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6-Hydroxy-10,11-dimethoxy-3,3,12-trimethyl-pyrano[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 c1781b8f-aaa9-4326-ba19-91f6bbb30d8d
Taxonomy Organoheterocyclic compounds > Quinolines and derivatives > Benzoquinolines > Acridines > Acridones
IUPAC Name 6-hydroxy-10,11-dimethoxy-3,3,12-trimethylpyrano[2,3-c]acridin-7-one
SMILES (Canonical) CC1(C=CC2=C(O1)C=C(C3=C2N(C4=C(C3=O)C=CC(=C4OC)OC)C)O)C
SMILES (Isomeric) CC1(C=CC2=C(O1)C=C(C3=C2N(C4=C(C3=O)C=CC(=C4OC)OC)C)O)C
InChI InChI=1S/C21H21NO5/c1-21(2)9-8-11-15(27-21)10-13(23)16-17(11)22(3)18-12(19(16)24)6-7-14(25-4)20(18)26-5/h6-10,23H,1-5H3
InChI Key OBCBNXMEAJGWOD-UHFFFAOYSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C21H21NO5
Molecular Weight 367.40 g/mol
Exact Mass 367.14197277 g/mol
Topological Polar Surface Area (TPSA) 68.20 Ų
XlogP 3.80
Atomic LogP (AlogP) 3.60
H-Bond Acceptor 6
H-Bond Donor 1
Rotatable Bonds 2

Synonyms

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CHEMBL452225
6-hydroxy-10,11-dimethoxy-3,3,12-trimethyl-pyrano[2,3-c]acridin-7-one
7H-Pyrano[2,3-c]acridin-7-one, 3,12-dihydro-6-hydroxy-10,11-dimethoxy-3,3,12-trimethyl-

2D Structure

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2D Structure of 6-Hydroxy-10,11-dimethoxy-3,3,12-trimethyl-pyrano[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 + 0.8885 88.85%
Caco-2 + 0.8704 87.04%
Blood Brain Barrier + 0.6000 60.00%
Human oral bioavailability + 0.5429 54.29%
Subcellular localzation Mitochondria 0.4024 40.24%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9258 92.58%
OATP1B3 inhibitior + 0.9550 95.50%
MATE1 inhibitior - 0.8400 84.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior + 0.7267 72.67%
P-glycoprotein inhibitior + 0.5740 57.40%
P-glycoprotein substrate - 0.5553 55.53%
CYP3A4 substrate + 0.6379 63.79%
CYP2C9 substrate - 0.7979 79.79%
CYP2D6 substrate - 0.8541 85.41%
CYP3A4 inhibition + 0.5247 52.47%
CYP2C9 inhibition - 0.8490 84.90%
CYP2C19 inhibition + 0.5804 58.04%
CYP2D6 inhibition - 0.7911 79.11%
CYP1A2 inhibition + 0.7609 76.09%
CYP2C8 inhibition + 0.4465 44.65%
CYP inhibitory promiscuity - 0.5120 51.20%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 0.9500 95.00%
Carcinogenicity (trinary) Danger 0.6001 60.01%
Eye corrosion - 0.9910 99.10%
Eye irritation + 0.7358 73.58%
Skin irritation - 0.8307 83.07%
Skin corrosion - 0.9542 95.42%
Ames mutagenesis + 0.6500 65.00%
Human Ether-a-go-go-Related Gene inhibition - 0.3932 39.32%
Micronuclear + 0.7100 71.00%
Hepatotoxicity + 0.5911 59.11%
skin sensitisation - 0.8745 87.45%
Respiratory toxicity + 0.5889 58.89%
Reproductive toxicity + 0.6778 67.78%
Mitochondrial toxicity + 0.7500 75.00%
Nephrotoxicity - 0.7674 76.74%
Acute Oral Toxicity (c) III 0.7299 72.99%
Estrogen receptor binding + 0.8309 83.09%
Androgen receptor binding + 0.5877 58.77%
Thyroid receptor binding + 0.8718 87.18%
Glucocorticoid receptor binding + 0.8227 82.27%
Aromatase binding + 0.6500 65.00%
PPAR gamma + 0.7143 71.43%
Honey bee toxicity - 0.8707 87.07%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.5000 50.00%
Fish aquatic toxicity + 0.7493 74.93%

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
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 98.02% 94.45%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.92% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.81% 96.09%
CHEMBL3192 Q9BY41 Histone deacetylase 8 95.17% 93.99%
CHEMBL2581 P07339 Cathepsin D 95.05% 98.95%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.86% 95.56%
CHEMBL1806 P11388 DNA topoisomerase II alpha 94.70% 89.00%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 94.50% 85.14%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 94.48% 94.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 90.97% 86.33%
CHEMBL1951 P21397 Monoamine oxidase A 90.90% 91.49%
CHEMBL2535 P11166 Glucose transporter 88.98% 98.75%
CHEMBL4208 P20618 Proteasome component C5 88.00% 90.00%
CHEMBL1255126 O15151 Protein Mdm4 87.19% 90.20%
CHEMBL1937 Q92769 Histone deacetylase 2 86.78% 94.75%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 85.07% 89.62%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 84.30% 99.15%
CHEMBL5409 Q8TDU6 G-protein coupled bile acid receptor 1 84.10% 93.65%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 83.81% 96.77%
CHEMBL2085 P14174 Macrophage migration inhibitory factor 83.65% 80.78%
CHEMBL3864 Q06124 Protein-tyrosine phosphatase 2C 81.66% 94.42%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 81.51% 97.14%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 81.10% 100.00%
CHEMBL3060 Q9Y345 Glycine transporter 2 80.39% 99.17%

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
Citrus maxima

Cross-Links

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PubChem 5494832
LOTUS LTS0273038
wikiData Q104396588