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(3S,4S,4aS,6R)-4-ethenyl-7-[2-[(3S)-3-hydroxy-2-oxo-1H-indol-3-yl]ethyl]-6-methoxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyridin-8-one

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 8bef908a-974c-456a-90ef-30f5e40b6a41
Taxonomy Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
IUPAC Name (3S,4S,4aS,6R)-4-ethenyl-7-[2-[(3S)-3-hydroxy-2-oxo-1H-indol-3-yl]ethyl]-6-methoxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyridin-8-one
SMILES (Canonical) COC1CC2C(C(OC=C2C(=O)N1CCC3(C4=CC=CC=C4NC3=O)O)OC5C(C(C(C(O5)CO)O)O)O)C=C
SMILES (Isomeric) CO[C@@H]1C[C@H]2[C@@H]([C@@H](OC=C2C(=O)N1CC[C@@]3(C4=CC=CC=C4NC3=O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C=C
InChI InChI=1S/C27H34N2O11/c1-3-13-14-10-19(37-2)29(9-8-27(36)16-6-4-5-7-17(16)28-26(27)35)23(34)15(14)12-38-24(13)40-25-22(33)21(32)20(31)18(11-30)39-25/h3-7,12-14,18-22,24-25,30-33,36H,1,8-11H2,2H3,(H,28,35)/t13-,14-,18+,19+,20+,21-,22+,24-,25-,27-/m0/s1
InChI Key XEQPPTNZKGNKKE-NDJXSGESSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C27H34N2O11
Molecular Weight 562.60 g/mol
Exact Mass 562.21625990 g/mol
Topological Polar Surface Area (TPSA) 187.00 Ų
XlogP -1.10
Atomic LogP (AlogP) -1.10
H-Bond Acceptor 11
H-Bond Donor 6
Rotatable Bonds 8

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (3S,4S,4aS,6R)-4-ethenyl-7-[2-[(3S)-3-hydroxy-2-oxo-1H-indol-3-yl]ethyl]-6-methoxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyridin-8-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.6142 61.42%
Caco-2 - 0.8652 86.52%
Blood Brain Barrier - 0.8750 87.50%
Human oral bioavailability - 0.8286 82.86%
Subcellular localzation Mitochondria 0.6430 64.30%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8264 82.64%
OATP1B3 inhibitior + 0.9349 93.49%
MATE1 inhibitior - 0.8400 84.00%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior - 0.6168 61.68%
P-glycoprotein inhibitior - 0.4416 44.16%
P-glycoprotein substrate + 0.5307 53.07%
CYP3A4 substrate + 0.7095 70.95%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8627 86.27%
CYP3A4 inhibition - 0.8344 83.44%
CYP2C9 inhibition - 0.7353 73.53%
CYP2C19 inhibition - 0.8385 83.85%
CYP2D6 inhibition - 0.9001 90.01%
CYP1A2 inhibition - 0.8352 83.52%
CYP2C8 inhibition + 0.5962 59.62%
CYP inhibitory promiscuity - 0.9233 92.33%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9500 95.00%
Carcinogenicity (trinary) Non-required 0.4645 46.45%
Eye corrosion - 0.9854 98.54%
Eye irritation - 0.9533 95.33%
Skin irritation - 0.7549 75.49%
Skin corrosion - 0.9265 92.65%
Ames mutagenesis - 0.5400 54.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4688 46.88%
Micronuclear + 0.8800 88.00%
Hepatotoxicity - 0.6091 60.91%
skin sensitisation - 0.8492 84.92%
Respiratory toxicity + 0.8889 88.89%
Reproductive toxicity + 1.0000 100.00%
Mitochondrial toxicity + 0.9625 96.25%
Nephrotoxicity - 0.5605 56.05%
Acute Oral Toxicity (c) III 0.5822 58.22%
Estrogen receptor binding + 0.8091 80.91%
Androgen receptor binding + 0.7101 71.01%
Thyroid receptor binding - 0.4900 49.00%
Glucocorticoid receptor binding + 0.6032 60.32%
Aromatase binding + 0.5190 51.90%
PPAR gamma + 0.6034 60.34%
Honey bee toxicity - 0.7498 74.98%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.5400 54.00%
Fish aquatic toxicity + 0.9206 92.06%

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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.39% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 97.48% 95.56%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 95.92% 91.11%
CHEMBL4208 P20618 Proteasome component C5 95.64% 90.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 94.05% 97.09%
CHEMBL2581 P07339 Cathepsin D 94.00% 98.95%
CHEMBL1293249 Q13887 Kruppel-like factor 5 93.04% 86.33%
CHEMBL253 P34972 Cannabinoid CB2 receptor 91.59% 97.25%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 89.46% 85.14%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 89.00% 95.83%
CHEMBL3524 P56524 Histone deacetylase 4 88.29% 92.97%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 85.99% 94.45%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 83.22% 86.92%
CHEMBL1806 P11388 DNA topoisomerase II alpha 83.11% 89.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 82.27% 95.89%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 80.44% 97.14%

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.
Cinnamodendron axillare

Cross-Links

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PubChem 162861350
LOTUS LTS0210757
wikiData Q105326546