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(1S,4aS,6S,7R,7aS)-1,4a,5,6,7,7a-Hexahydro-6,7-dihydroxy-1-[[6-O-[(2E)-3-(4-hydroxyphenyl)-1-oxo-2-propen-1-yl]-beta-D-glucopyranosyl]oxy]-7-methylcyclopenta[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 ba07a25b-f180-45ba-8074-afb1c734738f
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name (1S,4aS,6S,7R,7aS)-6,7-dihydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylic acid
SMILES (Canonical) CC1(C(CC2C1C(OC=C2C(=O)O)OC3C(C(C(C(O3)COC(=O)C=CC4=CC=C(C=C4)O)O)O)O)O)O
SMILES (Isomeric) C[C@@]1([C@H](C[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)COC(=O)/C=C/C4=CC=C(C=C4)O)O)O)O)O)O
InChI InChI=1S/C25H30O13/c1-25(34)16(27)8-13-14(22(32)33)9-36-23(18(13)25)38-24-21(31)20(30)19(29)15(37-24)10-35-17(28)7-4-11-2-5-12(26)6-3-11/h2-7,9,13,15-16,18-21,23-24,26-27,29-31,34H,8,10H2,1H3,(H,32,33)/b7-4+/t13-,15-,16+,18-,19-,20+,21-,23+,24+,25+/m1/s1
InChI Key QCPZTWAULZJVIK-YGPPJHJASA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C25H30O13
Molecular Weight 538.50 g/mol
Exact Mass 538.16864101 g/mol
Topological Polar Surface Area (TPSA) 213.00 Ų
XlogP -1.20
Atomic LogP (AlogP) -1.15
H-Bond Acceptor 12
H-Bond Donor 7
Rotatable Bonds 7

Synonyms

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(1S,4aS,6S,7R,7aS)-1,4a,5,6,7,7a-Hexahydro-6,7-dihydroxy-1-[[6-O-[(2E)-3-(4-hydroxyphenyl)-1-oxo-2-propen-1-yl]-beta-D-glucopyranosyl]oxy]-7-methylcyclopenta[c]pyran-4-carboxylic acid
220271-93-2

2D Structure

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2D Structure of (1S,4aS,6S,7R,7aS)-1,4a,5,6,7,7a-Hexahydro-6,7-dihydroxy-1-[[6-O-[(2E)-3-(4-hydroxyphenyl)-1-oxo-2-propen-1-yl]-beta-D-glucopyranosyl]oxy]-7-methylcyclopenta[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 + 0.8519 85.19%
Caco-2 - 0.8998 89.98%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.8571 85.71%
Subcellular localzation Mitochondria 0.6717 67.17%
OATP2B1 inhibitior - 0.8558 85.58%
OATP1B1 inhibitior + 0.7560 75.60%
OATP1B3 inhibitior + 0.9464 94.64%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior - 0.7327 73.27%
P-glycoprotein inhibitior - 0.6506 65.06%
P-glycoprotein substrate - 0.6269 62.69%
CYP3A4 substrate + 0.6805 68.05%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8803 88.03%
CYP3A4 inhibition - 0.9307 93.07%
CYP2C9 inhibition - 0.8060 80.60%
CYP2C19 inhibition - 0.8367 83.67%
CYP2D6 inhibition - 0.9012 90.12%
CYP1A2 inhibition - 0.7958 79.58%
CYP2C8 inhibition + 0.7541 75.41%
CYP inhibitory promiscuity - 0.8107 81.07%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5784 57.84%
Eye corrosion - 0.9911 99.11%
Eye irritation - 0.9348 93.48%
Skin irritation - 0.6787 67.87%
Skin corrosion - 0.9298 92.98%
Ames mutagenesis - 0.6300 63.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4472 44.72%
Micronuclear - 0.5841 58.41%
Hepatotoxicity - 0.7500 75.00%
skin sensitisation - 0.8110 81.10%
Respiratory toxicity + 0.6000 60.00%
Reproductive toxicity + 0.9222 92.22%
Mitochondrial toxicity + 0.8000 80.00%
Nephrotoxicity - 0.7924 79.24%
Acute Oral Toxicity (c) I 0.4046 40.46%
Estrogen receptor binding + 0.7393 73.93%
Androgen receptor binding + 0.6524 65.24%
Thyroid receptor binding + 0.5462 54.62%
Glucocorticoid receptor binding + 0.6430 64.30%
Aromatase binding + 0.5322 53.22%
PPAR gamma + 0.6919 69.19%
Honey bee toxicity - 0.7805 78.05%
Biodegradation - 0.7000 70.00%
Crustacea aquatic toxicity - 0.6000 60.00%
Fish aquatic toxicity + 0.9510 95.10%

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
CHEMBL1293249 Q13887 Kruppel-like factor 5 97.75% 86.33%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.87% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.08% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 94.96% 97.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 94.01% 89.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.45% 95.56%
CHEMBL1951 P21397 Monoamine oxidase A 90.67% 91.49%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 90.54% 96.00%
CHEMBL206 P03372 Estrogen receptor alpha 90.49% 97.64%
CHEMBL4208 P20618 Proteasome component C5 89.52% 90.00%
CHEMBL221 P23219 Cyclooxygenase-1 88.75% 90.17%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 88.28% 96.95%
CHEMBL3194 P02766 Transthyretin 86.20% 90.71%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 84.90% 94.62%
CHEMBL3060 Q9Y345 Glycine transporter 2 84.26% 99.17%
CHEMBL2179 P04062 Beta-glucocerebrosidase 84.16% 85.31%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 83.55% 97.21%
CHEMBL5608 Q16288 NT-3 growth factor receptor 82.77% 95.89%
CHEMBL4227 P25090 Lipoxin A4 receptor 82.54% 100.00%
CHEMBL5255 O00206 Toll-like receptor 4 81.91% 92.50%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 81.80% 94.45%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 80.57% 95.89%
CHEMBL1994 P08235 Mineralocorticoid receptor 80.25% 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.
Lippia origanoides

Cross-Links

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PubChem 162988849
LOTUS LTS0157665
wikiData Q105218448