Raddeamine

Details

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Internal ID 4632c3f2-23b5-4389-8bcc-a36d8bced8c3
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal alkaloids > Cerveratrum-type alkaloids
IUPAC Name (1R,2S,6S,9S,11S,14S,15S,18S,20S,23R,24S)-10,20-dihydroxy-6,10,23-trimethyl-4-azahexacyclo[12.11.0.02,11.04,9.015,24.018,23]pentacosan-17-one
SMILES (Canonical) CC1CCC2C(C3CCC4C(C3CN2C1)CC5C4CC(=O)C6C5(CCC(C6)O)C)(C)O
SMILES (Isomeric) C[C@H]1CC[C@H]2C([C@H]3CC[C@@H]4[C@H]([C@@H]3CN2C1)C[C@H]5[C@H]4CC(=O)[C@@H]6[C@@]5(CC[C@@H](C6)O)C)(C)O
InChI InChI=1S/C27H43NO3/c1-15-4-7-25-27(3,31)21-6-5-17-18(20(21)14-28(25)13-15)11-22-19(17)12-24(30)23-10-16(29)8-9-26(22,23)2/h15-23,25,29,31H,4-14H2,1-3H3/t15-,16-,17+,18+,19-,20-,21-,22-,23+,25-,26+,27?/m0/s1
InChI Key IQDIERHFZVCNRZ-DVFBZCKRSA-N
Popularity 64 references in papers

Physical and Chemical Properties

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Molecular Formula C27H43NO3
Molecular Weight 429.60 g/mol
Exact Mass 429.32429423 g/mol
Topological Polar Surface Area (TPSA) 60.80 Ų
XlogP 3.90
Atomic LogP (AlogP) 3.89
H-Bond Acceptor 4
H-Bond Donor 2
Rotatable Bonds 0

Synonyms

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C27-H43-N-O3
(3-beta,5-alpha)-3,20-Dihydroxycevan-6-one
5.alpha.-Cevan-6-one, 3.beta.,20-dihydroxy-

2D Structure

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2D Structure of Raddeamine

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9654 96.54%
Caco-2 - 0.5621 56.21%
Blood Brain Barrier + 0.8250 82.50%
Human oral bioavailability + 0.5857 58.57%
Subcellular localzation Lysosomes 0.5369 53.69%
OATP2B1 inhibitior - 0.5811 58.11%
OATP1B1 inhibitior + 0.9006 90.06%
OATP1B3 inhibitior + 0.9497 94.97%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.7000 70.00%
BSEP inhibitior + 0.6115 61.15%
P-glycoprotein inhibitior - 0.7821 78.21%
P-glycoprotein substrate + 0.5129 51.29%
CYP3A4 substrate + 0.7225 72.25%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate + 0.3948 39.48%
CYP3A4 inhibition - 0.7809 78.09%
CYP2C9 inhibition - 0.9076 90.76%
CYP2C19 inhibition - 0.9128 91.28%
CYP2D6 inhibition - 0.6125 61.25%
CYP1A2 inhibition - 0.9266 92.66%
CYP2C8 inhibition - 0.8049 80.49%
CYP inhibitory promiscuity - 0.9860 98.60%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6170 61.70%
Eye corrosion - 0.9882 98.82%
Eye irritation - 0.9488 94.88%
Skin irritation - 0.7323 73.23%
Skin corrosion - 0.8795 87.95%
Ames mutagenesis - 0.7756 77.56%
Human Ether-a-go-go-Related Gene inhibition - 0.5157 51.57%
Micronuclear - 0.6500 65.00%
Hepatotoxicity + 0.5836 58.36%
skin sensitisation - 0.8401 84.01%
Respiratory toxicity + 0.8222 82.22%
Reproductive toxicity + 0.8667 86.67%
Mitochondrial toxicity + 0.9750 97.50%
Nephrotoxicity + 0.5332 53.32%
Acute Oral Toxicity (c) III 0.6697 66.97%
Estrogen receptor binding + 0.7534 75.34%
Androgen receptor binding + 0.8169 81.69%
Thyroid receptor binding + 0.6174 61.74%
Glucocorticoid receptor binding + 0.7383 73.83%
Aromatase binding + 0.6017 60.17%
PPAR gamma + 0.5355 53.55%
Honey bee toxicity - 0.7922 79.22%
Biodegradation - 0.7000 70.00%
Crustacea aquatic toxicity + 0.7200 72.00%
Fish aquatic toxicity - 0.7381 73.81%

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 95.67% 96.09%
CHEMBL253 P34972 Cannabinoid CB2 receptor 91.50% 97.25%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.92% 97.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.83% 95.56%
CHEMBL1994 P08235 Mineralocorticoid receptor 89.79% 100.00%
CHEMBL325 Q13547 Histone deacetylase 1 88.71% 95.92%
CHEMBL1871 P10275 Androgen Receptor 88.63% 96.43%
CHEMBL3746 P80365 11-beta-hydroxysteroid dehydrogenase 2 87.85% 94.78%
CHEMBL2581 P07339 Cathepsin D 87.03% 98.95%
CHEMBL1293249 Q13887 Kruppel-like factor 5 86.19% 86.33%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 86.11% 96.77%
CHEMBL238 Q01959 Dopamine transporter 85.44% 95.88%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 83.98% 90.71%
CHEMBL299 P17252 Protein kinase C alpha 83.86% 98.03%
CHEMBL1937 Q92769 Histone deacetylase 2 83.85% 94.75%
CHEMBL1806 P11388 DNA topoisomerase II alpha 83.10% 89.00%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 82.53% 82.69%
CHEMBL5608 Q16288 NT-3 growth factor receptor 82.36% 95.89%
CHEMBL5255 O00206 Toll-like receptor 4 80.74% 92.50%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 80.53% 93.04%
CHEMBL5469 Q14289 Protein tyrosine kinase 2 beta 80.51% 91.03%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 80.19% 91.11%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 80.10% 95.89%

Cross-Links

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PubChem 102063129
NPASS NPC214237
LOTUS LTS0061086
wikiData Q104253424