2-[(4R,5S,7R,8R,9S,12S,13S,14S)-8,14,18,19-tetrahydroxy-7-(hydroxymethyl)-2,11,15-trioxo-5-(3,4,5-trihydroxybenzoyl)oxy-3,6,10,16-tetraoxatetracyclo[11.7.1.04,9.017,21]henicosa-1(20),17(21),18-trien-12-yl]acetic acid

Details

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Internal ID bfab8528-1f52-466a-b951-0875621c35d6
Taxonomy Phenylpropanoids and polyketides > Tannins > Hydrolyzable tannins
IUPAC Name 2-[(4R,5S,7R,8R,9S,12S,13S,14S)-8,14,18,19-tetrahydroxy-7-(hydroxymethyl)-2,11,15-trioxo-5-(3,4,5-trihydroxybenzoyl)oxy-3,6,10,16-tetraoxatetracyclo[11.7.1.04,9.017,21]henicosa-1(20),17(21),18-trien-12-yl]acetic acid
SMILES (Canonical) C1=C(C=C(C(=C1O)O)O)C(=O)OC2C3C(C(C(O2)CO)O)OC(=O)C(C4C(C(=O)OC5=C4C(=CC(=C5O)O)C(=O)O3)O)CC(=O)O
SMILES (Isomeric) C1=C(C=C(C(=C1O)O)O)C(=O)O[C@H]2[C@H]3[C@H]([C@@H]([C@H](O2)CO)O)OC(=O)[C@H]([C@@H]4[C@@H](C(=O)OC5=C4C(=CC(=C5O)O)C(=O)O3)O)CC(=O)O
InChI InChI=1S/C27H24O19/c28-5-12-18(36)21-22(27(42-12)46-23(38)6-1-9(29)16(34)10(30)2-6)45-24(39)7-3-11(31)17(35)20-15(7)14(19(37)26(41)43-20)8(4-13(32)33)25(40)44-21/h1-3,8,12,14,18-19,21-22,27-31,34-37H,4-5H2,(H,32,33)/t8-,12+,14-,18+,19-,21-,22+,27-/m0/s1
InChI Key DHIUETZAWAZMBO-WXAXTOTNSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C27H24O19
Molecular Weight 652.50 g/mol
Exact Mass 652.09117853 g/mol
Topological Polar Surface Area (TPSA) 314.00 Ų
XlogP -1.10
Atomic LogP (AlogP) -1.95
H-Bond Acceptor 18
H-Bond Donor 9
Rotatable Bonds 5

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of 2-[(4R,5S,7R,8R,9S,12S,13S,14S)-8,14,18,19-tetrahydroxy-7-(hydroxymethyl)-2,11,15-trioxo-5-(3,4,5-trihydroxybenzoyl)oxy-3,6,10,16-tetraoxatetracyclo[11.7.1.04,9.017,21]henicosa-1(20),17(21),18-trien-12-yl]acetic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.6430 64.30%
Caco-2 - 0.9031 90.31%
Blood Brain Barrier - 0.6750 67.50%
Human oral bioavailability - 0.7286 72.86%
Subcellular localzation Nucleus 0.4695 46.95%
OATP2B1 inhibitior - 0.8456 84.56%
OATP1B1 inhibitior - 0.3548 35.48%
OATP1B3 inhibitior + 0.9524 95.24%
MATE1 inhibitior - 0.8000 80.00%
OCT2 inhibitior - 0.7750 77.50%
BSEP inhibitior + 0.6387 63.87%
P-glycoprotein inhibitior + 0.6204 62.04%
P-glycoprotein substrate - 0.5931 59.31%
CYP3A4 substrate + 0.6384 63.84%
CYP2C9 substrate - 0.8024 80.24%
CYP2D6 substrate - 0.8618 86.18%
CYP3A4 inhibition - 0.9062 90.62%
CYP2C9 inhibition - 0.9617 96.17%
CYP2C19 inhibition - 0.9470 94.70%
CYP2D6 inhibition - 0.9416 94.16%
CYP1A2 inhibition - 0.9442 94.42%
CYP2C8 inhibition + 0.6025 60.25%
CYP inhibitory promiscuity - 0.9590 95.90%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.7212 72.12%
Eye corrosion - 0.9935 99.35%
Eye irritation - 0.8787 87.87%
Skin irritation - 0.8230 82.30%
Skin corrosion - 0.9644 96.44%
Ames mutagenesis - 0.5162 51.62%
Human Ether-a-go-go-Related Gene inhibition + 0.6628 66.28%
Micronuclear + 0.6133 61.33%
Hepatotoxicity - 0.6125 61.25%
skin sensitisation - 0.8891 88.91%
Respiratory toxicity + 0.7444 74.44%
Reproductive toxicity + 0.8444 84.44%
Mitochondrial toxicity + 0.7125 71.25%
Nephrotoxicity - 0.8489 84.89%
Acute Oral Toxicity (c) III 0.4701 47.01%
Estrogen receptor binding + 0.7907 79.07%
Androgen receptor binding + 0.7201 72.01%
Thyroid receptor binding - 0.5646 56.46%
Glucocorticoid receptor binding - 0.6238 62.38%
Aromatase binding - 0.5679 56.79%
PPAR gamma + 0.6150 61.50%
Honey bee toxicity - 0.7784 77.84%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity - 0.6100 61.00%
Fish aquatic toxicity + 0.7770 77.70%

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 99.39% 91.11%
CHEMBL1293249 Q13887 Kruppel-like factor 5 91.87% 86.33%
CHEMBL2581 P07339 Cathepsin D 91.69% 98.95%
CHEMBL3060 Q9Y345 Glycine transporter 2 90.60% 99.17%
CHEMBL1951 P21397 Monoamine oxidase A 89.50% 91.49%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 88.52% 95.56%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 87.54% 94.00%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 87.51% 96.09%
CHEMBL3194 P02766 Transthyretin 86.52% 90.71%
CHEMBL1806 P11388 DNA topoisomerase II alpha 86.48% 89.00%
CHEMBL3475 P05121 Plasminogen activator inhibitor-1 84.86% 83.00%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 84.71% 99.15%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 84.29% 99.23%
CHEMBL3401 O75469 Pregnane X receptor 82.96% 94.73%
CHEMBL1781 P11387 DNA topoisomerase I 82.22% 97.00%
CHEMBL5255 O00206 Toll-like receptor 4 81.74% 92.50%
CHEMBL3004 P33527 Multidrug resistance-associated protein 1 80.20% 96.37%

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.
Acalypha indica

Cross-Links

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PubChem 163188905
LOTUS LTS0206625
wikiData Q104980205