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(2R,3R,4R)-4-[(1R)-3-(1-carboxy-2,4,5,6-tetrahydroxyhexan-3-yl)oxycarbonyl-1-(3,4-dihydroxyphenyl)-6,7-dihydroxy-1,2-dihydronaphthalene-2-carbonyl]oxy-2-(1,2-dihydroxyethyl)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3,4-dihydro-2H-pyran-6-carboxylic acid

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 50956f4d-4c95-48b6-ad32-44124946df3b
Taxonomy Lignans, neolignans and related compounds > Aryltetralin lignans
IUPAC Name (2R,3R,4R)-4-[(1R)-3-(1-carboxy-2,4,5,6-tetrahydroxyhexan-3-yl)oxycarbonyl-1-(3,4-dihydroxyphenyl)-6,7-dihydroxy-1,2-dihydronaphthalene-2-carbonyl]oxy-2-(1,2-dihydroxyethyl)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3,4-dihydro-2H-pyran-6-carboxylic acid
SMILES (Canonical) C1=CC(=C(C=C1C=CC(=O)OC2C(C=C(OC2C(CO)O)C(=O)O)OC(=O)C3C(C4=CC(=C(C=C4C=C3C(=O)OC(C(CC(=O)O)O)C(C(CO)O)O)O)O)C5=CC(=C(C=C5)O)O)O)O
SMILES (Isomeric) C1=CC(=C(C=C1/C=C/C(=O)O[C@@H]2[C@@H](C=C(O[C@@H]2C(CO)O)C(=O)O)OC(=O)C3[C@@H](C4=CC(=C(C=C4C=C3C(=O)OC(C(CC(=O)O)O)C(C(CO)O)O)O)O)C5=CC(=C(C=C5)O)O)O)O
InChI InChI=1S/C42H42O23/c43-14-28(52)36(57)37(27(51)12-32(54)55)65-41(60)20-8-18-10-25(49)26(50)11-19(18)34(17-3-5-22(46)24(48)9-17)35(20)42(61)63-30-13-31(40(58)59)62-38(29(53)15-44)39(30)64-33(56)6-2-16-1-4-21(45)23(47)7-16/h1-11,13,27-30,34-39,43-53,57H,12,14-15H2,(H,54,55)(H,58,59)/b6-2+/t27?,28?,29?,30-,34-,35?,36?,37?,38-,39-/m1/s1
InChI Key MKLCPDMXKJGRLV-VENHLSGLSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C42H42O23
Molecular Weight 914.80 g/mol
Exact Mass 914.21168758 g/mol
Topological Polar Surface Area (TPSA) 406.00 Ų
XlogP -0.80
Atomic LogP (AlogP) -1.22
H-Bond Acceptor 21
H-Bond Donor 14
Rotatable Bonds 17

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2R,3R,4R)-4-[(1R)-3-(1-carboxy-2,4,5,6-tetrahydroxyhexan-3-yl)oxycarbonyl-1-(3,4-dihydroxyphenyl)-6,7-dihydroxy-1,2-dihydronaphthalene-2-carbonyl]oxy-2-(1,2-dihydroxyethyl)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3,4-dihydro-2H-pyran-6-carboxylic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.6677 66.77%
Caco-2 - 0.8895 88.95%
Blood Brain Barrier - 0.6500 65.00%
Human oral bioavailability - 0.7000 70.00%
Subcellular localzation Mitochondria 0.4753 47.53%
OATP2B1 inhibitior - 0.7111 71.11%
OATP1B1 inhibitior + 0.8394 83.94%
OATP1B3 inhibitior + 0.9599 95.99%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior + 0.8377 83.77%
P-glycoprotein inhibitior + 0.7112 71.12%
P-glycoprotein substrate + 0.6583 65.83%
CYP3A4 substrate + 0.7070 70.70%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8664 86.64%
CYP3A4 inhibition - 0.9218 92.18%
CYP2C9 inhibition - 0.8129 81.29%
CYP2C19 inhibition - 0.7832 78.32%
CYP2D6 inhibition - 0.8800 88.00%
CYP1A2 inhibition - 0.8162 81.62%
CYP2C8 inhibition + 0.8147 81.47%
CYP inhibitory promiscuity - 0.7520 75.20%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.7137 71.37%
Eye corrosion - 0.9913 99.13%
Eye irritation - 0.8994 89.94%
Skin irritation - 0.8151 81.51%
Skin corrosion - 0.9527 95.27%
Ames mutagenesis - 0.6223 62.23%
Human Ether-a-go-go-Related Gene inhibition + 0.7375 73.75%
Micronuclear + 0.6433 64.33%
Hepatotoxicity - 0.6625 66.25%
skin sensitisation - 0.8296 82.96%
Respiratory toxicity + 0.6778 67.78%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.7750 77.50%
Nephrotoxicity - 0.8650 86.50%
Acute Oral Toxicity (c) III 0.4118 41.18%
Estrogen receptor binding + 0.7436 74.36%
Androgen receptor binding + 0.7028 70.28%
Thyroid receptor binding + 0.5214 52.14%
Glucocorticoid receptor binding - 0.5684 56.84%
Aromatase binding - 0.5076 50.76%
PPAR gamma + 0.7215 72.15%
Honey bee toxicity - 0.6559 65.59%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.6300 63.00%
Fish aquatic toxicity + 0.9437 94.37%

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 99.79% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.43% 96.09%
CHEMBL3194 P02766 Transthyretin 96.59% 90.71%
CHEMBL221 P23219 Cyclooxygenase-1 96.57% 90.17%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 96.11% 99.15%
CHEMBL1293249 Q13887 Kruppel-like factor 5 94.19% 86.33%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.92% 97.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 92.98% 94.45%
CHEMBL1806 P11388 DNA topoisomerase II alpha 92.86% 89.00%
CHEMBL3060 Q9Y345 Glycine transporter 2 91.50% 99.17%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 91.03% 96.00%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 88.89% 86.92%
CHEMBL3475 P05121 Plasminogen activator inhibitor-1 88.75% 83.00%
CHEMBL2581 P07339 Cathepsin D 88.66% 98.95%
CHEMBL211 P08172 Muscarinic acetylcholine receptor M2 86.18% 94.97%
CHEMBL340 P08684 Cytochrome P450 3A4 85.43% 91.19%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 84.79% 85.14%
CHEMBL3004 P33527 Multidrug resistance-associated protein 1 84.53% 96.37%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 84.16% 95.56%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 83.74% 96.95%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 82.61% 95.50%
CHEMBL4227 P25090 Lipoxin A4 receptor 82.05% 100.00%
CHEMBL3922 P50579 Methionine aminopeptidase 2 81.14% 97.28%
CHEMBL3359 P21462 Formyl peptide receptor 1 80.42% 93.56%

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.
Bazzania trilobata

Cross-Links

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PubChem 101231537
LOTUS LTS0196708
wikiData Q105166060