(R)-3,4-Dihydro-8-hydroxy-3-(4-hydroxyphenyl)-1H-2-benzopyran-1-one

Details

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Internal ID 7cb6cbf7-5c1a-4953-ae72-bfa601f2c19b
Taxonomy Organoheterocyclic compounds > Benzopyrans > 2-benzopyrans
IUPAC Name (3R)-8-hydroxy-3-(4-hydroxyphenyl)-3,4-dihydroisochromen-1-one
SMILES (Canonical) C1C(OC(=O)C2=C1C=CC=C2O)C3=CC=C(C=C3)O
SMILES (Isomeric) C1[C@@H](OC(=O)C2=C1C=CC=C2O)C3=CC=C(C=C3)O
InChI InChI=1S/C15H12O4/c16-11-6-4-9(5-7-11)13-8-10-2-1-3-12(17)14(10)15(18)19-13/h1-7,13,16-17H,8H2/t13-/m1/s1
InChI Key DGKDFNDHPXVXHW-CYBMUJFWSA-N
Popularity 8 references in papers

Physical and Chemical Properties

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Molecular Formula C15H12O4
Molecular Weight 256.25 g/mol
Exact Mass 256.07355886 g/mol
Topological Polar Surface Area (TPSA) 66.80 Ų
XlogP 3.20
Atomic LogP (AlogP) 2.55
H-Bond Acceptor 4
H-Bond Donor 2
Rotatable Bonds 1

Synonyms

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CHEMBL1475427
HMS2198G14
NCGC00247503-01
SMR001397333
Q63392623
(R)-3,4-Dihydro-8-hydroxy-3-(4-hydroxyphenyl)-1H-2-benzopyran-1-one

2D Structure

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2D Structure of (R)-3,4-Dihydro-8-hydroxy-3-(4-hydroxyphenyl)-1H-2-benzopyran-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 + 0.9604 96.04%
Caco-2 - 0.6905 69.05%
Blood Brain Barrier - 0.9250 92.50%
Human oral bioavailability - 0.6286 62.86%
Subcellular localzation Mitochondria 0.7997 79.97%
OATP2B1 inhibitior - 0.7441 74.41%
OATP1B1 inhibitior + 0.8875 88.75%
OATP1B3 inhibitior + 0.9662 96.62%
MATE1 inhibitior - 0.8400 84.00%
OCT2 inhibitior - 0.9750 97.50%
BSEP inhibitior - 0.8263 82.63%
P-glycoprotein inhibitior - 0.9303 93.03%
P-glycoprotein substrate - 0.9242 92.42%
CYP3A4 substrate - 0.5059 50.59%
CYP2C9 substrate - 0.5266 52.66%
CYP2D6 substrate - 0.8254 82.54%
CYP3A4 inhibition - 0.7061 70.61%
CYP2C9 inhibition + 0.9060 90.60%
CYP2C19 inhibition - 0.5000 50.00%
CYP2D6 inhibition - 0.8644 86.44%
CYP1A2 inhibition - 0.5858 58.58%
CYP2C8 inhibition - 0.8378 83.78%
CYP inhibitory promiscuity - 0.6755 67.55%
UGT catelyzed + 0.9000 90.00%
Carcinogenicity (binary) - 0.9613 96.13%
Carcinogenicity (trinary) Non-required 0.5355 53.55%
Eye corrosion - 0.9916 99.16%
Eye irritation + 0.9209 92.09%
Skin irritation - 0.5178 51.78%
Skin corrosion - 0.9783 97.83%
Ames mutagenesis + 0.6600 66.00%
Human Ether-a-go-go-Related Gene inhibition - 0.7294 72.94%
Micronuclear + 0.8459 84.59%
Hepatotoxicity + 0.5125 51.25%
skin sensitisation - 0.9051 90.51%
Respiratory toxicity + 0.6667 66.67%
Reproductive toxicity + 0.8889 88.89%
Mitochondrial toxicity + 0.7500 75.00%
Nephrotoxicity + 0.7106 71.06%
Acute Oral Toxicity (c) I 0.4625 46.25%
Estrogen receptor binding + 0.7080 70.80%
Androgen receptor binding + 0.6917 69.17%
Thyroid receptor binding + 0.6158 61.58%
Glucocorticoid receptor binding - 0.5414 54.14%
Aromatase binding + 0.5869 58.69%
PPAR gamma + 0.8386 83.86%
Honey bee toxicity - 0.9154 91.54%
Biodegradation - 0.7000 70.00%
Crustacea aquatic toxicity - 0.5500 55.00%
Fish aquatic toxicity + 0.8865 88.65%

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 94.32% 91.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 93.81% 95.56%
CHEMBL3137262 O60341 LSD1/CoREST complex 92.99% 97.09%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 92.48% 99.23%
CHEMBL2581 P07339 Cathepsin D 91.96% 98.95%
CHEMBL217 P14416 Dopamine D2 receptor 87.96% 95.62%
CHEMBL3192 Q9BY41 Histone deacetylase 8 87.77% 93.99%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 87.02% 94.45%
CHEMBL1806 P11388 DNA topoisomerase II alpha 86.84% 89.00%
CHEMBL1951 P21397 Monoamine oxidase A 85.68% 91.49%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 80.71% 96.09%

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.
Hydrangea chinensis
Hydrangea macrophylla
Scorzonera psychrophila
Scorzonera tomentosa

Cross-Links

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PubChem 44144280
NPASS NPC301915
ChEMBL CHEMBL1475427
LOTUS LTS0242822
wikiData Q63392623