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(2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-2-[[(2S,3S,5S)-5-[(1R)-1-[(3S,5S,9R,10S,13S,14R,16S,17R)-3-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-16-hydroxy-10,13-dimethyl-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl]-3-ethyl-2-methyloxolan-2-yl]methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)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 5dd73215-a74b-4d75-91a8-fb531f9979f8
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
IUPAC Name (2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-2-[[(2S,3S,5S)-5-[(1R)-1-[(3S,5S,9R,10S,13S,14R,16S,17R)-3-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-16-hydroxy-10,13-dimethyl-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl]-3-ethyl-2-methyloxolan-2-yl]methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
SMILES (Canonical) CCC1CC(OC1(C)COC2C(C(C(C(O2)CO)O)O)OC3C(C(C(C(O3)CO)O)O)O)C(C)C4C(CC5C4(CCC6C5=CCC7C6(CCC(C7)OC8C(C(C(C(O8)CO)O)O)OC9C(C(C(C(O9)CO)O)O)O)C)C)O
SMILES (Isomeric) CC[C@H]1C[C@H](O[C@]1(C)CO[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)[C@H](C)[C@H]4[C@H](C[C@@H]5[C@@]4(CC[C@H]6C5=CC[C@@H]7[C@@]6(CC[C@@H](C7)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)C)C)O
InChI InChI=1S/C53H88O24/c1-6-22-14-29(77-53(22,5)20-69-49-45(41(65)37(61)32(18-56)73-49)75-47-43(67)39(63)35(59)30(16-54)71-47)21(2)34-28(58)15-27-25-8-7-23-13-24(9-11-51(23,3)26(25)10-12-52(27,34)4)70-50-46(42(66)38(62)33(19-57)74-50)76-48-44(68)40(64)36(60)31(17-55)72-48/h8,21-24,26-50,54-68H,6-7,9-20H2,1-5H3/t21-,22-,23-,24-,26-,27-,28-,29-,30+,31+,32+,33+,34-,35+,36+,37+,38+,39-,40-,41-,42-,43+,44+,45+,46+,47-,48-,49+,50+,51-,52-,53+/m0/s1
InChI Key CWLUVFCZEQBRPJ-KDIVADBSSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C53H88O24
Molecular Weight 1109.20 g/mol
Exact Mass 1108.56655367 g/mol
Topological Polar Surface Area (TPSA) 387.00 Ų
XlogP -1.60
Atomic LogP (AlogP) -3.60
H-Bond Acceptor 24
H-Bond Donor 15
Rotatable Bonds 16

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-2-[[(2S,3S,5S)-5-[(1R)-1-[(3S,5S,9R,10S,13S,14R,16S,17R)-3-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-16-hydroxy-10,13-dimethyl-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl]-3-ethyl-2-methyloxolan-2-yl]methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)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 + 0.8476 84.76%
Caco-2 - 0.8857 88.57%
Blood Brain Barrier - 0.6500 65.00%
Human oral bioavailability - 0.8286 82.86%
Subcellular localzation Mitochondria 0.6786 67.86%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8595 85.95%
OATP1B3 inhibitior + 0.9092 90.92%
MATE1 inhibitior - 0.9612 96.12%
OCT2 inhibitior - 0.5750 57.50%
BSEP inhibitior + 0.7178 71.78%
P-glycoprotein inhibitior + 0.7415 74.15%
P-glycoprotein substrate + 0.5302 53.02%
CYP3A4 substrate + 0.7176 71.76%
CYP2C9 substrate - 0.8037 80.37%
CYP2D6 substrate - 0.8331 83.31%
CYP3A4 inhibition - 0.8153 81.53%
CYP2C9 inhibition - 0.8962 89.62%
CYP2C19 inhibition - 0.8944 89.44%
CYP2D6 inhibition - 0.9249 92.49%
CYP1A2 inhibition - 0.9071 90.71%
CYP2C8 inhibition + 0.6347 63.47%
CYP inhibitory promiscuity - 0.8831 88.31%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.4991 49.91%
Eye corrosion - 0.9897 98.97%
Eye irritation - 0.9029 90.29%
Skin irritation + 0.5198 51.98%
Skin corrosion - 0.9404 94.04%
Ames mutagenesis - 0.7400 74.00%
Human Ether-a-go-go-Related Gene inhibition + 0.8421 84.21%
Micronuclear - 0.8500 85.00%
Hepatotoxicity - 0.6884 68.84%
skin sensitisation - 0.9194 91.94%
Respiratory toxicity + 0.5111 51.11%
Reproductive toxicity + 0.9333 93.33%
Mitochondrial toxicity + 0.5750 57.50%
Nephrotoxicity - 0.7521 75.21%
Acute Oral Toxicity (c) III 0.4540 45.40%
Estrogen receptor binding + 0.8496 84.96%
Androgen receptor binding + 0.7052 70.52%
Thyroid receptor binding + 0.5259 52.59%
Glucocorticoid receptor binding + 0.6944 69.44%
Aromatase binding + 0.6926 69.26%
PPAR gamma + 0.7957 79.57%
Honey bee toxicity - 0.6913 69.13%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.5900 59.00%
Fish aquatic toxicity + 0.9433 94.33%

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 98.36% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 97.05% 94.45%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.86% 96.09%
CHEMBL216 P11229 Muscarinic acetylcholine receptor M1 95.62% 94.23%
CHEMBL3137262 O60341 LSD1/CoREST complex 95.55% 97.09%
CHEMBL253 P34972 Cannabinoid CB2 receptor 95.41% 97.25%
CHEMBL218 P21554 Cannabinoid CB1 receptor 93.58% 96.61%
CHEMBL5608 Q16288 NT-3 growth factor receptor 92.79% 95.89%
CHEMBL226 P30542 Adenosine A1 receptor 92.43% 95.93%
CHEMBL2955 O95136 Sphingosine 1-phosphate receptor Edg-5 91.99% 92.86%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 90.20% 92.62%
CHEMBL3359 P21462 Formyl peptide receptor 1 88.92% 93.56%
CHEMBL1994 P08235 Mineralocorticoid receptor 88.60% 100.00%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 87.19% 95.50%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 86.57% 96.21%
CHEMBL3430907 Q96GD4 Aurora kinase B/Inner centromere protein 85.39% 97.50%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 84.42% 96.38%
CHEMBL237 P41145 Kappa opioid receptor 83.48% 98.10%
CHEMBL1937 Q92769 Histone deacetylase 2 82.74% 94.75%
CHEMBL3401 O75469 Pregnane X receptor 82.43% 94.73%
CHEMBL4227 P25090 Lipoxin A4 receptor 81.46% 100.00%
CHEMBL5163 Q9NY46 Sodium channel protein type III alpha subunit 81.10% 96.90%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 80.98% 94.00%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 80.69% 100.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 80.48% 89.00%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 80.34% 94.62%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 80.20% 94.08%

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.
Ajuga salicifolia

Cross-Links

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PubChem 101242574
LOTUS LTS0110800
wikiData Q104971357