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ethyl (2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8R,8aR,9R,10R,12aS,14aR,14bR)-9-acetyloxy-10-benzoyloxy-8-hydroxy-4,4,6a,6b,11,11,14b-heptamethyl-8a-[[(2R,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxymethyl]-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3-hydroxy-4,5-bis[[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy]oxane-2-carboxylate

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 c79e8546-6f12-4164-a9f3-c8c7a88d9260
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
IUPAC Name ethyl (2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8R,8aR,9R,10R,12aS,14aR,14bR)-9-acetyloxy-10-benzoyloxy-8-hydroxy-4,4,6a,6b,11,11,14b-heptamethyl-8a-[[(2R,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxymethyl]-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3-hydroxy-4,5-bis[[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy]oxane-2-carboxylate
SMILES (Canonical) CCOC(=O)C1C(C(C(C(O1)OC2CCC3(C(C2(C)C)CCC4(C3CC=C5C4(CC(C6(C5CC(C(C6OC(=O)C)OC(=O)C7=CC=CC=C7)(C)C)COC8C(C(C(C(O8)C)OC(=O)C)OC(=O)C)OC(=O)C)O)C)C)C)OC9C(C(C(C(O9)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC1C(C(C(C(O1)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)O
SMILES (Isomeric) CCOC(=O)[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@H]2CC[C@]3([C@H](C2(C)C)CC[C@@]4([C@@H]3CC=C5[C@]4(C[C@H]([C@@]6([C@H]5CC([C@H]([C@@H]6OC(=O)C)OC(=O)C7=CC=CC=C7)(C)C)CO[C@H]8[C@@H]([C@@H]([C@H]([C@@H](O8)C)OC(=O)C)OC(=O)C)OC(=O)C)O)C)C)C)O[C@H]9[C@@H]([C@H]([C@H]([C@H](O9)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)O[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)O
InChI InChI=1S/C87H120O38/c1-22-104-77(103)66-61(101)65(122-79-72(116-49(12)97)68(113-46(9)94)63(110-43(6)91)55(119-79)36-105-40(3)88)70(124-80-73(117-50(13)98)69(114-47(10)95)64(111-44(7)92)56(120-80)37-106-41(4)89)81(123-66)121-60-31-32-84(19)57(83(60,17)18)30-33-85(20)58(84)29-28-53-54-34-82(15,16)74(125-76(102)52-26-24-23-25-27-52)75(118-51(14)99)87(54,59(100)35-86(53,85)21)38-107-78-71(115-48(11)96)67(112-45(8)93)62(39(2)108-78)109-42(5)90/h23-28,39,54-75,78-81,100-101H,22,29-38H2,1-21H3/t39-,54-,55+,56+,57-,58+,59+,60-,61-,62-,63-,64-,65-,66-,67+,68-,69-,70+,71+,72+,73+,74-,75-,78+,79-,80-,81+,84-,85+,86+,87-/m0/s1
InChI Key SCMGCFOGZMBCEM-VVXIHMJLSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C87H120O38
Molecular Weight 1773.90 g/mol
Exact Mass 1772.7457594 g/mol
Topological Polar Surface Area (TPSA) 483.00 Ų
XlogP 7.20
Atomic LogP (AlogP) 5.66
H-Bond Acceptor 38
H-Bond Donor 2
Rotatable Bonds 27

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of ethyl (2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8R,8aR,9R,10R,12aS,14aR,14bR)-9-acetyloxy-10-benzoyloxy-8-hydroxy-4,4,6a,6b,11,11,14b-heptamethyl-8a-[[(2R,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxymethyl]-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3-hydroxy-4,5-bis[[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy]oxane-2-carboxylate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9740 97.40%
Caco-2 - 0.8565 85.65%
Blood Brain Barrier + 0.7000 70.00%
Human oral bioavailability - 0.6857 68.57%
Subcellular localzation Mitochondria 0.8628 86.28%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.7716 77.16%
OATP1B3 inhibitior + 0.7951 79.51%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.7526 75.26%
BSEP inhibitior + 0.9804 98.04%
P-glycoprotein inhibitior + 0.7428 74.28%
P-glycoprotein substrate + 0.6720 67.20%
CYP3A4 substrate + 0.7563 75.63%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8785 87.85%
CYP3A4 inhibition + 0.6051 60.51%
CYP2C9 inhibition - 0.8133 81.33%
CYP2C19 inhibition - 0.8258 82.58%
CYP2D6 inhibition - 0.9255 92.55%
CYP1A2 inhibition - 0.8142 81.42%
CYP2C8 inhibition + 0.8540 85.40%
CYP inhibitory promiscuity - 0.8921 89.21%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.5485 54.85%
Eye corrosion - 0.9918 99.18%
Eye irritation - 0.8957 89.57%
Skin irritation - 0.5782 57.82%
Skin corrosion - 0.9510 95.10%
Ames mutagenesis - 0.6800 68.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7271 72.71%
Micronuclear - 0.7500 75.00%
Hepatotoxicity - 0.7108 71.08%
skin sensitisation - 0.8874 88.74%
Respiratory toxicity + 0.6111 61.11%
Reproductive toxicity + 0.9000 90.00%
Mitochondrial toxicity + 0.5500 55.00%
Nephrotoxicity - 0.6856 68.56%
Acute Oral Toxicity (c) III 0.6599 65.99%
Estrogen receptor binding - 0.5111 51.11%
Androgen receptor binding + 0.7618 76.18%
Thyroid receptor binding + 0.7849 78.49%
Glucocorticoid receptor binding + 0.8352 83.52%
Aromatase binding + 0.7674 76.74%
PPAR gamma + 0.8104 81.04%
Honey bee toxicity - 0.6509 65.09%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity + 0.5100 51.00%
Fish aquatic toxicity + 0.9942 99.42%

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
CHEMBL221 P23219 Cyclooxygenase-1 96.18% 90.17%
CHEMBL1293249 Q13887 Kruppel-like factor 5 95.61% 86.33%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.12% 96.09%
CHEMBL2581 P07339 Cathepsin D 94.51% 98.95%
CHEMBL5028 O14672 ADAM10 91.37% 97.50%
CHEMBL2782 P35610 Acyl coenzyme A:cholesterol acyltransferase 1 91.29% 91.65%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 89.65% 99.23%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 87.97% 91.11%
CHEMBL1293277 O15118 Niemann-Pick C1 protein 87.83% 81.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 87.04% 95.56%
CHEMBL3401 O75469 Pregnane X receptor 86.73% 94.73%
CHEMBL1293294 P51151 Ras-related protein Rab-9A 85.62% 87.67%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 84.69% 95.50%
CHEMBL3475 P05121 Plasminogen activator inhibitor-1 84.23% 83.00%
CHEMBL226 P30542 Adenosine A1 receptor 83.40% 95.93%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 83.17% 96.21%
CHEMBL5255 O00206 Toll-like receptor 4 83.03% 92.50%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 82.74% 96.77%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 82.51% 82.69%
CHEMBL5608 Q16288 NT-3 growth factor receptor 82.34% 95.89%
CHEMBL3060 Q9Y345 Glycine transporter 2 82.27% 99.17%
CHEMBL3359 P21462 Formyl peptide receptor 1 82.05% 93.56%
CHEMBL1994 P08235 Mineralocorticoid receptor 81.92% 100.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 81.64% 89.00%
CHEMBL340 P08684 Cytochrome P450 3A4 81.59% 91.19%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 80.86% 97.21%
CHEMBL4227 P25090 Lipoxin A4 receptor 80.57% 100.00%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 80.37% 92.62%

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.
Petersianthus macrocarpus

Cross-Links

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PubChem 101635467
LOTUS LTS0271756
wikiData Q105250274