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methyl (1S,4aR,6S,7R,7aS)-4a,7-dihydroxy-7-methyl-6-[(Z)-3-phenylprop-2-enoyl]oxy-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 d82ae0ef-7e55-45bc-961a-d27b22017dcb
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name methyl (1S,4aR,6S,7R,7aS)-4a,7-dihydroxy-7-methyl-6-[(Z)-3-phenylprop-2-enoyl]oxy-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=CC=C4)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=CC=C4)O
InChI InChI=1S/C26H32O13/c1-25(33)16(38-17(28)9-8-13-6-4-3-5-7-13)10-26(34)14(22(32)35-2)12-36-24(21(25)26)39-23-20(31)19(30)18(29)15(11-27)37-23/h3-9,12,15-16,18-21,23-24,27,29-31,33-34H,10-11H2,1-2H3/b9-8-/t15-,16+,18-,19+,20-,21-,23+,24+,25+,26+/m1/s1
InChI Key YRARGBWFOYODHQ-NIMJLXNMSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C26H32O13
Molecular Weight 552.50 g/mol
Exact Mass 552.18429107 g/mol
Topological Polar Surface Area (TPSA) 202.00 Ų
XlogP -0.50
Atomic LogP (AlogP) -1.66
H-Bond Acceptor 13
H-Bond Donor 6
Rotatable Bonds 7

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of methyl (1S,4aR,6S,7R,7aS)-4a,7-dihydroxy-7-methyl-6-[(Z)-3-phenylprop-2-enoyl]oxy-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 + 0.7551 75.51%
Caco-2 - 0.8800 88.00%
Blood Brain Barrier - 0.5000 50.00%
Human oral bioavailability - 0.8714 87.14%
Subcellular localzation Mitochondria 0.5960 59.60%
OATP2B1 inhibitior - 0.8559 85.59%
OATP1B1 inhibitior + 0.8051 80.51%
OATP1B3 inhibitior + 0.9414 94.14%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior + 0.6388 63.88%
P-glycoprotein inhibitior - 0.5286 52.86%
P-glycoprotein substrate - 0.5802 58.02%
CYP3A4 substrate + 0.6828 68.28%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8809 88.09%
CYP3A4 inhibition - 0.8546 85.46%
CYP2C9 inhibition - 0.8904 89.04%
CYP2C19 inhibition - 0.9107 91.07%
CYP2D6 inhibition - 0.9094 90.94%
CYP1A2 inhibition - 0.8607 86.07%
CYP2C8 inhibition + 0.7256 72.56%
CYP inhibitory promiscuity - 0.8783 87.83%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6712 67.12%
Eye corrosion - 0.9906 99.06%
Eye irritation - 0.9403 94.03%
Skin irritation - 0.6995 69.95%
Skin corrosion - 0.9386 93.86%
Ames mutagenesis - 0.6270 62.70%
Human Ether-a-go-go-Related Gene inhibition - 0.4236 42.36%
Micronuclear - 0.6000 60.00%
Hepatotoxicity - 0.8086 80.86%
skin sensitisation - 0.8538 85.38%
Respiratory toxicity + 0.6667 66.67%
Reproductive toxicity + 0.9444 94.44%
Mitochondrial toxicity + 0.7875 78.75%
Nephrotoxicity - 0.8272 82.72%
Acute Oral Toxicity (c) III 0.4190 41.90%
Estrogen receptor binding + 0.7714 77.14%
Androgen receptor binding + 0.6541 65.41%
Thyroid receptor binding + 0.5705 57.05%
Glucocorticoid receptor binding + 0.6345 63.45%
Aromatase binding + 0.5577 55.77%
PPAR gamma + 0.6764 67.64%
Honey bee toxicity - 0.7679 76.79%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.6300 63.00%
Fish aquatic toxicity + 0.8172 81.72%

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 99.44% 91.11%
CHEMBL1293249 Q13887 Kruppel-like factor 5 97.49% 86.33%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.35% 96.09%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 97.09% 96.00%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 90.32% 95.50%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.15% 95.56%
CHEMBL221 P23219 Cyclooxygenase-1 88.90% 90.17%
CHEMBL2581 P07339 Cathepsin D 88.17% 98.95%
CHEMBL1806 P11388 DNA topoisomerase II alpha 87.14% 89.00%
CHEMBL5028 O14672 ADAM10 86.92% 97.50%
CHEMBL3401 O75469 Pregnane X receptor 86.01% 94.73%
CHEMBL3137262 O60341 LSD1/CoREST complex 84.83% 97.09%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 84.72% 94.08%
CHEMBL5678 P34947 G protein-coupled receptor kinase 5 83.14% 88.00%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 82.25% 95.83%
CHEMBL3060 Q9Y345 Glycine transporter 2 82.13% 99.17%

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 93473143
LOTUS LTS0113843
wikiData Q105352695