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(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[[(3S,8R,9S,10R,13R,14S,17R)-4,4,10,13,14-pentamethyl-17-[(2R)-6-methylhept-5-en-2-yl]-2,3,7,8,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]oxane-2-carboxylic acid

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 79d34aa5-7096-4746-8fbe-fe12fa71aff6
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
IUPAC Name (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[[(3S,8R,9S,10R,13R,14S,17R)-4,4,10,13,14-pentamethyl-17-[(2R)-6-methylhept-5-en-2-yl]-2,3,7,8,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]oxane-2-carboxylic acid
SMILES (Canonical) CC(CCC=C(C)C)C1CCC2(C1(CCC3C2CC=C4C3(CCC(C4(C)C)OC5C(C(C(C(O5)C(=O)O)O)O)O)C)C)C
SMILES (Isomeric) C[C@H](CCC=C(C)C)[C@H]1CC[C@@]2([C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4(C)C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)C(=O)O)O)O)O)C)C)C
InChI InChI=1S/C36H58O7/c1-20(2)10-9-11-21(3)22-14-18-36(8)24-12-13-25-33(4,5)26(16-17-34(25,6)23(24)15-19-35(22,36)7)42-32-29(39)27(37)28(38)30(43-32)31(40)41/h10,13,21-24,26-30,32,37-39H,9,11-12,14-19H2,1-8H3,(H,40,41)/t21-,22-,23+,24-,26+,27+,28+,29-,30+,32-,34-,35-,36+/m1/s1
InChI Key FPAKQFMQMIPGBZ-SQOFDNHTSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C36H58O7
Molecular Weight 602.80 g/mol
Exact Mass 602.41825418 g/mol
Topological Polar Surface Area (TPSA) 116.00 Ų
XlogP 8.00
Atomic LogP (AlogP) 6.25
H-Bond Acceptor 6
H-Bond Donor 4
Rotatable Bonds 7

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[[(3S,8R,9S,10R,13R,14S,17R)-4,4,10,13,14-pentamethyl-17-[(2R)-6-methylhept-5-en-2-yl]-2,3,7,8,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]oxane-2-carboxylic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9348 93.48%
Caco-2 - 0.8297 82.97%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.7143 71.43%
Subcellular localzation Mitochondria 0.6865 68.65%
OATP2B1 inhibitior - 0.8596 85.96%
OATP1B1 inhibitior + 0.8078 80.78%
OATP1B3 inhibitior - 0.2571 25.71%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.7250 72.50%
BSEP inhibitior - 0.4923 49.23%
P-glycoprotein inhibitior + 0.7684 76.84%
P-glycoprotein substrate - 0.6723 67.23%
CYP3A4 substrate + 0.7031 70.31%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8798 87.98%
CYP3A4 inhibition - 0.8271 82.71%
CYP2C9 inhibition - 0.8573 85.73%
CYP2C19 inhibition - 0.8860 88.60%
CYP2D6 inhibition - 0.9316 93.16%
CYP1A2 inhibition - 0.7845 78.45%
CYP2C8 inhibition + 0.6386 63.86%
CYP inhibitory promiscuity - 0.8722 87.22%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.6579 65.79%
Eye corrosion - 0.9911 99.11%
Eye irritation - 0.9263 92.63%
Skin irritation + 0.5074 50.74%
Skin corrosion - 0.9353 93.53%
Ames mutagenesis - 0.7400 74.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7371 73.71%
Micronuclear - 0.8000 80.00%
Hepatotoxicity - 0.6414 64.14%
skin sensitisation - 0.7972 79.72%
Respiratory toxicity + 0.7333 73.33%
Reproductive toxicity + 0.8667 86.67%
Mitochondrial toxicity + 0.7000 70.00%
Nephrotoxicity - 0.7643 76.43%
Acute Oral Toxicity (c) III 0.4006 40.06%
Estrogen receptor binding + 0.6837 68.37%
Androgen receptor binding + 0.7395 73.95%
Thyroid receptor binding - 0.5172 51.72%
Glucocorticoid receptor binding + 0.7429 74.29%
Aromatase binding + 0.7212 72.12%
PPAR gamma + 0.5966 59.66%
Honey bee toxicity - 0.7709 77.09%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.6255 62.55%
Fish aquatic toxicity + 0.9852 98.52%

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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.80% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 96.53% 94.45%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.10% 91.11%
CHEMBL2581 P07339 Cathepsin D 95.46% 98.95%
CHEMBL253 P34972 Cannabinoid CB2 receptor 95.44% 97.25%
CHEMBL3359 P21462 Formyl peptide receptor 1 92.16% 93.56%
CHEMBL4227 P25090 Lipoxin A4 receptor 88.44% 100.00%
CHEMBL1994 P08235 Mineralocorticoid receptor 88.19% 100.00%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 87.95% 90.71%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 86.73% 95.56%
CHEMBL5608 Q16288 NT-3 growth factor receptor 86.15% 95.89%
CHEMBL221 P23219 Cyclooxygenase-1 85.86% 90.17%
CHEMBL1806 P11388 DNA topoisomerase II alpha 84.87% 89.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 84.49% 86.33%
CHEMBL5028 O14672 ADAM10 82.81% 97.50%
CHEMBL3137262 O60341 LSD1/CoREST complex 82.51% 97.09%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 81.98% 92.62%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 80.73% 93.00%

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.
Glycyrrhiza glabra

Cross-Links

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PubChem 162880271
LOTUS LTS0275591
wikiData Q104999054