PlantaeDB Logo
Login Sign-up

1-[(3S,5S,8S,9R,10R,12R,13R,14R,17S)-5,8,14,17-tetrahydroxy-3-[(2R,4S,5R,6R)-5-[(2S,4S,5R,6R)-5-[(2S,4R,5R,6R)-5-[(2S,3R,4S,5R,6R)-3-hydroxy-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-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-12-[(E)-3-phenylprop-2-enoyl]oxy-2,3,4,9,11,12,15,16-octahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl (E)-2-methylbut-2-enoate

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

Top
Internal ID 1b2053f3-9d8e-4550-b720-2c2e9c57d529
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
IUPAC Name 1-[(3S,5S,8S,9R,10R,12R,13R,14R,17S)-5,8,14,17-tetrahydroxy-3-[(2R,4S,5R,6R)-5-[(2S,4S,5R,6R)-5-[(2S,4R,5R,6R)-5-[(2S,3R,4S,5R,6R)-3-hydroxy-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-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-12-[(E)-3-phenylprop-2-enoyl]oxy-2,3,4,9,11,12,15,16-octahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl (E)-2-methylbut-2-enoate
SMILES (Canonical) CC=C(C)C(=O)OC(C)C1(CCC2(C1(C(CC3C2(C=CC4(C3(CCC(C4)OC5CC(C(C(O5)C)OC6CC(C(C(O6)C)OC7CC(C(C(O7)C)OC8C(C(C(C(O8)C)OC9C(C(C(C(O9)CO)O)O)O)OC)O)OC)OC)OC)C)O)O)OC(=O)C=CC1=CC=CC=C1)C)O)O
SMILES (Isomeric) C/C=C(\C)/C(=O)OC(C)[C@@]1(CC[C@]2([C@@]1([C@@H](C[C@H]3[C@]2(C=C[C@@]4([C@@]3(CC[C@@H](C4)O[C@H]5C[C@@H]([C@@H]([C@H](O5)C)O[C@H]6C[C@@H]([C@@H]([C@H](O6)C)O[C@H]7C[C@H]([C@@H]([C@H](O7)C)O[C@H]8[C@@H]([C@@H]([C@@H]([C@H](O8)C)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)OC)O)OC)OC)OC)C)O)O)OC(=O)/C=C/C1=CC=CC=C1)C)O)O
InChI InChI=1S/C69H104O27/c1-14-34(2)61(76)89-39(7)67(78)26-27-69(80)65(67,9)47(92-48(71)21-20-40-18-16-15-17-19-40)31-46-64(8)23-22-41(32-66(64,77)24-25-68(46,69)79)90-49-28-42(81-10)56(35(3)85-49)93-50-29-43(82-11)57(36(4)86-50)94-51-30-44(83-12)58(37(5)87-51)95-63-55(75)60(84-13)59(38(6)88-63)96-62-54(74)53(73)52(72)45(33-70)91-62/h14-21,24-25,35-39,41-47,49-60,62-63,70,72-75,77-80H,22-23,26-33H2,1-13H3/b21-20+,34-14+/t35-,36-,37-,38-,39?,41+,42+,43+,44-,45-,46-,47-,49+,50+,51+,52-,53+,54-,55-,56-,57-,58-,59-,60+,62+,63+,64-,65-,66-,67-,68+,69-/m1/s1
InChI Key ZSVSPQCGTYJLNZ-VAUHWWNBSA-N
Popularity 0 references in papers

Physical and Chemical Properties

Top
Molecular Formula C69H104O27
Molecular Weight 1365.50 g/mol
Exact Mass 1364.67649804 g/mol
Topological Polar Surface Area (TPSA) 364.00 Ų
XlogP 2.30
Atomic LogP (AlogP) 2.31
H-Bond Acceptor 27
H-Bond Donor 9
Rotatable Bonds 21

Synonyms

Top
There are no found synonyms.

2D Structure

Top
2D Structure of 1-[(3S,5S,8S,9R,10R,12R,13R,14R,17S)-5,8,14,17-tetrahydroxy-3-[(2R,4S,5R,6R)-5-[(2S,4S,5R,6R)-5-[(2S,4R,5R,6R)-5-[(2S,3R,4S,5R,6R)-3-hydroxy-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-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-12-[(E)-3-phenylprop-2-enoyl]oxy-2,3,4,9,11,12,15,16-octahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl (E)-2-methylbut-2-enoate

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8058 80.58%
Caco-2 - 0.8590 85.90%
Blood Brain Barrier - 0.5500 55.00%
Human oral bioavailability - 0.8286 82.86%
Subcellular localzation Mitochondria 0.7408 74.08%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8086 80.86%
OATP1B3 inhibitior + 0.9112 91.12%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.7553 75.53%
BSEP inhibitior + 0.9755 97.55%
P-glycoprotein inhibitior + 0.7439 74.39%
P-glycoprotein substrate + 0.7861 78.61%
CYP3A4 substrate + 0.7482 74.82%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8906 89.06%
CYP3A4 inhibition - 0.7502 75.02%
CYP2C9 inhibition - 0.8886 88.86%
CYP2C19 inhibition - 0.9128 91.28%
CYP2D6 inhibition - 0.9419 94.19%
CYP1A2 inhibition - 0.8652 86.52%
CYP2C8 inhibition + 0.8069 80.69%
CYP inhibitory promiscuity - 0.9427 94.27%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6480 64.80%
Eye corrosion - 0.9920 99.20%
Eye irritation - 0.8967 89.67%
Skin irritation - 0.5458 54.58%
Skin corrosion - 0.9476 94.76%
Ames mutagenesis - 0.6440 64.40%
Human Ether-a-go-go-Related Gene inhibition + 0.8025 80.25%
Micronuclear - 0.7500 75.00%
Hepatotoxicity - 0.6387 63.87%
skin sensitisation - 0.9219 92.19%
Respiratory toxicity + 0.6889 68.89%
Reproductive toxicity + 0.9444 94.44%
Mitochondrial toxicity + 0.7125 71.25%
Nephrotoxicity - 0.9675 96.75%
Acute Oral Toxicity (c) I 0.6440 64.40%
Estrogen receptor binding + 0.6772 67.72%
Androgen receptor binding + 0.7696 76.96%
Thyroid receptor binding + 0.7351 73.51%
Glucocorticoid receptor binding + 0.8062 80.62%
Aromatase binding + 0.6831 68.31%
PPAR gamma + 0.8106 81.06%
Honey bee toxicity - 0.6181 61.81%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity + 0.6045 60.45%
Fish aquatic toxicity + 0.9638 96.38%

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
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 99.61% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.88% 96.09%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 97.73% 96.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 96.73% 86.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 95.74% 95.56%
CHEMBL4302 P08183 P-glycoprotein 1 94.75% 92.98%
CHEMBL2716 Q8WUI4 Histone deacetylase 7 94.20% 89.44%
CHEMBL1806 P11388 DNA topoisomerase II alpha 94.04% 89.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.06% 97.09%
CHEMBL2581 P07339 Cathepsin D 92.97% 98.95%
CHEMBL226 P30542 Adenosine A1 receptor 92.58% 95.93%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 91.63% 94.62%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 90.79% 93.00%
CHEMBL216 P11229 Muscarinic acetylcholine receptor M1 90.73% 94.23%
CHEMBL4227 P25090 Lipoxin A4 receptor 89.08% 100.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 88.24% 95.89%
CHEMBL5028 O14672 ADAM10 87.49% 97.50%
CHEMBL3359 P21462 Formyl peptide receptor 1 87.38% 93.56%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 87.03% 95.50%
CHEMBL1937 Q92769 Histone deacetylase 2 85.90% 94.75%
CHEMBL3714130 P46095 G-protein coupled receptor 6 85.53% 97.36%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 83.37% 92.62%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 83.09% 94.08%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 83.07% 100.00%
CHEMBL1994 P08235 Mineralocorticoid receptor 83.01% 100.00%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 82.33% 91.07%
CHEMBL3060 Q9Y345 Glycine transporter 2 81.81% 99.17%
CHEMBL221 P23219 Cyclooxygenase-1 81.69% 90.17%
CHEMBL2243 O00519 Anandamide amidohydrolase 81.41% 97.53%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 81.04% 97.14%
CHEMBL3130 O00329 PI3-kinase p110-delta subunit 80.88% 96.47%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 80.69% 99.23%
CHEMBL2563 Q9UQL6 Histone deacetylase 5 80.26% 89.67%

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.
Gymnema sylvestre

Cross-Links

Top
PubChem 101948681
LOTUS LTS0210256
wikiData Q105382755