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(1S,4aS,7aS)-7-[[(E,3R)-3-hydroxy-5-phenylpent-4-enoyl]oxymethyl]-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[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 b59910c9-72ae-4d5b-97b6-5222859efb5e
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name (1S,4aS,7aS)-7-[[(E,3R)-3-hydroxy-5-phenylpent-4-enoyl]oxymethyl]-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid
SMILES (Canonical) C1C=C(C2C1C(=COC2OC3C(C(C(C(O3)CO)O)O)O)C(=O)O)COC(=O)CC(C=CC4=CC=CC=C4)O
SMILES (Isomeric) C1C=C([C@@H]2[C@H]1C(=CO[C@H]2O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C(=O)O)COC(=O)C[C@H](/C=C/C4=CC=CC=C4)O
InChI InChI=1S/C27H32O12/c28-11-19-22(31)23(32)24(33)27(38-19)39-26-21-15(7-9-17(21)18(13-37-26)25(34)35)12-36-20(30)10-16(29)8-6-14-4-2-1-3-5-14/h1-8,13,16-17,19,21-24,26-29,31-33H,9-12H2,(H,34,35)/b8-6+/t16-,17+,19+,21+,22+,23-,24+,26-,27-/m0/s1
InChI Key UNWQLXACHOFSIS-CDZXDTOESA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C27H32O12
Molecular Weight 548.50 g/mol
Exact Mass 548.18937645 g/mol
Topological Polar Surface Area (TPSA) 192.00 Ų
XlogP -0.70
Atomic LogP (AlogP) -0.30
H-Bond Acceptor 11
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,7aS)-7-[[(E,3R)-3-hydroxy-5-phenylpent-4-enoyl]oxymethyl]-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[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 - 0.4824 48.24%
Caco-2 - 0.9020 90.20%
Blood Brain Barrier + 0.5250 52.50%
Human oral bioavailability - 0.7429 74.29%
Subcellular localzation Mitochondria 0.6824 68.24%
OATP2B1 inhibitior - 0.8498 84.98%
OATP1B1 inhibitior + 0.7812 78.12%
OATP1B3 inhibitior + 0.9625 96.25%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior + 0.6427 64.27%
P-glycoprotein inhibitior - 0.5189 51.89%
P-glycoprotein substrate - 0.7328 73.28%
CYP3A4 substrate + 0.6465 64.65%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8696 86.96%
CYP3A4 inhibition - 0.8654 86.54%
CYP2C9 inhibition - 0.9240 92.40%
CYP2C19 inhibition - 0.8060 80.60%
CYP2D6 inhibition - 0.8846 88.46%
CYP1A2 inhibition - 0.8600 86.00%
CYP2C8 inhibition + 0.7265 72.65%
CYP inhibitory promiscuity - 0.9126 91.26%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.7025 70.25%
Eye corrosion - 0.9899 98.99%
Eye irritation - 0.9245 92.45%
Skin irritation - 0.7999 79.99%
Skin corrosion - 0.9602 96.02%
Ames mutagenesis - 0.6400 64.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4048 40.48%
Micronuclear - 0.6700 67.00%
Hepatotoxicity - 0.7500 75.00%
skin sensitisation - 0.8650 86.50%
Respiratory toxicity + 0.6111 61.11%
Reproductive toxicity + 0.8556 85.56%
Mitochondrial toxicity + 0.6375 63.75%
Nephrotoxicity + 0.5137 51.37%
Acute Oral Toxicity (c) III 0.4435 44.35%
Estrogen receptor binding + 0.7475 74.75%
Androgen receptor binding + 0.6785 67.85%
Thyroid receptor binding - 0.5077 50.77%
Glucocorticoid receptor binding - 0.5000 50.00%
Aromatase binding + 0.5436 54.36%
PPAR gamma + 0.6663 66.63%
Honey bee toxicity - 0.7426 74.26%
Biodegradation - 0.7000 70.00%
Crustacea aquatic toxicity - 0.5951 59.51%
Fish aquatic toxicity + 0.9210 92.10%

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 98.40% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 94.62% 96.09%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 94.42% 94.62%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 94.02% 96.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 93.86% 95.56%
CHEMBL3060 Q9Y345 Glycine transporter 2 93.04% 99.17%
CHEMBL1293249 Q13887 Kruppel-like factor 5 92.24% 86.33%
CHEMBL3137262 O60341 LSD1/CoREST complex 91.83% 97.09%
CHEMBL3401 O75469 Pregnane X receptor 90.54% 94.73%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 90.46% 94.08%
CHEMBL1806 P11388 DNA topoisomerase II alpha 88.44% 89.00%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 88.08% 97.21%
CHEMBL2581 P07339 Cathepsin D 87.57% 98.95%
CHEMBL216 P11229 Muscarinic acetylcholine receptor M1 85.58% 94.23%
CHEMBL4227 P25090 Lipoxin A4 receptor 84.81% 100.00%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 83.25% 89.62%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 83.19% 96.95%
CHEMBL5028 O14672 ADAM10 82.94% 97.50%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 82.83% 95.50%
CHEMBL218 P21554 Cannabinoid CB1 receptor 81.66% 96.61%
CHEMBL3359 P21462 Formyl peptide receptor 1 80.08% 93.56%

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 162944404
LOTUS LTS0100679
wikiData Q105276178