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(2Z)-2-[(3R,4S,8S,9R,10S,13R,14R,16S)-3-hydroxy-4,10,14-trimethyl-11-oxo-16-propanoyloxy-2,3,4,5,6,7,8,9,12,13,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoic acid

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 9e9d5bd8-b331-4fbd-81f0-cad9fa491bae
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid esters
IUPAC Name (2Z)-2-[(3R,4S,8S,9R,10S,13R,14R,16S)-3-hydroxy-4,10,14-trimethyl-11-oxo-16-propanoyloxy-2,3,4,5,6,7,8,9,12,13,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoic acid
SMILES (Canonical) CCC(=O)OC1CC2(C3CCC4C(C(CCC4(C3C(=O)CC2C1=C(CCC=C(C)C)C(=O)O)C)O)C)C
SMILES (Isomeric) CCC(=O)O[C@H]\1C[C@@]2([C@H]3CCC4[C@@H]([C@@H](CC[C@@]4([C@@H]3C(=O)C[C@H]2/C1=C(\CCC=C(C)C)/C(=O)O)C)O)C)C
InChI InChI=1S/C31H46O6/c1-7-26(34)37-25-16-31(6)21-12-11-20-18(4)23(32)13-14-30(20,5)28(21)24(33)15-22(31)27(25)19(29(35)36)10-8-9-17(2)3/h9,18,20-23,25,28,32H,7-8,10-16H2,1-6H3,(H,35,36)/b27-19-/t18-,20?,21-,22-,23+,25-,28-,30-,31+/m0/s1
InChI Key ISLLRJYHCSQDTN-LFPDIBHUSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C31H46O6
Molecular Weight 514.70 g/mol
Exact Mass 514.32943918 g/mol
Topological Polar Surface Area (TPSA) 101.00 Ų
XlogP 5.30
Atomic LogP (AlogP) 5.87
H-Bond Acceptor 5
H-Bond Donor 2
Rotatable Bonds 6

Synonyms

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(2Z)-2-[(3R,4S,8S,9R,10S,13R,14R,16S)-3-hydroxy-4,10,14-trimethyl-11-oxo-16-propanoyloxy-2,3,4,5,6,7,8,9,12,13,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoic acid
11-Monoketofusidic acid
CHEBI:183845

2D Structure

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2D Structure of (2Z)-2-[(3R,4S,8S,9R,10S,13R,14R,16S)-3-hydroxy-4,10,14-trimethyl-11-oxo-16-propanoyloxy-2,3,4,5,6,7,8,9,12,13,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9958 99.58%
Caco-2 - 0.6269 62.69%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.5429 54.29%
Subcellular localzation Mitochondria 0.8401 84.01%
OATP2B1 inhibitior - 0.8598 85.98%
OATP1B1 inhibitior - 0.3332 33.32%
OATP1B3 inhibitior + 0.8046 80.46%
MATE1 inhibitior - 0.8600 86.00%
OCT2 inhibitior - 0.7500 75.00%
BSEP inhibitior + 0.9483 94.83%
P-glycoprotein inhibitior + 0.8046 80.46%
P-glycoprotein substrate + 0.5350 53.50%
CYP3A4 substrate + 0.7049 70.49%
CYP2C9 substrate - 0.7791 77.91%
CYP2D6 substrate - 0.9072 90.72%
CYP3A4 inhibition - 0.6075 60.75%
CYP2C9 inhibition - 0.8625 86.25%
CYP2C19 inhibition - 0.9129 91.29%
CYP2D6 inhibition - 0.9314 93.14%
CYP1A2 inhibition - 0.9459 94.59%
CYP2C8 inhibition + 0.4767 47.67%
CYP inhibitory promiscuity - 0.7191 71.91%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6928 69.28%
Eye corrosion - 0.9957 99.57%
Eye irritation - 0.9283 92.83%
Skin irritation + 0.6495 64.95%
Skin corrosion - 0.9606 96.06%
Ames mutagenesis - 0.7928 79.28%
Human Ether-a-go-go-Related Gene inhibition - 0.3800 38.00%
Micronuclear - 0.7600 76.00%
Hepatotoxicity + 0.5399 53.99%
skin sensitisation - 0.6939 69.39%
Respiratory toxicity + 0.7778 77.78%
Reproductive toxicity + 0.9889 98.89%
Mitochondrial toxicity + 1.0000 100.00%
Nephrotoxicity - 0.7829 78.29%
Acute Oral Toxicity (c) III 0.4334 43.34%
Estrogen receptor binding + 0.7663 76.63%
Androgen receptor binding + 0.7286 72.86%
Thyroid receptor binding + 0.5412 54.12%
Glucocorticoid receptor binding + 0.8339 83.39%
Aromatase binding + 0.7283 72.83%
PPAR gamma + 0.6010 60.10%
Honey bee toxicity - 0.6556 65.56%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity + 0.5400 54.00%
Fish aquatic toxicity + 1.0000 100.00%

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 97.61% 91.11%
CHEMBL221 P23219 Cyclooxygenase-1 95.31% 90.17%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 93.72% 96.09%
CHEMBL2581 P07339 Cathepsin D 91.39% 98.95%
CHEMBL1902 P62942 FK506-binding protein 1A 91.18% 97.05%
CHEMBL253 P34972 Cannabinoid CB2 receptor 87.51% 97.25%
CHEMBL1994 P08235 Mineralocorticoid receptor 86.19% 100.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 85.26% 95.89%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 84.47% 93.00%
CHEMBL299 P17252 Protein kinase C alpha 83.80% 98.03%
CHEMBL4227 P25090 Lipoxin A4 receptor 83.55% 100.00%
CHEMBL340 P08684 Cytochrome P450 3A4 83.41% 91.19%
CHEMBL1293249 Q13887 Kruppel-like factor 5 83.28% 86.33%
CHEMBL5255 O00206 Toll-like receptor 4 82.90% 92.50%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 82.71% 94.33%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 82.46% 94.45%
CHEMBL233 P35372 Mu opioid receptor 81.57% 97.93%
CHEMBL3137262 O60341 LSD1/CoREST complex 81.41% 97.09%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 80.23% 96.38%
CHEMBL1806 P11388 DNA topoisomerase II alpha 80.15% 89.00%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
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There are no matching plants.

Cross-Links

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PubChem 3082108
LOTUS LTS0243163
wikiData Q105119614