4,5,4'-Trihydroxy-7-methoxy-8-prenylflavan

Details

Top
Internal ID 4fe819e9-49da-4afc-828d-7c8c432836e4
Taxonomy Phenylpropanoids and polyketides > Flavonoids > Flavans > 8-prenylated flavans
IUPAC Name (2S,4R)-2-(4-hydroxyphenyl)-7-methoxy-8-(3-methylbut-2-enyl)-3,4-dihydro-2H-chromene-4,5-diol
SMILES (Canonical) CC(=CCC1=C(C=C(C2=C1OC(CC2O)C3=CC=C(C=C3)O)O)OC)C
SMILES (Isomeric) CC(=CCC1=C(C=C(C2=C1O[C@@H](C[C@H]2O)C3=CC=C(C=C3)O)O)OC)C
InChI InChI=1S/C21H24O5/c1-12(2)4-9-15-19(25-3)11-17(24)20-16(23)10-18(26-21(15)20)13-5-7-14(22)8-6-13/h4-8,11,16,18,22-24H,9-10H2,1-3H3/t16-,18+/m1/s1
InChI Key VLWJOYMOYMWONM-AEFFLSMTSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

Top
Molecular Formula C21H24O5
Molecular Weight 356.40 g/mol
Exact Mass 356.16237386 g/mol
Topological Polar Surface Area (TPSA) 79.20 Ų
XlogP 3.90
Atomic LogP (AlogP) 4.17
H-Bond Acceptor 5
H-Bond Donor 3
Rotatable Bonds 4

Synonyms

Top
CHEBI:186270
LMPK12020171
(2S,4R)-2-(4-hydroxyphenyl)-7-methoxy-8-(3-methylbut-2-enyl)-3,4-dihydro-2H-chromene-4,5-diol

2D Structure

Top
2D Structure of 4,5,4'-Trihydroxy-7-methoxy-8-prenylflavan

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9718 97.18%
Caco-2 + 0.8171 81.71%
Blood Brain Barrier + 0.6000 60.00%
Human oral bioavailability - 0.6571 65.71%
Subcellular localzation Mitochondria 0.5703 57.03%
OATP2B1 inhibitior - 0.8609 86.09%
OATP1B1 inhibitior + 0.8418 84.18%
OATP1B3 inhibitior + 0.9411 94.11%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior + 0.6819 68.19%
P-glycoprotein inhibitior + 0.5824 58.24%
P-glycoprotein substrate - 0.7207 72.07%
CYP3A4 substrate + 0.5875 58.75%
CYP2C9 substrate - 0.7907 79.07%
CYP2D6 substrate + 0.5123 51.23%
CYP3A4 inhibition + 0.5117 51.17%
CYP2C9 inhibition + 0.7038 70.38%
CYP2C19 inhibition + 0.8011 80.11%
CYP2D6 inhibition + 0.5342 53.42%
CYP1A2 inhibition + 0.7031 70.31%
CYP2C8 inhibition + 0.6381 63.81%
CYP inhibitory promiscuity + 0.9046 90.46%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.6342 63.42%
Eye corrosion - 0.9905 99.05%
Eye irritation - 0.8372 83.72%
Skin irritation - 0.7796 77.96%
Skin corrosion - 0.9390 93.90%
Ames mutagenesis + 0.5900 59.00%
Human Ether-a-go-go-Related Gene inhibition - 0.3809 38.09%
Micronuclear - 0.5400 54.00%
Hepatotoxicity - 0.5375 53.75%
skin sensitisation - 0.8137 81.37%
Respiratory toxicity + 0.5222 52.22%
Reproductive toxicity + 0.9000 90.00%
Mitochondrial toxicity + 0.7875 78.75%
Nephrotoxicity - 0.7847 78.47%
Acute Oral Toxicity (c) III 0.5327 53.27%
Estrogen receptor binding + 0.7095 70.95%
Androgen receptor binding + 0.6480 64.80%
Thyroid receptor binding + 0.7112 71.12%
Glucocorticoid receptor binding + 0.7550 75.50%
Aromatase binding - 0.5367 53.67%
PPAR gamma + 0.8104 81.04%
Honey bee toxicity - 0.7443 74.43%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity - 0.5100 51.00%
Fish aquatic toxicity + 0.9618 96.18%

Targets

Top

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 97.90% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.03% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 93.77% 94.45%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.02% 97.09%
CHEMBL3060 Q9Y345 Glycine transporter 2 92.11% 99.17%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 90.32% 89.62%
CHEMBL1293249 Q13887 Kruppel-like factor 5 88.48% 86.33%
CHEMBL241 Q14432 Phosphodiesterase 3A 88.35% 92.94%
CHEMBL4208 P20618 Proteasome component C5 88.23% 90.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 85.81% 95.89%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 83.83% 96.95%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 83.69% 95.56%
CHEMBL1951 P21397 Monoamine oxidase A 83.56% 91.49%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 83.50% 95.89%
CHEMBL301 P24941 Cyclin-dependent kinase 2 83.47% 91.23%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 82.78% 97.21%
CHEMBL3194 P02766 Transthyretin 82.65% 90.71%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 80.16% 94.00%

Plants that contains it

Top
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.
Marshallia obovata
Schisandra sphenanthera

Cross-Links

Top
PubChem 44257139
NPASS NPC270531
LOTUS LTS0088741
wikiData Q105288739