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

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 d7918c56-4a33-4208-96d7-44f958030ccd
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Hopanoids
IUPAC Name (2R,3R,4R,5S)-2-[[(3R,3aS,4S,5aS,5bR,7R,7aS,9S,11aS,11bS,13aS,13bS)-4-hydroxy-3-(2-hydroxypropan-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-7-[(2R,3S,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-1,2,3,3a,4,5,6,7,7a,9,10,11,11b,12,13,13a-hexadecahydrocyclopenta[a]chrysen-9-yl]oxy]oxane-3,4,5-triol
SMILES (Canonical) CC1(C(CCC2(C1C(CC3(C2CCC4C3(CC(C5C4(CCC5C(C)(C)O)C)O)C)C)OC6C(C(C(CO6)O)O)O)C)OC7C(C(C(CO7)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)O)C)O[C@@H]7[C@H]([C@H]([C@H](CO7)O)O)O)C)C)O)C(C)(C)O
InChI InChI=1S/C40H68O12/c1-35(2)26(52-34-31(47)29(45)22(43)18-50-34)12-14-38(6)25-10-9-24-37(5)13-11-19(36(3,4)48)27(37)20(41)15-39(24,7)40(25,8)16-23(32(35)38)51-33-30(46)28(44)21(42)17-49-33/h19-34,41-48H,9-18H2,1-8H3/t19-,20+,21+,22+,23-,24+,25+,26+,27-,28+,29-,30+,31-,32-,33-,34-,37+,38+,39+,40-/m1/s1
InChI Key WDNRGOKAQYUFRP-AKTWIABVSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C40H68O12
Molecular Weight 741.00 g/mol
Exact Mass 740.47107760 g/mol
Topological Polar Surface Area (TPSA) 199.00 Ų
XlogP 2.60
Atomic LogP (AlogP) 2.09
H-Bond Acceptor 12
H-Bond Donor 8
Rotatable Bonds 5

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2R,3R,4R,5S)-2-[[(3R,3aS,4S,5aS,5bR,7R,7aS,9S,11aS,11bS,13aS,13bS)-4-hydroxy-3-(2-hydroxypropan-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-7-[(2R,3S,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-1,2,3,3a,4,5,6,7,7a,9,10,11,11b,12,13,13a-hexadecahydrocyclopenta[a]chrysen-9-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 - 0.8539 85.39%
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 + 0.9008 90.08%
OATP1B3 inhibitior + 0.9056 90.56%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.6250 62.50%
BSEP inhibitior - 0.7154 71.54%
P-glycoprotein inhibitior + 0.7351 73.51%
P-glycoprotein substrate - 0.7059 70.59%
CYP3A4 substrate + 0.7128 71.28%
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 + 0.6064 60.64%
CYP inhibitory promiscuity - 0.9822 98.22%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.6337 63.37%
Eye corrosion - 0.9901 99.01%
Eye irritation - 0.9057 90.57%
Skin irritation - 0.7062 70.62%
Skin corrosion - 0.9456 94.56%
Ames mutagenesis - 0.5800 58.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7048 70.48%
Micronuclear - 0.8800 88.00%
Hepatotoxicity - 0.7500 75.00%
skin sensitisation - 0.9138 91.38%
Respiratory toxicity - 0.5556 55.56%
Reproductive toxicity + 0.7444 74.44%
Mitochondrial toxicity + 0.5750 57.50%
Nephrotoxicity - 0.9025 90.25%
Acute Oral Toxicity (c) I 0.4989 49.89%
Estrogen receptor binding + 0.5955 59.55%
Androgen receptor binding + 0.7285 72.85%
Thyroid receptor binding - 0.5745 57.45%
Glucocorticoid receptor binding + 0.5737 57.37%
Aromatase binding + 0.6667 66.67%
PPAR gamma + 0.6753 67.53%
Honey bee toxicity - 0.6516 65.16%
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
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.56% 91.11%
CHEMBL253 P34972 Cannabinoid CB2 receptor 96.03% 97.25%
CHEMBL241 Q14432 Phosphodiesterase 3A 92.57% 92.94%
CHEMBL1907605 P24864 Cyclin-dependent kinase 2/cyclin E1 91.40% 92.88%
CHEMBL5608 Q16288 NT-3 growth factor receptor 89.90% 95.89%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 88.55% 96.77%
CHEMBL3137262 O60341 LSD1/CoREST complex 87.97% 97.09%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 87.70% 96.09%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 86.75% 97.14%
CHEMBL1994 P08235 Mineralocorticoid receptor 85.49% 100.00%
CHEMBL2581 P07339 Cathepsin D 85.03% 98.95%
CHEMBL5888 Q99558 Mitogen-activated protein kinase kinase kinase 14 84.99% 100.00%
CHEMBL3713062 P10646 Tissue factor pathway inhibitor 84.58% 97.33%
CHEMBL1293249 Q13887 Kruppel-like factor 5 82.55% 86.33%
CHEMBL259 P32245 Melanocortin receptor 4 81.98% 95.38%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 81.26% 94.00%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 80.86% 85.14%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 80.79% 92.62%
CHEMBL1806 P11388 DNA topoisomerase II alpha 80.18% 89.00%

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.
Glinus lotoides

Cross-Links

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PubChem 162975027
LOTUS LTS0227924
wikiData Q105302557