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(1R,3aS,5aR,5bR,7aR,8S,9S,11aR,11bR,13aR,13bR)-5a,5b,8,11a-tetramethyl-1-prop-1-en-2-yl-9-sulfooxy-3a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-8-carboxylic acid

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 8eaa467a-8a72-4cc8-8d8e-a2daa23a0835
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
IUPAC Name (1R,3aS,5aR,5bR,7aR,8S,9S,11aR,11bR,13aR,13bR)-5a,5b,8,11a-tetramethyl-1-prop-1-en-2-yl-9-sulfooxy-3a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-8-carboxylic acid
SMILES (Canonical) CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C(=O)O)OS(=O)(=O)O)C)C(=O)OC6C(C(C(C(O6)CO)O)O)O
SMILES (Isomeric) CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]3CC[C@@H]4[C@]5(CC[C@@H]([C@@]([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C(=O)O)OS(=O)(=O)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O
InChI InChI=1S/C36H56O13S/c1-18(2)19-9-14-36(31(43)48-29-28(40)27(39)26(38)21(17-37)47-29)16-15-33(4)20(25(19)36)7-8-22-32(3)12-11-24(49-50(44,45)46)35(6,30(41)42)23(32)10-13-34(22,33)5/h19-29,37-40H,1,7-17H2,2-6H3,(H,41,42)(H,44,45,46)/t19-,20+,21+,22+,23+,24-,25+,26+,27-,28+,29-,32+,33+,34+,35-,36-/m0/s1
InChI Key OLMGVGQLCXKETP-JITVAQQKSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C36H56O13S
Molecular Weight 728.90 g/mol
Exact Mass 728.34416301 g/mol
Topological Polar Surface Area (TPSA) 226.00 Ų
XlogP 4.70
Atomic LogP (AlogP) 3.24
H-Bond Acceptor 11
H-Bond Donor 6
Rotatable Bonds 7

Synonyms

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RefChem:922656
(1R,3aS,5aR,5bR,7aR,8S,9S,11aR,11bR,13aR,13bR)-5a,5b,8,11a-tetramethyl-1-prop-1-en-2-yl-9-sulfooxy-3a-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxycarbonyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta(a)chrysene-8-carboxylic acid
947150-88-1

2D Structure

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2D Structure of (1R,3aS,5aR,5bR,7aR,8S,9S,11aR,11bR,13aR,13bR)-5a,5b,8,11a-tetramethyl-1-prop-1-en-2-yl-9-sulfooxy-3a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-8-carboxylic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8090 80.90%
Caco-2 - 0.8718 87.18%
Blood Brain Barrier + 0.5750 57.50%
Human oral bioavailability - 0.7143 71.43%
Subcellular localzation Mitochondria 0.4928 49.28%
OATP2B1 inhibitior - 0.7231 72.31%
OATP1B1 inhibitior + 0.8538 85.38%
OATP1B3 inhibitior + 0.9298 92.98%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.7798 77.98%
BSEP inhibitior - 0.6194 61.94%
P-glycoprotein inhibitior + 0.7320 73.20%
P-glycoprotein substrate - 0.5503 55.03%
CYP3A4 substrate + 0.7168 71.68%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8657 86.57%
CYP3A4 inhibition - 0.8508 85.08%
CYP2C9 inhibition - 0.7631 76.31%
CYP2C19 inhibition - 0.7328 73.28%
CYP2D6 inhibition - 0.8736 87.36%
CYP1A2 inhibition - 0.7323 73.23%
CYP2C8 inhibition + 0.7104 71.04%
CYP inhibitory promiscuity - 0.8763 87.63%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 0.5900 59.00%
Carcinogenicity (trinary) Non-required 0.6308 63.08%
Eye corrosion - 0.9772 97.72%
Eye irritation - 0.9129 91.29%
Skin irritation - 0.7533 75.33%
Skin corrosion - 0.9143 91.43%
Ames mutagenesis - 0.6234 62.34%
Human Ether-a-go-go-Related Gene inhibition + 0.7016 70.16%
Micronuclear + 0.5300 53.00%
Hepatotoxicity - 0.6973 69.73%
skin sensitisation - 0.8623 86.23%
Respiratory toxicity + 0.6000 60.00%
Reproductive toxicity + 0.8778 87.78%
Mitochondrial toxicity - 0.5125 51.25%
Nephrotoxicity - 0.8767 87.67%
Acute Oral Toxicity (c) III 0.5823 58.23%
Estrogen receptor binding + 0.7166 71.66%
Androgen receptor binding + 0.7632 76.32%
Thyroid receptor binding - 0.5902 59.02%
Glucocorticoid receptor binding + 0.6549 65.49%
Aromatase binding + 0.6165 61.65%
PPAR gamma + 0.6926 69.26%
Honey bee toxicity - 0.6508 65.08%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.6600 66.00%
Fish aquatic toxicity + 0.9957 99.57%

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
CHEMBL4040 P28482 MAP kinase ERK2 98.98% 83.82%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.14% 96.09%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 93.72% 96.38%
CHEMBL2581 P07339 Cathepsin D 92.56% 98.95%
CHEMBL241 Q14432 Phosphodiesterase 3A 91.70% 92.94%
CHEMBL233 P35372 Mu opioid receptor 91.64% 97.93%
CHEMBL340 P08684 Cytochrome P450 3A4 90.90% 91.19%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 90.76% 94.45%
CHEMBL1293316 Q9HBX9 Relaxin receptor 1 90.10% 82.50%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 89.65% 95.83%
CHEMBL218 P21554 Cannabinoid CB1 receptor 88.99% 96.61%
CHEMBL3524 P56524 Histone deacetylase 4 88.07% 92.97%
CHEMBL5255 O00206 Toll-like receptor 4 87.81% 92.50%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 87.49% 95.50%
CHEMBL1994 P08235 Mineralocorticoid receptor 87.07% 100.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 86.63% 95.56%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 86.61% 91.11%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 86.00% 95.89%
CHEMBL1966 Q02127 Dihydroorotate dehydrogenase 85.92% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 85.81% 97.09%
CHEMBL4588 P22894 Matrix metalloproteinase 8 85.60% 94.66%
CHEMBL237 P41145 Kappa opioid receptor 84.66% 98.10%
CHEMBL4227 P25090 Lipoxin A4 receptor 84.50% 100.00%
CHEMBL2095194 P08709 Coagulation factor VII/tissue factor 83.95% 99.17%
CHEMBL3713062 P10646 Tissue factor pathway inhibitor 83.93% 97.33%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 83.55% 91.24%
CHEMBL1293249 Q13887 Kruppel-like factor 5 82.60% 86.33%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 81.88% 94.33%
CHEMBL5888 Q99558 Mitogen-activated protein kinase kinase kinase 14 81.55% 100.00%
CHEMBL4302 P08183 P-glycoprotein 1 81.27% 92.98%
CHEMBL5608 Q16288 NT-3 growth factor receptor 81.07% 95.89%
CHEMBL226 P30542 Adenosine A1 receptor 81.05% 95.93%
CHEMBL5028 O14672 ADAM10 80.98% 97.50%
CHEMBL253 P34972 Cannabinoid CB2 receptor 80.96% 97.25%
CHEMBL5163 Q9NY46 Sodium channel protein type III alpha subunit 80.10% 96.90%

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.
Gypsophila repens

Cross-Links

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PubChem 102274702
LOTUS LTS0159624
wikiData Q105194024