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(16alpha,20R,24S)-2,16,20,25-tetrahydroxy-24-methoxycucurbita-1,5-diene-3,11,22-trione 2-O-beta-D-glucopyranoside

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 8925d6a4-46a9-4dec-a46b-ce16e13664c1
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
IUPAC Name (8S,9R,10R,13R,14S,16R,17R)-17-[(2R,5S)-2,6-dihydroxy-5-methoxy-6-methyl-3-oxoheptan-2-yl]-16-hydroxy-4,4,9,13,14-pentamethyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthrene-3,11-dione
SMILES (Canonical)
SMILES (Isomeric)
InChI InChI=1S/C37H56O13/c1-32(2)17-10-11-22-34(5)14-19(39)29(37(8,47)23(40)13-25(48-9)33(3,4)46)35(34,6)15-24(41)36(22,7)18(17)12-20(30(32)45)49-31-28(44)27(43)26(42)21(16-38)50-31/h10,12,18-19,21-22,25-29,31,38-39,42-44,46-47H,11,13-16H2,1-9H3/t18-,19-,21-,22+,25+,26-,27+,28-,29+,31-,34+,35-,36+,37+/m1/s1
InChI Key VFYMEDSYUASGPF-WLPFVFARSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C37H56O13
Molecular Weight 708.80 g/mol
Exact Mass 708.37209184 g/mol
Topological Polar Surface Area (TPSA) 221.00 Ų
XlogP 0.50
Atomic LogP (AlogP) 0.73
H-Bond Acceptor 13
H-Bond Donor 7
Rotatable Bonds 9

Synonyms

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(16alpha,20R,24S)-2,16,20,25-tetrahydroxy-24-methoxycucurbita-1,5-diene-3,11,22-trione 2-O-beta-D-glucopyranoside
CHEMBL1923784
DTXSID401103857
Q27137266
(4R,9beta,16alpha,24S)-16,20,25-trihydroxy-24-methoxy-9,10,14-trimethyl-1,11,22-trioxo-4,9-cyclo-9,10-secocholesta-2,5-dien-2-yl beta-D-glucopyranoside
1345690-58-5
19-Norlanosta-1,5-diene-3,11,22-trione, 2-(beta-D-glucopyranosyloxy)-16,20,25-trihydroxy-24-methoxy-9-methyl-, (9beta,10alpha,16alpha,24S)-

2D Structure

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2D Structure of (16alpha,20R,24S)-2,16,20,25-tetrahydroxy-24-methoxycucurbita-1,5-diene-3,11,22-trione 2-O-beta-D-glucopyranoside

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9006 90.06%
Caco-2 - 0.8585 85.85%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.8000 80.00%
Subcellular localzation Mitochondria 0.8010 80.10%
OATP2B1 inhibitior - 0.8644 86.44%
OATP1B1 inhibitior + 0.8423 84.23%
OATP1B3 inhibitior + 0.8991 89.91%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior - 0.5071 50.71%
P-glycoprotein inhibitior + 0.7349 73.49%
P-glycoprotein substrate - 0.5297 52.97%
CYP3A4 substrate + 0.7123 71.23%
CYP2C9 substrate - 0.8054 80.54%
CYP2D6 substrate - 0.8874 88.74%
CYP3A4 inhibition - 0.7697 76.97%
CYP2C9 inhibition - 0.8436 84.36%
CYP2C19 inhibition - 0.8971 89.71%
CYP2D6 inhibition - 0.9418 94.18%
CYP1A2 inhibition - 0.8531 85.31%
CYP2C8 inhibition + 0.6006 60.06%
CYP inhibitory promiscuity - 0.9309 93.09%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.6706 67.06%
Eye corrosion - 0.9893 98.93%
Eye irritation - 0.9107 91.07%
Skin irritation - 0.5968 59.68%
Skin corrosion - 0.9445 94.45%
Ames mutagenesis - 0.6700 67.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6716 67.16%
Micronuclear - 0.6600 66.00%
Hepatotoxicity - 0.6565 65.65%
skin sensitisation - 0.8904 89.04%
Respiratory toxicity + 0.6556 65.56%
Reproductive toxicity + 0.9556 95.56%
Mitochondrial toxicity + 0.7375 73.75%
Nephrotoxicity + 0.6159 61.59%
Acute Oral Toxicity (c) III 0.5338 53.38%
Estrogen receptor binding + 0.7153 71.53%
Androgen receptor binding + 0.7450 74.50%
Thyroid receptor binding + 0.5141 51.41%
Glucocorticoid receptor binding + 0.7654 76.54%
Aromatase binding + 0.6875 68.75%
PPAR gamma + 0.7030 70.30%
Honey bee toxicity - 0.6375 63.75%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.5400 54.00%
Fish aquatic toxicity + 0.9672 96.72%

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 99.14% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.41% 96.09%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 98.18% 85.14%
CHEMBL253 P34972 Cannabinoid CB2 receptor 97.31% 97.25%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 96.60% 94.45%
CHEMBL2581 P07339 Cathepsin D 96.38% 98.95%
CHEMBL3137262 O60341 LSD1/CoREST complex 95.64% 97.09%
CHEMBL218 P21554 Cannabinoid CB1 receptor 94.71% 96.61%
CHEMBL1293294 P51151 Ras-related protein Rab-9A 91.37% 87.67%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 90.97% 96.77%
CHEMBL3401 O75469 Pregnane X receptor 89.96% 94.73%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 87.92% 95.56%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 85.07% 96.95%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 83.72% 91.07%
CHEMBL2069156 Q14145 Kelch-like ECH-associated protein 1 83.17% 82.38%
CHEMBL4208 P20618 Proteasome component C5 82.80% 90.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 82.12% 89.00%
CHEMBL1994 P08235 Mineralocorticoid receptor 82.09% 100.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 80.49% 99.23%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.42% 95.89%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
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There are no matching plants.

Cross-Links

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PubChem 56833752
LOTUS LTS0242982
wikiData Q27137266