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(2S)-N-[(4S,4aR,6R,8S,8aR)-6-[(2S)-2,3-dihydroxypropyl]-8-hydroxy-7,7-dimethyl-4a,6,8,8a-tetrahydro-4H-pyrano[3,2-d][1,3]dioxin-4-yl]-2-hydroxy-2-[(2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl]acetamide

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 f537c9d3-0422-4295-9cbd-f6f82441253e
Taxonomy Organoheterocyclic compounds > Pyranodioxins
IUPAC Name (2S)-N-[(4S,4aR,6R,8S,8aR)-6-[(2S)-2,3-dihydroxypropyl]-8-hydroxy-7,7-dimethyl-4a,6,8,8a-tetrahydro-4H-pyrano[3,2-d][1,3]dioxin-4-yl]-2-hydroxy-2-[(2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl]acetamide
SMILES (Canonical) CC1C(OC(CC1=C)(C(C(=O)NC2C3C(C(C(C(O3)CC(CO)O)(C)C)O)OCO2)O)OC)C
SMILES (Isomeric) C[C@H]1[C@H](O[C@](CC1=C)([C@@H](C(=O)N[C@@H]2[C@H]3[C@@H]([C@H](C([C@H](O3)C[C@@H](CO)O)(C)C)O)OCO2)O)OC)C
InChI InChI=1S/C23H39NO10/c1-11-8-23(30-6,34-13(3)12(11)2)19(28)20(29)24-21-17-16(31-10-32-21)18(27)22(4,5)15(33-17)7-14(26)9-25/h12-19,21,25-28H,1,7-10H2,2-6H3,(H,24,29)/t12-,13-,14+,15-,16+,17-,18-,19-,21+,23-/m1/s1
InChI Key MPSRCJWTLGCJFM-GBFCGSDTSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C23H39NO10
Molecular Weight 489.60 g/mol
Exact Mass 489.25739644 g/mol
Topological Polar Surface Area (TPSA) 156.00 Ų
XlogP -0.70
Atomic LogP (AlogP) -0.60
H-Bond Acceptor 10
H-Bond Donor 5
Rotatable Bonds 7

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2S)-N-[(4S,4aR,6R,8S,8aR)-6-[(2S)-2,3-dihydroxypropyl]-8-hydroxy-7,7-dimethyl-4a,6,8,8a-tetrahydro-4H-pyrano[3,2-d][1,3]dioxin-4-yl]-2-hydroxy-2-[(2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl]acetamide

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.4652 46.52%
Caco-2 - 0.8303 83.03%
Blood Brain Barrier - 0.8500 85.00%
Human oral bioavailability - 0.6143 61.43%
Subcellular localzation Mitochondria 0.4662 46.62%
OATP2B1 inhibitior - 0.8574 85.74%
OATP1B1 inhibitior + 0.8873 88.73%
OATP1B3 inhibitior + 0.9344 93.44%
MATE1 inhibitior - 0.8800 88.00%
OCT2 inhibitior - 0.9750 97.50%
BSEP inhibitior - 0.9011 90.11%
P-glycoprotein inhibitior - 0.5849 58.49%
P-glycoprotein substrate + 0.5915 59.15%
CYP3A4 substrate + 0.6802 68.02%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8658 86.58%
CYP3A4 inhibition - 0.7947 79.47%
CYP2C9 inhibition - 0.8517 85.17%
CYP2C19 inhibition - 0.8567 85.67%
CYP2D6 inhibition - 0.9066 90.66%
CYP1A2 inhibition - 0.8268 82.68%
CYP2C8 inhibition - 0.5633 56.33%
CYP inhibitory promiscuity - 0.7823 78.23%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9500 95.00%
Carcinogenicity (trinary) Non-required 0.6138 61.38%
Eye corrosion - 0.9858 98.58%
Eye irritation - 0.9451 94.51%
Skin irritation - 0.7575 75.75%
Skin corrosion - 0.9283 92.83%
Ames mutagenesis + 0.5046 50.46%
Human Ether-a-go-go-Related Gene inhibition + 0.6819 68.19%
Micronuclear + 0.6300 63.00%
Hepatotoxicity + 0.5138 51.38%
skin sensitisation - 0.8204 82.04%
Respiratory toxicity - 0.5111 51.11%
Reproductive toxicity + 0.9444 94.44%
Mitochondrial toxicity + 0.8500 85.00%
Nephrotoxicity - 0.6220 62.20%
Acute Oral Toxicity (c) III 0.6220 62.20%
Estrogen receptor binding - 0.5090 50.90%
Androgen receptor binding + 0.5760 57.60%
Thyroid receptor binding + 0.5297 52.97%
Glucocorticoid receptor binding + 0.6795 67.95%
Aromatase binding + 0.6849 68.49%
PPAR gamma + 0.5653 56.53%
Honey bee toxicity - 0.6501 65.01%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.6200 62.00%
Fish aquatic toxicity - 0.4074 40.74%

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 99.06% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.73% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 95.12% 94.45%
CHEMBL2581 P07339 Cathepsin D 92.88% 98.95%
CHEMBL1907605 P24864 Cyclin-dependent kinase 2/cyclin E1 91.99% 92.88%
CHEMBL340 P08684 Cytochrome P450 3A4 91.04% 91.19%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 89.81% 91.24%
CHEMBL218 P21554 Cannabinoid CB1 receptor 88.66% 96.61%
CHEMBL3145 P42338 PI3-kinase p110-beta subunit 87.64% 98.75%
CHEMBL3060 Q9Y345 Glycine transporter 2 87.51% 99.17%
CHEMBL3267 P48736 PI3-kinase p110-gamma subunit 86.42% 95.71%
CHEMBL221 P23219 Cyclooxygenase-1 84.26% 90.17%
CHEMBL4051 P13569 Cystic fibrosis transmembrane conductance regulator 83.40% 95.71%
CHEMBL3401 O75469 Pregnane X receptor 83.18% 94.73%
CHEMBL3137262 O60341 LSD1/CoREST complex 83.08% 97.09%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 82.91% 96.77%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 82.38% 92.62%
CHEMBL1806 P11388 DNA topoisomerase II alpha 82.26% 89.00%
CHEMBL3130 O00329 PI3-kinase p110-delta subunit 81.92% 96.47%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 81.44% 94.33%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 81.05% 95.50%
CHEMBL5163 Q9NY46 Sodium channel protein type III alpha subunit 80.68% 96.90%
CHEMBL4227 P25090 Lipoxin A4 receptor 80.37% 100.00%
CHEMBL2563 Q9UQL6 Histone deacetylase 5 80.21% 89.67%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
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There are no matching plants.

Cross-Links

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PubChem 138319335
LOTUS LTS0034222
wikiData Q105169726