6-Hydroxy-6a,12a-dehydro-alpha-toxicarol

Details

Top
Internal ID a6205716-256d-4f21-a16c-15283d0073a6
Taxonomy Phenylpropanoids and polyketides > Isoflavonoids > Rotenoids > Rotenones
IUPAC Name 11,22-dihydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.03,12.04,9.015,20]docosa-1(14),3(12),4(9),5,10,15,17,19-octaen-13-one
SMILES (Canonical) CC1(C=CC2=C(O1)C=C(C3=C2OC4=C(C3=O)C5=CC(=C(C=C5OC4O)OC)OC)O)C
SMILES (Isomeric) CC1(C=CC2=C(O1)C=C(C3=C2OC4=C(C3=O)C5=CC(=C(C=C5OC4O)OC)OC)O)C
InChI InChI=1S/C23H20O8/c1-23(2)6-5-10-14(31-23)8-12(24)18-19(25)17-11-7-15(27-3)16(28-4)9-13(11)29-22(26)21(17)30-20(10)18/h5-9,22,24,26H,1-4H3
InChI Key NVIZHSSHHRHDLE-UHFFFAOYSA-N
Popularity 0 references in papers

Physical and Chemical Properties

Top
Molecular Formula C23H20O8
Molecular Weight 424.40 g/mol
Exact Mass 424.11581759 g/mol
Topological Polar Surface Area (TPSA) 104.00 Ų
XlogP 3.20
Atomic LogP (AlogP) 3.75
H-Bond Acceptor 8
H-Bond Donor 2
Rotatable Bonds 2

Synonyms

Top
LMPK12060075

2D Structure

Top
2D Structure of 6-Hydroxy-6a,12a-dehydro-alpha-toxicarol

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9612 96.12%
Caco-2 + 0.5599 55.99%
Blood Brain Barrier - 0.6750 67.50%
Human oral bioavailability - 0.5143 51.43%
Subcellular localzation Mitochondria 0.7071 70.71%
OATP2B1 inhibitior - 0.7150 71.50%
OATP1B1 inhibitior + 0.8810 88.10%
OATP1B3 inhibitior + 0.9231 92.31%
MATE1 inhibitior - 0.8000 80.00%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior + 0.8699 86.99%
P-glycoprotein inhibitior + 0.8780 87.80%
P-glycoprotein substrate + 0.5000 50.00%
CYP3A4 substrate + 0.6712 67.12%
CYP2C9 substrate - 0.6146 61.46%
CYP2D6 substrate - 0.8459 84.59%
CYP3A4 inhibition - 0.6773 67.73%
CYP2C9 inhibition - 0.8734 87.34%
CYP2C19 inhibition - 0.5440 54.40%
CYP2D6 inhibition - 0.7637 76.37%
CYP1A2 inhibition - 0.7245 72.45%
CYP2C8 inhibition + 0.6379 63.79%
CYP inhibitory promiscuity - 0.5786 57.86%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Danger 0.5641 56.41%
Eye corrosion - 0.9884 98.84%
Eye irritation - 0.7138 71.38%
Skin irritation - 0.7574 75.74%
Skin corrosion - 0.9626 96.26%
Ames mutagenesis + 0.5700 57.00%
Human Ether-a-go-go-Related Gene inhibition - 0.6291 62.91%
Micronuclear + 0.7000 70.00%
Hepatotoxicity + 0.5125 51.25%
skin sensitisation - 0.8472 84.72%
Respiratory toxicity + 0.6222 62.22%
Reproductive toxicity + 0.7444 74.44%
Mitochondrial toxicity + 0.5750 57.50%
Nephrotoxicity - 0.7483 74.83%
Acute Oral Toxicity (c) III 0.6252 62.52%
Estrogen receptor binding + 0.9116 91.16%
Androgen receptor binding + 0.6209 62.09%
Thyroid receptor binding + 0.7445 74.45%
Glucocorticoid receptor binding + 0.8668 86.68%
Aromatase binding + 0.7038 70.38%
PPAR gamma + 0.8594 85.94%
Honey bee toxicity - 0.6771 67.71%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity + 0.5151 51.51%
Fish aquatic toxicity + 0.9743 97.43%

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 97.92% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 95.14% 94.45%
CHEMBL1806 P11388 DNA topoisomerase II alpha 93.55% 89.00%
CHEMBL2581 P07339 Cathepsin D 93.14% 98.95%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 92.42% 94.00%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 91.16% 96.09%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 90.68% 96.21%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 90.55% 96.77%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 87.83% 85.14%
CHEMBL2535 P11166 Glucose transporter 87.02% 98.75%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 86.85% 95.56%
CHEMBL5608 Q16288 NT-3 growth factor receptor 86.62% 95.89%
CHEMBL1293249 Q13887 Kruppel-like factor 5 86.53% 86.33%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 86.34% 92.62%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 86.31% 97.14%
CHEMBL4051 P13569 Cystic fibrosis transmembrane conductance regulator 84.59% 95.71%
CHEMBL3060 Q9Y345 Glycine transporter 2 84.03% 99.17%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 83.62% 99.23%
CHEMBL3864 Q06124 Protein-tyrosine phosphatase 2C 81.31% 94.42%
CHEMBL2413 P32246 C-C chemokine receptor type 1 81.17% 89.50%
CHEMBL340 P08684 Cytochrome P450 3A4 80.31% 91.19%

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.
Millettia brandisiana

Cross-Links

Top
PubChem 44257423
LOTUS LTS0247519
wikiData Q105186261