[(6aR,9R,10S,10aR)-9,10-dihydroxy-6,6,9-trimethyl-11-oxo-7,8,10,10a-tetrahydro-6aH-isochromeno[4,3-c]quinolin-12-yl]methyl acetate

Details

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Internal ID 27a5b347-1549-4b25-9cec-659818b79103
Taxonomy Organoheterocyclic compounds > Quinolines and derivatives > Quinolones and derivatives > Pyranoquinolines
IUPAC Name [(6aR,9R,10S,10aR)-9,10-dihydroxy-6,6,9-trimethyl-11-oxo-7,8,10,10a-tetrahydro-6aH-isochromeno[4,3-c]quinolin-12-yl]methyl acetate
SMILES (Canonical) CC(=O)OCN1C2=CC=CC=C2C3=C(C1=O)C4C(CCC(C4O)(C)O)C(O3)(C)C
SMILES (Isomeric) CC(=O)OCN1C2=CC=CC=C2C3=C(C1=O)[C@H]4[C@@H](CC[C@@]([C@H]4O)(C)O)C(O3)(C)C
InChI InChI=1S/C22H27NO6/c1-12(24)28-11-23-15-8-6-5-7-13(15)18-17(20(23)26)16-14(21(2,3)29-18)9-10-22(4,27)19(16)25/h5-8,14,16,19,25,27H,9-11H2,1-4H3/t14-,16-,19+,22-/m1/s1
InChI Key WSNJPVCNURDQDC-NBHJVPQVSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C22H27NO6
Molecular Weight 401.50 g/mol
Exact Mass 401.18383758 g/mol
Topological Polar Surface Area (TPSA) 96.30 Ų
XlogP 1.30
Atomic LogP (AlogP) 2.30
H-Bond Acceptor 7
H-Bond Donor 2
Rotatable Bonds 2

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(6aR,9R,10S,10aR)-9,10-dihydroxy-6,6,9-trimethyl-11-oxo-7,8,10,10a-tetrahydro-6aH-isochromeno[4,3-c]quinolin-12-yl]methyl acetate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.5842 58.42%
Caco-2 - 0.6193 61.93%
Blood Brain Barrier - 0.6750 67.50%
Human oral bioavailability - 0.5571 55.71%
Subcellular localzation Mitochondria 0.4243 42.43%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8708 87.08%
OATP1B3 inhibitior + 0.9241 92.41%
MATE1 inhibitior - 0.8600 86.00%
OCT2 inhibitior - 0.7816 78.16%
BSEP inhibitior + 0.8805 88.05%
P-glycoprotein inhibitior - 0.5554 55.54%
P-glycoprotein substrate - 0.5878 58.78%
CYP3A4 substrate + 0.7404 74.04%
CYP2C9 substrate - 0.7968 79.68%
CYP2D6 substrate - 0.8477 84.77%
CYP3A4 inhibition + 0.6225 62.25%
CYP2C9 inhibition - 0.7625 76.25%
CYP2C19 inhibition - 0.7101 71.01%
CYP2D6 inhibition - 0.8985 89.85%
CYP1A2 inhibition - 0.5605 56.05%
CYP2C8 inhibition + 0.5249 52.49%
CYP inhibitory promiscuity - 0.7754 77.54%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.8900 89.00%
Carcinogenicity (trinary) Non-required 0.5449 54.49%
Eye corrosion - 0.9880 98.80%
Eye irritation - 0.9434 94.34%
Skin irritation - 0.8007 80.07%
Skin corrosion - 0.9364 93.64%
Ames mutagenesis + 0.5800 58.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5000 50.00%
Micronuclear + 0.6700 67.00%
Hepatotoxicity - 0.6073 60.73%
skin sensitisation - 0.8827 88.27%
Respiratory toxicity + 0.8778 87.78%
Reproductive toxicity + 0.8667 86.67%
Mitochondrial toxicity + 0.8500 85.00%
Nephrotoxicity - 0.7244 72.44%
Acute Oral Toxicity (c) III 0.6758 67.58%
Estrogen receptor binding + 0.7115 71.15%
Androgen receptor binding + 0.7653 76.53%
Thyroid receptor binding - 0.5899 58.99%
Glucocorticoid receptor binding + 0.8266 82.66%
Aromatase binding + 0.6687 66.87%
PPAR gamma + 0.6282 62.82%
Honey bee toxicity - 0.8313 83.13%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity + 0.6300 63.00%
Fish aquatic toxicity + 0.8813 88.13%

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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.39% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 96.15% 95.56%
CHEMBL253 P34972 Cannabinoid CB2 receptor 95.58% 97.25%
CHEMBL221 P23219 Cyclooxygenase-1 95.29% 90.17%
CHEMBL1806 P11388 DNA topoisomerase II alpha 95.13% 89.00%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 94.81% 91.11%
CHEMBL2581 P07339 Cathepsin D 89.72% 98.95%
CHEMBL1293249 Q13887 Kruppel-like factor 5 88.52% 86.33%
CHEMBL226 P30542 Adenosine A1 receptor 88.34% 95.93%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 86.85% 92.62%
CHEMBL3137262 O60341 LSD1/CoREST complex 86.04% 97.09%
CHEMBL255 P29275 Adenosine A2b receptor 84.84% 98.59%
CHEMBL5028 O14672 ADAM10 84.53% 97.50%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 83.42% 97.14%
CHEMBL3922 P50579 Methionine aminopeptidase 2 83.27% 97.28%
CHEMBL1994 P08235 Mineralocorticoid receptor 82.41% 100.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 81.68% 99.23%
CHEMBL4051 P13569 Cystic fibrosis transmembrane conductance regulator 81.26% 95.71%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 80.62% 94.45%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 80.09% 85.14%

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.
Halfordia kendack

Cross-Links

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PubChem 162864844
LOTUS LTS0102721
wikiData Q105311981