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

Details

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Internal ID 7ca2f838-0359-4810-9eb2-1e92b5e26410
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)-3,4,11,14-tetrahydroxy-10,13-dimethyl-12-oxo-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)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
InChI InChI=1S/C24H32O7/c1-22-9-8-16(25)19(27)15(22)5-4-14-18(22)20(28)21(29)23(2)13(7-10-24(14,23)30)12-3-6-17(26)31-11-12/h3,6,11,13-16,18-20,25,27-28,30H,4-5,7-10H2,1-2H3/t13-,14-,15+,16+,18-,19-,20+,22+,23+,24+/m1/s1
InChI Key RHIQPXHDMPKJGN-SIQGASHQSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C24H32O7
Molecular Weight 432.50 g/mol
Exact Mass 432.21480336 g/mol
Topological Polar Surface Area (TPSA) 124.00 Ų
XlogP 0.50
Atomic LogP (AlogP) 1.36
H-Bond Acceptor 7
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 5-[(3S,4R,5R,8R,9S,10S,11S,13R,14S,17R)-3,4,11,14-tetrahydroxy-10,13-dimethyl-12-oxo-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 + 0.9397 93.97%
Caco-2 - 0.7974 79.74%
Blood Brain Barrier - 0.6250 62.50%
Human oral bioavailability - 0.5857 58.57%
Subcellular localzation Mitochondria 0.7967 79.67%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8722 87.22%
OATP1B3 inhibitior + 0.8810 88.10%
MATE1 inhibitior - 0.8800 88.00%
OCT2 inhibitior - 0.9108 91.08%
BSEP inhibitior + 0.6429 64.29%
P-glycoprotein inhibitior - 0.7747 77.47%
P-glycoprotein substrate - 0.7850 78.50%
CYP3A4 substrate + 0.6742 67.42%
CYP2C9 substrate - 0.5942 59.42%
CYP2D6 substrate - 0.8554 85.54%
CYP3A4 inhibition - 0.7046 70.46%
CYP2C9 inhibition - 0.9170 91.70%
CYP2C19 inhibition - 0.8573 85.73%
CYP2D6 inhibition - 0.9590 95.90%
CYP1A2 inhibition - 0.6819 68.19%
CYP2C8 inhibition - 0.7882 78.82%
CYP inhibitory promiscuity - 0.9863 98.63%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9400 94.00%
Carcinogenicity (trinary) Non-required 0.5960 59.60%
Eye corrosion - 0.9936 99.36%
Eye irritation - 0.9659 96.59%
Skin irritation - 0.5760 57.60%
Skin corrosion - 0.8837 88.37%
Ames mutagenesis - 0.7800 78.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4788 47.88%
Micronuclear - 0.7800 78.00%
Hepatotoxicity + 0.5159 51.59%
skin sensitisation - 0.9070 90.70%
Respiratory toxicity + 0.8111 81.11%
Reproductive toxicity + 0.9000 90.00%
Mitochondrial toxicity + 0.9125 91.25%
Nephrotoxicity - 0.5574 55.74%
Acute Oral Toxicity (c) I 0.6464 64.64%
Estrogen receptor binding + 0.8668 86.68%
Androgen receptor binding + 0.7398 73.98%
Thyroid receptor binding + 0.5213 52.13%
Glucocorticoid receptor binding + 0.7097 70.97%
Aromatase binding + 0.7145 71.45%
PPAR gamma + 0.5425 54.25%
Honey bee toxicity - 0.8646 86.46%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity + 0.6100 61.00%
Fish aquatic toxicity + 0.9881 98.81%

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 93.87% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 93.79% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.40% 97.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 92.74% 94.45%
CHEMBL1994 P08235 Mineralocorticoid receptor 91.41% 100.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 91.06% 89.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.99% 95.56%
CHEMBL2581 P07339 Cathepsin D 88.77% 98.95%
CHEMBL5608 Q16288 NT-3 growth factor receptor 88.70% 95.89%
CHEMBL2553 Q15418 Ribosomal protein S6 kinase alpha 1 85.55% 85.11%
CHEMBL1293249 Q13887 Kruppel-like factor 5 84.43% 86.33%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 84.06% 93.04%
CHEMBL332 P03956 Matrix metalloproteinase-1 82.78% 94.50%
CHEMBL221 P23219 Cyclooxygenase-1 82.10% 90.17%
CHEMBL226 P30542 Adenosine A1 receptor 81.87% 95.93%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 81.00% 94.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 80.73% 99.23%
CHEMBL2563 Q9UQL6 Histone deacetylase 5 80.55% 89.67%
CHEMBL3922 P50579 Methionine aminopeptidase 2 80.12% 97.28%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 80.09% 96.38%

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 21579657
NPASS NPC191416