[(3S,5R,6S)-5-acetyloxy-6-[[(8R,9R,10S,13R,14S,16R,17R)-17-[(E,2R)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-2-hydroxy-4,4,9,13,14-pentamethyl-3-oxo-7,8,10,11,12,15,16,17-octahydrocyclopenta[a]phenanthren-16-yl]oxy]-4-hydroxyoxan-3-yl] acetate

Details

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Internal ID 6a998032-06bf-4f2c-a3b9-d51fa08c2a7f
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
IUPAC Name [(3S,5R,6S)-5-acetyloxy-6-[[(8R,9R,10S,13R,14S,16R,17R)-17-[(E,2R)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-2-hydroxy-4,4,9,13,14-pentamethyl-3-oxo-7,8,10,11,12,15,16,17-octahydrocyclopenta[a]phenanthren-16-yl]oxy]-4-hydroxyoxan-3-yl] acetate
SMILES (Canonical) CC(=O)OC1COC(C(C1O)OC(=O)C)OC2CC3(C4CC=C5C(C4(CCC3(C2C(C)(C(=O)C=CC(C)(C)O)O)C)C)C=C(C(=O)C5(C)C)O)C
SMILES (Isomeric) CC(=O)O[C@H]1CO[C@H]([C@@H](C1O)OC(=O)C)O[C@@H]2C[C@]3([C@@H]4CC=C5[C@H]([C@@]4(CC[C@@]3([C@H]2[C@](C)(C(=O)/C=C/C(C)(C)O)O)C)C)C=C(C(=O)C5(C)C)O)C
InChI InChI=1S/C39H56O12/c1-20(40)49-26-19-48-33(30(29(26)44)50-21(2)41)51-25-18-38(9)27-12-11-22-23(17-24(42)32(45)35(22,5)6)36(27,7)15-16-37(38,8)31(25)39(10,47)28(43)13-14-34(3,4)46/h11,13-14,17,23,25-27,29-31,33,42,44,46-47H,12,15-16,18-19H2,1-10H3/b14-13+/t23-,25-,26+,27-,29?,30-,31+,33+,36+,37-,38+,39+/m1/s1
InChI Key UODJOGKPOAZZHT-LDAOOKBTSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C39H56O12
Molecular Weight 716.90 g/mol
Exact Mass 716.37717722 g/mol
Topological Polar Surface Area (TPSA) 186.00 Ų
XlogP 3.40
Atomic LogP (AlogP) 4.05
H-Bond Acceptor 12
H-Bond Donor 4
Rotatable Bonds 8

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(3S,5R,6S)-5-acetyloxy-6-[[(8R,9R,10S,13R,14S,16R,17R)-17-[(E,2R)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-2-hydroxy-4,4,9,13,14-pentamethyl-3-oxo-7,8,10,11,12,15,16,17-octahydrocyclopenta[a]phenanthren-16-yl]oxy]-4-hydroxyoxan-3-yl] acetate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9715 97.15%
Caco-2 - 0.8391 83.91%
Blood Brain Barrier + 0.5250 52.50%
Human oral bioavailability - 0.7286 72.86%
Subcellular localzation Mitochondria 0.9002 90.02%
OATP2B1 inhibitior - 0.8574 85.74%
OATP1B1 inhibitior + 0.8103 81.03%
OATP1B3 inhibitior + 0.8682 86.82%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior + 0.5327 53.27%
BSEP inhibitior + 0.8977 89.77%
P-glycoprotein inhibitior + 0.7947 79.47%
P-glycoprotein substrate + 0.5585 55.85%
CYP3A4 substrate + 0.7368 73.68%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9015 90.15%
CYP3A4 inhibition - 0.8898 88.98%
CYP2C9 inhibition - 0.8032 80.32%
CYP2C19 inhibition - 0.9250 92.50%
CYP2D6 inhibition - 0.9426 94.26%
CYP1A2 inhibition - 0.6373 63.73%
CYP2C8 inhibition + 0.6983 69.83%
CYP inhibitory promiscuity - 0.9066 90.66%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.6151 61.51%
Eye corrosion - 0.9910 99.10%
Eye irritation - 0.9129 91.29%
Skin irritation + 0.5338 53.38%
Skin corrosion - 0.9405 94.05%
Ames mutagenesis + 0.5100 51.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5052 50.52%
Micronuclear - 0.7100 71.00%
Hepatotoxicity - 0.5750 57.50%
skin sensitisation - 0.8820 88.20%
Respiratory toxicity + 0.6778 67.78%
Reproductive toxicity + 0.9778 97.78%
Mitochondrial toxicity + 0.6000 60.00%
Nephrotoxicity - 0.6699 66.99%
Acute Oral Toxicity (c) III 0.4537 45.37%
Estrogen receptor binding + 0.7554 75.54%
Androgen receptor binding + 0.7292 72.92%
Thyroid receptor binding + 0.5802 58.02%
Glucocorticoid receptor binding + 0.7947 79.47%
Aromatase binding + 0.6858 68.58%
PPAR gamma + 0.7639 76.39%
Honey bee toxicity - 0.5907 59.07%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity + 0.5700 57.00%
Fish aquatic toxicity + 0.9911 99.11%

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 98.83% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 96.93% 94.45%
CHEMBL253 P34972 Cannabinoid CB2 receptor 96.88% 97.25%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 93.91% 96.77%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 91.37% 91.07%
CHEMBL2581 P07339 Cathepsin D 91.22% 98.95%
CHEMBL1806 P11388 DNA topoisomerase II alpha 90.47% 89.00%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 90.41% 94.08%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.90% 95.56%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 89.38% 96.09%
CHEMBL1293255 P15428 15-hydroxyprostaglandin dehydrogenase [NAD+] 87.48% 83.57%
CHEMBL1994 P08235 Mineralocorticoid receptor 85.26% 100.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 84.58% 99.23%
CHEMBL221 P23219 Cyclooxygenase-1 84.22% 90.17%
CHEMBL3137262 O60341 LSD1/CoREST complex 82.77% 97.09%
CHEMBL1293294 P51151 Ras-related protein Rab-9A 82.19% 87.67%
CHEMBL5608 Q16288 NT-3 growth factor receptor 81.77% 95.89%
CHEMBL2274 Q9H228 Sphingosine 1-phosphate receptor Edg-8 81.00% 100.00%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 80.05% 97.14%
CHEMBL5469 Q14289 Protein tyrosine kinase 2 beta 80.01% 91.03%

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.
Achyranthes bidentata
Bupleurum falcatum
Codonopsis pilosula
Platycodon grandiflorus
Trichosanthes kirilowii

Cross-Links

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PubChem 6326071
NPASS NPC84462