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(1S,4aS,5R,7S,7aS)-7-acetyloxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-7-methyl-1-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-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 1ff7773f-6688-439d-bcf2-8792ef8b8476
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name (1S,4aS,5R,7S,7aS)-7-acetyloxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-7-methyl-1-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylic acid
SMILES (Canonical) CC(=O)OC1(CC(C2C1C(OC=C2C(=O)O)OC3C(C(C(C(O3)CO)O)O)O)OC(=O)C=CC4=CC=C(C=C4)O)C
SMILES (Isomeric) CC(=O)O[C@]1(C[C@H]([C@H]2[C@@H]1[C@@H](OC=C2C(=O)O)O[C@H]3[C@@H]([C@H]([C@H]([C@H](O3)CO)O)O)O)OC(=O)/C=C/C4=CC=C(C=C4)O)C
InChI InChI=1S/C27H32O14/c1-12(29)41-27(2)9-16(38-18(31)8-5-13-3-6-14(30)7-4-13)19-15(24(35)36)11-37-25(20(19)27)40-26-23(34)22(33)21(32)17(10-28)39-26/h3-8,11,16-17,19-23,25-26,28,30,32-34H,9-10H2,1-2H3,(H,35,36)/b8-5+/t16-,17-,19+,20-,21+,22+,23-,25+,26+,27+/m1/s1
InChI Key XORDQNURMWOOGO-AFRZYKJDSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C27H32O14
Molecular Weight 580.50 g/mol
Exact Mass 580.17920569 g/mol
Topological Polar Surface Area (TPSA) 219.00 Ų
XlogP -0.10
Atomic LogP (AlogP) -0.58
H-Bond Acceptor 13
H-Bond Donor 6
Rotatable Bonds 8

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (1S,4aS,5R,7S,7aS)-7-acetyloxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-7-methyl-1-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-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 + 0.7143 71.43%
Caco-2 - 0.8950 89.50%
Blood Brain Barrier - 0.5750 57.50%
Human oral bioavailability - 0.8143 81.43%
Subcellular localzation Mitochondria 0.7079 70.79%
OATP2B1 inhibitior - 0.8610 86.10%
OATP1B1 inhibitior + 0.7682 76.82%
OATP1B3 inhibitior + 0.9196 91.96%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.8250 82.50%
BSEP inhibitior + 0.8789 87.89%
P-glycoprotein inhibitior - 0.4809 48.09%
P-glycoprotein substrate - 0.5187 51.87%
CYP3A4 substrate + 0.6736 67.36%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8797 87.97%
CYP3A4 inhibition - 0.8422 84.22%
CYP2C9 inhibition - 0.7724 77.24%
CYP2C19 inhibition - 0.8365 83.65%
CYP2D6 inhibition - 0.9279 92.79%
CYP1A2 inhibition - 0.8095 80.95%
CYP2C8 inhibition + 0.7369 73.69%
CYP inhibitory promiscuity - 0.6721 67.21%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5853 58.53%
Eye corrosion - 0.9909 99.09%
Eye irritation - 0.9396 93.96%
Skin irritation - 0.7275 72.75%
Skin corrosion - 0.9399 93.99%
Ames mutagenesis - 0.6200 62.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6674 66.74%
Micronuclear - 0.5400 54.00%
Hepatotoxicity - 0.7913 79.13%
skin sensitisation - 0.8327 83.27%
Respiratory toxicity + 0.5889 58.89%
Reproductive toxicity + 0.8667 86.67%
Mitochondrial toxicity + 0.7125 71.25%
Nephrotoxicity + 0.5882 58.82%
Acute Oral Toxicity (c) III 0.4104 41.04%
Estrogen receptor binding + 0.7982 79.82%
Androgen receptor binding + 0.6667 66.67%
Thyroid receptor binding + 0.5478 54.78%
Glucocorticoid receptor binding + 0.7286 72.86%
Aromatase binding - 0.5203 52.03%
PPAR gamma + 0.7005 70.05%
Honey bee toxicity - 0.6882 68.82%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.6900 69.00%
Fish aquatic toxicity + 0.9530 95.30%

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 98.82% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.92% 96.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 97.43% 86.33%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 94.56% 94.62%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 94.31% 94.08%
CHEMBL1806 P11388 DNA topoisomerase II alpha 92.86% 89.00%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 92.82% 96.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.74% 97.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 90.51% 94.45%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.76% 95.56%
CHEMBL2581 P07339 Cathepsin D 86.52% 98.95%
CHEMBL5608 Q16288 NT-3 growth factor receptor 85.49% 95.89%
CHEMBL3401 O75469 Pregnane X receptor 84.51% 94.73%
CHEMBL3060 Q9Y345 Glycine transporter 2 84.09% 99.17%
CHEMBL216 P11229 Muscarinic acetylcholine receptor M1 84.09% 94.23%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 83.88% 95.50%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 83.51% 96.95%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 83.36% 95.89%
CHEMBL4208 P20618 Proteasome component C5 83.28% 90.00%
CHEMBL211 P08172 Muscarinic acetylcholine receptor M2 82.57% 94.97%
CHEMBL221 P23219 Cyclooxygenase-1 81.31% 90.17%
CHEMBL4040 P28482 MAP kinase ERK2 80.84% 83.82%
CHEMBL1994 P08235 Mineralocorticoid receptor 80.66% 100.00%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 80.60% 93.00%

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

Cross-Links

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PubChem 154496086
LOTUS LTS0225978
wikiData Q105337884