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[(2R,3R,4S,5R,6R)-5-acetyloxy-6-[[(1S,3R,8S,9S,10R,13S,14S,17S)-1-acetyloxy-17-[(1R)-1-acetyloxy-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-3,4-bis[[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy]oxan-2-yl]methyl acetate

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 1ccb7a1a-248c-4d08-a9dd-90c5878b47c3
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives > Withanolide glycosides and derivatives
IUPAC Name [(2R,3R,4S,5R,6R)-5-acetyloxy-6-[[(1S,3R,8S,9S,10R,13S,14S,17S)-1-acetyloxy-17-[(1R)-1-acetyloxy-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-3,4-bis[[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy]oxan-2-yl]methyl acetate
SMILES (Canonical) CC1=C(C(=O)OC(C1)C(C)(C2CCC3C2(CCC4C3CC=C5C4(C(CC(C5)OC6C(C(C(C(O6)COC(=O)C)OC7C(C(C(C(O7)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC8C(C(C(C(O8)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)C)C)OC(=O)C)C
SMILES (Isomeric) CC1=C(C(=O)O[C@H](C1)[C@@](C)([C@H]2CC[C@@H]3[C@@]2(CC[C@H]4[C@H]3CC=C5[C@@]4([C@H](C[C@@H](C5)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)COC(=O)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)C)C)OC(=O)C)C
InChI InChI=1S/C70H96O32/c1-30-24-54(99-64(83)31(30)2)70(17,102-43(14)82)52-21-20-47-46-19-18-44-25-45(26-53(87-35(6)74)69(44,16)48(46)22-23-68(47,52)15)95-65-63(94-42(13)81)60(101-67-62(93-41(12)80)59(91-39(10)78)56(89-37(8)76)50(98-67)28-85-33(4)72)57(51(96-65)29-86-34(5)73)100-66-61(92-40(11)79)58(90-38(9)77)55(88-36(7)75)49(97-66)27-84-32(3)71/h18,45-63,65-67H,19-29H2,1-17H3/t45-,46+,47+,48+,49-,50-,51-,52+,53+,54-,55-,56-,57-,58+,59+,60+,61-,62-,63-,65-,66+,67+,68+,69+,70-/m1/s1
InChI Key GWCAPZYWQIVMDS-ZLOLQBMJSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C70H96O32
Molecular Weight 1449.50 g/mol
Exact Mass 1448.5884709 g/mol
Topological Polar Surface Area (TPSA) 397.00 Ų
XlogP 4.50
Atomic LogP (AlogP) 4.62
H-Bond Acceptor 32
H-Bond Donor 0
Rotatable Bonds 23

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(2R,3R,4S,5R,6R)-5-acetyloxy-6-[[(1S,3R,8S,9S,10R,13S,14S,17S)-1-acetyloxy-17-[(1R)-1-acetyloxy-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-3,4-bis[[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy]oxan-2-yl]methyl acetate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9718 97.18%
Caco-2 - 0.8554 85.54%
Blood Brain Barrier + 0.8000 80.00%
Human oral bioavailability - 0.6286 62.86%
Subcellular localzation Mitochondria 0.8310 83.10%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8443 84.43%
OATP1B3 inhibitior + 0.9151 91.51%
MATE1 inhibitior - 0.7400 74.00%
OCT2 inhibitior - 0.6250 62.50%
BSEP inhibitior + 0.9938 99.38%
P-glycoprotein inhibitior + 0.7494 74.94%
P-glycoprotein substrate + 0.5753 57.53%
CYP3A4 substrate + 0.7705 77.05%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9053 90.53%
CYP3A4 inhibition - 0.8906 89.06%
CYP2C9 inhibition - 0.9475 94.75%
CYP2C19 inhibition - 0.9449 94.49%
CYP2D6 inhibition - 0.9532 95.32%
CYP1A2 inhibition - 0.8869 88.69%
CYP2C8 inhibition + 0.7503 75.03%
CYP inhibitory promiscuity - 0.8647 86.47%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.5497 54.97%
Eye corrosion - 0.9883 98.83%
Eye irritation - 0.8970 89.70%
Skin irritation - 0.5296 52.96%
Skin corrosion - 0.9379 93.79%
Ames mutagenesis - 0.7000 70.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7134 71.34%
Micronuclear - 0.6900 69.00%
Hepatotoxicity - 0.5423 54.23%
skin sensitisation - 0.8901 89.01%
Respiratory toxicity + 0.8444 84.44%
Reproductive toxicity + 0.8889 88.89%
Mitochondrial toxicity + 0.5375 53.75%
Nephrotoxicity + 0.4829 48.29%
Acute Oral Toxicity (c) III 0.4047 40.47%
Estrogen receptor binding + 0.7503 75.03%
Androgen receptor binding + 0.7705 77.05%
Thyroid receptor binding + 0.6407 64.07%
Glucocorticoid receptor binding + 0.7531 75.31%
Aromatase binding + 0.6971 69.71%
PPAR gamma + 0.7703 77.03%
Honey bee toxicity - 0.6590 65.90%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity + 0.6900 69.00%
Fish aquatic toxicity + 0.9850 98.50%

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 97.05% 85.14%
CHEMBL253 P34972 Cannabinoid CB2 receptor 96.89% 97.25%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.30% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 94.75% 91.11%
CHEMBL226 P30542 Adenosine A1 receptor 94.13% 95.93%
CHEMBL1293249 Q13887 Kruppel-like factor 5 93.94% 86.33%
CHEMBL1806 P11388 DNA topoisomerase II alpha 93.82% 89.00%
CHEMBL1937 Q92769 Histone deacetylase 2 91.36% 94.75%
CHEMBL1994 P08235 Mineralocorticoid receptor 91.23% 100.00%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 90.88% 93.04%
CHEMBL5255 O00206 Toll-like receptor 4 90.54% 92.50%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.97% 97.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.30% 95.56%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 88.66% 94.45%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 88.60% 94.00%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 87.79% 95.89%
CHEMBL2782 P35610 Acyl coenzyme A:cholesterol acyltransferase 1 86.87% 91.65%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 86.68% 99.23%
CHEMBL1871 P10275 Androgen Receptor 86.28% 96.43%
CHEMBL340 P08684 Cytochrome P450 3A4 86.17% 91.19%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 85.15% 96.95%
CHEMBL5028 O14672 ADAM10 84.88% 97.50%
CHEMBL3359 P21462 Formyl peptide receptor 1 84.23% 93.56%
CHEMBL3401 O75469 Pregnane X receptor 83.91% 94.73%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 83.06% 97.14%
CHEMBL5103 Q969S8 Histone deacetylase 10 82.75% 90.08%
CHEMBL3475 P05121 Plasminogen activator inhibitor-1 82.60% 83.00%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 82.28% 92.62%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 81.16% 91.07%

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.
Eriolarynx australis

Cross-Links

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PubChem 163023940
LOTUS LTS0251522
wikiData Q105022163