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

Details

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Internal ID 3a351fe8-9ffa-4433-bce3-494cc7b17cd3
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives
IUPAC Name 3-[(3S,5R,8R,10S,13R,14S,16S,17R)-3,14,16-trihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
SMILES (Canonical) CC12CCC(CC1CCC3C2CCC4(C3(CC(C4C5=CC(=O)OC5)O)O)C)O
SMILES (Isomeric) C[C@]12CC[C@@H](C[C@H]1CC[C@@H]3C2CC[C@]4([C@@]3(C[C@@H]([C@@H]4C5=CC(=O)OC5)O)O)C)O
InChI InChI=1S/C23H34O5/c1-21-7-5-15(24)10-14(21)3-4-17-16(21)6-8-22(2)20(13-9-19(26)28-12-13)18(25)11-23(17,22)27/h9,14-18,20,24-25,27H,3-8,10-12H2,1-2H3/t14-,15+,16?,17-,18+,20+,21+,22-,23+/m1/s1
InChI Key PVAMXWLZJKTXFW-ZGSFGNQMSA-N
Popularity 7 references in papers

Physical and Chemical Properties

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Molecular Formula C23H34O5
Molecular Weight 390.50 g/mol
Exact Mass 390.24062418 g/mol
Topological Polar Surface Area (TPSA) 87.00 Ų
XlogP 1.60
Atomic LogP (AlogP) 2.58
H-Bond Acceptor 5
H-Bond Donor 3
Rotatable Bonds 1

Synonyms

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CHEMBL1434641
HMS2219C08
SMR001397373

2D Structure

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2D Structure of 3-[(3S,5R,8R,10S,13R,14S,16S,17R)-3,14,16-trihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[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 - 0.5373 53.73%
Blood Brain Barrier - 0.6189 61.89%
Human oral bioavailability + 0.5857 58.57%
Subcellular localzation Mitochondria 0.8004 80.04%
OATP2B1 inhibitior - 0.8643 86.43%
OATP1B1 inhibitior + 0.9095 90.95%
OATP1B3 inhibitior + 0.9615 96.15%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.7493 74.93%
BSEP inhibitior + 0.8043 80.43%
P-glycoprotein inhibitior - 0.8868 88.68%
P-glycoprotein substrate + 0.7207 72.07%
CYP3A4 substrate + 0.7146 71.46%
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 - 0.7932 79.32%
CYP inhibitory promiscuity - 0.8702 87.02%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5443 54.43%
Eye corrosion - 0.9913 99.13%
Eye irritation - 0.9601 96.01%
Skin irritation - 0.5181 51.81%
Skin corrosion - 0.9360 93.60%
Ames mutagenesis - 0.6424 64.24%
Human Ether-a-go-go-Related Gene inhibition - 0.5191 51.91%
Micronuclear - 0.8400 84.00%
Hepatotoxicity + 0.5199 51.99%
skin sensitisation - 0.8828 88.28%
Respiratory toxicity + 0.9111 91.11%
Reproductive toxicity + 0.9222 92.22%
Mitochondrial toxicity + 0.8750 87.50%
Nephrotoxicity - 0.6437 64.37%
Acute Oral Toxicity (c) I 0.5853 58.53%
Estrogen receptor binding + 0.8766 87.66%
Androgen receptor binding + 0.8473 84.73%
Thyroid receptor binding + 0.5737 57.37%
Glucocorticoid receptor binding + 0.8692 86.92%
Aromatase binding + 0.7665 76.65%
PPAR gamma - 0.5828 58.28%
Honey bee toxicity - 0.7548 75.48%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity + 0.5900 59.00%
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
CHEMBL1994 P08235 Mineralocorticoid receptor 95.49% 100.00%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 94.49% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 93.37% 91.11%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 92.69% 82.69%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 91.43% 94.45%
CHEMBL1871 P10275 Androgen Receptor 90.71% 96.43%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.38% 97.09%
CHEMBL253 P34972 Cannabinoid CB2 receptor 90.07% 97.25%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 88.61% 95.56%
CHEMBL5608 Q16288 NT-3 growth factor receptor 87.02% 95.89%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 86.86% 93.04%
CHEMBL1293249 Q13887 Kruppel-like factor 5 85.94% 86.33%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 84.09% 99.23%
CHEMBL2581 P07339 Cathepsin D 81.09% 98.95%

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.
Nerium oleander
Tribulus terrestris

Cross-Links

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PubChem 44144286
NPASS NPC46575