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3-[(3S,5S,8R,9S,10R,12R,13S,14S,17R)-5,12,14-trihydroxy-10-(hydroxymethyl)-13-methyl-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-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 4be349c0-15eb-4414-b082-0519cabde127
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
IUPAC Name 3-[(3S,5S,8R,9S,10R,12R,13S,14S,17R)-5,12,14-trihydroxy-10-(hydroxymethyl)-13-methyl-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-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) CC1C(C(C(C(O1)OC2CCC3(C4CC(C5(C(CCC5(C4CCC3(C2)O)O)C6=CC(=O)OC6)C)O)CO)O)O)O
SMILES (Isomeric) C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2CC[C@@]3([C@H]4C[C@H]([C@@]5([C@H](CC[C@@]5([C@@H]4CC[C@@]3(C2)O)O)C6=CC(=O)OC6)C)O)CO)O)O)O
InChI InChI=1S/C29H44O11/c1-14-22(33)23(34)24(35)25(39-14)40-16-3-6-27(13-30)19-10-20(31)26(2)17(15-9-21(32)38-12-15)5-8-29(26,37)18(19)4-7-28(27,36)11-16/h9,14,16-20,22-25,30-31,33-37H,3-8,10-13H2,1-2H3/t14-,16-,17+,18+,19-,20+,22-,23+,24+,25-,26-,27-,28-,29-/m0/s1
InChI Key KYNXIMRHBXPXLL-KRRSKSLRSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C29H44O11
Molecular Weight 568.70 g/mol
Exact Mass 568.28836222 g/mol
Topological Polar Surface Area (TPSA) 186.00 Ų
XlogP -1.80
Atomic LogP (AlogP) -0.49
H-Bond Acceptor 11
H-Bond Donor 7
Rotatable Bonds 4

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of 3-[(3S,5S,8R,9S,10R,12R,13S,14S,17R)-5,12,14-trihydroxy-10-(hydroxymethyl)-13-methyl-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-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 + 0.7905 79.05%
Caco-2 - 0.8577 85.77%
Blood Brain Barrier - 0.6750 67.50%
Human oral bioavailability - 0.7714 77.14%
Subcellular localzation Mitochondria 0.8521 85.21%
OATP2B1 inhibitior - 0.6477 64.77%
OATP1B1 inhibitior + 0.9320 93.20%
OATP1B3 inhibitior + 0.9521 95.21%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior - 0.7623 76.23%
P-glycoprotein inhibitior - 0.5140 51.40%
P-glycoprotein substrate + 0.6100 61.00%
CYP3A4 substrate + 0.6759 67.59%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9010 90.10%
CYP3A4 inhibition - 0.9516 95.16%
CYP2C9 inhibition - 0.9310 93.10%
CYP2C19 inhibition - 0.9254 92.54%
CYP2D6 inhibition - 0.9192 91.92%
CYP1A2 inhibition - 0.9043 90.43%
CYP2C8 inhibition - 0.7071 70.71%
CYP inhibitory promiscuity - 0.9136 91.36%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6262 62.62%
Eye corrosion - 0.9900 99.00%
Eye irritation - 0.9381 93.81%
Skin irritation - 0.6105 61.05%
Skin corrosion - 0.9410 94.10%
Ames mutagenesis - 0.6370 63.70%
Human Ether-a-go-go-Related Gene inhibition + 0.9228 92.28%
Micronuclear - 0.8400 84.00%
Hepatotoxicity - 0.7101 71.01%
skin sensitisation - 0.9048 90.48%
Respiratory toxicity + 0.8556 85.56%
Reproductive toxicity + 0.9000 90.00%
Mitochondrial toxicity + 0.5250 52.50%
Nephrotoxicity - 0.7725 77.25%
Acute Oral Toxicity (c) I 0.7772 77.72%
Estrogen receptor binding + 0.8584 85.84%
Androgen receptor binding + 0.8123 81.23%
Thyroid receptor binding - 0.5882 58.82%
Glucocorticoid receptor binding + 0.5751 57.51%
Aromatase binding + 0.7221 72.21%
PPAR gamma + 0.5534 55.34%
Honey bee toxicity - 0.7630 76.30%
Biodegradation - 0.6750 67.50%
Crustacea aquatic toxicity - 0.5800 58.00%
Fish aquatic toxicity + 0.9023 90.23%

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 98.86% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.52% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 96.49% 97.09%
CHEMBL253 P34972 Cannabinoid CB2 receptor 95.37% 97.25%
CHEMBL1994 P08235 Mineralocorticoid receptor 95.15% 100.00%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 93.74% 85.14%
CHEMBL1293249 Q13887 Kruppel-like factor 5 93.46% 86.33%
CHEMBL3714130 P46095 G-protein coupled receptor 6 92.19% 97.36%
CHEMBL226 P30542 Adenosine A1 receptor 91.47% 95.93%
CHEMBL1937 Q92769 Histone deacetylase 2 90.10% 94.75%
CHEMBL1806 P11388 DNA topoisomerase II alpha 88.08% 89.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 85.38% 95.89%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 84.92% 95.56%
CHEMBL2581 P07339 Cathepsin D 84.63% 98.95%
CHEMBL3038469 P24941 CDK2/Cyclin A 84.26% 91.38%
CHEMBL2072 P35499 Sodium channel protein type IV alpha subunit 84.04% 92.32%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 83.98% 94.45%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 82.59% 94.00%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 81.53% 82.69%
CHEMBL4208 P20618 Proteasome component C5 81.16% 90.00%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 81.08% 96.77%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 80.21% 93.04%

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.
Antiaris toxicaria

Cross-Links

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PubChem 73356794
LOTUS LTS0069028
wikiData Q105147810