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[(1S)-1-[(2S,5R)-5-[(S)-hydroxy-[(2R)-6-oxo-2,3-dihydropyran-2-yl]methyl]oxolan-2-yl]ethyl] (E)-3-(4-hydroxyphenyl)prop-2-enoate

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 bce095f2-1352-4555-bc58-361d96fad339
Taxonomy Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acid esters > Coumaric acid esters
IUPAC Name [(1S)-1-[(2S,5R)-5-[(S)-hydroxy-[(2R)-6-oxo-2,3-dihydropyran-2-yl]methyl]oxolan-2-yl]ethyl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
SMILES (Canonical) CC(C1CCC(O1)C(C2CC=CC(=O)O2)O)OC(=O)C=CC3=CC=C(C=C3)O
SMILES (Isomeric) C[C@@H]([C@@H]1CC[C@@H](O1)[C@@H]([C@H]2CC=CC(=O)O2)O)OC(=O)/C=C/C3=CC=C(C=C3)O
InChI InChI=1S/C21H24O7/c1-13(26-20(24)12-7-14-5-8-15(22)9-6-14)16-10-11-18(27-16)21(25)17-3-2-4-19(23)28-17/h2,4-9,12-13,16-18,21-22,25H,3,10-11H2,1H3/b12-7+/t13-,16-,17+,18+,21+/m0/s1
InChI Key DEEHWRGXKJRSMV-WMOYMDCYSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C21H24O7
Molecular Weight 388.40 g/mol
Exact Mass 388.15220310 g/mol
Topological Polar Surface Area (TPSA) 102.00 Ų
XlogP 2.70
Atomic LogP (AlogP) 2.12
H-Bond Acceptor 7
H-Bond Donor 2
Rotatable Bonds 6

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(1S)-1-[(2S,5R)-5-[(S)-hydroxy-[(2R)-6-oxo-2,3-dihydropyran-2-yl]methyl]oxolan-2-yl]ethyl] (E)-3-(4-hydroxyphenyl)prop-2-enoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9211 92.11%
Caco-2 - 0.6894 68.94%
Blood Brain Barrier - 0.5500 55.00%
Human oral bioavailability - 0.8286 82.86%
Subcellular localzation Mitochondria 0.9043 90.43%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8760 87.60%
OATP1B3 inhibitior + 0.8497 84.97%
MATE1 inhibitior - 0.8600 86.00%
OCT2 inhibitior - 0.8000 80.00%
BSEP inhibitior + 0.6367 63.67%
P-glycoprotein inhibitior - 0.6482 64.82%
P-glycoprotein substrate - 0.5529 55.29%
CYP3A4 substrate + 0.6278 62.78%
CYP2C9 substrate - 0.8165 81.65%
CYP2D6 substrate - 0.8767 87.67%
CYP3A4 inhibition - 0.8183 81.83%
CYP2C9 inhibition - 0.7567 75.67%
CYP2C19 inhibition - 0.6395 63.95%
CYP2D6 inhibition - 0.8650 86.50%
CYP1A2 inhibition - 0.5900 59.00%
CYP2C8 inhibition + 0.4774 47.74%
CYP inhibitory promiscuity - 0.7244 72.44%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9328 93.28%
Carcinogenicity (trinary) Danger 0.4386 43.86%
Eye corrosion - 0.9809 98.09%
Eye irritation - 0.9362 93.62%
Skin irritation - 0.6976 69.76%
Skin corrosion - 0.8904 89.04%
Ames mutagenesis - 0.7000 70.00%
Human Ether-a-go-go-Related Gene inhibition - 0.3651 36.51%
Micronuclear - 0.7700 77.00%
Hepatotoxicity - 0.6731 67.31%
skin sensitisation - 0.8814 88.14%
Respiratory toxicity + 0.5556 55.56%
Reproductive toxicity + 0.7333 73.33%
Mitochondrial toxicity + 0.6125 61.25%
Nephrotoxicity + 0.7821 78.21%
Acute Oral Toxicity (c) III 0.3986 39.86%
Estrogen receptor binding + 0.7577 75.77%
Androgen receptor binding + 0.5685 56.85%
Thyroid receptor binding - 0.5216 52.16%
Glucocorticoid receptor binding + 0.6514 65.14%
Aromatase binding + 0.5368 53.68%
PPAR gamma + 0.6448 64.48%
Honey bee toxicity - 0.8451 84.51%
Biodegradation - 0.5500 55.00%
Crustacea aquatic toxicity - 0.5600 56.00%
Fish aquatic toxicity + 0.9473 94.73%

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 95.50% 91.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.71% 95.56%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 94.22% 94.45%
CHEMBL1806 P11388 DNA topoisomerase II alpha 93.62% 89.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.27% 97.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 89.23% 86.33%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 88.70% 96.09%
CHEMBL2581 P07339 Cathepsin D 87.22% 98.95%
CHEMBL3060 Q9Y345 Glycine transporter 2 86.56% 99.17%
CHEMBL1907605 P24864 Cyclin-dependent kinase 2/cyclin E1 86.09% 92.88%
CHEMBL5608 Q16288 NT-3 growth factor receptor 86.04% 95.89%
CHEMBL3194 P02766 Transthyretin 85.52% 90.71%
CHEMBL3830 Q2M2I8 Adaptor-associated kinase 85.07% 83.10%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 84.81% 90.71%
CHEMBL4208 P20618 Proteasome component C5 84.37% 90.00%
CHEMBL3359 P21462 Formyl peptide receptor 1 82.44% 93.56%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 82.22% 96.00%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 81.09% 89.62%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 80.97% 99.23%
CHEMBL5966 P55899 IgG receptor FcRn large subunit p51 80.73% 90.93%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 80.26% 91.07%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 80.01% 97.14%

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.
Hyptis brevipes

Cross-Links

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PubChem 137636436
LOTUS LTS0068954
wikiData Q103815881