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[2-[4a-Hydroxy-8-oxo-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4,5,6-tetrahydropyrano[3,4-c]pyran-4-yl]-2-hydroxyethyl] 6-hydroxy-7-methyl-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate

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 2f55fc8c-0131-4328-9794-4a03cde63a19
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name [2-[4a-hydroxy-8-oxo-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4,5,6-tetrahydropyrano[3,4-c]pyran-4-yl]-2-hydroxyethyl] 6-hydroxy-7-methyl-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
SMILES (Canonical) CC1C(CC2C1C(OC=C2C(=O)OCC(C3C(OC=C4C3(CCOC4=O)O)OC5C(C(C(C(O5)CO)O)O)O)O)OC6C(C(C(C(O6)CO)O)O)O)O
SMILES (Isomeric) CC1C(CC2C1C(OC=C2C(=O)OCC(C3C(OC=C4C3(CCOC4=O)O)OC5C(C(C(C(O5)CO)O)O)O)O)OC6C(C(C(C(O6)CO)O)O)O)O
InChI InChI=1S/C32H46O21/c1-10-14(35)4-11-12(7-48-28(18(10)11)52-30-24(41)22(39)20(37)16(5-33)50-30)26(43)47-9-15(36)19-29(49-8-13-27(44)46-3-2-32(13,19)45)53-31-25(42)23(40)21(38)17(6-34)51-31/h7-8,10-11,14-25,28-31,33-42,45H,2-6,9H2,1H3
InChI Key WKWUCUUUPMTTOU-UHFFFAOYSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C32H46O21
Molecular Weight 766.70 g/mol
Exact Mass 766.25315847 g/mol
Topological Polar Surface Area (TPSA) 331.00 Ų
XlogP -4.30
Atomic LogP (AlogP) -6.07
H-Bond Acceptor 21
H-Bond Donor 11
Rotatable Bonds 10

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [2-[4a-Hydroxy-8-oxo-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4,5,6-tetrahydropyrano[3,4-c]pyran-4-yl]-2-hydroxyethyl] 6-hydroxy-7-methyl-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.6658 66.58%
Caco-2 - 0.8941 89.41%
Blood Brain Barrier + 0.5296 52.96%
Human oral bioavailability - 0.7857 78.57%
Subcellular localzation Mitochondria 0.8276 82.76%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior - 0.3249 32.49%
OATP1B3 inhibitior + 0.9088 90.88%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.6651 66.51%
BSEP inhibitior - 0.4664 46.64%
P-glycoprotein inhibitior + 0.6431 64.31%
P-glycoprotein substrate + 0.5200 52.00%
CYP3A4 substrate + 0.7039 70.39%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8771 87.71%
CYP3A4 inhibition - 0.9646 96.46%
CYP2C9 inhibition - 0.9107 91.07%
CYP2C19 inhibition - 0.9194 91.94%
CYP2D6 inhibition - 0.9252 92.52%
CYP1A2 inhibition - 0.8891 88.91%
CYP2C8 inhibition + 0.5259 52.59%
CYP inhibitory promiscuity - 0.9562 95.62%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6186 61.86%
Eye corrosion - 0.9892 98.92%
Eye irritation - 0.9172 91.72%
Skin irritation - 0.6092 60.92%
Skin corrosion - 0.9341 93.41%
Ames mutagenesis - 0.6254 62.54%
Human Ether-a-go-go-Related Gene inhibition + 0.8157 81.57%
Micronuclear - 0.7800 78.00%
Hepatotoxicity - 0.5726 57.26%
skin sensitisation - 0.8986 89.86%
Respiratory toxicity + 0.7333 73.33%
Reproductive toxicity + 0.9000 90.00%
Mitochondrial toxicity + 0.6375 63.75%
Nephrotoxicity - 0.8118 81.18%
Acute Oral Toxicity (c) III 0.4745 47.45%
Estrogen receptor binding + 0.8302 83.02%
Androgen receptor binding + 0.6864 68.64%
Thyroid receptor binding - 0.5549 55.49%
Glucocorticoid receptor binding + 0.5764 57.64%
Aromatase binding + 0.5964 59.64%
PPAR gamma + 0.6710 67.10%
Honey bee toxicity - 0.7099 70.99%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.7800 78.00%
Fish aquatic toxicity + 0.7677 76.77%

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
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 98.45% 85.14%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.07% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.07% 96.09%
CHEMBL253 P34972 Cannabinoid CB2 receptor 97.49% 97.25%
CHEMBL3137262 O60341 LSD1/CoREST complex 96.51% 97.09%
CHEMBL218 P21554 Cannabinoid CB1 receptor 94.92% 96.61%
CHEMBL1806 P11388 DNA topoisomerase II alpha 94.11% 89.00%
CHEMBL2581 P07339 Cathepsin D 93.55% 98.95%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 88.84% 86.92%
CHEMBL3401 O75469 Pregnane X receptor 87.00% 94.73%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 86.59% 95.83%
CHEMBL1293249 Q13887 Kruppel-like factor 5 85.82% 86.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 85.18% 95.56%
CHEMBL1994 P08235 Mineralocorticoid receptor 82.76% 100.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 81.25% 95.89%
CHEMBL4208 P20618 Proteasome component C5 81.20% 90.00%
CHEMBL299 P17252 Protein kinase C alpha 80.91% 98.03%

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.
Gentiana olivieri
Gentiana septemfida

Cross-Links

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PubChem 163192477
LOTUS LTS0138278
wikiData Q105307769