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(3R,4aR,12bS)-9-[(1R,3R,5S,8S,10R,12R,14R)-5,14-dimethyl-6-oxo-2,4,9,13-tetraoxatricyclo[8.4.0.03,8]tetradecan-12-yl]-4a,8,12b-trihydroxy-3-methyl-3-[(2S,5S,6S)-6-methyl-5-[[(2R,6S)-6-methyl-5-oxo-2H-pyran-2-yl]oxy]oxan-2-yl]oxy-2,4-dihydrobenzo[a]anthracene-1,7,12-trione

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 a7a30b44-495a-420d-ac20-476d223b7a3c
Taxonomy Phenylpropanoids and polyketides > Angucyclines
IUPAC Name (3R,4aR,12bS)-9-[(1R,3R,5S,8S,10R,12R,14R)-5,14-dimethyl-6-oxo-2,4,9,13-tetraoxatricyclo[8.4.0.03,8]tetradecan-12-yl]-4a,8,12b-trihydroxy-3-methyl-3-[(2S,5S,6S)-6-methyl-5-[[(2R,6S)-6-methyl-5-oxo-2H-pyran-2-yl]oxy]oxan-2-yl]oxy-2,4-dihydrobenzo[a]anthracene-1,7,12-trione
SMILES (Canonical) CC1C(CCC(O1)OC2(CC(=O)C3(C4=C(C=CC3(C2)O)C(=O)C5=C(C4=O)C=CC(=C5O)C6CC7C(C(O6)C)OC8C(O7)CC(=O)C(O8)C)O)C)OC9C=CC(=O)C(O9)C
SMILES (Isomeric) C[C@H]1[C@H](CC[C@@H](O1)O[C@]2(CC(=O)[C@@]3(C4=C(C=C[C@@]3(C2)O)C(=O)C5=C(C4=O)C=CC(=C5O)[C@H]6C[C@@H]7[C@@H]([C@H](O6)C)O[C@H]8[C@@H](O7)CC(=O)[C@@H](O8)C)O)C)O[C@H]9C=CC(=O)[C@@H](O9)C
InChI InChI=1S/C43H48O16/c1-18-25(44)8-10-32(53-18)57-27-9-11-33(54-20(27)3)59-41(5)16-31(46)43(51)35-24(12-13-42(43,50)17-41)37(48)34-23(38(35)49)7-6-22(36(34)47)28-15-29-39(21(4)52-28)58-40-30(56-29)14-26(45)19(2)55-40/h6-8,10,12-13,18-21,27-30,32-33,39-40,47,50-51H,9,11,14-17H2,1-5H3/t18-,19-,20-,21+,27-,28+,29+,30-,32-,33-,39+,40-,41-,42-,43-/m0/s1
InChI Key WUQKUPKWGZHYBN-NIVOMPQSSA-N
Popularity 8 references in papers

Physical and Chemical Properties

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Molecular Formula C43H48O16
Molecular Weight 820.80 g/mol
Exact Mass 820.29423544 g/mol
Topological Polar Surface Area (TPSA) 220.00 Ų
XlogP 1.40
Atomic LogP (AlogP) 2.72
H-Bond Acceptor 16
H-Bond Donor 3
Rotatable Bonds 5

Synonyms

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RefChem:931268
(3R,4aR,12bS)-9-((2S,4aS,5aR,7R,9R,9aR,10aR)-2,9-dimethyl-3-oxo-4,4a,5a,6,7,9,9a,10a-octahydrodipyrano(4,2-a:4',3'-e)(1,4)dioxin-7-yl)-4a,8,12b-trihydroxy-3-methyl-3-((2S,5S,6S)-6-methyl-5-(((2R,6S)-6-methyl-5-oxo-2H-pyran-2-yl)oxy)oxan-2-yl)oxy-2,4-dihydrobenzo(a)anthracene-1,7,12-trione
9-(5,14-dimethyl-6-oxo-2,4,9,13-tetraoxatricyclo(8.4.0.03,8)tetradecan-12-yl)-4a,8,12b-trihydroxy-3-methyl-3-(6-methyl-5-((6-methyl-5-oxo-2H-pyran-2-yl)oxy)oxan-2-yl)oxy-2,4-dihydrobenzo(a)anthracene-1,7,12-trione
99260-67-0
CHEMBL451284
SCHEMBL29884689
CHEBI:225311
HY-126803
(3R,4aR,12bS)-9-[(1R,3R,5S,8S,10R,12R,14R)-5,14-dimethyl-6-oxo-2,4,9,13-tetraoxatricyclo[8.4.0.03,8]tetradecan-12-yl]-4a,8,12b-trihydroxy-3-methyl-3-[(2S,5S,6S)-6-methyl-5-[[(2R,6S)-6-methyl-5-oxo-2H-pyran-2-yl]oxy]oxan-2-yl]oxy-2,4-dihydrobenzo[a]anthracene-1,7,12-trione

2D Structure

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2D Structure of (3R,4aR,12bS)-9-[(1R,3R,5S,8S,10R,12R,14R)-5,14-dimethyl-6-oxo-2,4,9,13-tetraoxatricyclo[8.4.0.03,8]tetradecan-12-yl]-4a,8,12b-trihydroxy-3-methyl-3-[(2S,5S,6S)-6-methyl-5-[[(2R,6S)-6-methyl-5-oxo-2H-pyran-2-yl]oxy]oxan-2-yl]oxy-2,4-dihydrobenzo[a]anthracene-1,7,12-trione

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9659 96.59%
Caco-2 - 0.8574 85.74%
Blood Brain Barrier - 0.6500 65.00%
Human oral bioavailability - 0.7286 72.86%
Subcellular localzation Mitochondria 0.7890 78.90%
OATP2B1 inhibitior - 0.7214 72.14%
OATP1B1 inhibitior + 0.8158 81.58%
OATP1B3 inhibitior - 0.2746 27.46%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.7821 78.21%
BSEP inhibitior + 0.9734 97.34%
P-glycoprotein inhibitior + 0.7739 77.39%
P-glycoprotein substrate + 0.8032 80.32%
CYP3A4 substrate + 0.7520 75.20%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8721 87.21%
CYP3A4 inhibition - 0.8817 88.17%
CYP2C9 inhibition - 0.8078 80.78%
CYP2C19 inhibition - 0.8323 83.23%
CYP2D6 inhibition - 0.9291 92.91%
CYP1A2 inhibition - 0.7137 71.37%
CYP2C8 inhibition + 0.7969 79.69%
CYP inhibitory promiscuity - 0.9388 93.88%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9400 94.00%
Carcinogenicity (trinary) Non-required 0.5453 54.53%
Eye corrosion - 0.9908 99.08%
Eye irritation - 0.9094 90.94%
Skin irritation - 0.6269 62.69%
Skin corrosion - 0.9211 92.11%
Ames mutagenesis + 0.6146 61.46%
Human Ether-a-go-go-Related Gene inhibition + 0.6499 64.99%
Micronuclear - 0.6000 60.00%
Hepatotoxicity + 0.5875 58.75%
skin sensitisation - 0.8425 84.25%
Respiratory toxicity + 0.6889 68.89%
Reproductive toxicity + 0.9556 95.56%
Mitochondrial toxicity + 0.8000 80.00%
Nephrotoxicity + 0.6610 66.10%
Acute Oral Toxicity (c) I 0.4742 47.42%
Estrogen receptor binding + 0.8589 85.89%
Androgen receptor binding + 0.7542 75.42%
Thyroid receptor binding + 0.5719 57.19%
Glucocorticoid receptor binding + 0.8032 80.32%
Aromatase binding + 0.7074 70.74%
PPAR gamma + 0.7856 78.56%
Honey bee toxicity - 0.6900 69.00%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity + 0.5500 55.00%
Fish aquatic toxicity + 0.9924 99.24%

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 99.23% 91.11%
CHEMBL2581 P07339 Cathepsin D 95.91% 98.95%
CHEMBL3137262 O60341 LSD1/CoREST complex 94.88% 97.09%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 94.78% 99.23%
CHEMBL5608 Q16288 NT-3 growth factor receptor 94.18% 95.89%
CHEMBL2996 Q05655 Protein kinase C delta 93.91% 97.79%
CHEMBL253 P34972 Cannabinoid CB2 receptor 93.38% 97.25%
CHEMBL1951 P21397 Monoamine oxidase A 93.37% 91.49%
CHEMBL226 P30542 Adenosine A1 receptor 93.17% 95.93%
CHEMBL1966 Q02127 Dihydroorotate dehydrogenase 93.08% 96.09%
CHEMBL1994 P08235 Mineralocorticoid receptor 91.46% 100.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 91.34% 89.00%
CHEMBL3713062 P10646 Tissue factor pathway inhibitor 90.65% 97.33%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 90.31% 96.09%
CHEMBL1902 P62942 FK506-binding protein 1A 89.61% 97.05%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 88.77% 93.04%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 88.50% 95.56%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 88.49% 85.14%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 88.21% 96.38%
CHEMBL2378 P30307 Dual specificity phosphatase Cdc25C 87.95% 96.67%
CHEMBL262 P49841 Glycogen synthase kinase-3 beta 87.50% 95.72%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 87.37% 94.45%
CHEMBL301 P24941 Cyclin-dependent kinase 2 87.25% 91.23%
CHEMBL241 Q14432 Phosphodiesterase 3A 86.33% 92.94%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 84.38% 94.00%
CHEMBL2345 P51812 Ribosomal protein S6 kinase alpha 3 83.95% 95.64%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 83.76% 96.77%
CHEMBL1293249 Q13887 Kruppel-like factor 5 83.23% 86.33%
CHEMBL2553 Q15418 Ribosomal protein S6 kinase alpha 1 81.14% 85.11%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 80.57% 90.71%
CHEMBL2069156 Q14145 Kelch-like ECH-associated protein 1 80.17% 82.38%
CHEMBL238 Q01959 Dopamine transporter 80.05% 95.88%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
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There are no matching plants.

Cross-Links

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PubChem 44587771
LOTUS LTS0264945
wikiData Q104401512