4'-O-demethylknipholone-4'-O-beta-D-glucopyranoside

Details

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Internal ID f015e909-447e-4969-b7d1-dd1ab36286c0
Taxonomy Benzenoids > Anthracenes > Anthraquinones
IUPAC Name 1-[3-acetyl-2,6-dihydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-4,5-dihydroxy-2-methylanthracene-9,10-dione
SMILES (Canonical) CC1=CC(=C2C(=C1C3=C(C(=C(C=C3O)OC4C(C(C(C(O4)CO)O)O)O)C(=O)C)O)C(=O)C5=C(C2=O)C(=CC=C5)O)O
SMILES (Isomeric) CC1=CC(=C2C(=C1C3=C(C(=C(C=C3O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)C(=O)C)O)C(=O)C5=C(C2=O)C(=CC=C5)O)O
InChI InChI=1S/C29H26O13/c1-9-6-13(33)21-22(23(35)11-4-3-5-12(32)19(11)26(21)38)17(9)20-14(34)7-15(18(10(2)31)25(20)37)41-29-28(40)27(39)24(36)16(8-30)42-29/h3-7,16,24,27-30,32-34,36-37,39-40H,8H2,1-2H3/t16-,24-,27+,28-,29-/m1/s1
InChI Key AOJYFODHRHWWEN-GQUXZSRASA-N
Popularity 4 references in papers

Physical and Chemical Properties

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Molecular Formula C29H26O13
Molecular Weight 582.50 g/mol
Exact Mass 582.13734088 g/mol
Topological Polar Surface Area (TPSA) 232.00 Ų
XlogP 2.10
Atomic LogP (AlogP) 0.64
H-Bond Acceptor 13
H-Bond Donor 8
Rotatable Bonds 5

Synonyms

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4'-O-demethylknipholone-4'-O-beta-D-glucopyranoside
CHEBI:65741
2-acetyl-4-(4,5-dihydroxy-2-methyl-9,10-dioxo-9,10-dihydroanthracen-1-yl)-3,5-dihydroxyphenyl beta-D-glucopyranoside
CHEMBL447622
Q27134223
1-[3-acetyl-2,6-dihydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-4,5-dihydroxy-2-methylanthracene-9,10-dione

2D Structure

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2D Structure of 4'-O-demethylknipholone-4'-O-beta-D-glucopyranoside

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.5246 52.46%
Caco-2 - 0.9013 90.13%
Blood Brain Barrier - 0.8500 85.00%
Human oral bioavailability - 0.6429 64.29%
Subcellular localzation Mitochondria 0.6463 64.63%
OATP2B1 inhibitior - 0.5633 56.33%
OATP1B1 inhibitior + 0.8539 85.39%
OATP1B3 inhibitior + 0.9495 94.95%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.7750 77.50%
BSEP inhibitior + 0.8238 82.38%
P-glycoprotein inhibitior - 0.5000 50.00%
P-glycoprotein substrate - 0.6251 62.51%
CYP3A4 substrate + 0.6494 64.94%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8669 86.69%
CYP3A4 inhibition - 0.8899 88.99%
CYP2C9 inhibition - 0.8748 87.48%
CYP2C19 inhibition - 0.9223 92.23%
CYP2D6 inhibition - 0.9640 96.40%
CYP1A2 inhibition - 0.8023 80.23%
CYP2C8 inhibition + 0.6332 63.32%
CYP inhibitory promiscuity - 0.7830 78.30%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.7472 74.72%
Eye corrosion - 0.9924 99.24%
Eye irritation - 0.9042 90.42%
Skin irritation - 0.8502 85.02%
Skin corrosion - 0.9582 95.82%
Ames mutagenesis + 0.7936 79.36%
Human Ether-a-go-go-Related Gene inhibition + 0.7013 70.13%
Micronuclear + 0.6733 67.33%
Hepatotoxicity - 0.6250 62.50%
skin sensitisation - 0.9385 93.85%
Respiratory toxicity + 0.5444 54.44%
Reproductive toxicity + 0.8333 83.33%
Mitochondrial toxicity + 0.7000 70.00%
Nephrotoxicity + 0.4580 45.80%
Acute Oral Toxicity (c) III 0.5595 55.95%
Estrogen receptor binding + 0.7921 79.21%
Androgen receptor binding - 0.4819 48.19%
Thyroid receptor binding - 0.5583 55.83%
Glucocorticoid receptor binding + 0.6041 60.41%
Aromatase binding - 0.5299 52.99%
PPAR gamma + 0.7016 70.16%
Honey bee toxicity - 0.8311 83.11%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity - 0.7100 71.00%
Fish aquatic toxicity + 0.9169 91.69%

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 98.62% 91.11%
CHEMBL2581 P07339 Cathepsin D 98.22% 98.95%
CHEMBL1806 P11388 DNA topoisomerase II alpha 96.95% 89.00%
CHEMBL3401 O75469 Pregnane X receptor 95.79% 94.73%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 93.74% 95.56%
CHEMBL1293249 Q13887 Kruppel-like factor 5 93.04% 86.33%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 92.87% 94.00%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 92.66% 96.21%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 91.71% 96.09%
CHEMBL3060 Q9Y345 Glycine transporter 2 88.74% 99.17%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 88.64% 99.23%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 87.80% 99.15%
CHEMBL220 P22303 Acetylcholinesterase 87.33% 94.45%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 87.31% 96.00%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 85.33% 95.50%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 85.09% 97.21%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 83.56% 96.95%
CHEMBL4208 P20618 Proteasome component C5 81.71% 90.00%
CHEMBL1293255 P15428 15-hydroxyprostaglandin dehydrogenase [NAD+] 80.88% 83.57%

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.
Bulbine frutescens
Bulbinella floribunda

Cross-Links

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PubChem 10008440
NPASS NPC114257
LOTUS LTS0119724
wikiData Q27134223