3-[(3S,5S,8S,9R,10R,13R,14R,17R)-3,5,8,14-tetrahydroxy-10,13-dimethyl-1,2,3,4,6,7,9,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one

Details

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Internal ID 19843821-bece-4fb3-a987-131c602b58f9
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives
IUPAC Name 3-[(3S,5S,8S,9R,10R,13R,14R,17R)-3,5,8,14-tetrahydroxy-10,13-dimethyl-1,2,3,4,6,7,9,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
SMILES (Canonical) CC12CCC3C4(CCC(CC4(CCC3(C1(CCC2C5=CC(=O)OC5)O)O)O)O)C
SMILES (Isomeric) C[C@]12CC[C@@H]3[C@]4(CC[C@@H](C[C@]4(CC[C@]3([C@]1(CC[C@@H]2C5=CC(=O)OC5)O)O)O)O)C
InChI InChI=1S/C23H34O6/c1-19-7-5-17-20(2)6-3-15(24)12-21(20,26)9-10-22(17,27)23(19,28)8-4-16(19)14-11-18(25)29-13-14/h11,15-17,24,26-28H,3-10,12-13H2,1-2H3/t15-,16+,17+,19+,20+,21-,22-,23+/m0/s1
InChI Key MGNCIZDGYCWTJX-YSFBYOPPSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C23H34O6
Molecular Weight 406.50 g/mol
Exact Mass 406.23553880 g/mol
Topological Polar Surface Area (TPSA) 107.00 Ų
XlogP 0.70
Atomic LogP (AlogP) 1.83
H-Bond Acceptor 6
H-Bond Donor 4
Rotatable Bonds 1

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of 3-[(3S,5S,8S,9R,10R,13R,14R,17R)-3,5,8,14-tetrahydroxy-10,13-dimethyl-1,2,3,4,6,7,9,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9673 96.73%
Caco-2 - 0.5913 59.13%
Blood Brain Barrier - 0.6966 69.66%
Human oral bioavailability + 0.5857 58.57%
Subcellular localzation Mitochondria 0.8122 81.22%
OATP2B1 inhibitior - 0.8653 86.53%
OATP1B1 inhibitior + 0.9321 93.21%
OATP1B3 inhibitior + 0.9639 96.39%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.8542 85.42%
BSEP inhibitior + 0.8497 84.97%
P-glycoprotein inhibitior - 0.9216 92.16%
P-glycoprotein substrate + 0.5816 58.16%
CYP3A4 substrate + 0.6470 64.70%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9026 90.26%
CYP3A4 inhibition - 0.8873 88.73%
CYP2C9 inhibition - 0.8997 89.97%
CYP2C19 inhibition - 0.9050 90.50%
CYP2D6 inhibition - 0.9285 92.85%
CYP1A2 inhibition - 0.8992 89.92%
CYP2C8 inhibition - 0.8465 84.65%
CYP inhibitory promiscuity - 0.9371 93.71%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5566 55.66%
Eye corrosion - 0.9909 99.09%
Eye irritation - 0.9388 93.88%
Skin irritation + 0.5136 51.36%
Skin corrosion - 0.9329 93.29%
Ames mutagenesis - 0.6970 69.70%
Human Ether-a-go-go-Related Gene inhibition - 0.4368 43.68%
Micronuclear - 0.8400 84.00%
Hepatotoxicity - 0.5621 56.21%
skin sensitisation - 0.8933 89.33%
Respiratory toxicity + 0.7556 75.56%
Reproductive toxicity + 0.9000 90.00%
Mitochondrial toxicity + 0.8375 83.75%
Nephrotoxicity - 0.7279 72.79%
Acute Oral Toxicity (c) I 0.6339 63.39%
Estrogen receptor binding + 0.8892 88.92%
Androgen receptor binding + 0.7594 75.94%
Thyroid receptor binding + 0.6258 62.58%
Glucocorticoid receptor binding + 0.7821 78.21%
Aromatase binding + 0.7566 75.66%
PPAR gamma + 0.5554 55.54%
Honey bee toxicity - 0.7991 79.91%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity + 0.5100 51.00%
Fish aquatic toxicity + 0.9868 98.68%

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 95.61% 91.11%
CHEMBL1994 P08235 Mineralocorticoid receptor 94.39% 100.00%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 94.33% 82.69%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 93.84% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 90.68% 94.45%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.24% 95.56%
CHEMBL2581 P07339 Cathepsin D 88.47% 98.95%
CHEMBL253 P34972 Cannabinoid CB2 receptor 88.15% 97.25%
CHEMBL5608 Q16288 NT-3 growth factor receptor 86.20% 95.89%
CHEMBL3137262 O60341 LSD1/CoREST complex 84.84% 97.09%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 84.06% 96.77%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 84.02% 85.14%
CHEMBL1293249 Q13887 Kruppel-like factor 5 83.90% 86.33%

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.
Periploca forrestii

Cross-Links

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PubChem 101575836
LOTUS LTS0196603
wikiData Q104999068