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methyl (1S,4aS,5R,7S,7aS)-7-acetyloxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-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-4-carboxylate

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 29f56e99-f8db-45d9-af9e-76d2f7d2d8f8
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name methyl (1S,4aS,5R,7S,7aS)-7-acetyloxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-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-4-carboxylate
SMILES (Canonical)
SMILES (Isomeric)
InChI InChI=1S/C28H34O14/c1-13(30)42-28(2)10-17(39-19(32)9-6-14-4-7-15(31)8-5-14)20-16(25(36)37-3)12-38-26(21(20)28)41-27-24(35)23(34)22(33)18(11-29)40-27/h4-9,12,17-18,20-24,26-27,29,31,33-35H,10-11H2,1-3H3/b9-6+/t17-,18-,20+,21-,22-,23+,24-,26+,27+,28+/m1/s1
InChI Key VWZXXWQOKCWKSB-PSVLUTBBSA-N
Popularity 3 references in papers

Physical and Chemical Properties

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Molecular Formula C28H34O14
Molecular Weight 594.60 g/mol
Exact Mass 594.19485575 g/mol
Topological Polar Surface Area (TPSA) 208.00 Ų
XlogP 0.30
Atomic LogP (AlogP) -0.50
H-Bond Acceptor 14
H-Bond Donor 5
Rotatable Bonds 8

Synonyms

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ACon1_002403
NCGC00169878-01
BRD-K99996186-001-01-0

2D Structure

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2D Structure of methyl (1S,4aS,5R,7S,7aS)-7-acetyloxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-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-4-carboxylate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7228 72.28%
Caco-2 - 0.8739 87.39%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.8286 82.86%
Subcellular localzation Mitochondria 0.6090 60.90%
OATP2B1 inhibitior - 0.8651 86.51%
OATP1B1 inhibitior + 0.7806 78.06%
OATP1B3 inhibitior + 0.8976 89.76%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.8500 85.00%
BSEP inhibitior + 0.8842 88.42%
P-glycoprotein inhibitior + 0.6136 61.36%
P-glycoprotein substrate + 0.5632 56.32%
CYP3A4 substrate + 0.7056 70.56%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8782 87.82%
CYP3A4 inhibition - 0.8228 82.28%
CYP2C9 inhibition - 0.8076 80.76%
CYP2C19 inhibition - 0.8355 83.55%
CYP2D6 inhibition - 0.9283 92.83%
CYP1A2 inhibition - 0.8186 81.86%
CYP2C8 inhibition + 0.7812 78.12%
CYP inhibitory promiscuity - 0.7389 73.89%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5629 56.29%
Eye corrosion - 0.9897 98.97%
Eye irritation - 0.9381 93.81%
Skin irritation - 0.7354 73.54%
Skin corrosion - 0.9445 94.45%
Ames mutagenesis - 0.5937 59.37%
Human Ether-a-go-go-Related Gene inhibition + 0.7039 70.39%
Micronuclear - 0.5600 56.00%
Hepatotoxicity - 0.7922 79.22%
skin sensitisation - 0.8481 84.81%
Respiratory toxicity + 0.5667 56.67%
Reproductive toxicity + 0.8889 88.89%
Mitochondrial toxicity + 0.6750 67.50%
Nephrotoxicity + 0.6067 60.67%
Acute Oral Toxicity (c) III 0.3916 39.16%
Estrogen receptor binding + 0.8051 80.51%
Androgen receptor binding + 0.6758 67.58%
Thyroid receptor binding + 0.5754 57.54%
Glucocorticoid receptor binding + 0.7671 76.71%
Aromatase binding - 0.5063 50.63%
PPAR gamma + 0.7204 72.04%
Honey bee toxicity - 0.6838 68.38%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.6700 67.00%
Fish aquatic toxicity + 0.9144 91.44%

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 99.42% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.23% 96.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 96.34% 86.33%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 93.75% 96.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 93.24% 94.45%
CHEMBL1806 P11388 DNA topoisomerase II alpha 90.76% 89.00%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 89.65% 85.14%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.62% 97.09%
CHEMBL4040 P28482 MAP kinase ERK2 88.36% 83.82%
CHEMBL3401 O75469 Pregnane X receptor 87.79% 94.73%
CHEMBL4208 P20618 Proteasome component C5 87.74% 90.00%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 87.20% 94.08%
CHEMBL3922 P50579 Methionine aminopeptidase 2 87.01% 97.28%
CHEMBL5608 Q16288 NT-3 growth factor receptor 86.27% 95.89%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 85.41% 95.89%
CHEMBL3060 Q9Y345 Glycine transporter 2 84.58% 99.17%
CHEMBL2107 P61073 C-X-C chemokine receptor type 4 82.49% 93.10%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 82.39% 96.95%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 82.14% 95.50%
CHEMBL221 P23219 Cyclooxygenase-1 81.98% 90.17%
CHEMBL2581 P07339 Cathepsin D 81.59% 98.95%
CHEMBL226 P30542 Adenosine A1 receptor 81.01% 95.93%
CHEMBL1994 P08235 Mineralocorticoid receptor 80.72% 100.00%

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.
Barleria lupulina
Barleria prionitis

Cross-Links

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PubChem 24096431
LOTUS LTS0128034
wikiData Q105298376