(r)-3,4-Dihydro-4,8-dihydroxy-6-methoxy-4,5-dimethyl-3-methyleneisochromen-1-one

Details

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Internal ID 6a20b102-a42b-48dd-b939-02edfa65a28f
Taxonomy Organoheterocyclic compounds > Benzopyrans > 2-benzopyrans
IUPAC Name (4R)-4,8-dihydroxy-6-methoxy-4,5-dimethyl-3-methylideneisochromen-1-one
SMILES (Canonical) CC1=C(C=C(C2=C1C(C(=C)OC2=O)(C)O)O)OC
SMILES (Isomeric) CC1=C(C=C(C2=C1[C@@](C(=C)OC2=O)(C)O)O)OC
InChI InChI=1S/C13H14O5/c1-6-9(17-4)5-8(14)10-11(6)13(3,16)7(2)18-12(10)15/h5,14,16H,2H2,1,3-4H3/t13-/m0/s1
InChI Key KVGGUNZKZGOZHC-ZDUSSCGKSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C13H14O5
Molecular Weight 250.25 g/mol
Exact Mass 250.08412354 g/mol
Topological Polar Surface Area (TPSA) 76.00 Ų
XlogP 1.90
Atomic LogP (AlogP) 1.60
H-Bond Acceptor 5
H-Bond Donor 2
Rotatable Bonds 1

Synonyms

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(r)-3,4-dihydro-4,8-dihydroxy-6-methoxy-4,5-dimethyl-3-methyleneisochromen-1-one
CHEMBL1765568
Q27136245
4,8-di-hydroxy-6-methoxy-4,5-dimethyl-3-methyleneisochroman-1-one

2D Structure

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2D Structure of (r)-3,4-Dihydro-4,8-dihydroxy-6-methoxy-4,5-dimethyl-3-methyleneisochromen-1-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9699 96.99%
Caco-2 - 0.7156 71.56%
Blood Brain Barrier - 0.7750 77.50%
Human oral bioavailability + 0.7571 75.71%
Subcellular localzation Mitochondria 0.6221 62.21%
OATP2B1 inhibitior - 0.8593 85.93%
OATP1B1 inhibitior + 0.8776 87.76%
OATP1B3 inhibitior + 0.9385 93.85%
MATE1 inhibitior - 0.6600 66.00%
OCT2 inhibitior - 0.9500 95.00%
BSEP inhibitior - 0.9290 92.90%
P-glycoprotein inhibitior - 0.8561 85.61%
P-glycoprotein substrate - 0.9317 93.17%
CYP3A4 substrate + 0.5579 55.79%
CYP2C9 substrate - 0.5796 57.96%
CYP2D6 substrate - 0.8509 85.09%
CYP3A4 inhibition - 0.5714 57.14%
CYP2C9 inhibition - 0.9332 93.32%
CYP2C19 inhibition - 0.5114 51.14%
CYP2D6 inhibition - 0.8907 89.07%
CYP1A2 inhibition - 0.5891 58.91%
CYP2C8 inhibition - 0.7385 73.85%
CYP inhibitory promiscuity + 0.5105 51.05%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9718 97.18%
Carcinogenicity (trinary) Non-required 0.4663 46.63%
Eye corrosion - 0.9780 97.80%
Eye irritation + 0.7548 75.48%
Skin irritation - 0.6464 64.64%
Skin corrosion - 0.9483 94.83%
Ames mutagenesis - 0.6500 65.00%
Human Ether-a-go-go-Related Gene inhibition - 0.8543 85.43%
Micronuclear + 0.7000 70.00%
Hepatotoxicity + 0.6750 67.50%
skin sensitisation - 0.7881 78.81%
Respiratory toxicity + 0.5556 55.56%
Reproductive toxicity + 0.8111 81.11%
Mitochondrial toxicity + 0.5875 58.75%
Nephrotoxicity + 0.5896 58.96%
Acute Oral Toxicity (c) III 0.4324 43.24%
Estrogen receptor binding - 0.5345 53.45%
Androgen receptor binding - 0.5885 58.85%
Thyroid receptor binding - 0.5358 53.58%
Glucocorticoid receptor binding - 0.6173 61.73%
Aromatase binding + 0.5252 52.52%
PPAR gamma + 0.5469 54.69%
Honey bee toxicity - 0.8856 88.56%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.6200 62.00%
Fish aquatic toxicity + 0.9762 97.62%

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
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.23% 91.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 95.89% 95.56%
CHEMBL1293249 Q13887 Kruppel-like factor 5 93.83% 86.33%
CHEMBL2581 P07339 Cathepsin D 92.05% 98.95%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 91.02% 94.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 90.20% 94.45%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 89.75% 99.23%
CHEMBL2535 P11166 Glucose transporter 86.15% 98.75%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 85.59% 96.21%
CHEMBL1255126 O15151 Protein Mdm4 84.91% 90.20%
CHEMBL1806 P11388 DNA topoisomerase II alpha 84.32% 89.00%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 83.85% 91.07%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 83.49% 95.50%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 82.54% 99.15%
CHEMBL3192 Q9BY41 Histone deacetylase 8 82.25% 93.99%
CHEMBL2069156 Q14145 Kelch-like ECH-associated protein 1 80.65% 82.38%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 80.39% 93.03%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 80.34% 85.14%

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 54584238
LOTUS LTS0198467
wikiData Q27136245