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(1R,5R,7S,14R)-14-hydroxy-17,18-dimethoxy-6,6-dimethyl-2,8,21-trioxahexacyclo[12.8.0.03,12.04,9.05,7.015,20]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 cbc144a1-7ed0-4fe7-9a0e-256c9b012c89
Taxonomy Phenylpropanoids and polyketides > Isoflavonoids > Rotenoids > Rotenones
IUPAC Name (1R,5R,7S,14R)-14-hydroxy-17,18-dimethoxy-6,6-dimethyl-2,8,21-trioxahexacyclo[12.8.0.03,12.04,9.05,7.015,20]docosa-3(12),4(9),10,15,17,19-hexaen-13-one
SMILES (Canonical) CC1(C2C1OC3=C2C4=C(C=C3)C(=O)C5(C(O4)COC6=CC(=C(C=C65)OC)OC)O)C
SMILES (Isomeric) CC1([C@H]2[C@@H]1OC3=C2C4=C(C=C3)C(=O)[C@@]5([C@H](O4)COC6=CC(=C(C=C65)OC)OC)O)C
InChI InChI=1S/C23H22O7/c1-22(2)18-17-12(29-21(18)22)6-5-10-19(17)30-16-9-28-13-8-15(27-4)14(26-3)7-11(13)23(16,25)20(10)24/h5-8,16,18,21,25H,9H2,1-4H3/t16-,18-,21+,23-/m1/s1
InChI Key HJDODWXISWRQIF-ANNUPHGVSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C23H22O7
Molecular Weight 410.40 g/mol
Exact Mass 410.13655304 g/mol
Topological Polar Surface Area (TPSA) 83.50 Ų
XlogP 2.90
Atomic LogP (AlogP) 2.81
H-Bond Acceptor 7
H-Bond Donor 1
Rotatable Bonds 2

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (1R,5R,7S,14R)-14-hydroxy-17,18-dimethoxy-6,6-dimethyl-2,8,21-trioxahexacyclo[12.8.0.03,12.04,9.05,7.015,20]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 + 0.9859 98.59%
Caco-2 + 0.5910 59.10%
Blood Brain Barrier + 0.5500 55.00%
Human oral bioavailability - 0.5714 57.14%
Subcellular localzation Mitochondria 0.8297 82.97%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9161 91.61%
OATP1B3 inhibitior + 0.9599 95.99%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.9500 95.00%
BSEP inhibitior - 0.4608 46.08%
P-glycoprotein inhibitior + 0.7629 76.29%
P-glycoprotein substrate - 0.5000 50.00%
CYP3A4 substrate + 0.6513 65.13%
CYP2C9 substrate - 0.7795 77.95%
CYP2D6 substrate - 0.7722 77.22%
CYP3A4 inhibition + 0.5827 58.27%
CYP2C9 inhibition - 0.6666 66.66%
CYP2C19 inhibition + 0.7240 72.40%
CYP2D6 inhibition - 0.7216 72.16%
CYP1A2 inhibition + 0.6456 64.56%
CYP2C8 inhibition + 0.4571 45.71%
CYP inhibitory promiscuity - 0.6422 64.22%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5016 50.16%
Eye corrosion - 0.9885 98.85%
Eye irritation - 0.8191 81.91%
Skin irritation - 0.8193 81.93%
Skin corrosion - 0.9593 95.93%
Ames mutagenesis - 0.5154 51.54%
Human Ether-a-go-go-Related Gene inhibition - 0.6866 68.66%
Micronuclear + 0.6559 65.59%
Hepatotoxicity - 0.6000 60.00%
skin sensitisation - 0.7450 74.50%
Respiratory toxicity + 0.6222 62.22%
Reproductive toxicity + 0.8333 83.33%
Mitochondrial toxicity + 0.6000 60.00%
Nephrotoxicity - 0.6228 62.28%
Acute Oral Toxicity (c) III 0.6056 60.56%
Estrogen receptor binding + 0.8838 88.38%
Androgen receptor binding + 0.6765 67.65%
Thyroid receptor binding + 0.7751 77.51%
Glucocorticoid receptor binding + 0.7914 79.14%
Aromatase binding + 0.5440 54.40%
PPAR gamma + 0.8054 80.54%
Honey bee toxicity - 0.7370 73.70%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity + 0.6151 61.51%
Fish aquatic toxicity + 0.8282 82.82%

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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 93.75% 96.09%
CHEMBL241 Q14432 Phosphodiesterase 3A 92.86% 92.94%
CHEMBL1293249 Q13887 Kruppel-like factor 5 92.56% 86.33%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 91.67% 91.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.32% 95.56%
CHEMBL1937 Q92769 Histone deacetylase 2 88.12% 94.75%
CHEMBL2581 P07339 Cathepsin D 87.77% 98.95%
CHEMBL3192 Q9BY41 Histone deacetylase 8 87.25% 93.99%
CHEMBL1994 P08235 Mineralocorticoid receptor 87.15% 100.00%
CHEMBL4208 P20618 Proteasome component C5 87.08% 90.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 86.62% 89.00%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 86.62% 97.14%
CHEMBL5608 Q16288 NT-3 growth factor receptor 86.47% 95.89%
CHEMBL3137262 O60341 LSD1/CoREST complex 86.03% 97.09%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 85.83% 94.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 85.58% 94.45%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 84.87% 92.62%
CHEMBL4247 Q9UM73 ALK tyrosine kinase receptor 83.38% 96.86%
CHEMBL5697 Q9GZT9 Egl nine homolog 1 82.62% 93.40%
CHEMBL2413 P32246 C-C chemokine receptor type 1 82.23% 89.50%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 80.75% 96.77%
CHEMBL340 P08684 Cytochrome P450 3A4 80.44% 91.19%
CHEMBL5311 P37023 Serine/threonine-protein kinase receptor R3 80.30% 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.
Sarcolobus globosus

Cross-Links

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PubChem 26203653
LOTUS LTS0242968
wikiData Q105029166