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(3R)-8-hydroxy-3-[(E)-2-(7-hydroxy-2-oxochromen-8-yl)ethenyl]-10-methoxy-3,12-dimethyl-2H-[1,4]dioxino[2,3-c]acridin-7-one

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 c33d32f6-d07a-4e5a-b8e0-e0799909b118
Taxonomy Organoheterocyclic compounds > Quinolines and derivatives > Benzoquinolines > Acridines > Acridones
IUPAC Name (3R)-8-hydroxy-3-[(E)-2-(7-hydroxy-2-oxochromen-8-yl)ethenyl]-10-methoxy-3,12-dimethyl-2H-[1,4]dioxino[2,3-c]acridin-7-one
SMILES (Canonical) CC1(COC2=C(O1)C=CC3=C2N(C4=C(C3=O)C(=CC(=C4)OC)O)C)C=CC5=C(C=CC6=C5OC(=O)C=C6)O
SMILES (Isomeric) C[C@]1(COC2=C(O1)C=CC3=C2N(C4=C(C3=O)C(=CC(=C4)OC)O)C)/C=C/C5=C(C=CC6=C5OC(=O)C=C6)O
InChI InChI=1S/C29H23NO8/c1-29(11-10-17-20(31)7-4-15-5-9-23(33)37-27(15)17)14-36-28-22(38-29)8-6-18-25(28)30(2)19-12-16(35-3)13-21(32)24(19)26(18)34/h4-13,31-32H,14H2,1-3H3/b11-10+/t29-/m1/s1
InChI Key AEXHLHGCDOTWGS-WBKPCLEFSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C29H23NO8
Molecular Weight 513.50 g/mol
Exact Mass 513.14236669 g/mol
Topological Polar Surface Area (TPSA) 115.00 Ų
XlogP 5.00
Atomic LogP (AlogP) 4.46
H-Bond Acceptor 9
H-Bond Donor 2
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (3R)-8-hydroxy-3-[(E)-2-(7-hydroxy-2-oxochromen-8-yl)ethenyl]-10-methoxy-3,12-dimethyl-2H-[1,4]dioxino[2,3-c]acridin-7-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.5945 59.45%
Caco-2 - 0.7289 72.89%
Blood Brain Barrier - 0.6500 65.00%
Human oral bioavailability - 0.6571 65.71%
Subcellular localzation Nucleus 0.4227 42.27%
OATP2B1 inhibitior - 0.8517 85.17%
OATP1B1 inhibitior + 0.8953 89.53%
OATP1B3 inhibitior + 0.9199 91.99%
MATE1 inhibitior - 0.8400 84.00%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior + 0.9778 97.78%
P-glycoprotein inhibitior + 0.8915 89.15%
P-glycoprotein substrate + 0.5900 59.00%
CYP3A4 substrate + 0.6662 66.62%
CYP2C9 substrate - 0.5729 57.29%
CYP2D6 substrate - 0.8737 87.37%
CYP3A4 inhibition - 0.8587 85.87%
CYP2C9 inhibition - 0.8231 82.31%
CYP2C19 inhibition - 0.6983 69.83%
CYP2D6 inhibition - 0.8492 84.92%
CYP1A2 inhibition + 0.5305 53.05%
CYP2C8 inhibition + 0.7275 72.75%
CYP inhibitory promiscuity - 0.7810 78.10%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Danger 0.4405 44.05%
Eye corrosion - 0.9904 99.04%
Eye irritation - 0.8876 88.76%
Skin irritation - 0.8350 83.50%
Skin corrosion - 0.9500 95.00%
Ames mutagenesis + 0.6000 60.00%
Human Ether-a-go-go-Related Gene inhibition + 0.8515 85.15%
Micronuclear + 0.6974 69.74%
Hepatotoxicity + 0.5216 52.16%
skin sensitisation - 0.8758 87.58%
Respiratory toxicity + 0.6444 64.44%
Reproductive toxicity + 0.8000 80.00%
Mitochondrial toxicity + 0.8000 80.00%
Nephrotoxicity - 0.5530 55.30%
Acute Oral Toxicity (c) III 0.6953 69.53%
Estrogen receptor binding + 0.8086 80.86%
Androgen receptor binding + 0.8827 88.27%
Thyroid receptor binding + 0.6533 65.33%
Glucocorticoid receptor binding + 0.8539 85.39%
Aromatase binding + 0.6843 68.43%
PPAR gamma + 0.7537 75.37%
Honey bee toxicity - 0.7887 78.87%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity + 0.6500 65.00%
Fish aquatic toxicity + 0.8291 82.91%

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
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 98.60% 95.56%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 98.52% 94.45%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.31% 91.11%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 95.56% 99.15%
CHEMBL3192 Q9BY41 Histone deacetylase 8 95.38% 93.99%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 95.15% 94.00%
CHEMBL2581 P07339 Cathepsin D 94.69% 98.95%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 94.20% 96.77%
CHEMBL1806 P11388 DNA topoisomerase II alpha 94.17% 89.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 93.64% 99.23%
CHEMBL3864 Q06124 Protein-tyrosine phosphatase 2C 93.06% 94.42%
CHEMBL2085 P14174 Macrophage migration inhibitory factor 92.95% 80.78%
CHEMBL1937 Q92769 Histone deacetylase 2 91.47% 94.75%
CHEMBL1293249 Q13887 Kruppel-like factor 5 90.08% 86.33%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 88.23% 96.09%
CHEMBL4940 P07195 L-lactate dehydrogenase B chain 87.53% 95.53%
CHEMBL4208 P20618 Proteasome component C5 87.30% 90.00%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 85.96% 96.00%
CHEMBL3401 O75469 Pregnane X receptor 84.84% 94.73%
CHEMBL2535 P11166 Glucose transporter 83.64% 98.75%
CHEMBL4224 P49759 Dual specificty protein kinase CLK1 83.49% 85.30%
CHEMBL3713062 P10646 Tissue factor pathway inhibitor 81.82% 97.33%
CHEMBL5697 Q9GZT9 Egl nine homolog 1 81.35% 93.40%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 81.11% 100.00%
CHEMBL4829 O00763 Acetyl-CoA carboxylase 2 80.70% 98.00%

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.
Citrus × aurantium

Cross-Links

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PubChem 163188888
LOTUS LTS0181655
wikiData Q104910741