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(2R,3R,4S,5S,6R)-2-[(3R,5R)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)heptan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol

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 2cec48db-c384-4c01-a735-a8816b0f1bab
Taxonomy Phenylpropanoids and polyketides > Diarylheptanoids > Linear diarylheptanoids > Curcuminoids
IUPAC Name (2R,3R,4S,5S,6R)-2-[(3R,5R)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)heptan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
SMILES (Canonical) COC1=C(C=CC(=C1)CCC(CC(CCC2=CC=C(C=C2)O)O)OC3C(C(C(C(O3)CO)O)O)O)O
SMILES (Isomeric) COC1=C(C=CC(=C1)CC[C@H](C[C@@H](CCC2=CC=C(C=C2)O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O
InChI InChI=1S/C26H36O10/c1-34-21-12-16(6-11-20(21)30)5-10-19(13-18(29)9-4-15-2-7-17(28)8-3-15)35-26-25(33)24(32)23(31)22(14-27)36-26/h2-3,6-8,11-12,18-19,22-33H,4-5,9-10,13-14H2,1H3/t18-,19-,22-,23-,24+,25-,26-/m1/s1
InChI Key XCZCCUNORLFCBF-DJAAXWDZSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C26H36O10
Molecular Weight 508.60 g/mol
Exact Mass 508.23084734 g/mol
Topological Polar Surface Area (TPSA) 169.00 Ų
XlogP 1.60
Atomic LogP (AlogP) 0.61
H-Bond Acceptor 10
H-Bond Donor 7
Rotatable Bonds 12

Synonyms

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[(1R,3R)-1-(3-Methoxy-4-hydroxyphenethyl)-3-hydroxy-5-(4-hydroxyphenyl)pentyl]beta-D-glucopyranoside

2D Structure

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2D Structure of (2R,3R,4S,5S,6R)-2-[(3R,5R)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)heptan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.6901 69.01%
Caco-2 - 0.8508 85.08%
Blood Brain Barrier - 0.6000 60.00%
Human oral bioavailability - 0.7857 78.57%
Subcellular localzation Mitochondria 0.7860 78.60%
OATP2B1 inhibitior - 0.8626 86.26%
OATP1B1 inhibitior + 0.8672 86.72%
OATP1B3 inhibitior + 0.9400 94.00%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.7292 72.92%
BSEP inhibitior + 0.6452 64.52%
P-glycoprotein inhibitior - 0.5668 56.68%
P-glycoprotein substrate + 0.5592 55.92%
CYP3A4 substrate + 0.6380 63.80%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.7717 77.17%
CYP3A4 inhibition - 0.8482 84.82%
CYP2C9 inhibition - 0.8514 85.14%
CYP2C19 inhibition - 0.8277 82.77%
CYP2D6 inhibition - 0.8722 87.22%
CYP1A2 inhibition - 0.8093 80.93%
CYP2C8 inhibition + 0.7241 72.41%
CYP inhibitory promiscuity - 0.8825 88.25%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9500 95.00%
Carcinogenicity (trinary) Non-required 0.7433 74.33%
Eye corrosion - 0.9917 99.17%
Eye irritation - 0.9404 94.04%
Skin irritation - 0.8102 81.02%
Skin corrosion - 0.9532 95.32%
Ames mutagenesis - 0.6100 61.00%
Human Ether-a-go-go-Related Gene inhibition + 0.9294 92.94%
Micronuclear - 0.7200 72.00%
Hepatotoxicity - 0.7718 77.18%
skin sensitisation - 0.8617 86.17%
Respiratory toxicity + 0.6111 61.11%
Reproductive toxicity + 0.6000 60.00%
Mitochondrial toxicity - 0.5625 56.25%
Nephrotoxicity - 0.8296 82.96%
Acute Oral Toxicity (c) III 0.7423 74.23%
Estrogen receptor binding + 0.8165 81.65%
Androgen receptor binding + 0.6008 60.08%
Thyroid receptor binding + 0.5809 58.09%
Glucocorticoid receptor binding + 0.5374 53.74%
Aromatase binding + 0.5978 59.78%
PPAR gamma + 0.6314 63.14%
Honey bee toxicity - 0.7194 71.94%
Biodegradation - 0.7000 70.00%
Crustacea aquatic toxicity - 0.6400 64.00%
Fish aquatic toxicity + 0.7066 70.66%

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 99.50% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.34% 96.09%
CHEMBL2581 P07339 Cathepsin D 96.49% 98.95%
CHEMBL3060 Q9Y345 Glycine transporter 2 95.93% 99.17%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 92.63% 95.89%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 91.42% 86.92%
CHEMBL1293249 Q13887 Kruppel-like factor 5 90.14% 86.33%
CHEMBL5608 Q16288 NT-3 growth factor receptor 87.81% 95.89%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 87.25% 85.14%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 86.96% 94.00%
CHEMBL5939 Q9NZ08 Endoplasmic reticulum aminopeptidase 1 86.61% 100.00%
CHEMBL2535 P11166 Glucose transporter 86.35% 98.75%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 84.93% 94.45%
CHEMBL3401 O75469 Pregnane X receptor 84.36% 94.73%
CHEMBL5852 Q96P65 Pyroglutamylated RFamide peptide receptor 83.83% 85.00%
CHEMBL1255126 O15151 Protein Mdm4 83.22% 90.20%
CHEMBL3137262 O60341 LSD1/CoREST complex 82.90% 97.09%
CHEMBL242 Q92731 Estrogen receptor beta 81.84% 98.35%
CHEMBL241 Q14432 Phosphodiesterase 3A 81.72% 92.94%
CHEMBL2274 Q9H228 Sphingosine 1-phosphate receptor Edg-8 81.56% 100.00%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 81.28% 99.15%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 81.22% 90.71%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 81.00% 89.62%
CHEMBL3194 P02766 Transthyretin 80.66% 90.71%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 80.54% 95.56%
CHEMBL1907 P15144 Aminopeptidase N 80.04% 93.31%

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.
Anthriscus sylvestris
Tacca chantrieri

Cross-Links

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PubChem 10973237
NPASS NPC199459
LOTUS LTS0130687
wikiData Q105325566