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[(1S,4aR,5R,7S,7aS)-7-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-5-yl] (2E,4E)-3-methyl-5-[(1R,3S,6R)-1,3,6-trihydroxy-2,2,6-trimethylcyclohexyl]penta-2,4-dienoate

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 9bd52bac-c745-4659-95f8-e310092179f2
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name [(1S,4aR,5R,7S,7aS)-7-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-5-yl] (2E,4E)-3-methyl-5-[(1R,3S,6R)-1,3,6-trihydroxy-2,2,6-trimethylcyclohexyl]penta-2,4-dienoate
SMILES (Canonical)
SMILES (Isomeric)
InChI InChI=1S/C30H46O13/c1-15(6-10-30(39)27(2,3)19(32)7-9-29(30,5)38)12-20(33)41-17-13-28(4,37)21-16(17)8-11-40-25(21)43-26-24(36)23(35)22(34)18(14-31)42-26/h6,8,10-12,16-19,21-26,31-32,34-39H,7,9,13-14H2,1-5H3/b10-6+,15-12+/t16-,17+,18+,19-,21+,22+,23-,24+,25-,26-,28-,29+,30+/m0/s1
InChI Key XAYXKOKRFVFDAF-CFWMCNMYSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C30H46O13
Molecular Weight 614.70 g/mol
Exact Mass 614.29384152 g/mol
Topological Polar Surface Area (TPSA) 216.00 Ų
XlogP -0.30
Atomic LogP (AlogP) -0.86
H-Bond Acceptor 13
H-Bond Donor 8
Rotatable Bonds 7

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(1S,4aR,5R,7S,7aS)-7-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-5-yl] (2E,4E)-3-methyl-5-[(1R,3S,6R)-1,3,6-trihydroxy-2,2,6-trimethylcyclohexyl]penta-2,4-dienoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8201 82.01%
Caco-2 - 0.8672 86.72%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.8571 85.71%
Subcellular localzation Mitochondria 0.7565 75.65%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8395 83.95%
OATP1B3 inhibitior + 0.8315 83.15%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.7776 77.76%
BSEP inhibitior + 0.8611 86.11%
P-glycoprotein inhibitior + 0.6197 61.97%
P-glycoprotein substrate - 0.5424 54.24%
CYP3A4 substrate + 0.7296 72.96%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8935 89.35%
CYP3A4 inhibition - 0.8973 89.73%
CYP2C9 inhibition - 0.8076 80.76%
CYP2C19 inhibition - 0.9170 91.70%
CYP2D6 inhibition - 0.9246 92.46%
CYP1A2 inhibition - 0.8709 87.09%
CYP2C8 inhibition + 0.6050 60.50%
CYP inhibitory promiscuity - 0.8853 88.53%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6421 64.21%
Eye corrosion - 0.9909 99.09%
Eye irritation - 0.9264 92.64%
Skin irritation - 0.5391 53.91%
Skin corrosion - 0.9310 93.10%
Ames mutagenesis - 0.6900 69.00%
Human Ether-a-go-go-Related Gene inhibition - 0.3881 38.81%
Micronuclear - 0.8600 86.00%
Hepatotoxicity - 0.6925 69.25%
skin sensitisation - 0.8763 87.63%
Respiratory toxicity - 0.5000 50.00%
Reproductive toxicity + 0.9000 90.00%
Mitochondrial toxicity + 0.5125 51.25%
Nephrotoxicity - 0.8050 80.50%
Acute Oral Toxicity (c) III 0.6272 62.72%
Estrogen receptor binding + 0.7996 79.96%
Androgen receptor binding + 0.6573 65.73%
Thyroid receptor binding + 0.5641 56.41%
Glucocorticoid receptor binding + 0.6220 62.20%
Aromatase binding + 0.6239 62.39%
PPAR gamma + 0.6469 64.69%
Honey bee toxicity - 0.6073 60.73%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.5455 54.55%
Fish aquatic toxicity + 0.8176 81.76%

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 97.59% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.58% 96.09%
CHEMBL221 P23219 Cyclooxygenase-1 93.24% 90.17%
CHEMBL3137262 O60341 LSD1/CoREST complex 91.48% 97.09%
CHEMBL1994 P08235 Mineralocorticoid receptor 89.53% 100.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 88.46% 89.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 87.61% 86.33%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 86.76% 91.24%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 85.91% 95.50%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 85.53% 96.00%
CHEMBL1937 Q92769 Histone deacetylase 2 85.26% 94.75%
CHEMBL226 P30542 Adenosine A1 receptor 84.51% 95.93%
CHEMBL220 P22303 Acetylcholinesterase 84.37% 94.45%
CHEMBL5255 O00206 Toll-like receptor 4 83.81% 92.50%
CHEMBL2061 P19793 Retinoid X receptor alpha 83.59% 91.67%
CHEMBL4227 P25090 Lipoxin A4 receptor 83.04% 100.00%
CHEMBL241 Q14432 Phosphodiesterase 3A 82.77% 92.94%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 82.54% 94.45%
CHEMBL259 P32245 Melanocortin receptor 4 82.48% 95.38%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 82.06% 95.83%
CHEMBL5608 Q16288 NT-3 growth factor receptor 81.54% 95.89%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 81.44% 95.89%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 81.38% 96.95%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 81.08% 94.33%
CHEMBL3922 P50579 Methionine aminopeptidase 2 80.89% 97.28%
CHEMBL253 P34972 Cannabinoid CB2 receptor 80.70% 97.25%
CHEMBL340 P08684 Cytochrome P450 3A4 80.42% 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.
There are no matching plants.

Cross-Links

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PubChem 101603365
LOTUS LTS0022341
wikiData Q105324242