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(2Z,6S)-5,6-dihydroxy-4-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-[[2,3,4-trihydroxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]-6-oxo-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohexa-1,4-dien-1-yl]methylidene]cyclohex-4-ene-1,3-dione

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 5fe6087d-44fb-4b91-9e1a-00b87347a60f
Taxonomy Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives
IUPAC Name (2Z,6S)-5,6-dihydroxy-4-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-[[2,3,4-trihydroxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]-6-oxo-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohexa-1,4-dien-1-yl]methylidene]cyclohex-4-ene-1,3-dione
SMILES (Canonical) C1=CC(=CC=C1C=CC(=O)C2=C(C(C(=C(C2=O)C=C3C(=O)C(=C(C(C3=O)(C4C(C(C(C(O4)CO)O)O)O)O)O)C(=O)C=CC5=CC=C(C=C5)O)O)(C6C(C(C(C(O6)CO)O)O)O)O)O)O
SMILES (Isomeric) C1=CC(=CC=C1/C=C/C(=O)C2=C([C@](C(=O)/C(=C\C3=C(C(C(=C(C3=O)C(=O)/C=C/C4=CC=C(C=C4)O)O)([C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)O)/C2=O)([C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O)O)O
InChI InChI=1S/C43H42O22/c44-14-24-30(52)32(54)34(56)40(64-24)42(62)36(58)20(28(50)26(38(42)60)22(48)11-5-16-1-7-18(46)8-2-16)13-21-29(51)27(23(49)12-6-17-3-9-19(47)10-4-17)39(61)43(63,37(21)59)41-35(57)33(55)31(53)25(15-45)65-41/h1-13,24-25,30-35,40-41,44-47,52-58,60-63H,14-15H2/b11-5+,12-6+,21-13-/t24-,25-,30-,31-,32+,33+,34-,35-,40-,41-,42?,43-/m1/s1
InChI Key WLYGSPLCNKYESI-CIYWHUEBSA-N
Popularity 59 references in papers

Physical and Chemical Properties

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Molecular Formula C43H42O22
Molecular Weight 910.80 g/mol
Exact Mass 910.21677296 g/mol
Topological Polar Surface Area (TPSA) 407.00 Ų
XlogP -2.50
Atomic LogP (AlogP) -3.79
H-Bond Acceptor 22
H-Bond Donor 15
Rotatable Bonds 11

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2Z,6S)-5,6-dihydroxy-4-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-[[2,3,4-trihydroxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]-6-oxo-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohexa-1,4-dien-1-yl]methylidene]cyclohex-4-ene-1,3-dione

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.5080 50.80%
Caco-2 - 0.8755 87.55%
Blood Brain Barrier - 0.6129 61.29%
Human oral bioavailability - 0.6000 60.00%
Subcellular localzation Mitochondria 0.6948 69.48%
OATP2B1 inhibitior - 0.5713 57.13%
OATP1B1 inhibitior + 0.8251 82.51%
OATP1B3 inhibitior + 0.9689 96.89%
MATE1 inhibitior - 0.8600 86.00%
OCT2 inhibitior - 0.8500 85.00%
BSEP inhibitior + 0.8221 82.21%
P-glycoprotein inhibitior + 0.7195 71.95%
P-glycoprotein substrate - 0.6338 63.38%
CYP3A4 substrate + 0.6200 62.00%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8594 85.94%
CYP3A4 inhibition - 0.8977 89.77%
CYP2C9 inhibition - 0.7578 75.78%
CYP2C19 inhibition - 0.7948 79.48%
CYP2D6 inhibition - 0.9309 93.09%
CYP1A2 inhibition - 0.8862 88.62%
CYP2C8 inhibition + 0.6011 60.11%
CYP inhibitory promiscuity - 0.7590 75.90%
UGT catelyzed + 0.9000 90.00%
Carcinogenicity (binary) - 0.9000 90.00%
Carcinogenicity (trinary) Non-required 0.6328 63.28%
Eye corrosion - 0.9903 99.03%
Eye irritation - 0.8954 89.54%
Skin irritation - 0.8177 81.77%
Skin corrosion - 0.9396 93.96%
Ames mutagenesis - 0.5644 56.44%
Human Ether-a-go-go-Related Gene inhibition + 0.7496 74.96%
Micronuclear + 0.5259 52.59%
Hepatotoxicity - 0.7000 70.00%
skin sensitisation - 0.7844 78.44%
Respiratory toxicity - 0.5222 52.22%
Reproductive toxicity + 0.7000 70.00%
Mitochondrial toxicity + 0.5125 51.25%
Nephrotoxicity + 0.7070 70.70%
Acute Oral Toxicity (c) III 0.4998 49.98%
Estrogen receptor binding + 0.7943 79.43%
Androgen receptor binding + 0.6641 66.41%
Thyroid receptor binding + 0.5423 54.23%
Glucocorticoid receptor binding - 0.5204 52.04%
Aromatase binding + 0.5323 53.23%
PPAR gamma + 0.7294 72.94%
Honey bee toxicity - 0.7543 75.43%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity - 0.7000 70.00%
Fish aquatic toxicity + 0.8608 86.08%

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 98.65% 91.11%
CHEMBL1806 P11388 DNA topoisomerase II alpha 94.42% 89.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 91.76% 97.09%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 90.98% 96.00%
CHEMBL2563 Q9UQL6 Histone deacetylase 5 90.95% 89.67%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.26% 95.56%
CHEMBL1293249 Q13887 Kruppel-like factor 5 87.54% 86.33%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 86.89% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 86.22% 94.45%
CHEMBL2288 Q13526 Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 86.11% 91.71%
CHEMBL2107 P61073 C-X-C chemokine receptor type 4 85.68% 93.10%
CHEMBL3194 P02766 Transthyretin 84.64% 90.71%
CHEMBL5852 Q96P65 Pyroglutamylated RFamide peptide receptor 83.89% 85.00%
CHEMBL3401 O75469 Pregnane X receptor 83.88% 94.73%
CHEMBL2581 P07339 Cathepsin D 83.81% 98.95%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 82.68% 86.92%
CHEMBL1994 P08235 Mineralocorticoid receptor 82.27% 100.00%

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.
Carthamus tinctorius

Cross-Links

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PubChem 137208345
LOTUS LTS0004753
wikiData Q104250525