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methyl (1S,4aS,6S,7S,7aS)-7-methyl-6-[(2E,4E)-5-phenylpenta-2,4-dienoyl]oxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[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 134b187f-c56e-43d4-a0fb-61a7636f6b74
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name methyl (1S,4aS,6S,7S,7aS)-7-methyl-6-[(2E,4E)-5-phenylpenta-2,4-dienoyl]oxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
SMILES (Canonical) CC1C(CC2C1C(OC=C2C(=O)OC)OC3C(C(C(C(O3)CO)O)O)O)OC(=O)C=CC=CC4=CC=CC=C4
SMILES (Isomeric) C[C@@H]1[C@H](C[C@H]2[C@@H]1[C@@H](OC=C2C(=O)OC)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)OC(=O)/C=C/C=C/C4=CC=CC=C4
InChI InChI=1S/C28H34O11/c1-15-19(37-21(30)11-7-6-10-16-8-4-3-5-9-16)12-17-18(26(34)35-2)14-36-27(22(15)17)39-28-25(33)24(32)23(31)20(13-29)38-28/h3-11,14-15,17,19-20,22-25,27-29,31-33H,12-13H2,1-2H3/b10-6+,11-7+/t15-,17-,19+,20-,22-,23-,24+,25-,27+,28+/m1/s1
InChI Key OCFVEUFRRHOHAR-CFJSNBGRSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C28H34O11
Molecular Weight 546.60 g/mol
Exact Mass 546.21011190 g/mol
Topological Polar Surface Area (TPSA) 161.00 Ų
XlogP 1.90
Atomic LogP (AlogP) 0.67
H-Bond Acceptor 11
H-Bond Donor 4
Rotatable Bonds 8

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of methyl (1S,4aS,6S,7S,7aS)-7-methyl-6-[(2E,4E)-5-phenylpenta-2,4-dienoyl]oxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[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 + 0.6762 67.62%
Caco-2 - 0.8594 85.94%
Blood Brain Barrier - 0.5500 55.00%
Human oral bioavailability - 0.8714 87.14%
Subcellular localzation Mitochondria 0.6428 64.28%
OATP2B1 inhibitior - 0.8578 85.78%
OATP1B1 inhibitior - 0.3326 33.26%
OATP1B3 inhibitior + 0.9455 94.55%
MATE1 inhibitior - 0.9412 94.12%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior + 0.8968 89.68%
P-glycoprotein inhibitior - 0.4341 43.41%
P-glycoprotein substrate - 0.5531 55.31%
CYP3A4 substrate + 0.6822 68.22%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8842 88.42%
CYP3A4 inhibition - 0.8616 86.16%
CYP2C9 inhibition - 0.8524 85.24%
CYP2C19 inhibition - 0.8717 87.17%
CYP2D6 inhibition - 0.8936 89.36%
CYP1A2 inhibition - 0.8322 83.22%
CYP2C8 inhibition + 0.7590 75.90%
CYP inhibitory promiscuity - 0.7509 75.09%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.7152 71.52%
Eye corrosion - 0.9899 98.99%
Eye irritation - 0.9546 95.46%
Skin irritation - 0.7635 76.35%
Skin corrosion - 0.9521 95.21%
Ames mutagenesis - 0.5270 52.70%
Human Ether-a-go-go-Related Gene inhibition + 0.6958 69.58%
Micronuclear - 0.6000 60.00%
Hepatotoxicity - 0.7750 77.50%
skin sensitisation - 0.8692 86.92%
Respiratory toxicity + 0.6778 67.78%
Reproductive toxicity + 0.8556 85.56%
Mitochondrial toxicity + 0.6625 66.25%
Nephrotoxicity - 0.7872 78.72%
Acute Oral Toxicity (c) III 0.5075 50.75%
Estrogen receptor binding + 0.8097 80.97%
Androgen receptor binding + 0.5322 53.22%
Thyroid receptor binding - 0.5000 50.00%
Glucocorticoid receptor binding + 0.5975 59.75%
Aromatase binding - 0.6220 62.20%
PPAR gamma + 0.7080 70.80%
Honey bee toxicity - 0.7942 79.42%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.6100 61.00%
Fish aquatic toxicity + 0.8700 87.00%

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 98.90% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.54% 96.09%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 95.50% 96.00%
CHEMBL221 P23219 Cyclooxygenase-1 94.68% 90.17%
CHEMBL1293249 Q13887 Kruppel-like factor 5 94.08% 86.33%
CHEMBL4040 P28482 MAP kinase ERK2 93.10% 83.82%
CHEMBL3401 O75469 Pregnane X receptor 90.76% 94.73%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.61% 97.09%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 88.76% 86.92%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 88.18% 95.56%
CHEMBL5028 O14672 ADAM10 88.10% 97.50%
CHEMBL2581 P07339 Cathepsin D 88.06% 98.95%
CHEMBL3060 Q9Y345 Glycine transporter 2 88.01% 99.17%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 87.94% 94.08%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 86.95% 95.83%
CHEMBL1806 P11388 DNA topoisomerase II alpha 83.79% 89.00%
CHEMBL4208 P20618 Proteasome component C5 82.12% 90.00%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 81.91% 95.50%

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.
Avicennia marina

Cross-Links

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PubChem 163193467
LOTUS LTS0227075
wikiData Q105189339