[(2R,3S,4S,5R,6R)-6-[[(1S,2R,3R,5S,8R,9S,10R,13R,14R,17S)-17-[(2R)-2,5-dihydroxy-6-methylhept-6-en-2-yl]-1,2-dihydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate

Details

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Internal ID a49afdf0-c00e-4bef-b221-985492a3620a
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
IUPAC Name [(2R,3S,4S,5R,6R)-6-[[(1S,2R,3R,5S,8R,9S,10R,13R,14R,17S)-17-[(2R)-2,5-dihydroxy-6-methylhept-6-en-2-yl]-1,2-dihydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate
SMILES (Canonical) CC(=C)C(CCC(C)(C1CCC2(C1CCC3C2(CCC4C3(C(C(C(C4(C)C)OC5C(C(C(C(O5)COC(=O)C)O)O)O)O)O)C)C)C)O)O
SMILES (Isomeric) CC(=C)C(CC[C@](C)([C@H]1CC[C@@]2([C@@H]1CC[C@H]3[C@]2(CC[C@@H]4[C@@]3([C@@H]([C@H]([C@@H](C4(C)C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)COC(=O)C)O)O)O)O)O)C)C)C)O)O
InChI InChI=1S/C38H64O11/c1-19(2)23(40)13-17-37(8,46)22-12-15-35(6)21(22)10-11-26-36(35,7)16-14-25-34(4,5)32(30(44)31(45)38(25,26)9)49-33-29(43)28(42)27(41)24(48-33)18-47-20(3)39/h21-33,40-46H,1,10-18H2,2-9H3/t21-,22+,23?,24-,25+,26+,27-,28+,29-,30-,31-,32+,33+,35-,36-,37-,38+/m1/s1
InChI Key AKUSREPTEAYSBY-ZBZQTYFVSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C38H64O11
Molecular Weight 696.90 g/mol
Exact Mass 696.44486285 g/mol
Topological Polar Surface Area (TPSA) 186.00 Ų
XlogP 4.00
Atomic LogP (AlogP) 2.84
H-Bond Acceptor 11
H-Bond Donor 7
Rotatable Bonds 9

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(2R,3S,4S,5R,6R)-6-[[(1S,2R,3R,5S,8R,9S,10R,13R,14R,17S)-17-[(2R)-2,5-dihydroxy-6-methylhept-6-en-2-yl]-1,2-dihydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8843 88.43%
Caco-2 - 0.8765 87.65%
Blood Brain Barrier - 0.6500 65.00%
Human oral bioavailability - 0.7429 74.29%
Subcellular localzation Mitochondria 0.7991 79.91%
OATP2B1 inhibitior - 0.8654 86.54%
OATP1B1 inhibitior + 0.8351 83.51%
OATP1B3 inhibitior + 0.8467 84.67%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.7818 78.18%
BSEP inhibitior - 0.5841 58.41%
P-glycoprotein inhibitior + 0.7666 76.66%
P-glycoprotein substrate - 0.5597 55.97%
CYP3A4 substrate + 0.7205 72.05%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8900 89.00%
CYP3A4 inhibition - 0.8568 85.68%
CYP2C9 inhibition - 0.7252 72.52%
CYP2C19 inhibition - 0.7966 79.66%
CYP2D6 inhibition - 0.9332 93.32%
CYP1A2 inhibition - 0.7767 77.67%
CYP2C8 inhibition + 0.6238 62.38%
CYP inhibitory promiscuity - 0.9111 91.11%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.7225 72.25%
Eye corrosion - 0.9908 99.08%
Eye irritation - 0.9120 91.20%
Skin irritation + 0.5495 54.95%
Skin corrosion - 0.9409 94.09%
Ames mutagenesis - 0.6537 65.37%
Human Ether-a-go-go-Related Gene inhibition + 0.6605 66.05%
Micronuclear - 0.8600 86.00%
Hepatotoxicity - 0.6175 61.75%
skin sensitisation - 0.8713 87.13%
Respiratory toxicity + 0.6000 60.00%
Reproductive toxicity + 0.8444 84.44%
Mitochondrial toxicity + 0.7375 73.75%
Nephrotoxicity - 0.7308 73.08%
Acute Oral Toxicity (c) III 0.4191 41.91%
Estrogen receptor binding + 0.6896 68.96%
Androgen receptor binding + 0.7422 74.22%
Thyroid receptor binding - 0.6076 60.76%
Glucocorticoid receptor binding + 0.6320 63.20%
Aromatase binding + 0.6736 67.36%
PPAR gamma + 0.6866 68.66%
Honey bee toxicity - 0.6626 66.26%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity - 0.5500 55.00%
Fish aquatic toxicity + 0.9890 98.90%

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
CHEMBL253 P34972 Cannabinoid CB2 receptor 99.85% 97.25%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.93% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.54% 96.09%
CHEMBL218 P21554 Cannabinoid CB1 receptor 95.87% 96.61%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 95.50% 94.45%
CHEMBL2581 P07339 Cathepsin D 95.38% 98.95%
CHEMBL3137262 O60341 LSD1/CoREST complex 94.78% 97.09%
CHEMBL5608 Q16288 NT-3 growth factor receptor 89.39% 95.89%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 89.37% 85.14%
CHEMBL4227 P25090 Lipoxin A4 receptor 88.89% 100.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 88.25% 86.33%
CHEMBL1994 P08235 Mineralocorticoid receptor 87.94% 100.00%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 87.36% 95.89%
CHEMBL2179 P04062 Beta-glucocerebrosidase 86.63% 85.31%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 85.98% 93.04%
CHEMBL3401 O75469 Pregnane X receptor 85.95% 94.73%
CHEMBL3130 O00329 PI3-kinase p110-delta subunit 84.11% 96.47%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 83.92% 97.14%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 82.80% 96.95%
CHEMBL5028 O14672 ADAM10 81.99% 97.50%
CHEMBL2274 Q9H228 Sphingosine 1-phosphate receptor Edg-8 81.78% 100.00%
CHEMBL4051 P13569 Cystic fibrosis transmembrane conductance regulator 81.72% 95.71%
CHEMBL1293316 Q9HBX9 Relaxin receptor 1 81.01% 82.50%
CHEMBL3359 P21462 Formyl peptide receptor 1 80.73% 93.56%
CHEMBL3060 Q9Y345 Glycine transporter 2 80.23% 99.17%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 80.02% 92.62%
CHEMBL340 P08684 Cytochrome P450 3A4 80.01% 91.19%

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.
Rhoiptelea chiliantha

Cross-Links

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PubChem 10842401
LOTUS LTS0193109
wikiData Q104913862