Glycocitrine-Iv

Details

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Internal ID 48d8fc23-db98-4691-92fe-26e387d18323
Taxonomy Organoheterocyclic compounds > Quinolines and derivatives > Benzoquinolines > Acridines > Acridones
IUPAC Name 1,3,5-trihydroxy-4-methoxy-10-methyl-2-(3-methylbut-2-enyl)acridin-9-one
SMILES (Canonical) CC(=CCC1=C(C2=C(C(=C1O)OC)N(C3=C(C2=O)C=CC=C3O)C)O)C
SMILES (Isomeric) CC(=CCC1=C(C2=C(C(=C1O)OC)N(C3=C(C2=O)C=CC=C3O)C)O)C
InChI InChI=1S/C20H21NO5/c1-10(2)8-9-12-18(24)14-16(20(26-4)19(12)25)21(3)15-11(17(14)23)6-5-7-13(15)22/h5-8,22,24-25H,9H2,1-4H3
InChI Key GKBPFZFFEMNSRA-UHFFFAOYSA-N
Popularity 5 references in papers

Physical and Chemical Properties

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Molecular Formula C20H21NO5
Molecular Weight 355.40 g/mol
Exact Mass 355.14197277 g/mol
Topological Polar Surface Area (TPSA) 90.20 Ų
XlogP 4.50
Atomic LogP (AlogP) 3.33
H-Bond Acceptor 6
H-Bond Donor 3
Rotatable Bonds 3

Synonyms

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CHEMBL463652
Glycocitrine IV
DTXSID801344354
BDBM50336478
1,3,5-trihydroxy-4-methoxy-2-(3-methylbut-2-enyl)-10-methyl-9-acridone
1,3,5-Trihydroxy-4-methoxy-10-methyl-2-(3-methyl-2-buten-1-yl)-9(10H)-acridinone
262359-05-7

2D Structure

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2D Structure of Glycocitrine-Iv

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9270 92.70%
Caco-2 + 0.7508 75.08%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability + 0.7143 71.43%
Subcellular localzation Nucleus 0.7368 73.68%
OATP2B1 inhibitior - 0.7123 71.23%
OATP1B1 inhibitior + 0.8868 88.68%
OATP1B3 inhibitior + 0.9287 92.87%
MATE1 inhibitior - 0.6800 68.00%
OCT2 inhibitior - 0.8500 85.00%
BSEP inhibitior - 0.4791 47.91%
P-glycoprotein inhibitior - 0.6441 64.41%
P-glycoprotein substrate - 0.6227 62.27%
CYP3A4 substrate + 0.6249 62.49%
CYP2C9 substrate - 0.6000 60.00%
CYP2D6 substrate - 0.8372 83.72%
CYP3A4 inhibition - 0.8026 80.26%
CYP2C9 inhibition - 0.6918 69.18%
CYP2C19 inhibition - 0.5340 53.40%
CYP2D6 inhibition - 0.5620 56.20%
CYP1A2 inhibition + 0.6612 66.12%
CYP2C8 inhibition - 0.7048 70.48%
CYP inhibitory promiscuity + 0.7590 75.90%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5343 53.43%
Eye corrosion - 0.9897 98.97%
Eye irritation + 0.7031 70.31%
Skin irritation - 0.8154 81.54%
Skin corrosion - 0.9413 94.13%
Ames mutagenesis + 0.5600 56.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4677 46.77%
Micronuclear + 0.7000 70.00%
Hepatotoxicity + 0.5711 57.11%
skin sensitisation - 0.8654 86.54%
Respiratory toxicity + 0.8111 81.11%
Reproductive toxicity + 0.8667 86.67%
Mitochondrial toxicity + 0.7500 75.00%
Nephrotoxicity - 0.9175 91.75%
Acute Oral Toxicity (c) III 0.6831 68.31%
Estrogen receptor binding + 0.8121 81.21%
Androgen receptor binding - 0.5000 50.00%
Thyroid receptor binding + 0.6259 62.59%
Glucocorticoid receptor binding + 0.7607 76.07%
Aromatase binding - 0.5307 53.07%
PPAR gamma + 0.8318 83.18%
Honey bee toxicity - 0.9050 90.50%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity - 0.5500 55.00%
Fish aquatic toxicity + 0.8848 88.48%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
CHEMBL3272 O60911 Cathepsin L2 2200 nM
IC50
PMID: 21277783

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL2581 P07339 Cathepsin D 98.72% 98.95%
CHEMBL3192 Q9BY41 Histone deacetylase 8 98.11% 93.99%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.04% 91.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 97.40% 95.56%
CHEMBL1951 P21397 Monoamine oxidase A 95.54% 91.49%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 94.07% 94.45%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 93.61% 96.09%
CHEMBL1937 Q92769 Histone deacetylase 2 93.04% 94.75%
CHEMBL1293249 Q13887 Kruppel-like factor 5 92.01% 86.33%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 90.08% 85.14%
CHEMBL3401 O75469 Pregnane X receptor 88.76% 94.73%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 88.34% 94.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 85.66% 89.00%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 83.31% 96.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 83.08% 99.23%
CHEMBL3060 Q9Y345 Glycine transporter 2 82.49% 99.17%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 81.31% 97.21%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 80.38% 99.15%

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.
Clematis flammula
Gentianella magellanica
Glycosmis parviflora
Hortia brasiliana
Swinglea glutinosa

Cross-Links

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PubChem 9998312
NPASS NPC7560
ChEMBL CHEMBL463652
LOTUS LTS0071849
wikiData Q104167241