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(3S,8S,9R,10R,13R,14S,17S)-3-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4,4,9,13,14-pentamethyl-17-[(2S,5S)-2-methyl-5-[2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropan-2-yl]oxolan-2-yl]-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-11-one

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 c0cabedc-f35d-4567-a3b5-00e7c9ccbd08
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
IUPAC Name (3S,8S,9R,10R,13R,14S,17S)-3-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4,4,9,13,14-pentamethyl-17-[(2S,5S)-2-methyl-5-[2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropan-2-yl]oxolan-2-yl]-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-11-one
SMILES (Canonical)
SMILES (Isomeric)
InChI InChI=1S/C48H78O19/c1-43(2)21-9-11-27-45(5)15-13-26(47(7)16-14-30(66-47)44(3,4)67-41-38(60)35(57)32(54)24(19-50)62-41)46(45,6)17-28(52)48(27,8)22(21)10-12-29(43)64-42-39(36(58)33(55)25(20-51)63-42)65-40-37(59)34(56)31(53)23(18-49)61-40/h9,22-27,29-42,49-51,53-60H,10-20H2,1-8H3/t22-,23-,24-,25-,26+,27+,29+,30+,31-,32-,33-,34+,35+,36+,37-,38-,39-,40+,41+,42+,45+,46-,47+,48+/m1/s1
InChI Key NPQCOVKWQISDMU-WJBSUBJXSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C48H78O19
Molecular Weight 959.10 g/mol
Exact Mass 958.51373025 g/mol
Topological Polar Surface Area (TPSA) 304.00 Ų
XlogP -0.10
Atomic LogP (AlogP) -0.69
H-Bond Acceptor 19
H-Bond Donor 11
Rotatable Bonds 11

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (3S,8S,9R,10R,13R,14S,17S)-3-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4,4,9,13,14-pentamethyl-17-[(2S,5S)-2-methyl-5-[2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropan-2-yl]oxolan-2-yl]-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-11-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8694 86.94%
Caco-2 - 0.8865 88.65%
Blood Brain Barrier - 0.7250 72.50%
Human oral bioavailability - 0.8143 81.43%
Subcellular localzation Mitochondria 0.8845 88.45%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8494 84.94%
OATP1B3 inhibitior - 0.2282 22.82%
MATE1 inhibitior - 0.9812 98.12%
OCT2 inhibitior - 0.8500 85.00%
BSEP inhibitior + 0.7222 72.22%
P-glycoprotein inhibitior + 0.7517 75.17%
P-glycoprotein substrate - 0.6435 64.35%
CYP3A4 substrate + 0.7262 72.62%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8635 86.35%
CYP3A4 inhibition - 0.9206 92.06%
CYP2C9 inhibition - 0.8544 85.44%
CYP2C19 inhibition - 0.8999 89.99%
CYP2D6 inhibition - 0.9317 93.17%
CYP1A2 inhibition - 0.8951 89.51%
CYP2C8 inhibition + 0.6297 62.97%
CYP inhibitory promiscuity - 0.8562 85.62%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.5400 54.00%
Eye corrosion - 0.9883 98.83%
Eye irritation - 0.9043 90.43%
Skin irritation - 0.6077 60.77%
Skin corrosion - 0.9396 93.96%
Ames mutagenesis - 0.8000 80.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7859 78.59%
Micronuclear - 0.8600 86.00%
Hepatotoxicity + 0.5041 50.41%
skin sensitisation - 0.9079 90.79%
Respiratory toxicity + 0.5222 52.22%
Reproductive toxicity + 0.8889 88.89%
Mitochondrial toxicity - 0.6000 60.00%
Nephrotoxicity - 0.7482 74.82%
Acute Oral Toxicity (c) III 0.4439 44.39%
Estrogen receptor binding + 0.7953 79.53%
Androgen receptor binding + 0.7597 75.97%
Thyroid receptor binding - 0.5000 50.00%
Glucocorticoid receptor binding + 0.7257 72.57%
Aromatase binding + 0.6559 65.59%
PPAR gamma + 0.7918 79.18%
Honey bee toxicity - 0.6995 69.95%
Biodegradation - 0.7000 70.00%
Crustacea aquatic toxicity - 0.5600 56.00%
Fish aquatic toxicity + 0.9766 97.66%

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
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.88% 91.11%
CHEMBL218 P21554 Cannabinoid CB1 receptor 95.41% 96.61%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 92.87% 96.09%
CHEMBL253 P34972 Cannabinoid CB2 receptor 90.92% 97.25%
CHEMBL1293249 Q13887 Kruppel-like factor 5 90.75% 86.33%
CHEMBL2581 P07339 Cathepsin D 90.70% 98.95%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.60% 95.56%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.07% 97.09%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 89.55% 94.00%
CHEMBL259 P32245 Melanocortin receptor 4 86.60% 95.38%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 85.79% 93.04%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.74% 100.00%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 84.38% 96.21%
CHEMBL5255 O00206 Toll-like receptor 4 84.18% 92.50%
CHEMBL5608 Q16288 NT-3 growth factor receptor 83.51% 95.89%
CHEMBL1937 Q92769 Histone deacetylase 2 82.98% 94.75%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 82.27% 92.62%
CHEMBL5888 Q99558 Mitogen-activated protein kinase kinase kinase 14 81.72% 100.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 80.10% 94.45%

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.
Gratiola officinalis

Cross-Links

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PubChem 21575885
LOTUS LTS0255065
wikiData Q105183307