5-[(1R,2R)-2-carboxy-3-[(2S,3S,4S,5S)-3-[(3S,4R)-3-carboxy-4-(3,4-dihydroxyphenyl)-6,7-dihydroxy-3,4-dihydronaphthalene-2-carbonyl]oxy-2-(carboxymethyl)-5-hydroxyoxan-4-yl]oxycarbonyl-6,7-dihydroxy-1,2-dihydronaphthalen-1-yl]-6-oxopyran-2-carboxylic acid

Details

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Internal ID 96e1d9ff-6edc-482b-b8ca-70cf033d4d03
Taxonomy Lignans, neolignans and related compounds > Lignan lactones
IUPAC Name 5-[(1R,2R)-2-carboxy-3-[(2S,3S,4S,5S)-3-[(3S,4R)-3-carboxy-4-(3,4-dihydroxyphenyl)-6,7-dihydroxy-3,4-dihydronaphthalene-2-carbonyl]oxy-2-(carboxymethyl)-5-hydroxyoxan-4-yl]oxycarbonyl-6,7-dihydroxy-1,2-dihydronaphthalen-1-yl]-6-oxopyran-2-carboxylic acid
SMILES (Canonical) C1C(C(C(C(O1)CC(=O)O)OC(=O)C2=CC3=CC(=C(C=C3C(C2C(=O)O)C4=CC(=C(C=C4)O)O)O)O)OC(=O)C5=CC6=CC(=C(C=C6C(C5C(=O)O)C7=CC=C(OC7=O)C(=O)O)O)O)O
SMILES (Isomeric) C1[C@@H]([C@@H]([C@H]([C@@H](O1)CC(=O)O)OC(=O)C2=CC3=CC(=C(C=C3[C@H]([C@@H]2C(=O)O)C4=CC(=C(C=C4)O)O)O)O)OC(=O)C5=CC6=CC(=C(C=C6[C@@H]([C@H]5C(=O)O)C7=CC=C(OC7=O)C(=O)O)O)O)O
InChI InChI=1S/C43H34O22/c44-22-3-1-14(7-23(22)45)32-18-10-26(48)24(46)8-15(18)5-20(34(32)39(55)56)43(61)65-37-30(12-31(51)52)62-13-28(50)36(37)64-42(60)21-6-16-9-25(47)27(49)11-19(16)33(35(21)40(57)58)17-2-4-29(38(53)54)63-41(17)59/h1-11,28,30,32-37,44-50H,12-13H2,(H,51,52)(H,53,54)(H,55,56)(H,57,58)/t28-,30-,32+,33-,34+,35-,36-,37-/m0/s1
InChI Key VMWRMZUOUIDYCS-ARUDPIHHSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C43H34O22
Molecular Weight 902.70 g/mol
Exact Mass 902.15417271 g/mol
Topological Polar Surface Area (TPSA) 379.00 Ų
XlogP 1.50
Atomic LogP (AlogP) 1.79
H-Bond Acceptor 18
H-Bond Donor 11
Rotatable Bonds 11

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of 5-[(1R,2R)-2-carboxy-3-[(2S,3S,4S,5S)-3-[(3S,4R)-3-carboxy-4-(3,4-dihydroxyphenyl)-6,7-dihydroxy-3,4-dihydronaphthalene-2-carbonyl]oxy-2-(carboxymethyl)-5-hydroxyoxan-4-yl]oxycarbonyl-6,7-dihydroxy-1,2-dihydronaphthalen-1-yl]-6-oxopyran-2-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 + 0.9236 92.36%
Caco-2 - 0.8838 88.38%
Blood Brain Barrier - 0.7750 77.50%
Human oral bioavailability - 0.6714 67.14%
Subcellular localzation Mitochondria 0.7911 79.11%
OATP2B1 inhibitior - 0.7116 71.16%
OATP1B1 inhibitior + 0.8590 85.90%
OATP1B3 inhibitior + 0.9183 91.83%
MATE1 inhibitior - 0.8400 84.00%
OCT2 inhibitior - 0.8250 82.50%
BSEP inhibitior + 0.7075 70.75%
P-glycoprotein inhibitior + 0.7236 72.36%
P-glycoprotein substrate + 0.5531 55.31%
CYP3A4 substrate + 0.6678 66.78%
CYP2C9 substrate - 0.5973 59.73%
CYP2D6 substrate - 0.8588 85.88%
CYP3A4 inhibition - 0.8068 80.68%
CYP2C9 inhibition - 0.5696 56.96%
CYP2C19 inhibition - 0.6301 63.01%
CYP2D6 inhibition - 0.8419 84.19%
CYP1A2 inhibition - 0.7747 77.47%
CYP2C8 inhibition + 0.7407 74.07%
CYP inhibitory promiscuity - 0.6994 69.94%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.6583 65.83%
Eye corrosion - 0.9894 98.94%
Eye irritation - 0.8989 89.89%
Skin irritation - 0.7979 79.79%
Skin corrosion - 0.9543 95.43%
Ames mutagenesis + 0.5436 54.36%
Human Ether-a-go-go-Related Gene inhibition + 0.6463 64.63%
Micronuclear + 0.7418 74.18%
Hepatotoxicity - 0.6415 64.15%
skin sensitisation - 0.7856 78.56%
Respiratory toxicity + 0.7222 72.22%
Reproductive toxicity + 0.8111 81.11%
Mitochondrial toxicity + 0.7625 76.25%
Nephrotoxicity - 0.9412 94.12%
Acute Oral Toxicity (c) III 0.4922 49.22%
Estrogen receptor binding + 0.7669 76.69%
Androgen receptor binding + 0.7368 73.68%
Thyroid receptor binding + 0.5170 51.70%
Glucocorticoid receptor binding - 0.5360 53.60%
Aromatase binding + 0.5578 55.78%
PPAR gamma + 0.7290 72.90%
Honey bee toxicity - 0.7111 71.11%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity - 0.6250 62.50%
Fish aquatic toxicity + 0.9871 98.71%

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 99.70% 91.11%
CHEMBL2581 P07339 Cathepsin D 96.17% 98.95%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 95.97% 94.45%
CHEMBL3137262 O60341 LSD1/CoREST complex 94.17% 97.09%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 93.89% 99.15%
CHEMBL335 P18031 Protein-tyrosine phosphatase 1B 93.43% 95.17%
CHEMBL1951 P21397 Monoamine oxidase A 93.40% 91.49%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 92.11% 96.09%
CHEMBL4040 P28482 MAP kinase ERK2 91.39% 83.82%
CHEMBL3194 P02766 Transthyretin 90.79% 90.71%
CHEMBL3922 P50579 Methionine aminopeptidase 2 89.92% 97.28%
CHEMBL340 P08684 Cytochrome P450 3A4 89.50% 91.19%
CHEMBL5608 Q16288 NT-3 growth factor receptor 89.43% 95.89%
CHEMBL1293249 Q13887 Kruppel-like factor 5 86.09% 86.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 86.00% 95.56%
CHEMBL2563 Q9UQL6 Histone deacetylase 5 85.09% 89.67%
CHEMBL3492 P49721 Proteasome Macropain subunit 84.01% 90.24%
CHEMBL3475 P05121 Plasminogen activator inhibitor-1 83.66% 83.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 83.37% 89.00%
CHEMBL3060 Q9Y345 Glycine transporter 2 83.27% 99.17%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 82.90% 85.14%
CHEMBL2288 Q13526 Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 80.51% 91.71%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 80.08% 94.00%

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.
Bazzania trilobata

Cross-Links

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PubChem 101231536
LOTUS LTS0106649
wikiData Q105289352