4'-Methylsigmoidin B

Details

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Internal ID a17e1fc0-7840-42e9-9615-587a19d0497d
Taxonomy Phenylpropanoids and polyketides > Flavonoids > Flavans > 3-prenylated flavans > 3-prenylated flavanones
IUPAC Name 5,7-dihydroxy-2-[3-hydroxy-4-methoxy-5-(3-methylbut-2-enyl)phenyl]-2,3-dihydrochromen-4-one
SMILES (Canonical) CC(=CCC1=C(C(=CC(=C1)C2CC(=O)C3=C(C=C(C=C3O2)O)O)O)OC)C
SMILES (Isomeric) CC(=CCC1=C(C(=CC(=C1)C2CC(=O)C3=C(C=C(C=C3O2)O)O)O)OC)C
InChI InChI=1S/C21H22O6/c1-11(2)4-5-12-6-13(7-17(25)21(12)26-3)18-10-16(24)20-15(23)8-14(22)9-19(20)27-18/h4,6-9,18,22-23,25H,5,10H2,1-3H3
InChI Key UYGBXGAZUCKDDV-UHFFFAOYSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C21H22O6
Molecular Weight 370.40 g/mol
Exact Mass 370.14163842 g/mol
Topological Polar Surface Area (TPSA) 96.20 Ų
XlogP 4.30
Atomic LogP (AlogP) 4.03
H-Bond Acceptor 6
H-Bond Donor 3
Rotatable Bonds 4

Synonyms

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Sigmoidin B 3'-methyl ether
114340-00-0
LMPK12140383

2D Structure

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2D Structure of 4'-Methylsigmoidin B

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9645 96.45%
Caco-2 + 0.7724 77.24%
Blood Brain Barrier + 0.5750 57.50%
Human oral bioavailability - 0.7143 71.43%
Subcellular localzation Mitochondria 0.5849 58.49%
OATP2B1 inhibitior - 0.7214 72.14%
OATP1B1 inhibitior + 0.9222 92.22%
OATP1B3 inhibitior + 0.9271 92.71%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior + 0.6938 69.38%
P-glycoprotein inhibitior - 0.5957 59.57%
P-glycoprotein substrate - 0.8283 82.83%
CYP3A4 substrate + 0.5831 58.31%
CYP2C9 substrate - 0.7977 79.77%
CYP2D6 substrate - 0.7912 79.12%
CYP3A4 inhibition - 0.5408 54.08%
CYP2C9 inhibition + 0.8503 85.03%
CYP2C19 inhibition + 0.8903 89.03%
CYP2D6 inhibition + 0.6856 68.56%
CYP1A2 inhibition + 0.7766 77.66%
CYP2C8 inhibition - 0.6221 62.21%
CYP inhibitory promiscuity + 0.9196 91.96%
UGT catelyzed + 0.9000 90.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6700 67.00%
Eye corrosion - 0.9898 98.98%
Eye irritation - 0.5892 58.92%
Skin irritation - 0.7665 76.65%
Skin corrosion - 0.9476 94.76%
Ames mutagenesis - 0.5800 58.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6637 66.37%
Micronuclear - 0.5200 52.00%
Hepatotoxicity + 0.5928 59.28%
skin sensitisation - 0.8251 82.51%
Respiratory toxicity + 0.5444 54.44%
Reproductive toxicity + 0.8889 88.89%
Mitochondrial toxicity + 0.7375 73.75%
Nephrotoxicity + 0.4661 46.61%
Acute Oral Toxicity (c) III 0.5538 55.38%
Estrogen receptor binding + 0.9391 93.91%
Androgen receptor binding - 0.5000 50.00%
Thyroid receptor binding + 0.6835 68.35%
Glucocorticoid receptor binding + 0.8196 81.96%
Aromatase binding + 0.5569 55.69%
PPAR gamma + 0.8820 88.20%
Honey bee toxicity - 0.7269 72.69%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.5900 59.00%
Fish aquatic toxicity + 0.9733 97.33%

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 99.61% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 96.36% 94.45%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.09% 96.09%
CHEMBL1929 P47989 Xanthine dehydrogenase 94.07% 96.12%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 93.25% 85.14%
CHEMBL2581 P07339 Cathepsin D 90.26% 98.95%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.10% 97.09%
CHEMBL215 P09917 Arachidonate 5-lipoxygenase 89.35% 92.68%
CHEMBL1293249 Q13887 Kruppel-like factor 5 88.66% 86.33%
CHEMBL3060 Q9Y345 Glycine transporter 2 88.40% 99.17%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 87.81% 99.23%
CHEMBL4040 P28482 MAP kinase ERK2 86.93% 83.82%
CHEMBL3401 O75469 Pregnane X receptor 86.01% 94.73%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 85.95% 95.56%
CHEMBL4208 P20618 Proteasome component C5 85.91% 90.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 85.36% 89.00%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 84.52% 92.62%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 83.14% 96.95%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 80.73% 94.00%
CHEMBL1994 P08235 Mineralocorticoid receptor 80.72% 100.00%
CHEMBL5697 Q9GZT9 Egl nine homolog 1 80.16% 93.40%

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.
Erythrina burttii
Erythrina velutina

Cross-Links

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PubChem 21721826
LOTUS LTS0126671
wikiData Q105281403