Rheagenine

Details

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Internal ID acba0199-0ffd-421b-a1f5-cdfa2ebcab0d
Taxonomy Alkaloids and derivatives > Rhoeadine alkaloids
IUPAC Name (1R,14R,24S)-13-methyl-5,7,19,21,25-pentaoxa-13-azahexacyclo[12.11.0.02,10.04,8.015,23.018,22]pentacosa-2,4(8),9,15(23),16,18(22)-hexaen-24-ol
SMILES (Canonical) CN1CCC2=CC3=C(C=C2C4C1C5=C(C(O4)O)C6=C(C=C5)OCO6)OCO3
SMILES (Isomeric) CN1CCC2=CC3=C(C=C2[C@@H]4[C@H]1C5=C([C@H](O4)O)C6=C(C=C5)OCO6)OCO3
InChI InChI=1S/C20H19NO6/c1-21-5-4-10-6-14-15(25-8-24-14)7-12(10)18-17(21)11-2-3-13-19(26-9-23-13)16(11)20(22)27-18/h2-3,6-7,17-18,20,22H,4-5,8-9H2,1H3/t17-,18-,20+/m1/s1
InChI Key XUYAYNRYVXHNOQ-GGPKGHCWSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C20H19NO6
Molecular Weight 369.40 g/mol
Exact Mass 369.12123733 g/mol
Topological Polar Surface Area (TPSA) 69.60 Ų
XlogP 1.90
Atomic LogP (AlogP) 2.44
H-Bond Acceptor 7
H-Bond Donor 1
Rotatable Bonds 0

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of Rheagenine

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9307 93.07%
Caco-2 + 0.7347 73.47%
Blood Brain Barrier + 0.7000 70.00%
Human oral bioavailability - 0.6571 65.71%
Subcellular localzation Lysosomes 0.4717 47.17%
OATP2B1 inhibitior - 0.8666 86.66%
OATP1B1 inhibitior + 0.9246 92.46%
OATP1B3 inhibitior + 0.9523 95.23%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.7000 70.00%
BSEP inhibitior + 0.7265 72.65%
P-glycoprotein inhibitior - 0.6139 61.39%
P-glycoprotein substrate - 0.7282 72.82%
CYP3A4 substrate + 0.5891 58.91%
CYP2C9 substrate - 0.5862 58.62%
CYP2D6 substrate + 0.5770 57.70%
CYP3A4 inhibition - 0.8117 81.17%
CYP2C9 inhibition - 0.7780 77.80%
CYP2C19 inhibition + 0.5055 50.55%
CYP2D6 inhibition + 0.6130 61.30%
CYP1A2 inhibition + 0.6591 65.91%
CYP2C8 inhibition - 0.8776 87.76%
CYP inhibitory promiscuity - 0.8561 85.61%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.5903 59.03%
Eye corrosion - 0.9871 98.71%
Eye irritation - 0.9600 96.00%
Skin irritation - 0.7571 75.71%
Skin corrosion - 0.9260 92.60%
Ames mutagenesis + 0.6500 65.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5809 58.09%
Micronuclear + 0.5500 55.00%
Hepatotoxicity - 0.6875 68.75%
skin sensitisation - 0.8471 84.71%
Respiratory toxicity + 0.9000 90.00%
Reproductive toxicity + 0.8111 81.11%
Mitochondrial toxicity + 0.8750 87.50%
Nephrotoxicity - 0.8044 80.44%
Acute Oral Toxicity (c) III 0.6868 68.68%
Estrogen receptor binding + 0.6528 65.28%
Androgen receptor binding + 0.6484 64.84%
Thyroid receptor binding + 0.5372 53.72%
Glucocorticoid receptor binding + 0.7346 73.46%
Aromatase binding - 0.5991 59.91%
PPAR gamma + 0.8346 83.46%
Honey bee toxicity - 0.9156 91.56%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity + 0.6000 60.00%
Fish aquatic toxicity - 0.5000 50.00%

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 97.77% 96.09%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 95.76% 96.77%
CHEMBL2581 P07339 Cathepsin D 95.74% 98.95%
CHEMBL5697 Q9GZT9 Egl nine homolog 1 94.35% 93.40%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.22% 95.56%
CHEMBL1293249 Q13887 Kruppel-like factor 5 90.58% 86.33%
CHEMBL4040 P28482 MAP kinase ERK2 88.85% 83.82%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 88.84% 91.11%
CHEMBL2056 P21728 Dopamine D1 receptor 85.28% 91.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 84.84% 95.89%
CHEMBL5311 P37023 Serine/threonine-protein kinase receptor R3 84.77% 82.67%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 83.34% 92.62%
CHEMBL3227 P41594 Metabotropic glutamate receptor 5 82.06% 96.42%
CHEMBL1806 P11388 DNA topoisomerase II alpha 81.78% 89.00%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 81.24% 95.89%
CHEMBL2095226 P05556 Integrin alpha-5/beta-1 80.70% 96.39%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 80.68% 100.00%
CHEMBL1994 P08235 Mineralocorticoid receptor 80.50% 100.00%

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.
Fumaria parviflora
Papaver atlanticum
Papaver lateritium
Papaver persicum subsp. tauricola
Papaver rhoeas
Papaver somniferum subsp. setigerum

Cross-Links

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PubChem 12304373
LOTUS LTS0049085
wikiData Q104252463