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[(2R,3R,4R,5R,6S)-2-[[(1S,4aR,5S,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-5-yl]oxy]-4,5-dihydroxy-6-methyloxan-3-yl] (E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate

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 17ecef37-7bfc-47d8-bb91-94d82915af50
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name [(2R,3R,4R,5R,6S)-2-[[(1S,4aR,5S,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-5-yl]oxy]-4,5-dihydroxy-6-methyloxan-3-yl] (E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate
SMILES (Canonical) CC1C(C(C(C(O1)OC2C=C(C3C2C=COC3OC4C(C(C(C(O4)CO)O)O)O)CO)OC(=O)C=CC5=CC(=C(C=C5)OC)O)O)O
SMILES (Isomeric) C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2C=C([C@@H]3[C@H]2C=CO[C@H]3O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)CO)OC(=O)/C=C/C5=CC(=C(C=C5)OC)O)O)O
InChI InChI=1S/C31H40O16/c1-13-23(36)26(39)28(46-21(35)6-4-14-3-5-18(41-2)17(34)9-14)31(43-13)44-19-10-15(11-32)22-16(19)7-8-42-29(22)47-30-27(40)25(38)24(37)20(12-33)45-30/h3-10,13,16,19-20,22-34,36-40H,11-12H2,1-2H3/b6-4+/t13-,16-,19+,20+,22+,23-,24+,25-,26+,27+,28+,29-,30-,31-/m0/s1
InChI Key VMKDGEXOTBXACB-REKXUBECSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C31H40O16
Molecular Weight 668.60 g/mol
Exact Mass 668.23163518 g/mol
Topological Polar Surface Area (TPSA) 244.00 Ų
XlogP -1.80
Atomic LogP (AlogP) -1.97
H-Bond Acceptor 16
H-Bond Donor 8
Rotatable Bonds 10

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(2R,3R,4R,5R,6S)-2-[[(1S,4aR,5S,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-5-yl]oxy]-4,5-dihydroxy-6-methyloxan-3-yl] (E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.6784 67.84%
Caco-2 - 0.8881 88.81%
Blood Brain Barrier - 0.6750 67.50%
Human oral bioavailability - 0.8000 80.00%
Subcellular localzation Mitochondria 0.5787 57.87%
OATP2B1 inhibitior - 0.8607 86.07%
OATP1B1 inhibitior + 0.8300 83.00%
OATP1B3 inhibitior + 0.9710 97.10%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior - 0.4719 47.19%
P-glycoprotein inhibitior - 0.5000 50.00%
P-glycoprotein substrate + 0.5968 59.68%
CYP3A4 substrate + 0.6835 68.35%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8696 86.96%
CYP3A4 inhibition - 0.8699 86.99%
CYP2C9 inhibition - 0.8350 83.50%
CYP2C19 inhibition - 0.6454 64.54%
CYP2D6 inhibition - 0.8471 84.71%
CYP1A2 inhibition - 0.8311 83.11%
CYP2C8 inhibition + 0.7369 73.69%
CYP inhibitory promiscuity + 0.5231 52.31%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6980 69.80%
Eye corrosion - 0.9885 98.85%
Eye irritation - 0.9236 92.36%
Skin irritation - 0.8010 80.10%
Skin corrosion - 0.9538 95.38%
Ames mutagenesis - 0.5637 56.37%
Human Ether-a-go-go-Related Gene inhibition - 0.3808 38.08%
Micronuclear + 0.5233 52.33%
Hepatotoxicity - 0.8000 80.00%
skin sensitisation - 0.8067 80.67%
Respiratory toxicity - 0.6111 61.11%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.5750 57.50%
Nephrotoxicity - 0.9336 93.36%
Acute Oral Toxicity (c) III 0.5747 57.47%
Estrogen receptor binding + 0.7480 74.80%
Androgen receptor binding - 0.4899 48.99%
Thyroid receptor binding - 0.5293 52.93%
Glucocorticoid receptor binding + 0.5913 59.13%
Aromatase binding - 0.5717 57.17%
PPAR gamma + 0.6615 66.15%
Honey bee toxicity - 0.7001 70.01%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity - 0.6255 62.55%
Fish aquatic toxicity + 0.7948 79.48%

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 99.29% 91.11%
CHEMBL1293249 Q13887 Kruppel-like factor 5 97.63% 86.33%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.94% 96.09%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 96.80% 96.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 95.96% 89.00%
CHEMBL1951 P21397 Monoamine oxidase A 94.76% 91.49%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 93.93% 95.56%
CHEMBL3194 P02766 Transthyretin 91.33% 90.71%
CHEMBL3714130 P46095 G-protein coupled receptor 6 89.61% 97.36%
CHEMBL3060 Q9Y345 Glycine transporter 2 88.65% 99.17%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 87.47% 86.92%
CHEMBL4208 P20618 Proteasome component C5 84.05% 90.00%
CHEMBL241 Q14432 Phosphodiesterase 3A 83.97% 92.94%
CHEMBL3401 O75469 Pregnane X receptor 83.04% 94.73%
CHEMBL2288 Q13526 Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 82.52% 91.71%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 81.41% 95.50%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 81.36% 95.89%
CHEMBL2085 P14174 Macrophage migration inhibitory factor 80.93% 80.78%
CHEMBL4829 O00763 Acetyl-CoA carboxylase 2 80.88% 98.00%
CHEMBL2581 P07339 Cathepsin D 80.52% 98.95%
CHEMBL3137262 O60341 LSD1/CoREST complex 80.07% 97.09%

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.
Verbascum nigrum

Cross-Links

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PubChem 44715579
LOTUS LTS0072153
wikiData Q105289027