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

Details

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Internal ID 70e0c146-9adb-48ff-b944-c31d5e8ec0db
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives
IUPAC Name 3-[(3S,5R,7S,8R,9S,10R,13R,14S,17R)-3,5,7,14-tetrahydroxy-10,13-dimethyl-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
SMILES (Canonical) CC12CCC(CC1(CC(C3C2CCC4(C3(CCC4C5=CC(=O)OC5)O)C)O)O)O
SMILES (Isomeric) C[C@]12CC[C@@H](C[C@]1(C[C@@H]([C@H]3[C@@H]2CC[C@]4([C@@]3(CC[C@@H]4C5=CC(=O)OC5)O)C)O)O)O
InChI InChI=1S/C23H34O6/c1-20-6-3-14(24)10-22(20,27)11-17(25)19-16(20)4-7-21(2)15(5-8-23(19,21)28)13-9-18(26)29-12-13/h9,14-17,19,24-25,27-28H,3-8,10-12H2,1-2H3/t14-,15+,16-,17-,19+,20+,21+,22+,23-/m0/s1
InChI Key GHZTYACAVBAZKG-RTDLGUASSA-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 0.40
Atomic LogP (AlogP) 1.69
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,5R,7S,8R,9S,10R,13R,14S,17R)-3,5,7,14-tetrahydroxy-10,13-dimethyl-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[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 + 0.9875 98.75%
Caco-2 - 0.5877 58.77%
Blood Brain Barrier - 0.6189 61.89%
Human oral bioavailability + 0.6714 67.14%
Subcellular localzation Mitochondria 0.8004 80.04%
OATP2B1 inhibitior - 0.8614 86.14%
OATP1B1 inhibitior + 0.9326 93.26%
OATP1B3 inhibitior + 0.9615 96.15%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.7493 74.93%
BSEP inhibitior + 0.8491 84.91%
P-glycoprotein inhibitior - 0.9007 90.07%
P-glycoprotein substrate + 0.5809 58.09%
CYP3A4 substrate + 0.6793 67.93%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9060 90.60%
CYP3A4 inhibition - 0.8310 83.10%
CYP2C9 inhibition - 0.9099 90.99%
CYP2C19 inhibition - 0.9256 92.56%
CYP2D6 inhibition - 0.9362 93.62%
CYP1A2 inhibition - 0.9046 90.46%
CYP2C8 inhibition - 0.7193 71.93%
CYP inhibitory promiscuity - 0.8702 87.02%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5443 54.43%
Eye corrosion - 0.9913 99.13%
Eye irritation - 0.9587 95.87%
Skin irritation - 0.5181 51.81%
Skin corrosion - 0.9360 93.60%
Ames mutagenesis - 0.6670 66.70%
Human Ether-a-go-go-Related Gene inhibition + 0.6502 65.02%
Micronuclear - 0.8400 84.00%
Hepatotoxicity - 0.5746 57.46%
skin sensitisation - 0.8828 88.28%
Respiratory toxicity + 0.8556 85.56%
Reproductive toxicity + 0.9222 92.22%
Mitochondrial toxicity + 0.8750 87.50%
Nephrotoxicity - 0.7074 70.74%
Acute Oral Toxicity (c) I 0.5853 58.53%
Estrogen receptor binding + 0.8860 88.60%
Androgen receptor binding + 0.8145 81.45%
Thyroid receptor binding + 0.5228 52.28%
Glucocorticoid receptor binding + 0.7678 76.78%
Aromatase binding + 0.7201 72.01%
PPAR gamma - 0.5709 57.09%
Honey bee toxicity - 0.7941 79.41%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity + 0.5300 53.00%
Fish aquatic toxicity + 0.9889 98.89%

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
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 97.87% 85.14%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.21% 91.11%
CHEMBL1994 P08235 Mineralocorticoid receptor 96.06% 100.00%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.04% 96.09%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 94.66% 82.69%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 91.29% 94.45%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.73% 97.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 88.91% 95.56%
CHEMBL1293249 Q13887 Kruppel-like factor 5 88.08% 86.33%
CHEMBL5608 Q16288 NT-3 growth factor receptor 86.90% 95.89%
CHEMBL1871 P10275 Androgen Receptor 85.39% 96.43%
CHEMBL2581 P07339 Cathepsin D 85.35% 98.95%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 84.42% 93.04%
CHEMBL4208 P20618 Proteasome component C5 84.18% 90.00%
CHEMBL253 P34972 Cannabinoid CB2 receptor 83.21% 97.25%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 82.39% 96.77%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 81.87% 97.14%
CHEMBL1293277 O15118 Niemann-Pick C1 protein 81.18% 81.11%

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 162866528
LOTUS LTS0160466
wikiData Q105008823