroxy-6-[(E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoyl]oxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

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Internal ID 67e4c58c-2f20-4f2a-a436-3490a556afb3
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name methyl (1S,4aR,6S,7R,7aS)-4a,7-dihydroxy-6-[(E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoyl]oxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
SMILES (Canonical) CC1(C(CC2(C1C(OC=C2C(=O)OC)OC3C(C(C(C(O3)CO)O)O)O)O)OC(=O)C=CC4=CC(=C(C=C4)OC)O)O
SMILES (Isomeric) C[C@@]1([C@H](C[C@]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)OC(=O)/C=C/C4=CC(=C(C=C4)OC)O)O
InChI InChI=1S/C27H34O15/c1-26(35)17(41-18(30)7-5-12-4-6-15(37-2)14(29)8-12)9-27(36)13(23(34)38-3)11-39-25(22(26)27)42-24-21(33)20(32)19(31)16(10-28)40-24/h4-8,11,16-17,19-22,24-25,28-29,31-33,35-36H,9-10H2,1-3H3/b7-5+/t16-,17+,19-,20+,21-,22-,24+,25+,26+,27+/m1/s1
InChI Key RWRMUTIGNCFJFX-SWONWTSQSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C27H34O15
Molecular Weight 598.50 g/mol
Exact Mass 598.18977037 g/mol
Topological Polar Surface Area (TPSA) 231.00 Ų
XlogP -0.90
Atomic LogP (AlogP) -1.94
H-Bond Acceptor 15
H-Bond Donor 7
Rotatable Bonds 8

Synonyms

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ACon1_000384
NCGC00169128-01
BRD-K35111359-001-01-4

2D Structure

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2D Structure of methyl (1S,4aR,6S,7R,7aS)-4a,7-dihydroxy-6-[(E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoyl]oxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8454 84.54%
Caco-2 - 0.8826 88.26%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.8286 82.86%
Subcellular localzation Mitochondria 0.4658 46.58%
OATP2B1 inhibitior - 0.8634 86.34%
OATP1B1 inhibitior + 0.8372 83.72%
OATP1B3 inhibitior + 0.9271 92.71%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior - 0.4767 47.67%
P-glycoprotein inhibitior - 0.4508 45.08%
P-glycoprotein substrate + 0.5396 53.96%
CYP3A4 substrate + 0.6917 69.17%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8700 87.00%
CYP3A4 inhibition - 0.8810 88.10%
CYP2C9 inhibition - 0.8487 84.87%
CYP2C19 inhibition - 0.8786 87.86%
CYP2D6 inhibition - 0.9044 90.44%
CYP1A2 inhibition - 0.7251 72.51%
CYP2C8 inhibition + 0.7431 74.31%
CYP inhibitory promiscuity - 0.8573 85.73%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6674 66.74%
Eye corrosion - 0.9901 99.01%
Eye irritation - 0.9329 93.29%
Skin irritation - 0.7165 71.65%
Skin corrosion - 0.9390 93.90%
Ames mutagenesis - 0.6300 63.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6842 68.42%
Micronuclear - 0.5600 56.00%
Hepatotoxicity - 0.7664 76.64%
skin sensitisation - 0.8386 83.86%
Respiratory toxicity + 0.5444 54.44%
Reproductive toxicity + 0.9778 97.78%
Mitochondrial toxicity + 0.7875 78.75%
Nephrotoxicity - 0.8734 87.34%
Acute Oral Toxicity (c) III 0.3878 38.78%
Estrogen receptor binding + 0.7808 78.08%
Androgen receptor binding + 0.6588 65.88%
Thyroid receptor binding + 0.5758 57.58%
Glucocorticoid receptor binding + 0.7025 70.25%
Aromatase binding + 0.6130 61.30%
PPAR gamma + 0.7035 70.35%
Honey bee toxicity - 0.7574 75.74%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.7100 71.00%
Fish aquatic toxicity + 0.9007 90.07%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 99.72% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.30% 96.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 97.18% 86.33%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 96.82% 96.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 94.11% 94.45%
CHEMBL1806 P11388 DNA topoisomerase II alpha 93.79% 89.00%
CHEMBL3060 Q9Y345 Glycine transporter 2 87.88% 99.17%
CHEMBL5608 Q16288 NT-3 growth factor receptor 87.30% 95.89%
CHEMBL1951 P21397 Monoamine oxidase A 87.26% 91.49%
CHEMBL3922 P50579 Methionine aminopeptidase 2 86.51% 97.28%
CHEMBL3137262 O60341 LSD1/CoREST complex 86.46% 97.09%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 86.33% 95.50%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 86.23% 95.56%
CHEMBL4208 P20618 Proteasome component C5 84.78% 90.00%
CHEMBL2581 P07339 Cathepsin D 83.51% 98.95%
CHEMBL3401 O75469 Pregnane X receptor 82.48% 94.73%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 82.36% 91.07%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 81.82% 97.14%
CHEMBL241 Q14432 Phosphodiesterase 3A 81.20% 92.94%
CHEMBL2413 P32246 C-C chemokine receptor type 1 81.04% 89.50%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 80.73% 92.62%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Duranta erecta

Cross-Links

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PubChem 23786422
LOTUS LTS0005100
wikiData Q105246693