(2S,3R,4S,5S)-2-[[(3S,3aS,4S,5aR,5bR,7S,7aR,9S,11aR,11bR,13aR,13bR)-9-[(2S,3R,4S,5S)-3,5-dihydroxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-7-hydroxy-3-(2-hydroxypropan-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-1,2,3,3a,4,5,6,7,7a,9,10,11,11b,12,13,13a-hexadecahydrocyclopenta[a]chrysen-4-yl]oxy]oxane-3,4,5-triol

Details

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Internal ID ccb69bf7-3482-4d12-befe-0b3b5216a09a
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Hopanoids
IUPAC Name (2S,3R,4S,5S)-2-[[(3S,3aS,4S,5aR,5bR,7S,7aR,9S,11aR,11bR,13aR,13bR)-9-[(2S,3R,4S,5S)-3,5-dihydroxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-7-hydroxy-3-(2-hydroxypropan-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-1,2,3,3a,4,5,6,7,7a,9,10,11,11b,12,13,13a-hexadecahydrocyclopenta[a]chrysen-4-yl]oxy]oxane-3,4,5-triol
SMILES (Canonical) CC1(C(CCC2(C1C(CC3(C2CCC4C3(CC(C5C4(CCC5C(C)(C)O)C)OC6C(C(C(CO6)O)O)O)C)C)O)C)OC7C(C(C(CO7)O)OC8C(C(C(CO8)O)O)O)O)C
SMILES (Isomeric) C[C@]12CC[C@@H]([C@@H]1[C@H](C[C@@]3([C@@H]2CC[C@H]4[C@]3(C[C@@H]([C@@H]5[C@@]4(CC[C@@H](C5(C)C)O[C@H]6[C@@H]([C@H]([C@H](CO6)O)O[C@H]7[C@@H]([C@H]([C@@H](CO7)O)O)O)O)C)O)C)C)O[C@H]8[C@@H]([C@H]([C@H](CO8)O)O)O)C(C)(C)O
InChI InChI=1S/C45H76O16/c1-40(2)28(60-39-34(54)35(24(49)19-58-39)61-38-33(53)31(51)23(48)18-57-38)12-14-43(6)27-10-9-26-42(5)13-11-20(41(3,4)55)29(42)25(59-37-32(52)30(50)22(47)17-56-37)16-45(26,8)44(27,7)15-21(46)36(40)43/h20-39,46-55H,9-19H2,1-8H3/t20-,21-,22-,23+,24-,25-,26+,27+,28-,29+,30-,31-,32+,33+,34+,35-,36-,37-,38-,39-,42+,43+,44+,45+/m0/s1
InChI Key XLPWHCKLGKFHCL-GSHBARKISA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C45H76O16
Molecular Weight 873.10 g/mol
Exact Mass 872.51333633 g/mol
Topological Polar Surface Area (TPSA) 258.00 Ų
XlogP 1.10
Atomic LogP (AlogP) 0.55
H-Bond Acceptor 16
H-Bond Donor 10
Rotatable Bonds 7

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2S,3R,4S,5S)-2-[[(3S,3aS,4S,5aR,5bR,7S,7aR,9S,11aR,11bR,13aR,13bR)-9-[(2S,3R,4S,5S)-3,5-dihydroxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-7-hydroxy-3-(2-hydroxypropan-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-1,2,3,3a,4,5,6,7,7a,9,10,11,11b,12,13,13a-hexadecahydrocyclopenta[a]chrysen-4-yl]oxy]oxane-3,4,5-triol

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.5910 59.10%
Caco-2 - 0.8821 88.21%
Blood Brain Barrier - 0.6000 60.00%
Human oral bioavailability - 0.6000 60.00%
Subcellular localzation Mitochondria 0.6634 66.34%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8841 88.41%
OATP1B3 inhibitior + 0.9056 90.56%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.6250 62.50%
BSEP inhibitior - 0.6365 63.65%
P-glycoprotein inhibitior + 0.7520 75.20%
P-glycoprotein substrate - 0.5684 56.84%
CYP3A4 substrate + 0.7168 71.68%
CYP2C9 substrate - 0.7981 79.81%
CYP2D6 substrate - 0.8283 82.83%
CYP3A4 inhibition - 0.9691 96.91%
CYP2C9 inhibition - 0.9021 90.21%
CYP2C19 inhibition - 0.8903 89.03%
CYP2D6 inhibition - 0.9560 95.60%
CYP1A2 inhibition - 0.9021 90.21%
CYP2C8 inhibition + 0.5989 59.89%
CYP inhibitory promiscuity - 0.9822 98.22%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.6337 63.37%
Eye corrosion - 0.9901 99.01%
Eye irritation - 0.9062 90.62%
Skin irritation - 0.7062 70.62%
Skin corrosion - 0.9456 94.56%
Ames mutagenesis - 0.6100 61.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7429 74.29%
Micronuclear - 0.8800 88.00%
Hepatotoxicity - 0.7125 71.25%
skin sensitisation - 0.9138 91.38%
Respiratory toxicity - 0.5222 52.22%
Reproductive toxicity + 0.7444 74.44%
Mitochondrial toxicity + 0.5750 57.50%
Nephrotoxicity - 0.9213 92.13%
Acute Oral Toxicity (c) I 0.4989 49.89%
Estrogen receptor binding + 0.7343 73.43%
Androgen receptor binding + 0.7312 73.12%
Thyroid receptor binding - 0.5765 57.65%
Glucocorticoid receptor binding + 0.5920 59.20%
Aromatase binding + 0.6579 65.79%
PPAR gamma + 0.7407 74.07%
Honey bee toxicity - 0.6208 62.08%
Biodegradation - 0.7000 70.00%
Crustacea aquatic toxicity + 0.5200 52.00%
Fish aquatic toxicity + 0.8551 85.51%

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 97.49% 97.25%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.02% 91.11%
CHEMBL1907605 P24864 Cyclin-dependent kinase 2/cyclin E1 93.72% 92.88%
CHEMBL241 Q14432 Phosphodiesterase 3A 93.19% 92.94%
CHEMBL1937 Q92769 Histone deacetylase 2 91.95% 94.75%
CHEMBL5608 Q16288 NT-3 growth factor receptor 91.51% 95.89%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 90.96% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.71% 97.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 89.43% 94.45%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 87.53% 96.77%
CHEMBL3922 P50579 Methionine aminopeptidase 2 87.32% 97.28%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 87.19% 97.14%
CHEMBL2581 P07339 Cathepsin D 86.50% 98.95%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.03% 100.00%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 84.00% 94.00%
CHEMBL2179 P04062 Beta-glucocerebrosidase 83.98% 85.31%
CHEMBL325 Q13547 Histone deacetylase 1 83.67% 95.92%
CHEMBL2815 P04629 Nerve growth factor receptor Trk-A 83.29% 87.16%
CHEMBL1806 P11388 DNA topoisomerase II alpha 82.39% 89.00%
CHEMBL2274 Q9H228 Sphingosine 1-phosphate receptor Edg-8 81.30% 100.00%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 81.15% 85.14%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 80.67% 82.69%
CHEMBL1293249 Q13887 Kruppel-like factor 5 80.54% 86.33%
CHEMBL3746 P80365 11-beta-hydroxysteroid dehydrogenase 2 80.27% 94.78%
CHEMBL5888 Q99558 Mitogen-activated protein kinase kinase kinase 14 80.22% 100.00%
CHEMBL1974 P36888 Tyrosine-protein kinase receptor FLT3 80.05% 91.83%

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.
Polycarpon succulentum
Polypodium vulgare

Cross-Links

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PubChem 102438588
LOTUS LTS0187454
wikiData Q105278871