Crotalarin

Details

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Internal ID fa1fc6f1-1e36-428f-bacf-507e31a1caa7
Taxonomy Phenylpropanoids and polyketides > Isoflavonoids > Pyranoisoflavonoids
IUPAC Name 5-hydroxy-3-(4-hydroxyphenyl)-8,8-dimethyl-9,10-dihydropyrano[2,3-h]chromen-4-one
SMILES (Canonical) CC1(CCC2=C(O1)C=C(C3=C2OC=C(C3=O)C4=CC=C(C=C4)O)O)C
SMILES (Isomeric) CC1(CCC2=C(O1)C=C(C3=C2OC=C(C3=O)C4=CC=C(C=C4)O)O)C
InChI InChI=1S/C20H18O5/c1-20(2)8-7-13-16(25-20)9-15(22)17-18(23)14(10-24-19(13)17)11-3-5-12(21)6-4-11/h3-6,9-10,21-22H,7-8H2,1-2H3
InChI Key XIQJWMALSPXBMN-UHFFFAOYSA-N
Popularity 3 references in papers

Physical and Chemical Properties

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Molecular Formula C20H18O5
Molecular Weight 338.40 g/mol
Exact Mass 338.11542367 g/mol
Topological Polar Surface Area (TPSA) 76.00 Ų
XlogP 4.00
Atomic LogP (AlogP) 3.97
H-Bond Acceptor 5
H-Bond Donor 2
Rotatable Bonds 1

Synonyms

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109517-68-2
5-hydroxy-3-(4-hydroxyphenyl)-8,8-dimethyl-9,10-dihydropyrano[2,3-h]chromen-4-one
DTXSID90148960
CHEBI:187371
LMPK12050208
4H,8H-Benzo(1,2-b:3,4-b')dipyran-4-one, 9,10-dihydro-5-hydroxy-3-(4-hydroxyphenyl)-8,8-dimethyl-

2D Structure

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2D Structure of Crotalarin

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9870 98.70%
Caco-2 + 0.7162 71.62%
Blood Brain Barrier - 0.6750 67.50%
Human oral bioavailability - 0.7143 71.43%
Subcellular localzation Mitochondria 0.8715 87.15%
OATP2B1 inhibitior + 0.5638 56.38%
OATP1B1 inhibitior + 0.9238 92.38%
OATP1B3 inhibitior + 0.9740 97.40%
MATE1 inhibitior - 0.7600 76.00%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior + 0.5953 59.53%
P-glycoprotein inhibitior - 0.5272 52.72%
P-glycoprotein substrate - 0.8728 87.28%
CYP3A4 substrate + 0.6226 62.26%
CYP2C9 substrate - 0.5914 59.14%
CYP2D6 substrate - 0.8089 80.89%
CYP3A4 inhibition - 0.6176 61.76%
CYP2C9 inhibition - 0.5301 53.01%
CYP2C19 inhibition - 0.7376 73.76%
CYP2D6 inhibition - 0.8514 85.14%
CYP1A2 inhibition + 0.5205 52.05%
CYP2C8 inhibition + 0.6976 69.76%
CYP inhibitory promiscuity - 0.7883 78.83%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6391 63.91%
Eye corrosion - 0.9913 99.13%
Eye irritation + 0.7487 74.87%
Skin irritation - 0.7212 72.12%
Skin corrosion - 0.9187 91.87%
Ames mutagenesis - 0.6100 61.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5844 58.44%
Micronuclear - 0.6500 65.00%
Hepatotoxicity - 0.5121 51.21%
skin sensitisation - 0.8527 85.27%
Respiratory toxicity + 0.5778 57.78%
Reproductive toxicity + 0.6667 66.67%
Mitochondrial toxicity + 0.6000 60.00%
Nephrotoxicity + 0.5879 58.79%
Acute Oral Toxicity (c) III 0.7626 76.26%
Estrogen receptor binding + 0.9074 90.74%
Androgen receptor binding + 0.8440 84.40%
Thyroid receptor binding + 0.7443 74.43%
Glucocorticoid receptor binding + 0.8857 88.57%
Aromatase binding + 0.7754 77.54%
PPAR gamma + 0.8966 89.66%
Honey bee toxicity - 0.8693 86.93%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity + 0.5700 57.00%
Fish aquatic toxicity + 0.9619 96.19%

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 99.25% 91.11%
CHEMBL2581 P07339 Cathepsin D 98.26% 98.95%
CHEMBL242 Q92731 Estrogen receptor beta 97.28% 98.35%
CHEMBL1806 P11388 DNA topoisomerase II alpha 93.88% 89.00%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 91.31% 94.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 90.48% 86.33%
CHEMBL1937 Q92769 Histone deacetylase 2 89.85% 94.75%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.79% 95.56%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 88.46% 94.45%
CHEMBL2288 Q13526 Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 87.96% 91.71%
CHEMBL5339 Q5NUL3 G-protein coupled receptor 120 84.76% 95.78%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 84.71% 96.09%
CHEMBL2107 P61073 C-X-C chemokine receptor type 4 84.67% 93.10%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 84.25% 99.15%
CHEMBL5697 Q9GZT9 Egl nine homolog 1 83.57% 93.40%
CHEMBL3192 Q9BY41 Histone deacetylase 8 83.08% 93.99%
CHEMBL4940 P07195 L-lactate dehydrogenase B chain 82.59% 95.53%
CHEMBL2553 Q15418 Ribosomal protein S6 kinase alpha 1 82.57% 85.11%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 82.26% 99.23%
CHEMBL2345 P51812 Ribosomal protein S6 kinase alpha 3 80.61% 95.64%
CHEMBL1994 P08235 Mineralocorticoid receptor 80.55% 100.00%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 80.23% 90.71%

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.
Crotalaria madurensis

Cross-Links

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PubChem 5489401
LOTUS LTS0217408
wikiData Q83014623