[(7S,8R)-7-[(Z)-2-methylbut-2-enoyl]oxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2S)-3-acetyloxy-2-hydroxy-2-[(1S)-1-methoxyethyl]-3-methylbutanoate

Details

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Internal ID 1ca8d6d8-2c4b-4f02-9fdd-5a6abdb30dc9
Taxonomy Alkaloids and derivatives
IUPAC Name [(7S,8R)-7-[(Z)-2-methylbut-2-enoyl]oxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2S)-3-acetyloxy-2-hydroxy-2-[(1S)-1-methoxyethyl]-3-methylbutanoate
SMILES (Canonical) CC=C(C)C(=O)OC1CCN2C1C(=CC2)COC(=O)C(C(C)OC)(C(C)(C)OC(=O)C)O
SMILES (Isomeric) C/C=C(/C)\C(=O)O[C@H]1CCN2[C@@H]1C(=CC2)COC(=O)[C@]([C@H](C)OC)(C(C)(C)OC(=O)C)O
InChI InChI=1S/C23H35NO8/c1-8-14(2)20(26)31-18-10-12-24-11-9-17(19(18)24)13-30-21(27)23(28,15(3)29-7)22(5,6)32-16(4)25/h8-9,15,18-19,28H,10-13H2,1-7H3/b14-8-/t15-,18-,19+,23+/m0/s1
InChI Key XGLOPSNBSMBXSE-PSBUCHAKSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C23H35NO8
Molecular Weight 453.50 g/mol
Exact Mass 453.23626707 g/mol
Topological Polar Surface Area (TPSA) 112.00 Ų
XlogP 1.00
Atomic LogP (AlogP) 1.53
H-Bond Acceptor 9
H-Bond Donor 1
Rotatable Bonds 9

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(7S,8R)-7-[(Z)-2-methylbut-2-enoyl]oxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2S)-3-acetyloxy-2-hydroxy-2-[(1S)-1-methoxyethyl]-3-methylbutanoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7817 78.17%
Caco-2 - 0.5465 54.65%
Blood Brain Barrier + 0.6750 67.50%
Human oral bioavailability - 0.7429 74.29%
Subcellular localzation Mitochondria 0.7715 77.15%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8819 88.19%
OATP1B3 inhibitior + 0.9354 93.54%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.6750 67.50%
BSEP inhibitior + 0.8810 88.10%
P-glycoprotein inhibitior + 0.6776 67.76%
P-glycoprotein substrate + 0.6069 60.69%
CYP3A4 substrate + 0.6486 64.86%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8157 81.57%
CYP3A4 inhibition - 0.9658 96.58%
CYP2C9 inhibition - 0.9039 90.39%
CYP2C19 inhibition - 0.9031 90.31%
CYP2D6 inhibition - 0.7588 75.88%
CYP1A2 inhibition - 0.8868 88.68%
CYP2C8 inhibition - 0.6148 61.48%
CYP inhibitory promiscuity - 0.9555 95.55%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9500 95.00%
Carcinogenicity (trinary) Danger 0.7015 70.15%
Eye corrosion - 0.9783 97.83%
Eye irritation - 0.9596 95.96%
Skin irritation - 0.7543 75.43%
Skin corrosion - 0.9135 91.35%
Ames mutagenesis + 0.7500 75.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5000 50.00%
Micronuclear + 0.7500 75.00%
Hepatotoxicity + 1.0000 100.00%
skin sensitisation - 0.8111 81.11%
Respiratory toxicity + 0.6222 62.22%
Reproductive toxicity + 0.6778 67.78%
Mitochondrial toxicity + 0.8500 85.00%
Nephrotoxicity + 0.7014 70.14%
Acute Oral Toxicity (c) II 0.5526 55.26%
Estrogen receptor binding + 0.5781 57.81%
Androgen receptor binding + 0.5978 59.78%
Thyroid receptor binding + 0.5751 57.51%
Glucocorticoid receptor binding + 0.7789 77.89%
Aromatase binding + 0.5854 58.54%
PPAR gamma - 0.5268 52.68%
Honey bee toxicity - 0.7718 77.18%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.5800 58.00%
Fish aquatic toxicity - 0.6640 66.40%

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 99.15% 96.09%
CHEMBL2581 P07339 Cathepsin D 97.21% 98.95%
CHEMBL253 P34972 Cannabinoid CB2 receptor 94.47% 97.25%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 92.36% 94.45%
CHEMBL3060 Q9Y345 Glycine transporter 2 88.53% 99.17%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 87.42% 95.89%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 86.15% 89.62%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 85.87% 91.11%
CHEMBL5608 Q16288 NT-3 growth factor receptor 85.29% 95.89%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 85.24% 97.21%
CHEMBL3137262 O60341 LSD1/CoREST complex 84.58% 97.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 82.42% 95.56%
CHEMBL1293249 Q13887 Kruppel-like factor 5 81.84% 86.33%
CHEMBL2274 Q9H228 Sphingosine 1-phosphate receptor Edg-8 81.74% 100.00%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 81.59% 93.00%
CHEMBL340 P08684 Cytochrome P450 3A4 81.17% 91.19%

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.
Heliotropium bovei

Cross-Links

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PubChem 162901632
LOTUS LTS0178181
wikiData Q105327657