(2S,3S,5S)-7-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)heptane-2,3,5-triol

Details

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Internal ID 908d9e1d-6819-47d4-808d-68df166e1598
Taxonomy Phenylpropanoids and polyketides > Diarylheptanoids > Linear diarylheptanoids > Curcuminoids
IUPAC Name (2S,3S,5S)-7-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)heptane-2,3,5-triol
SMILES (Canonical) COC1=C(C=CC(=C1)CCC(CC(C(CC2=CC=C(C=C2)O)O)O)O)O
SMILES (Isomeric) COC1=C(C=CC(=C1)CC[C@@H](C[C@@H]([C@H](CC2=CC=C(C=C2)O)O)O)O)O
InChI InChI=1S/C20H26O6/c1-26-20-11-14(5-9-17(20)23)4-8-16(22)12-19(25)18(24)10-13-2-6-15(21)7-3-13/h2-3,5-7,9,11,16,18-19,21-25H,4,8,10,12H2,1H3/t16-,18-,19-/m0/s1
InChI Key HMULPILLJJIZBE-WDSOQIARSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C20H26O6
Molecular Weight 362.40 g/mol
Exact Mass 362.17293854 g/mol
Topological Polar Surface Area (TPSA) 110.00 Ų
XlogP 2.30
Atomic LogP (AlogP) 1.75
H-Bond Acceptor 6
H-Bond Donor 5
Rotatable Bonds 9

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2S,3S,5S)-7-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)heptane-2,3,5-triol

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8160 81.60%
Caco-2 - 0.6770 67.70%
Blood Brain Barrier - 0.7500 75.00%
Human oral bioavailability - 0.8143 81.43%
Subcellular localzation Mitochondria 0.8112 81.12%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9073 90.73%
OATP1B3 inhibitior + 0.9527 95.27%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.8250 82.50%
BSEP inhibitior - 0.6378 63.78%
P-glycoprotein inhibitior - 0.7952 79.52%
P-glycoprotein substrate + 0.5848 58.48%
CYP3A4 substrate + 0.5401 54.01%
CYP2C9 substrate - 0.8032 80.32%
CYP2D6 substrate + 0.4513 45.13%
CYP3A4 inhibition - 0.7413 74.13%
CYP2C9 inhibition - 0.7005 70.05%
CYP2C19 inhibition - 0.5868 58.68%
CYP2D6 inhibition - 0.8253 82.53%
CYP1A2 inhibition + 0.6648 66.48%
CYP2C8 inhibition + 0.7271 72.71%
CYP inhibitory promiscuity - 0.7301 73.01%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 0.8500 85.00%
Carcinogenicity (trinary) Non-required 0.6521 65.21%
Eye corrosion - 0.9850 98.50%
Eye irritation - 0.8456 84.56%
Skin irritation - 0.6655 66.55%
Skin corrosion - 0.8146 81.46%
Ames mutagenesis - 0.6800 68.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7639 76.39%
Micronuclear - 0.6682 66.82%
Hepatotoxicity - 0.6125 61.25%
skin sensitisation - 0.7143 71.43%
Respiratory toxicity + 0.6556 65.56%
Reproductive toxicity + 0.6556 65.56%
Mitochondrial toxicity + 0.5625 56.25%
Nephrotoxicity - 0.8244 82.44%
Acute Oral Toxicity (c) III 0.7373 73.73%
Estrogen receptor binding + 0.8147 81.47%
Androgen receptor binding + 0.7248 72.48%
Thyroid receptor binding + 0.6115 61.15%
Glucocorticoid receptor binding + 0.6450 64.50%
Aromatase binding + 0.5984 59.84%
PPAR gamma + 0.5908 59.08%
Honey bee toxicity - 0.8543 85.43%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.5400 54.00%
Fish aquatic toxicity + 0.8709 87.09%

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 97.54% 91.11%
CHEMBL2581 P07339 Cathepsin D 97.45% 98.95%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.64% 96.09%
CHEMBL1255126 O15151 Protein Mdm4 95.09% 90.20%
CHEMBL242 Q92731 Estrogen receptor beta 94.65% 98.35%
CHEMBL3060 Q9Y345 Glycine transporter 2 94.35% 99.17%
CHEMBL2535 P11166 Glucose transporter 93.12% 98.75%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 90.73% 94.45%
CHEMBL1293249 Q13887 Kruppel-like factor 5 90.51% 86.33%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 89.39% 99.15%
CHEMBL301 P24941 Cyclin-dependent kinase 2 89.27% 91.23%
CHEMBL335 P18031 Protein-tyrosine phosphatase 1B 88.06% 95.17%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 85.31% 95.89%
CHEMBL1907 P15144 Aminopeptidase N 84.40% 93.31%
CHEMBL5939 Q9NZ08 Endoplasmic reticulum aminopeptidase 1 83.67% 100.00%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 82.46% 94.00%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 82.43% 90.71%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 81.61% 95.50%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 81.38% 95.56%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.40% 95.89%

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.
Rhoiptelea chiliantha

Cross-Links

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PubChem 102445611
LOTUS LTS0114946
wikiData Q105030693