[(E,6R)-6-hydroxy-2-methyl-5-oxo-6-[(7S,8S,9S,10R,13R,14S,16R,17R)-2,7,16-trihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthren-17-yl]hept-3-en-2-yl] acetate

Details

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Internal ID 613c8919-b929-4d01-981a-4dd755df1900
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Cucurbitacins
IUPAC Name [(E,6R)-6-hydroxy-2-methyl-5-oxo-6-[(7S,8S,9S,10R,13R,14S,16R,17R)-2,7,16-trihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthren-17-yl]hept-3-en-2-yl] acetate
SMILES (Canonical) CC(=O)OC(C)(C)C=CC(=O)C(C)(C1C(CC2(C1(CC(=O)C3(C2C(C=C4C3C=C(C(=O)C4(C)C)O)O)C)C)C)O)O
SMILES (Isomeric) CC(=O)OC(C)(C)/C=C/C(=O)[C@@](C)([C@H]1[C@@H](C[C@@]2([C@@]1(CC(=O)[C@@]3([C@H]2[C@H](C=C4[C@H]3C=C(C(=O)C4(C)C)O)O)C)C)C)O)O
InChI InChI=1S/C32H44O9/c1-16(33)41-27(2,3)11-10-22(37)32(9,40)25-21(36)14-29(6)24-19(34)12-17-18(13-20(35)26(39)28(17,4)5)31(24,8)23(38)15-30(25,29)7/h10-13,18-19,21,24-25,34-36,40H,14-15H2,1-9H3/b11-10+/t18-,19+,21-,24+,25+,29+,30-,31-,32+/m1/s1
InChI Key SGUCHYFOTGXDTG-IEPPCUIASA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C32H44O9
Molecular Weight 572.70 g/mol
Exact Mass 572.29853298 g/mol
Topological Polar Surface Area (TPSA) 158.00 Ų
XlogP 2.10
Atomic LogP (AlogP) 3.16
H-Bond Acceptor 9
H-Bond Donor 4
Rotatable Bonds 5

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(E,6R)-6-hydroxy-2-methyl-5-oxo-6-[(7S,8S,9S,10R,13R,14S,16R,17R)-2,7,16-trihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthren-17-yl]hept-3-en-2-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 + 0.9856 98.56%
Caco-2 - 0.7819 78.19%
Blood Brain Barrier + 0.6250 62.50%
Human oral bioavailability - 0.6571 65.71%
Subcellular localzation Mitochondria 0.7731 77.31%
OATP2B1 inhibitior + 0.5644 56.44%
OATP1B1 inhibitior + 0.8287 82.87%
OATP1B3 inhibitior + 0.8366 83.66%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior + 0.7452 74.52%
P-glycoprotein inhibitior + 0.7109 71.09%
P-glycoprotein substrate + 0.5146 51.46%
CYP3A4 substrate + 0.7204 72.04%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9119 91.19%
CYP3A4 inhibition - 0.7135 71.35%
CYP2C9 inhibition - 0.8849 88.49%
CYP2C19 inhibition - 0.9079 90.79%
CYP2D6 inhibition - 0.9475 94.75%
CYP1A2 inhibition - 0.8531 85.31%
CYP2C8 inhibition + 0.5940 59.40%
CYP inhibitory promiscuity - 0.8940 89.40%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5810 58.10%
Eye corrosion - 0.9922 99.22%
Eye irritation - 0.8986 89.86%
Skin irritation + 0.6111 61.11%
Skin corrosion - 0.9452 94.52%
Ames mutagenesis - 0.6600 66.00%
Human Ether-a-go-go-Related Gene inhibition - 0.6070 60.70%
Micronuclear - 0.5900 59.00%
Hepatotoxicity - 0.5125 51.25%
skin sensitisation - 0.7520 75.20%
Respiratory toxicity + 0.7444 74.44%
Reproductive toxicity + 0.9667 96.67%
Mitochondrial toxicity + 0.9500 95.00%
Nephrotoxicity - 0.5885 58.85%
Acute Oral Toxicity (c) I 0.7875 78.75%
Estrogen receptor binding + 0.7425 74.25%
Androgen receptor binding + 0.7123 71.23%
Thyroid receptor binding + 0.6109 61.09%
Glucocorticoid receptor binding + 0.7516 75.16%
Aromatase binding + 0.7425 74.25%
PPAR gamma + 0.6326 63.26%
Honey bee toxicity - 0.6593 65.93%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.5300 53.00%
Fish aquatic toxicity + 0.9969 99.69%

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
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 98.95% 85.14%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.63% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 95.22% 94.45%
CHEMBL2581 P07339 Cathepsin D 94.99% 98.95%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 93.68% 96.09%
CHEMBL1902 P62942 FK506-binding protein 1A 93.16% 97.05%
CHEMBL1293249 Q13887 Kruppel-like factor 5 91.23% 86.33%
CHEMBL217 P14416 Dopamine D2 receptor 88.69% 95.62%
CHEMBL3137262 O60341 LSD1/CoREST complex 88.68% 97.09%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 86.09% 99.23%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 85.93% 95.56%
CHEMBL1994 P08235 Mineralocorticoid receptor 85.68% 100.00%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 84.99% 96.95%
CHEMBL253 P34972 Cannabinoid CB2 receptor 82.80% 97.25%
CHEMBL340 P08684 Cytochrome P450 3A4 82.00% 91.19%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.97% 95.89%
CHEMBL1951 P21397 Monoamine oxidase A 80.13% 91.49%
CHEMBL1293294 P51151 Ras-related protein Rab-9A 80.03% 87.67%

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.
Aglaia elliptica
Bacopa monnieri
Catananche caerulea
Cirsium wallichii
Corydalis calliantha
Fritillaria cirrhosa
Phebalium whitei
Quassia indica
Rosa agrestis
Rumex nepalensis
Salvia urolepis
Strychnos lucida
Vitis betulifolia

Cross-Links

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PubChem 16216753
NPASS NPC309140
LOTUS LTS0187554
wikiData Q105252622