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(1R,5S,6S,14R)-6,11,14-trihydroxy-5,17,18-trimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.03,12.04,9.015,20]docosa-3(12),4(9),10,15,17,19-hexaen-13-one

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

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Internal ID 9352df75-8a15-43fe-a4ba-793cd5fb1d4c
Taxonomy Phenylpropanoids and polyketides > Isoflavonoids > Rotenoids > Rotenones
IUPAC Name (1R,5S,6S,14R)-6,11,14-trihydroxy-5,17,18-trimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.03,12.04,9.015,20]docosa-3(12),4(9),10,15,17,19-hexaen-13-one
SMILES (Canonical) CC1(C(C(C2=C(O1)C=C(C3=C2OC4COC5=CC(=C(C=C5C4(C3=O)O)OC)OC)O)OC)O)C
SMILES (Isomeric) CC1([C@H]([C@H](C2=C(O1)C=C(C3=C2O[C@@H]4COC5=CC(=C(C=C5[C@@]4(C3=O)O)OC)OC)O)OC)O)C
InChI InChI=1S/C24H26O10/c1-23(2)22(27)20(31-5)18-15(34-23)7-11(25)17-19(18)33-16-9-32-12-8-14(30-4)13(29-3)6-10(12)24(16,28)21(17)26/h6-8,16,20,22,25,27-28H,9H2,1-5H3/t16-,20+,22+,24-/m1/s1
InChI Key RTUABMSWXKMPKI-UCLSJRGTSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C24H26O10
Molecular Weight 474.50 g/mol
Exact Mass 474.15259702 g/mol
Topological Polar Surface Area (TPSA) 133.00 Ų
XlogP 1.70
Atomic LogP (AlogP) 1.85
H-Bond Acceptor 10
H-Bond Donor 3
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (1R,5S,6S,14R)-6,11,14-trihydroxy-5,17,18-trimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.03,12.04,9.015,20]docosa-3(12),4(9),10,15,17,19-hexaen-13-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9685 96.85%
Caco-2 - 0.5714 57.14%
Blood Brain Barrier - 0.7000 70.00%
Human oral bioavailability - 0.6857 68.57%
Subcellular localzation Mitochondria 0.8191 81.91%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9006 90.06%
OATP1B3 inhibitior + 0.9351 93.51%
MATE1 inhibitior - 0.8800 88.00%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior + 0.6056 60.56%
P-glycoprotein inhibitior + 0.6825 68.25%
P-glycoprotein substrate - 0.5387 53.87%
CYP3A4 substrate + 0.6627 66.27%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8056 80.56%
CYP3A4 inhibition - 0.7524 75.24%
CYP2C9 inhibition - 0.8369 83.69%
CYP2C19 inhibition + 0.6054 60.54%
CYP2D6 inhibition - 0.7151 71.51%
CYP1A2 inhibition + 0.7617 76.17%
CYP2C8 inhibition + 0.5663 56.63%
CYP inhibitory promiscuity - 0.7878 78.78%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6213 62.13%
Eye corrosion - 0.9888 98.88%
Eye irritation - 0.8190 81.90%
Skin irritation - 0.8358 83.58%
Skin corrosion - 0.9644 96.44%
Ames mutagenesis + 0.5146 51.46%
Human Ether-a-go-go-Related Gene inhibition - 0.8465 84.65%
Micronuclear + 0.6159 61.59%
Hepatotoxicity - 0.7500 75.00%
skin sensitisation - 0.8482 84.82%
Respiratory toxicity + 0.7222 72.22%
Reproductive toxicity + 0.7222 72.22%
Mitochondrial toxicity + 0.5125 51.25%
Nephrotoxicity + 0.6221 62.21%
Acute Oral Toxicity (c) III 0.7601 76.01%
Estrogen receptor binding + 0.8228 82.28%
Androgen receptor binding + 0.6480 64.80%
Thyroid receptor binding + 0.7179 71.79%
Glucocorticoid receptor binding + 0.7849 78.49%
Aromatase binding + 0.6231 62.31%
PPAR gamma + 0.8021 80.21%
Honey bee toxicity - 0.6866 68.66%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.5849 58.49%
Fish aquatic toxicity + 0.7882 78.82%

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
CHEMBL4040 P28482 MAP kinase ERK2 99.52% 83.82%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 99.22% 91.11%
CHEMBL241 Q14432 Phosphodiesterase 3A 95.88% 92.94%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 95.05% 94.45%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 93.03% 96.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 92.91% 89.00%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 92.21% 85.14%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.72% 95.56%
CHEMBL1293249 Q13887 Kruppel-like factor 5 91.27% 86.33%
CHEMBL1937 Q92769 Histone deacetylase 2 88.49% 94.75%
CHEMBL4208 P20618 Proteasome component C5 87.50% 90.00%
CHEMBL2581 P07339 Cathepsin D 87.49% 98.95%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 87.10% 92.62%
CHEMBL340 P08684 Cytochrome P450 3A4 86.46% 91.19%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 85.48% 94.00%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 85.40% 96.77%
CHEMBL2413 P32246 C-C chemokine receptor type 1 85.11% 89.50%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.76% 100.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 84.71% 99.23%
CHEMBL5608 Q16288 NT-3 growth factor receptor 83.73% 95.89%
CHEMBL5697 Q9GZT9 Egl nine homolog 1 83.64% 93.40%
CHEMBL3137262 O60341 LSD1/CoREST complex 83.02% 97.09%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 82.34% 97.14%
CHEMBL5311 P37023 Serine/threonine-protein kinase receptor R3 80.62% 82.67%

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.
Tephrosia sinapou

Cross-Links

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PubChem 162889173
LOTUS LTS0179934
wikiData Q105245407