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(1S,4aS,7R,7aS)-1-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(E)-3-(4-methoxyphenyl)prop-2-enoyl]oxyoxan-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 ac786959-68ff-4c2b-a2df-92efa6884489
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name (1S,4aS,7R,7aS)-1-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(E)-3-(4-methoxyphenyl)prop-2-enoyl]oxyoxan-2-yl]oxy-7-hydroxy-7-methyl-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylic acid
SMILES (Canonical) CC1(CCC2C1C(OC=C2C(=O)O)OC3C(C(C(C(O3)CO)O)O)OC(=O)C=CC4=CC=C(C=C4)OC)O
SMILES (Isomeric) C[C@]1(CC[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)OC(=O)/C=C/C4=CC=C(C=C4)OC)O
InChI InChI=1S/C26H32O12/c1-26(33)10-9-15-16(23(31)32)12-35-24(19(15)26)38-25-22(21(30)20(29)17(11-27)36-25)37-18(28)8-5-13-3-6-14(34-2)7-4-13/h3-8,12,15,17,19-22,24-25,27,29-30,33H,9-11H2,1-2H3,(H,31,32)/b8-5+/t15-,17-,19-,20-,21+,22-,24+,25+,26-/m1/s1
InChI Key CGQHDMQVSGXNLP-LDTLPTRKSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C26H32O12
Molecular Weight 536.50 g/mol
Exact Mass 536.18937645 g/mol
Topological Polar Surface Area (TPSA) 181.00 Ų
XlogP 0.70
Atomic LogP (AlogP) 0.18
H-Bond Acceptor 11
H-Bond Donor 5
Rotatable Bonds 8

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (1S,4aS,7R,7aS)-1-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(E)-3-(4-methoxyphenyl)prop-2-enoyl]oxyoxan-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 + 0.8196 81.96%
Caco-2 - 0.8805 88.05%
Blood Brain Barrier - 0.5500 55.00%
Human oral bioavailability - 0.8000 80.00%
Subcellular localzation Mitochondria 0.6582 65.82%
OATP2B1 inhibitior - 0.8578 85.78%
OATP1B1 inhibitior + 0.7621 76.21%
OATP1B3 inhibitior + 0.9195 91.95%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.8375 83.75%
BSEP inhibitior - 0.6530 65.30%
P-glycoprotein inhibitior - 0.5000 50.00%
P-glycoprotein substrate - 0.6715 67.15%
CYP3A4 substrate + 0.6851 68.51%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8751 87.51%
CYP3A4 inhibition - 0.8013 80.13%
CYP2C9 inhibition - 0.8342 83.42%
CYP2C19 inhibition - 0.8759 87.59%
CYP2D6 inhibition - 0.9017 90.17%
CYP1A2 inhibition - 0.7961 79.61%
CYP2C8 inhibition + 0.6538 65.38%
CYP inhibitory promiscuity - 0.8704 87.04%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.6211 62.11%
Eye corrosion - 0.9907 99.07%
Eye irritation - 0.9428 94.28%
Skin irritation - 0.6519 65.19%
Skin corrosion - 0.9297 92.97%
Ames mutagenesis - 0.6270 62.70%
Human Ether-a-go-go-Related Gene inhibition + 0.7337 73.37%
Micronuclear - 0.7200 72.00%
Hepatotoxicity - 0.7566 75.66%
skin sensitisation - 0.8797 87.97%
Respiratory toxicity + 0.6778 67.78%
Reproductive toxicity + 0.9556 95.56%
Mitochondrial toxicity + 0.7750 77.50%
Nephrotoxicity - 0.7892 78.92%
Acute Oral Toxicity (c) I 0.5231 52.31%
Estrogen receptor binding + 0.7713 77.13%
Androgen receptor binding + 0.6277 62.77%
Thyroid receptor binding + 0.5762 57.62%
Glucocorticoid receptor binding + 0.7033 70.33%
Aromatase binding + 0.5327 53.27%
PPAR gamma + 0.6450 64.50%
Honey bee toxicity - 0.8019 80.19%
Biodegradation - 0.6750 67.50%
Crustacea aquatic toxicity - 0.7400 74.00%
Fish aquatic toxicity + 0.9000 90.00%

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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.48% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.86% 91.11%
CHEMBL3137262 O60341 LSD1/CoREST complex 96.22% 97.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 95.50% 86.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 95.19% 95.56%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 94.91% 96.00%
CHEMBL4208 P20618 Proteasome component C5 94.11% 90.00%
CHEMBL221 P23219 Cyclooxygenase-1 93.92% 90.17%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 88.85% 93.00%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 87.26% 94.08%
CHEMBL211 P08172 Muscarinic acetylcholine receptor M2 86.84% 94.97%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 86.62% 86.92%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 86.58% 95.89%
CHEMBL5608 Q16288 NT-3 growth factor receptor 86.53% 95.89%
CHEMBL1806 P11388 DNA topoisomerase II alpha 85.38% 89.00%
CHEMBL226 P30542 Adenosine A1 receptor 85.37% 95.93%
CHEMBL1966 Q02127 Dihydroorotate dehydrogenase 85.24% 96.09%
CHEMBL5255 O00206 Toll-like receptor 4 83.96% 92.50%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 82.34% 94.45%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 81.84% 91.07%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 80.93% 92.62%
CHEMBL3060 Q9Y345 Glycine transporter 2 80.79% 99.17%
CHEMBL1994 P08235 Mineralocorticoid receptor 80.74% 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.
Avicennia marina

Cross-Links

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PubChem 162908307
LOTUS LTS0010501
wikiData Q104958032