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5-[(3S,4R,5R,8R,9S,10S,11S,13R,14S,17R)-4,11,14-trihydroxy-10,13-dimethyl-12-oxo-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-2,3,4,5,6,7,8,9,11,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]pyran-2-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 09dcddce-6081-4eb3-9214-9cede965a780
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Bufanolides and derivatives
IUPAC Name 5-[(3S,4R,5R,8R,9S,10S,11S,13R,14S,17R)-4,11,14-trihydroxy-10,13-dimethyl-12-oxo-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-2,3,4,5,6,7,8,9,11,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]pyran-2-one
SMILES (Canonical) CC12CCC(C(C1CCC3C2C(C(=O)C4(C3(CCC4C5=COC(=O)C=C5)O)C)O)O)OC6C(C(C(CO6)O)O)O
SMILES (Isomeric) C[C@]12CC[C@@H]([C@@H]([C@@H]1CC[C@@H]3[C@@H]2[C@@H](C(=O)[C@]4([C@@]3(CC[C@@H]4C5=COC(=O)C=C5)O)C)O)O)O[C@H]6[C@@H]([C@H]([C@@H](CO6)O)O)O
InChI InChI=1S/C29H40O11/c1-27-9-8-18(40-26-24(35)22(33)17(30)12-39-26)21(32)16(27)5-4-15-20(27)23(34)25(36)28(2)14(7-10-29(15,28)37)13-3-6-19(31)38-11-13/h3,6,11,14-18,20-24,26,30,32-35,37H,4-5,7-10,12H2,1-2H3/t14-,15-,16+,17-,18+,20-,21-,22+,23+,24-,26+,27+,28+,29+/m1/s1
InChI Key MLZPINQGGDBAKV-YYZAXNALSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C29H40O11
Molecular Weight 564.60 g/mol
Exact Mass 564.25706209 g/mol
Topological Polar Surface Area (TPSA) 183.00 Ų
XlogP -1.00
Atomic LogP (AlogP) -0.17
H-Bond Acceptor 11
H-Bond Donor 6
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of 5-[(3S,4R,5R,8R,9S,10S,11S,13R,14S,17R)-4,11,14-trihydroxy-10,13-dimethyl-12-oxo-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-2,3,4,5,6,7,8,9,11,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]pyran-2-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8295 82.95%
Caco-2 - 0.9056 90.56%
Blood Brain Barrier - 0.6500 65.00%
Human oral bioavailability - 0.6429 64.29%
Subcellular localzation Mitochondria 0.8144 81.44%
OATP2B1 inhibitior - 0.7226 72.26%
OATP1B1 inhibitior + 0.8719 87.19%
OATP1B3 inhibitior + 0.9301 93.01%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.8787 87.87%
BSEP inhibitior - 0.5671 56.71%
P-glycoprotein inhibitior - 0.5293 52.93%
P-glycoprotein substrate - 0.6591 65.91%
CYP3A4 substrate + 0.7154 71.54%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8762 87.62%
CYP3A4 inhibition - 0.7984 79.84%
CYP2C9 inhibition - 0.9250 92.50%
CYP2C19 inhibition - 0.9193 91.93%
CYP2D6 inhibition - 0.9465 94.65%
CYP1A2 inhibition - 0.8673 86.73%
CYP2C8 inhibition + 0.4476 44.76%
CYP inhibitory promiscuity - 0.9662 96.62%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.6321 63.21%
Eye corrosion - 0.9922 99.22%
Eye irritation - 0.9420 94.20%
Skin irritation - 0.7011 70.11%
Skin corrosion - 0.9359 93.59%
Ames mutagenesis - 0.5800 58.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6471 64.71%
Micronuclear - 0.7600 76.00%
Hepatotoxicity - 0.6324 63.24%
skin sensitisation - 0.9268 92.68%
Respiratory toxicity + 0.7778 77.78%
Reproductive toxicity + 0.8889 88.89%
Mitochondrial toxicity + 0.8125 81.25%
Nephrotoxicity - 0.6896 68.96%
Acute Oral Toxicity (c) I 0.5180 51.80%
Estrogen receptor binding + 0.8436 84.36%
Androgen receptor binding + 0.7268 72.68%
Thyroid receptor binding - 0.5532 55.32%
Glucocorticoid receptor binding + 0.6309 63.09%
Aromatase binding + 0.6567 65.67%
PPAR gamma + 0.6320 63.20%
Honey bee toxicity - 0.7657 76.57%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity + 0.6400 64.00%
Fish aquatic toxicity + 0.9817 98.17%

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 96.71% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.32% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 94.63% 94.45%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.67% 97.09%
CHEMBL2581 P07339 Cathepsin D 90.93% 98.95%
CHEMBL221 P23219 Cyclooxygenase-1 90.55% 90.17%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.25% 95.56%
CHEMBL1994 P08235 Mineralocorticoid receptor 89.07% 100.00%
CHEMBL3922 P50579 Methionine aminopeptidase 2 88.96% 97.28%
CHEMBL5608 Q16288 NT-3 growth factor receptor 88.93% 95.89%
CHEMBL1806 P11388 DNA topoisomerase II alpha 87.85% 89.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 87.74% 86.33%
CHEMBL2563 Q9UQL6 Histone deacetylase 5 87.12% 89.67%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 86.56% 94.00%
CHEMBL4040 P28482 MAP kinase ERK2 84.51% 83.82%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 83.95% 96.38%
CHEMBL332 P03956 Matrix metalloproteinase-1 83.19% 94.50%
CHEMBL4145 Q9UKV0 Histone deacetylase 9 82.27% 85.49%
CHEMBL3713062 P10646 Tissue factor pathway inhibitor 82.04% 97.33%
CHEMBL1907605 P24864 Cyclin-dependent kinase 2/cyclin E1 81.22% 92.88%
CHEMBL226 P30542 Adenosine A1 receptor 80.32% 95.93%
CHEMBL5255 O00206 Toll-like receptor 4 80.08% 92.50%

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.
Acacia mearnsii
Cinnamomum aromaticum
Dioscorea panthaica

Cross-Links

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PubChem 21579656
NPASS NPC45008