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(1S,4aS,7R,7aS)-1-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(E)-3-(4-hydroxyphenyl)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 c95ea21e-e46c-4317-9aa0-7aaa5a2d03db
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-hydroxyphenyl)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)
SMILES (Isomeric)
InChI InChI=1S/C25H30O12/c1-25(33)9-8-14-15(22(31)32)11-34-23(18(14)25)37-24-21(20(30)19(29)16(10-26)35-24)36-17(28)7-4-12-2-5-13(27)6-3-12/h2-7,11,14,16,18-21,23-24,26-27,29-30,33H,8-10H2,1H3,(H,31,32)/b7-4+/t14-,16-,18-,19-,20+,21-,23+,24+,25-/m1/s1
InChI Key LWORTIDRRYUBBP-KGLXQJFJSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C25H30O12
Molecular Weight 522.50 g/mol
Exact Mass 522.17372639 g/mol
Topological Polar Surface Area (TPSA) 192.00 Ų
XlogP 0.30
Atomic LogP (AlogP) -0.13
H-Bond Acceptor 11
H-Bond Donor 6
Rotatable Bonds 7

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-hydroxyphenyl)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 + 0.8275 82.75%
Caco-2 - 0.8980 89.80%
Blood Brain Barrier - 0.5500 55.00%
Human oral bioavailability - 0.8429 84.29%
Subcellular localzation Mitochondria 0.7306 73.06%
OATP2B1 inhibitior - 0.8528 85.28%
OATP1B1 inhibitior + 0.7323 73.23%
OATP1B3 inhibitior + 0.9205 92.05%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.7651 76.51%
BSEP inhibitior - 0.6223 62.23%
P-glycoprotein inhibitior - 0.5833 58.33%
P-glycoprotein substrate - 0.6686 66.86%
CYP3A4 substrate + 0.6793 67.93%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8789 87.89%
CYP3A4 inhibition - 0.8426 84.26%
CYP2C9 inhibition - 0.8157 81.57%
CYP2C19 inhibition - 0.8532 85.32%
CYP2D6 inhibition - 0.9025 90.25%
CYP1A2 inhibition - 0.7887 78.87%
CYP2C8 inhibition + 0.7413 74.13%
CYP inhibitory promiscuity - 0.8459 84.59%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.5793 57.93%
Eye corrosion - 0.9914 99.14%
Eye irritation - 0.9340 93.40%
Skin irritation - 0.6258 62.58%
Skin corrosion - 0.9276 92.76%
Ames mutagenesis - 0.6270 62.70%
Human Ether-a-go-go-Related Gene inhibition + 0.6824 68.24%
Micronuclear - 0.7500 75.00%
Hepatotoxicity - 0.7976 79.76%
skin sensitisation - 0.8732 87.32%
Respiratory toxicity + 0.6667 66.67%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.7750 77.50%
Nephrotoxicity - 0.7323 73.23%
Acute Oral Toxicity (c) I 0.4504 45.04%
Estrogen receptor binding + 0.7794 77.94%
Androgen receptor binding + 0.6413 64.13%
Thyroid receptor binding + 0.5778 57.78%
Glucocorticoid receptor binding + 0.6501 65.01%
Aromatase binding + 0.5730 57.30%
PPAR gamma + 0.6245 62.45%
Honey bee toxicity - 0.7986 79.86%
Biodegradation - 0.5750 57.50%
Crustacea aquatic toxicity - 0.6700 67.00%
Fish aquatic toxicity + 0.9345 93.45%

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 97.59% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.40% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 95.11% 97.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 94.85% 86.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 93.24% 95.56%
CHEMBL1806 P11388 DNA topoisomerase II alpha 92.12% 89.00%
CHEMBL206 P03372 Estrogen receptor alpha 90.77% 97.64%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 89.91% 96.00%
CHEMBL4208 P20618 Proteasome component C5 88.90% 90.00%
CHEMBL216 P11229 Muscarinic acetylcholine receptor M1 88.16% 94.23%
CHEMBL242 Q92731 Estrogen receptor beta 87.41% 98.35%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 87.34% 94.62%
CHEMBL5255 O00206 Toll-like receptor 4 86.55% 92.50%
CHEMBL3194 P02766 Transthyretin 86.01% 90.71%
CHEMBL1994 P08235 Mineralocorticoid receptor 85.97% 100.00%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 85.01% 93.00%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 84.77% 94.08%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 84.66% 95.89%
CHEMBL4227 P25090 Lipoxin A4 receptor 84.61% 100.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 84.54% 94.45%
CHEMBL5608 Q16288 NT-3 growth factor receptor 84.04% 95.89%
CHEMBL1966 Q02127 Dihydroorotate dehydrogenase 84.03% 96.09%
CHEMBL2581 P07339 Cathepsin D 83.77% 98.95%
CHEMBL226 P30542 Adenosine A1 receptor 83.54% 95.93%
CHEMBL211 P08172 Muscarinic acetylcholine receptor M2 82.09% 94.97%
CHEMBL2996 Q05655 Protein kinase C delta 81.05% 97.79%

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 163022016
LOTUS LTS0181432
wikiData Q105158454