Isoschimawalin A

Details

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Internal ID e122e925-e0d3-4727-b71b-d7c26911f1f6
Taxonomy Phenylpropanoids and polyketides > Tannins > Hydrolyzable tannins
IUPAC Name 2-[[3,4,11,17,18,19-hexahydroxy-9,14-dioxo-10-[3-oxo-1-(3,4,5-trihydroxybenzoyl)oxy-2-[3,4,5-trihydroxy-2-[(7,13,14-trihydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),4,6,8(16),11,13-hexaen-6-yl)oxy]benzoyl]oxypropyl]-8,13-dioxatricyclo[13.4.0.02,7]nonadeca-1(19),2,4,6,15,17-hexaen-5-yl]oxy]-3,4,5-trihydroxybenzoic acid
SMILES (Canonical) C1C(C(C(=O)OC2=CC(=C(C(=C2C3=C(C(=C(C=C3C(=O)O1)O)O)O)O)O)OC4=C(C(=C(C=C4C(=O)O)O)O)O)C(C(C=O)OC(=O)C5=CC(=C(C(=C5OC6=C(C7=C8C(=C6)C(=O)OC9=C8C(=CC(=C9O)O)C(=O)O7)O)O)O)O)OC(=O)C1=CC(=C(C(=C1)O)O)O)O
SMILES (Isomeric) C1C(C(C(=O)OC2=CC(=C(C(=C2C3=C(C(=C(C=C3C(=O)O1)O)O)O)O)O)OC4=C(C(=C(C=C4C(=O)O)O)O)O)C(C(C=O)OC(=O)C5=CC(=C(C(=C5OC6=C(C7=C8C(=C6)C(=O)OC9=C8C(=CC(=C9O)O)C(=O)O7)O)O)O)O)OC(=O)C1=CC(=C(C(=C1)O)O)O)O
InChI InChI=1S/C55H34O35/c56-9-27(87-54(81)16-6-21(61)36(67)43(74)45(16)84-25-7-14-30-29-13(52(79)90-48(30)39(25)70)4-22(62)37(68)47(29)89-53(14)80)46(88-50(77)11-1-17(57)33(64)18(58)2-11)31-23(63)10-83-51(78)12-3-19(59)34(65)40(71)28(12)32-24(86-55(31)82)8-26(38(69)41(32)72)85-44-15(49(75)76)5-20(60)35(66)42(44)73/h1-9,23,27,31,46,57-74H,10H2,(H,75,76)
InChI Key QHUFBIOFLFOWEC-UHFFFAOYSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C55H34O35
Molecular Weight 1254.80 g/mol
Exact Mass 1254.0880628 g/mol
Topological Polar Surface Area (TPSA) 595.00 Ų
XlogP 2.20
Atomic LogP (AlogP) 3.14
H-Bond Acceptor 34
H-Bond Donor 19
Rotatable Bonds 12

Synonyms

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143201-45-0
D-Glucose, cyclic 4-2:6-2'-((1S)-4-(6-carboxy-2,3,4-trihydroxyphenoxy)-4',5,5',6,6'-pentahydroxy(1,1'-biphenyl)-2,2'-dicarboxylate) 2-(2-((5,10-dihydro-3,7,8-trihydroxy-5,10-dioxo(1)benzopyrano(5,4,3-cde)(1)benzopyran-2-yl)oxy)-3,4,5-trihydroxybenzoate)-3-(3,4,5-trihydroxybenzoate)
2-[hexahydroxy-dioxo-[3-oxo-1-(3,4,5-trihydroxybenzoyl)oxy-2-[3,4,5-trihydroxy-2-[trihydroxy(dioxo)[?]yl]oxy-benzoyl]oxy-propyl][?]yl]oxy-3,4,5-trihydroxy-benzoic acid
D-Glucose, cyclic 4.fwdarw.2:6.fwdarw.2'-[(1S)-4-(6-carboxy-2,3,4-trihydroxyphenoxy)-4',5,5',6,6'-pentahydroxy[1,1'-biphenyl]-2,2'-dicarboxylate] 2-[2-[(5,10-dihydro-3,7,8-trihydroxy-5,10-dioxo[1]benzopyrano[5,4,3-cde][1]benzopyran-2-yl)oxy]-3,4,5-trihydroxybenzoate]-3-(3,4,5-trihydroxybenzoate)

2D Structure

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2D Structure of Isoschimawalin A

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.6759 67.59%
Caco-2 - 0.8634 86.34%
Blood Brain Barrier - 0.7250 72.50%
Human oral bioavailability - 0.6286 62.86%
Subcellular localzation Mitochondria 0.5320 53.20%
OATP2B1 inhibitior - 0.5718 57.18%
OATP1B1 inhibitior + 0.7833 78.33%
OATP1B3 inhibitior + 0.8874 88.74%
MATE1 inhibitior - 0.8200 82.00%
OCT2 inhibitior - 0.8250 82.50%
BSEP inhibitior + 0.9159 91.59%
P-glycoprotein inhibitior + 0.7425 74.25%
P-glycoprotein substrate + 0.6880 68.80%
CYP3A4 substrate + 0.6918 69.18%
CYP2C9 substrate - 0.5951 59.51%
CYP2D6 substrate - 0.8620 86.20%
CYP3A4 inhibition - 0.8728 87.28%
CYP2C9 inhibition - 0.9390 93.90%
CYP2C19 inhibition - 0.9245 92.45%
CYP2D6 inhibition - 0.9176 91.76%
CYP1A2 inhibition - 0.8856 88.56%
CYP2C8 inhibition + 0.8583 85.83%
CYP inhibitory promiscuity - 0.9531 95.31%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6950 69.50%
Eye corrosion - 0.9912 99.12%
Eye irritation - 0.8969 89.69%
Skin irritation - 0.7772 77.72%
Skin corrosion - 0.9518 95.18%
Ames mutagenesis + 0.5400 54.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7255 72.55%
Micronuclear + 0.7933 79.33%
Hepatotoxicity - 0.5468 54.68%
skin sensitisation - 0.8283 82.83%
Respiratory toxicity + 0.8000 80.00%
Reproductive toxicity + 0.7778 77.78%
Mitochondrial toxicity + 0.6375 63.75%
Nephrotoxicity - 0.9395 93.95%
Acute Oral Toxicity (c) III 0.5736 57.36%
Estrogen receptor binding + 0.7644 76.44%
Androgen receptor binding + 0.7733 77.33%
Thyroid receptor binding + 0.5713 57.13%
Glucocorticoid receptor binding + 0.5569 55.69%
Aromatase binding + 0.6213 62.13%
PPAR gamma + 0.7420 74.20%
Honey bee toxicity - 0.6398 63.98%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity - 0.6400 64.00%
Fish aquatic toxicity + 0.8471 84.71%

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
CHEMBL1951 P21397 Monoamine oxidase A 99.89% 91.49%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 99.54% 91.11%
CHEMBL1293267 Q9HC97 G-protein coupled receptor 35 98.35% 89.34%
CHEMBL335 P18031 Protein-tyrosine phosphatase 1B 98.31% 95.17%
CHEMBL3475 P05121 Plasminogen activator inhibitor-1 97.59% 83.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 96.29% 99.23%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 95.89% 95.56%
CHEMBL2581 P07339 Cathepsin D 95.33% 98.95%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 95.14% 95.50%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 95.00% 99.15%
CHEMBL3194 P02766 Transthyretin 94.23% 90.71%
CHEMBL1806 P11388 DNA topoisomerase II alpha 94.18% 89.00%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 93.24% 96.21%
CHEMBL1163125 O60885 Bromodomain-containing protein 4 93.21% 97.31%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 92.51% 94.00%
CHEMBL1811 P34995 Prostanoid EP1 receptor 92.49% 95.71%
CHEMBL1293249 Q13887 Kruppel-like factor 5 92.10% 86.33%
CHEMBL3864 Q06124 Protein-tyrosine phosphatase 2C 90.83% 94.42%
CHEMBL3060 Q9Y345 Glycine transporter 2 90.17% 99.17%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 89.63% 97.21%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 89.28% 93.00%
CHEMBL2535 P11166 Glucose transporter 89.20% 98.75%
CHEMBL4361 Q07820 Induced myeloid leukemia cell differentiation protein Mcl-1 88.61% 95.52%
CHEMBL340 P08684 Cytochrome P450 3A4 87.53% 91.19%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 87.39% 92.62%
CHEMBL3891 P07384 Calpain 1 84.53% 93.04%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 83.41% 94.45%
CHEMBL213 P08588 Beta-1 adrenergic receptor 81.58% 95.56%
CHEMBL3401 O75469 Pregnane X receptor 81.03% 94.73%
CHEMBL2413 P32246 C-C chemokine receptor type 1 80.76% 89.50%
CHEMBL2179 P04062 Beta-glucocerebrosidase 80.70% 85.31%
CHEMBL4530 P00488 Coagulation factor XIII 80.48% 96.00%
CHEMBL4208 P20618 Proteasome component C5 80.39% 90.00%

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.
Woodfordia fruticosa

Cross-Links

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PubChem 16130370
LOTUS LTS0041488
wikiData Q105221145