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(1S,4aS,7S,7aS)-1-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-3-(4-hydroxybenzoyl)oxy-6-[[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxymethyl]oxan-2-yl]oxy-7-hydroxy-7-methyl-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-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 37f1be47-a023-4459-9371-db5fea855f76
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name (1S,4aS,7S,7aS)-1-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-3-(4-hydroxybenzoyl)oxy-6-[[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxymethyl]oxan-2-yl]oxy-7-hydroxy-7-methyl-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylic acid
SMILES (Canonical)
SMILES (Isomeric)
InChI InChI=1S/C33H36O15/c1-33(42)12-11-19-20(29(39)40)14-45-31(25(19)33)48-32-28(47-30(41)17-5-7-18(34)8-6-17)27(38)26(37)23(46-32)15-44-24(36)10-4-16-3-9-21(35)22(13-16)43-2/h3-10,13-14,19,23,25-28,31-32,34-35,37-38,42H,11-12,15H2,1-2H3,(H,39,40)/b10-4+/t19-,23-,25-,26-,27+,28-,31+,32+,33+/m1/s1
InChI Key WNQDGXDEZSWXSE-PBAPIZBRSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C33H36O15
Molecular Weight 672.60 g/mol
Exact Mass 672.20542044 g/mol
Topological Polar Surface Area (TPSA) 228.00 Ų
XlogP 1.60
Atomic LogP (AlogP) 1.45
H-Bond Acceptor 14
H-Bond Donor 6
Rotatable Bonds 10

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (1S,4aS,7S,7aS)-1-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-3-(4-hydroxybenzoyl)oxy-6-[[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxymethyl]oxan-2-yl]oxy-7-hydroxy-7-methyl-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-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 + 0.9087 90.87%
Caco-2 - 0.8816 88.16%
Blood Brain Barrier - 0.6000 60.00%
Human oral bioavailability - 0.7429 74.29%
Subcellular localzation Mitochondria 0.7446 74.46%
OATP2B1 inhibitior - 0.7236 72.36%
OATP1B1 inhibitior + 0.7694 76.94%
OATP1B3 inhibitior + 0.9117 91.17%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.8319 83.19%
BSEP inhibitior + 0.6263 62.63%
P-glycoprotein inhibitior + 0.6946 69.46%
P-glycoprotein substrate + 0.5532 55.32%
CYP3A4 substrate + 0.7124 71.24%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8730 87.30%
CYP3A4 inhibition - 0.8303 83.03%
CYP2C9 inhibition - 0.7404 74.04%
CYP2C19 inhibition - 0.8073 80.73%
CYP2D6 inhibition - 0.8753 87.53%
CYP1A2 inhibition - 0.5662 56.62%
CYP2C8 inhibition + 0.8781 87.81%
CYP inhibitory promiscuity - 0.8690 86.90%
UGT catelyzed + 0.9000 90.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.5994 59.94%
Eye corrosion - 0.9913 99.13%
Eye irritation - 0.9208 92.08%
Skin irritation - 0.7028 70.28%
Skin corrosion - 0.9298 92.98%
Ames mutagenesis - 0.5870 58.70%
Human Ether-a-go-go-Related Gene inhibition + 0.6658 66.58%
Micronuclear - 0.6700 67.00%
Hepatotoxicity - 0.7476 74.76%
skin sensitisation - 0.8604 86.04%
Respiratory toxicity + 0.6556 65.56%
Reproductive toxicity + 0.9889 98.89%
Mitochondrial toxicity + 0.8625 86.25%
Nephrotoxicity - 0.9043 90.43%
Acute Oral Toxicity (c) I 0.5192 51.92%
Estrogen receptor binding + 0.8054 80.54%
Androgen receptor binding + 0.6841 68.41%
Thyroid receptor binding + 0.5848 58.48%
Glucocorticoid receptor binding + 0.7243 72.43%
Aromatase binding + 0.5326 53.26%
PPAR gamma + 0.7157 71.57%
Honey bee toxicity - 0.7603 76.03%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.5800 58.00%
Fish aquatic toxicity + 0.9811 98.11%

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
CHEMBL1951 P21397 Monoamine oxidase A 99.20% 91.49%
CHEMBL1293249 Q13887 Kruppel-like factor 5 99.16% 86.33%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.45% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.09% 96.09%
CHEMBL3194 P02766 Transthyretin 97.51% 90.71%
CHEMBL4208 P20618 Proteasome component C5 96.05% 90.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 95.60% 89.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 94.18% 97.09%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 93.77% 96.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 93.25% 95.89%
CHEMBL2179 P04062 Beta-glucocerebrosidase 92.90% 85.31%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.60% 95.56%
CHEMBL5255 O00206 Toll-like receptor 4 91.56% 92.50%
CHEMBL241 Q14432 Phosphodiesterase 3A 90.67% 92.94%
CHEMBL4630 O14757 Serine/threonine-protein kinase Chk1 90.55% 97.03%
CHEMBL3060 Q9Y345 Glycine transporter 2 90.05% 99.17%
CHEMBL1994 P08235 Mineralocorticoid receptor 87.61% 100.00%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 86.79% 89.62%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 86.19% 96.95%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 85.67% 95.89%
CHEMBL340 P08684 Cytochrome P450 3A4 84.88% 91.19%
CHEMBL206 P03372 Estrogen receptor alpha 83.33% 97.64%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 82.84% 97.21%
CHEMBL4829 O00763 Acetyl-CoA carboxylase 2 81.18% 98.00%
CHEMBL4227 P25090 Lipoxin A4 receptor 81.03% 100.00%
CHEMBL221 P23219 Cyclooxygenase-1 80.97% 90.17%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 80.66% 96.21%
CHEMBL226 P30542 Adenosine A1 receptor 80.45% 95.93%
CHEMBL242 Q92731 Estrogen receptor beta 80.02% 98.35%

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.
Vitex altissima

Cross-Links

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PubChem 11181450
LOTUS LTS0181246
wikiData Q105309226