24-methylenecholesteryl beta-D-glucoside

Details

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Internal ID 05a67717-4a91-4076-ab68-c53ee17e582d
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
IUPAC Name (2R,3R,4S,5S,6R)-2-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
SMILES (Canonical) CC(C)C(=C)CCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)OC5C(C(C(C(O5)CO)O)O)O)C)C
SMILES (Isomeric) C[C@H](CCC(=C)C(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C)C
InChI InChI=1S/C34H56O6/c1-19(2)20(3)7-8-21(4)25-11-12-26-24-10-9-22-17-23(13-15-33(22,5)27(24)14-16-34(25,26)6)39-32-31(38)30(37)29(36)28(18-35)40-32/h9,19,21,23-32,35-38H,3,7-8,10-18H2,1-2,4-6H3/t21-,23+,24+,25-,26+,27+,28-,29-,30+,31-,32-,33+,34-/m1/s1
InChI Key YQEUTOSZVKSYTM-UYRRFJMQSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C34H56O6
Molecular Weight 560.80 g/mol
Exact Mass 560.40768950 g/mol
Topological Polar Surface Area (TPSA) 99.40 Ų
XlogP 7.00
Atomic LogP (AlogP) 5.38
H-Bond Acceptor 6
H-Bond Donor 4
Rotatable Bonds 8

Synonyms

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CHEBI:145114
24-methylene cholesteryl beta-D-glucoside
(17R)-ergosta-5,24(28)-dien-3beta-yl beta-D-glucopyranoside
(2R,3R,4S,5S,6R)-2-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-Dimethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

2D Structure

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2D Structure of 24-methylenecholesteryl beta-D-glucoside

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8104 81.04%
Caco-2 - 0.8397 83.97%
Blood Brain Barrier - 0.6250 62.50%
Human oral bioavailability - 0.7286 72.86%
Subcellular localzation Mitochondria 0.7601 76.01%
OATP2B1 inhibitior - 0.5770 57.70%
OATP1B1 inhibitior + 0.8946 89.46%
OATP1B3 inhibitior - 0.2618 26.18%
MATE1 inhibitior - 0.9612 96.12%
OCT2 inhibitior - 0.6500 65.00%
BSEP inhibitior - 0.7229 72.29%
P-glycoprotein inhibitior + 0.6351 63.51%
P-glycoprotein substrate - 0.5059 50.59%
CYP3A4 substrate + 0.7353 73.53%
CYP2C9 substrate - 0.8025 80.25%
CYP2D6 substrate - 0.8264 82.64%
CYP3A4 inhibition - 0.8656 86.56%
CYP2C9 inhibition - 0.7750 77.50%
CYP2C19 inhibition - 0.8471 84.71%
CYP2D6 inhibition - 0.9320 93.20%
CYP1A2 inhibition - 0.7785 77.85%
CYP2C8 inhibition + 0.5879 58.79%
CYP inhibitory promiscuity - 0.8352 83.52%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.7086 70.86%
Eye corrosion - 0.9885 98.85%
Eye irritation - 0.9358 93.58%
Skin irritation - 0.5725 57.25%
Skin corrosion - 0.9406 94.06%
Ames mutagenesis - 0.8670 86.70%
Human Ether-a-go-go-Related Gene inhibition + 0.7545 75.45%
Micronuclear - 0.8500 85.00%
Hepatotoxicity - 0.7481 74.81%
skin sensitisation - 0.8930 89.30%
Respiratory toxicity + 0.7778 77.78%
Reproductive toxicity + 0.8778 87.78%
Mitochondrial toxicity - 0.5750 57.50%
Nephrotoxicity - 0.7919 79.19%
Acute Oral Toxicity (c) III 0.6706 67.06%
Estrogen receptor binding + 0.6979 69.79%
Androgen receptor binding + 0.7040 70.40%
Thyroid receptor binding - 0.5744 57.44%
Glucocorticoid receptor binding + 0.5698 56.98%
Aromatase binding + 0.5873 58.73%
PPAR gamma + 0.5415 54.15%
Honey bee toxicity - 0.6850 68.50%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.6000 60.00%
Fish aquatic toxicity + 0.9828 98.28%

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 99.01% 91.11%
CHEMBL253 P34972 Cannabinoid CB2 receptor 98.57% 97.25%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.47% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 95.02% 94.45%
CHEMBL2581 P07339 Cathepsin D 94.95% 98.95%
CHEMBL3137262 O60341 LSD1/CoREST complex 94.38% 97.09%
CHEMBL237 P41145 Kappa opioid receptor 93.35% 98.10%
CHEMBL226 P30542 Adenosine A1 receptor 92.51% 95.93%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 92.44% 95.89%
CHEMBL1994 P08235 Mineralocorticoid receptor 92.11% 100.00%
CHEMBL4681 P42330 Aldo-keto-reductase family 1 member C3 90.21% 89.05%
CHEMBL5608 Q16288 NT-3 growth factor receptor 87.27% 95.89%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 86.60% 92.62%
CHEMBL3359 P21462 Formyl peptide receptor 1 86.11% 93.56%
CHEMBL218 P21554 Cannabinoid CB1 receptor 84.30% 96.61%
CHEMBL4227 P25090 Lipoxin A4 receptor 82.19% 100.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 82.04% 89.00%
CHEMBL3401 O75469 Pregnane X receptor 81.86% 94.73%
CHEMBL220 P22303 Acetylcholinesterase 81.62% 94.45%
CHEMBL3060 Q9Y345 Glycine transporter 2 81.26% 99.17%
CHEMBL2094135 Q96BI3 Gamma-secretase 81.04% 98.05%
CHEMBL216 P11229 Muscarinic acetylcholine receptor M1 80.23% 94.23%

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.
Cedrela odorata

Cross-Links

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PubChem 12895793
LOTUS LTS0133780
wikiData Q105352202