[(3S,8R,9S,10R,12R,13S,14S,17S)-17-acetyl-14,17-dihydroxy-3-[(2R,4S,5R,6R)-5-[(2S,4R,5S,6S)-5-[(2S,4R,5S,6S)-5-[(2S,4S,5R,6R)-5-[(2S,4S,5S,6R)-4-hydroxy-5-[(2S,4R,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-10,13-dimethyl-2,3,4,7,8,9,11,12,15,16-decahydro-1H-cyclopenta[a]phenanthren-12-yl] acetate

Details

Top
Internal ID e7d3f614-e9cf-4dd6-99ab-c97dc77d7872
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
IUPAC Name [(3S,8R,9S,10R,12R,13S,14S,17S)-17-acetyl-14,17-dihydroxy-3-[(2R,4S,5R,6R)-5-[(2S,4R,5S,6S)-5-[(2S,4R,5S,6S)-5-[(2S,4S,5R,6R)-5-[(2S,4S,5S,6R)-4-hydroxy-5-[(2S,4R,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-10,13-dimethyl-2,3,4,7,8,9,11,12,15,16-decahydro-1H-cyclopenta[a]phenanthren-12-yl] acetate
SMILES (Canonical) CC1C(C(CC(O1)OC2C(OC(CC2O)OC3C(OC(CC3OC)OC4C(OC(CC4OC)OC5C(OC(CC5OC)OC6C(OC(CC6OC)OC7CCC8(C9CC(C1(C(C9CC=C8C7)(CCC1(C(=O)C)O)O)C)OC(=O)C)C)C)C)C)C)C)OC)O
SMILES (Isomeric) C[C@H]1[C@@H]([C@@H](C[C@@H](O1)O[C@@H]2[C@H](O[C@H](C[C@@H]2O)O[C@@H]3[C@H](O[C@H](C[C@@H]3OC)O[C@H]4[C@@H](O[C@H](C[C@H]4OC)O[C@H]5[C@@H](O[C@H](C[C@H]5OC)O[C@@H]6[C@H](O[C@H](C[C@@H]6OC)O[C@H]7CC[C@@]8([C@H]9C[C@H]([C@]1([C@@]([C@@H]9CC=C8C7)(CC[C@]1(C(=O)C)O)O)C)OC(=O)C)C)C)C)C)C)C)OC)O
InChI InChI=1S/C64H104O24/c1-30-55(68)43(71-11)25-51(76-30)84-56-31(2)77-49(24-42(56)67)85-57-33(4)79-52(27-45(57)73-13)87-59-35(6)81-54(29-47(59)75-15)88-60-34(5)80-53(28-46(60)74-14)86-58-32(3)78-50(26-44(58)72-12)83-39-18-19-61(9)38(22-39)16-17-40-41(61)23-48(82-37(8)66)62(10)63(69,36(7)65)20-21-64(40,62)70/h16,30-35,39-60,67-70H,17-29H2,1-15H3/t30-,31+,32+,33+,34-,35-,39-,40+,41-,42-,43+,44-,45-,46+,47+,48+,49-,50-,51-,52-,53-,54-,55-,56+,57+,58+,59-,60-,61-,62+,63+,64-/m0/s1
InChI Key NGBYNFODEMEVDO-VEUWDPGSSA-N
Popularity 0 references in papers

Physical and Chemical Properties

Top
Molecular Formula C64H104O24
Molecular Weight 1257.50 g/mol
Exact Mass 1256.69175418 g/mol
Topological Polar Surface Area (TPSA) 281.00 Ų
XlogP 3.20
Atomic LogP (AlogP) 4.84
H-Bond Acceptor 24
H-Bond Donor 4
Rotatable Bonds 19

Synonyms

Top
There are no found synonyms.

2D Structure

Top
2D Structure of [(3S,8R,9S,10R,12R,13S,14S,17S)-17-acetyl-14,17-dihydroxy-3-[(2R,4S,5R,6R)-5-[(2S,4R,5S,6S)-5-[(2S,4R,5S,6S)-5-[(2S,4S,5R,6R)-5-[(2S,4S,5S,6R)-4-hydroxy-5-[(2S,4R,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-10,13-dimethyl-2,3,4,7,8,9,11,12,15,16-decahydro-1H-cyclopenta[a]phenanthren-12-yl] acetate

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9426 94.26%
Caco-2 - 0.8636 86.36%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.5714 57.14%
Subcellular localzation Mitochondria 0.7305 73.05%
OATP2B1 inhibitior - 0.8713 87.13%
OATP1B1 inhibitior + 0.8830 88.30%
OATP1B3 inhibitior + 0.9218 92.18%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.6374 63.74%
BSEP inhibitior + 0.9805 98.05%
P-glycoprotein inhibitior + 0.7488 74.88%
P-glycoprotein substrate + 0.6976 69.76%
CYP3A4 substrate + 0.7396 73.96%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8921 89.21%
CYP3A4 inhibition - 0.8515 85.15%
CYP2C9 inhibition - 0.9153 91.53%
CYP2C19 inhibition - 0.9382 93.82%
CYP2D6 inhibition - 0.9466 94.66%
CYP1A2 inhibition - 0.8666 86.66%
CYP2C8 inhibition + 0.5876 58.76%
CYP inhibitory promiscuity - 0.9532 95.32%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.5261 52.61%
Eye corrosion - 0.9910 99.10%
Eye irritation - 0.9004 90.04%
Skin irritation + 0.5649 56.49%
Skin corrosion - 0.9199 91.99%
Ames mutagenesis - 0.5900 59.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7690 76.90%
Micronuclear - 0.6900 69.00%
Hepatotoxicity - 0.6250 62.50%
skin sensitisation - 0.8778 87.78%
Respiratory toxicity + 0.6222 62.22%
Reproductive toxicity + 0.9889 98.89%
Mitochondrial toxicity + 0.8875 88.75%
Nephrotoxicity - 0.7806 78.06%
Acute Oral Toxicity (c) I 0.3844 38.44%
Estrogen receptor binding + 0.8225 82.25%
Androgen receptor binding + 0.7709 77.09%
Thyroid receptor binding + 0.6285 62.85%
Glucocorticoid receptor binding + 0.8074 80.74%
Aromatase binding + 0.7285 72.85%
PPAR gamma + 0.8411 84.11%
Honey bee toxicity - 0.6334 63.34%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity + 0.5900 59.00%
Fish aquatic toxicity + 0.9550 95.50%

Targets

Top

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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 99.28% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.28% 91.11%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 96.53% 85.14%
CHEMBL1994 P08235 Mineralocorticoid receptor 93.97% 100.00%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 90.70% 95.89%
CHEMBL1806 P11388 DNA topoisomerase II alpha 90.23% 89.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.14% 97.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 88.95% 94.45%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 88.91% 91.07%
CHEMBL1293249 Q13887 Kruppel-like factor 5 86.75% 86.33%
CHEMBL340 P08684 Cytochrome P450 3A4 85.00% 91.19%
CHEMBL5608 Q16288 NT-3 growth factor receptor 84.14% 95.89%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 83.94% 97.14%
CHEMBL5255 O00206 Toll-like receptor 4 83.39% 92.50%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 83.35% 92.62%
CHEMBL241 Q14432 Phosphodiesterase 3A 82.62% 92.94%
CHEMBL5028 O14672 ADAM10 81.67% 97.50%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 81.64% 94.00%
CHEMBL253 P34972 Cannabinoid CB2 receptor 80.62% 97.25%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 80.28% 99.23%
CHEMBL4040 P28482 MAP kinase ERK2 80.25% 83.82%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 80.11% 95.56%

Plants that contains it

Top
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.
Carthamus tinctorius

Cross-Links

Top
PubChem 163191889
LOTUS LTS0190141
wikiData Q105300830