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methyl (1S,4aS,7aS)-1-[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4S,5S,6R)-6-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-7-(hydroxymethyl)-1,4a,5,7a-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 dce98f7b-bc97-463d-8992-d3ff7477cda5
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name methyl (1S,4aS,7aS)-1-[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4S,5S,6R)-6-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
SMILES (Canonical)
SMILES (Isomeric)
InChI InChI=1S/C32H40O18/c1-44-29(43)16-10-46-30(22-14(9-33)4-5-15(16)22)50-32-28(42)26(40)24(38)20(49-32)12-47-31-27(41)25(39)23(37)19(48-31)11-45-21(36)7-3-13-2-6-17(34)18(35)8-13/h2-4,6-8,10,15,19-20,22-28,30-35,37-42H,5,9,11-12H2,1H3/b7-3+/t15-,19-,20-,22-,23-,24-,25+,26+,27-,28-,30+,31-,32+/m1/s1
InChI Key CSRRWPAMFHNUSX-DALANRPMSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C32H40O18
Molecular Weight 712.60 g/mol
Exact Mass 712.22146442 g/mol
Topological Polar Surface Area (TPSA) 281.00 Ų
XlogP -3.10
Atomic LogP (AlogP) -2.73
H-Bond Acceptor 18
H-Bond Donor 9
Rotatable Bonds 11

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of methyl (1S,4aS,7aS)-1-[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4S,5S,6R)-6-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-7-(hydroxymethyl)-1,4a,5,7a-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 + 0.6717 67.17%
Caco-2 - 0.8948 89.48%
Blood Brain Barrier - 0.5750 57.50%
Human oral bioavailability - 0.7857 78.57%
Subcellular localzation Mitochondria 0.6719 67.19%
OATP2B1 inhibitior - 0.8610 86.10%
OATP1B1 inhibitior + 0.8329 83.29%
OATP1B3 inhibitior + 0.9726 97.26%
MATE1 inhibitior - 0.8600 86.00%
OCT2 inhibitior - 0.8000 80.00%
BSEP inhibitior + 0.5827 58.27%
P-glycoprotein inhibitior + 0.5946 59.46%
P-glycoprotein substrate - 0.5247 52.47%
CYP3A4 substrate + 0.6839 68.39%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8632 86.32%
CYP3A4 inhibition - 0.8659 86.59%
CYP2C9 inhibition - 0.8485 84.85%
CYP2C19 inhibition - 0.6560 65.60%
CYP2D6 inhibition - 0.8862 88.62%
CYP1A2 inhibition - 0.7804 78.04%
CYP2C8 inhibition + 0.7492 74.92%
CYP inhibitory promiscuity - 0.7360 73.60%
UGT catelyzed - 0.5638 56.38%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6692 66.92%
Eye corrosion - 0.9884 98.84%
Eye irritation - 0.9149 91.49%
Skin irritation - 0.8109 81.09%
Skin corrosion - 0.9522 95.22%
Ames mutagenesis - 0.5337 53.37%
Human Ether-a-go-go-Related Gene inhibition + 0.6925 69.25%
Micronuclear - 0.5900 59.00%
Hepatotoxicity - 0.7875 78.75%
skin sensitisation - 0.8105 81.05%
Respiratory toxicity + 0.5556 55.56%
Reproductive toxicity + 0.8778 87.78%
Mitochondrial toxicity + 0.6625 66.25%
Nephrotoxicity - 0.5615 56.15%
Acute Oral Toxicity (c) III 0.4978 49.78%
Estrogen receptor binding + 0.7775 77.75%
Androgen receptor binding + 0.6493 64.93%
Thyroid receptor binding - 0.5358 53.58%
Glucocorticoid receptor binding + 0.6306 63.06%
Aromatase binding + 0.6181 61.81%
PPAR gamma + 0.7042 70.42%
Honey bee toxicity - 0.7652 76.52%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.6600 66.00%
Fish aquatic toxicity + 0.9481 94.81%

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 99.76% 91.11%
CHEMBL1951 P21397 Monoamine oxidase A 99.10% 91.49%
CHEMBL1293249 Q13887 Kruppel-like factor 5 96.34% 86.33%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.63% 96.09%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 94.61% 96.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 92.95% 89.00%
CHEMBL3401 O75469 Pregnane X receptor 90.77% 94.73%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.39% 97.09%
CHEMBL4208 P20618 Proteasome component C5 88.17% 90.00%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 87.26% 89.62%
CHEMBL3060 Q9Y345 Glycine transporter 2 87.17% 99.17%
CHEMBL226 P30542 Adenosine A1 receptor 86.76% 95.93%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 85.74% 95.83%
CHEMBL5255 O00206 Toll-like receptor 4 85.37% 92.50%
CHEMBL5608 Q16288 NT-3 growth factor receptor 84.63% 95.89%
CHEMBL2581 P07339 Cathepsin D 84.36% 98.95%
CHEMBL5028 O14672 ADAM10 82.39% 97.50%
CHEMBL218 P21554 Cannabinoid CB1 receptor 81.10% 96.61%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 80.72% 95.56%
CHEMBL3194 P02766 Transthyretin 80.36% 90.71%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 80.06% 94.45%

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.
Gardenia jasminoides

Cross-Links

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PubChem 71552449
NPASS NPC69367
LOTUS LTS0033793
wikiData Q104969525