Racemodine

Details

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Internal ID d233e3ca-5ffe-4c1b-b270-04a83d5e06bf
Taxonomy Organic acids and derivatives > Carboxylic acids and derivatives > Tricarboxylic acids and derivatives
IUPAC Name [(1S,7R,8R)-7-[(Z)-2-methylbut-2-enoyl]oxy-2,3,5,6,7,8-hexahydro-1H-pyrrolizin-1-yl]methyl (Z)-2-[(3-hydroxy-3-methylbutanoyl)oxymethyl]but-2-enoate
SMILES (Canonical) CC=C(C)C(=O)OC1CCN2C1C(CC2)COC(=O)C(=CC)COC(=O)CC(C)(C)O
SMILES (Isomeric) C/C=C(/C)\C(=O)O[C@@H]1CCN2[C@@H]1[C@H](CC2)COC(=O)/C(=C\C)/COC(=O)CC(C)(C)O
InChI InChI=1S/C23H35NO7/c1-6-15(3)21(26)31-18-9-11-24-10-8-17(20(18)24)14-30-22(27)16(7-2)13-29-19(25)12-23(4,5)28/h6-7,17-18,20,28H,8-14H2,1-5H3/b15-6-,16-7-/t17-,18-,20-/m1/s1
InChI Key IFOJBJYZVQYKHB-HEWCMQNGSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C23H35NO7
Molecular Weight 437.50 g/mol
Exact Mass 437.24135246 g/mol
Topological Polar Surface Area (TPSA) 102.00 Ų
XlogP 2.30
Atomic LogP (AlogP) 2.15
H-Bond Acceptor 8
H-Bond Donor 1
Rotatable Bonds 9

Synonyms

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147554-28-7
[(1S,7R,8R)-7-[(Z)-2-methylbut-2-enoyl]oxy-2,3,5,6,7,8-hexahydro-1H-pyrrolizin-1-yl]methyl (Z)-2-[(3-hydroxy-3-methylbutanoyl)oxymethyl]but-2-enoate

2D Structure

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2D Structure of Racemodine

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9561 95.61%
Caco-2 - 0.6456 64.56%
Blood Brain Barrier + 0.6500 65.00%
Human oral bioavailability - 0.6429 64.29%
Subcellular localzation Mitochondria 0.6398 63.98%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9120 91.20%
OATP1B3 inhibitior + 0.9365 93.65%
MATE1 inhibitior - 0.8800 88.00%
OCT2 inhibitior - 0.7250 72.50%
BSEP inhibitior + 0.8956 89.56%
P-glycoprotein inhibitior + 0.7030 70.30%
P-glycoprotein substrate + 0.5191 51.91%
CYP3A4 substrate + 0.6321 63.21%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8232 82.32%
CYP3A4 inhibition - 0.9561 95.61%
CYP2C9 inhibition - 0.9278 92.78%
CYP2C19 inhibition - 0.9014 90.14%
CYP2D6 inhibition - 0.8439 84.39%
CYP1A2 inhibition - 0.8759 87.59%
CYP2C8 inhibition - 0.7519 75.19%
CYP inhibitory promiscuity - 0.9734 97.34%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9100 91.00%
Carcinogenicity (trinary) Danger 0.5607 56.07%
Eye corrosion - 0.9786 97.86%
Eye irritation - 0.9685 96.85%
Skin irritation - 0.7185 71.85%
Skin corrosion - 0.9001 90.01%
Ames mutagenesis - 0.6654 66.54%
Human Ether-a-go-go-Related Gene inhibition + 0.7213 72.13%
Micronuclear + 0.6300 63.00%
Hepatotoxicity + 0.9000 90.00%
skin sensitisation - 0.7863 78.63%
Respiratory toxicity + 0.5556 55.56%
Reproductive toxicity + 0.6333 63.33%
Mitochondrial toxicity + 0.8250 82.50%
Nephrotoxicity + 0.4755 47.55%
Acute Oral Toxicity (c) III 0.6566 65.66%
Estrogen receptor binding - 0.5400 54.00%
Androgen receptor binding - 0.6262 62.62%
Thyroid receptor binding - 0.5000 50.00%
Glucocorticoid receptor binding + 0.6949 69.49%
Aromatase binding - 0.5638 56.38%
PPAR gamma - 0.5809 58.09%
Honey bee toxicity - 0.7513 75.13%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.6200 62.00%
Fish aquatic toxicity + 0.7072 70.72%

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
CHEMBL4040 P28482 MAP kinase ERK2 98.32% 83.82%
CHEMBL253 P34972 Cannabinoid CB2 receptor 98.09% 97.25%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.87% 96.09%
CHEMBL284 P27487 Dipeptidyl peptidase IV 91.07% 95.69%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 90.97% 94.45%
CHEMBL2581 P07339 Cathepsin D 89.15% 98.95%
CHEMBL3137262 O60341 LSD1/CoREST complex 88.64% 97.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 88.60% 91.11%
CHEMBL5608 Q16288 NT-3 growth factor receptor 88.53% 95.89%
CHEMBL228 P31645 Serotonin transporter 86.95% 95.51%
CHEMBL1937 Q92769 Histone deacetylase 2 86.39% 94.75%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 85.85% 93.04%
CHEMBL3437 Q16853 Amine oxidase, copper containing 85.27% 94.00%
CHEMBL5469 Q14289 Protein tyrosine kinase 2 beta 84.69% 91.03%
CHEMBL5103 Q969S8 Histone deacetylase 10 84.12% 90.08%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 83.65% 93.03%
CHEMBL2781 P19634 Sodium/hydrogen exchanger 1 83.49% 90.24%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 82.71% 93.00%
CHEMBL3130 O00329 PI3-kinase p110-delta subunit 82.20% 96.47%
CHEMBL4227 P25090 Lipoxin A4 receptor 81.52% 100.00%
CHEMBL2274 Q9H228 Sphingosine 1-phosphate receptor Edg-8 80.89% 100.00%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 80.75% 94.33%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 80.42% 82.69%

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.
Ligularia fischeri

Cross-Links

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PubChem 10433214
LOTUS LTS0141694
wikiData Q105112274