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methyl 2-chloro-6,8-dihydroxy-9-[(1S)-1-(2-hydroxyacetyl)oxyethyl]-1-methoxy-3-methyl-7,12-dioxobenzo[a]anthracene-10-carboxylate

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 c2928285-37f5-442e-817d-83af5e518c9f
Taxonomy Phenylpropanoids and polyketides > Angucyclines
IUPAC Name methyl 2-chloro-6,8-dihydroxy-9-[(1S)-1-(2-hydroxyacetyl)oxyethyl]-1-methoxy-3-methyl-7,12-dioxobenzo[a]anthracene-10-carboxylate
SMILES (Canonical) CC1=CC2=CC(=C3C(=C2C(=C1Cl)OC)C(=O)C4=CC(=C(C(=C4C3=O)O)C(C)OC(=O)CO)C(=O)OC)O
SMILES (Isomeric) CC1=CC2=CC(=C3C(=C2C(=C1Cl)OC)C(=O)C4=CC(=C(C(=C4C3=O)O)[C@H](C)OC(=O)CO)C(=O)OC)O
InChI InChI=1S/C26H21ClO10/c1-9-5-11-6-14(29)19-20(17(11)25(35-3)21(9)27)22(31)12-7-13(26(34)36-4)16(10(2)37-15(30)8-28)23(32)18(12)24(19)33/h5-7,10,28-29,32H,8H2,1-4H3/t10-/m0/s1
InChI Key LMNHPKWXMIGBEL-JTQLQIEISA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C26H21ClO10
Molecular Weight 528.90 g/mol
Exact Mass 528.0823246 g/mol
Topological Polar Surface Area (TPSA) 157.00 Ų
XlogP 4.20
Atomic LogP (AlogP) 3.38
H-Bond Acceptor 10
H-Bond Donor 3
Rotatable Bonds 5

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of methyl 2-chloro-6,8-dihydroxy-9-[(1S)-1-(2-hydroxyacetyl)oxyethyl]-1-methoxy-3-methyl-7,12-dioxobenzo[a]anthracene-10-carboxylate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9770 97.70%
Caco-2 - 0.6931 69.31%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.5143 51.43%
Subcellular localzation Mitochondria 0.7492 74.92%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8142 81.42%
OATP1B3 inhibitior - 0.2728 27.28%
MATE1 inhibitior - 0.8400 84.00%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior + 0.9394 93.94%
P-glycoprotein inhibitior + 0.6485 64.85%
P-glycoprotein substrate - 0.5352 53.52%
CYP3A4 substrate + 0.6543 65.43%
CYP2C9 substrate - 0.8105 81.05%
CYP2D6 substrate - 0.8699 86.99%
CYP3A4 inhibition - 0.6917 69.17%
CYP2C9 inhibition + 0.5285 52.85%
CYP2C19 inhibition - 0.7284 72.84%
CYP2D6 inhibition - 0.9116 91.16%
CYP1A2 inhibition - 0.5360 53.60%
CYP2C8 inhibition + 0.6047 60.47%
CYP inhibitory promiscuity - 0.6543 65.43%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.8012 80.12%
Carcinogenicity (trinary) Non-required 0.6276 62.76%
Eye corrosion - 0.9888 98.88%
Eye irritation - 0.8852 88.52%
Skin irritation - 0.7914 79.14%
Skin corrosion - 0.9516 95.16%
Ames mutagenesis - 0.5200 52.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4208 42.08%
Micronuclear + 0.5633 56.33%
Hepatotoxicity + 0.5348 53.48%
skin sensitisation - 0.8226 82.26%
Respiratory toxicity + 0.6778 67.78%
Reproductive toxicity + 0.6556 65.56%
Mitochondrial toxicity + 0.5625 56.25%
Nephrotoxicity - 0.7504 75.04%
Acute Oral Toxicity (c) III 0.6381 63.81%
Estrogen receptor binding + 0.7892 78.92%
Androgen receptor binding + 0.6495 64.95%
Thyroid receptor binding + 0.5165 51.65%
Glucocorticoid receptor binding + 0.7736 77.36%
Aromatase binding + 0.5206 52.06%
PPAR gamma + 0.6673 66.73%
Honey bee toxicity - 0.8760 87.60%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.6827 68.27%
Fish aquatic toxicity + 0.9820 98.20%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
CHEMBL235 P37231 Peroxisome proliferator-activated receptor gamma 90 nM
 IC50
 via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 99.26% 91.11%
CHEMBL2581 P07339 Cathepsin D 97.33% 98.95%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 94.32% 99.15%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 94.07% 94.45%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 93.65% 94.00%
CHEMBL3401 O75469 Pregnane X receptor 90.84% 94.73%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 90.73% 96.21%
CHEMBL3864 Q06124 Protein-tyrosine phosphatase 2C 89.51% 94.42%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 89.24% 90.71%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 88.73% 96.09%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 88.41% 96.00%
CHEMBL4208 P20618 Proteasome component C5 87.81% 90.00%
CHEMBL2535 P11166 Glucose transporter 87.55% 98.75%
CHEMBL3060 Q9Y345 Glycine transporter 2 87.36% 99.17%
CHEMBL3359 P21462 Formyl peptide receptor 1 86.93% 93.56%
CHEMBL335 P18031 Protein-tyrosine phosphatase 1B 86.49% 95.17%
CHEMBL2378 P30307 Dual specificity phosphatase Cdc25C 85.98% 96.67%
CHEMBL1293249 Q13887 Kruppel-like factor 5 85.11% 86.33%
CHEMBL1293267 Q9HC97 G-protein coupled receptor 35 84.64% 89.34%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 84.38% 86.92%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 84.27% 93.03%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 84.15% 95.56%
CHEMBL5163 Q9NY46 Sodium channel protein type III alpha subunit 83.01% 96.90%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 81.74% 85.14%
CHEMBL1907591 P30926 Neuronal acetylcholine receptor; alpha4/beta4 81.71% 100.00%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 81.61% 95.50%
CHEMBL4581 P52732 Kinesin-like protein 1 80.39% 93.18%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 80.34% 96.38%

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 162969254
LOTUS LTS0093543
wikiData Q105154064