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(1S,4aS,6R,7R,7aS)-1-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-3-[(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-(3-hydroxybenzoyl)oxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[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 bc2c21dd-203f-4645-8f08-c0696547397f
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name (1S,4aS,6R,7R,7aS)-1-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-3-[(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-(3-hydroxybenzoyl)oxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid
SMILES (Canonical) CC1C(CC2C1C(OC=C2C(=O)O)OC3C(C(C(C(O3)CO)O)O)OC(=O)C=CC4=CC(=C(C(=C4)OC)O)OC)OC(=O)C5=CC(=CC=C5)O
SMILES (Isomeric) C[C@H]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)CO)O)O)OC(=O)/C=C/C4=CC(=C(C(=C4)OC)O)OC)OC(=O)C5=CC(=CC=C5)O
InChI InChI=1S/C34H38O16/c1-15-21(47-32(43)17-5-4-6-18(36)11-17)12-19-20(31(41)42)14-46-33(26(15)19)50-34-30(29(40)28(39)24(13-35)48-34)49-25(37)8-7-16-9-22(44-2)27(38)23(10-16)45-3/h4-11,14-15,19,21,24,26,28-30,33-36,38-40H,12-13H2,1-3H3,(H,41,42)/b8-7+/t15-,19+,21+,24+,26+,28+,29-,30+,33-,34-/m0/s1
InChI Key LPSKMPVDZRGUPK-CWTUTKDHSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C34H38O16
Molecular Weight 702.70 g/mol
Exact Mass 702.21598512 g/mol
Topological Polar Surface Area (TPSA) 237.00 Ų
XlogP 2.40
Atomic LogP (AlogP) 1.32
H-Bond Acceptor 15
H-Bond Donor 6
Rotatable Bonds 11

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (1S,4aS,6R,7R,7aS)-1-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-3-[(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-(3-hydroxybenzoyl)oxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[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 + 0.7444 74.44%
Caco-2 - 0.8813 88.13%
Blood Brain Barrier - 0.5750 57.50%
Human oral bioavailability - 0.8000 80.00%
Subcellular localzation Mitochondria 0.5204 52.04%
OATP2B1 inhibitior - 0.5758 57.58%
OATP1B1 inhibitior + 0.6941 69.41%
OATP1B3 inhibitior + 0.9414 94.14%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.8000 80.00%
BSEP inhibitior + 0.6910 69.10%
P-glycoprotein inhibitior + 0.7007 70.07%
P-glycoprotein substrate + 0.6470 64.70%
CYP3A4 substrate + 0.6999 69.99%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8699 86.99%
CYP3A4 inhibition - 0.8875 88.75%
CYP2C9 inhibition - 0.7885 78.85%
CYP2C19 inhibition - 0.8026 80.26%
CYP2D6 inhibition - 0.8881 88.81%
CYP1A2 inhibition - 0.7296 72.96%
CYP2C8 inhibition + 0.8288 82.88%
CYP inhibitory promiscuity - 0.7140 71.40%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.7169 71.69%
Eye corrosion - 0.9899 98.99%
Eye irritation - 0.9201 92.01%
Skin irritation - 0.7837 78.37%
Skin corrosion - 0.9468 94.68%
Ames mutagenesis - 0.5200 52.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7545 75.45%
Micronuclear - 0.5200 52.00%
Hepatotoxicity - 0.6476 64.76%
skin sensitisation - 0.8521 85.21%
Respiratory toxicity + 0.7333 73.33%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.6625 66.25%
Nephrotoxicity - 0.9508 95.08%
Acute Oral Toxicity (c) III 0.4732 47.32%
Estrogen receptor binding + 0.8534 85.34%
Androgen receptor binding + 0.6350 63.50%
Thyroid receptor binding + 0.5414 54.14%
Glucocorticoid receptor binding + 0.7207 72.07%
Aromatase binding - 0.4853 48.53%
PPAR gamma + 0.7205 72.05%
Honey bee toxicity - 0.7373 73.73%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.6300 63.00%
Fish aquatic toxicity + 0.9641 96.41%

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 97.66% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.57% 96.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 97.49% 86.33%
CHEMBL3137262 O60341 LSD1/CoREST complex 96.26% 97.09%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 95.85% 96.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 95.83% 95.56%
CHEMBL1806 P11388 DNA topoisomerase II alpha 95.22% 89.00%
CHEMBL3194 P02766 Transthyretin 92.15% 90.71%
CHEMBL3060 Q9Y345 Glycine transporter 2 91.74% 99.17%
CHEMBL2581 P07339 Cathepsin D 91.20% 98.95%
CHEMBL221 P23219 Cyclooxygenase-1 87.81% 90.17%
CHEMBL3401 O75469 Pregnane X receptor 87.42% 94.73%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 86.78% 86.92%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 86.72% 96.95%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 85.09% 99.23%
CHEMBL340 P08684 Cytochrome P450 3A4 85.03% 91.19%
CHEMBL4208 P20618 Proteasome component C5 84.90% 90.00%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 84.40% 95.89%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 84.15% 97.21%
CHEMBL5255 O00206 Toll-like receptor 4 83.44% 92.50%
CHEMBL1966 Q02127 Dihydroorotate dehydrogenase 83.02% 96.09%
CHEMBL3713062 P10646 Tissue factor pathway inhibitor 81.81% 97.33%
CHEMBL1994 P08235 Mineralocorticoid receptor 81.03% 100.00%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 80.84% 94.08%
CHEMBL5678 P34947 G protein-coupled receptor kinase 5 80.56% 88.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.48% 95.89%

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.
Swertia franchetiana
Swertia japonica

Cross-Links

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PubChem 102397460
NPASS NPC164406
LOTUS LTS0079852
wikiData Q104399092