10-Methoxyibogamine

Details

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Internal ID a65095ad-03e4-433f-9ff9-797df5b720f6
Taxonomy Alkaloids and derivatives > Ibogan-type alkaloids
IUPAC Name (1R,15S,17S,18S)-17-ethyl-7-methoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4(9),5,7-tetraene
SMILES (Canonical) CCC1CC2CC3C1N(C2)CCC4=C3NC5=C4C=C(C=C5)OC
SMILES (Isomeric) CC[C@H]1C[C@H]2C[C@@H]3[C@H]1N(C2)CCC4=C3NC5=C4C=C(C=C5)OC
InChI InChI=1S/C20H26N2O/c1-3-13-8-12-9-17-19-15(6-7-22(11-12)20(13)17)16-10-14(23-2)4-5-18(16)21-19/h4-5,10,12-13,17,20-21H,3,6-9,11H2,1-2H3/t12-,13-,17-,20-/m0/s1
InChI Key HSIBGVUMFOSJPD-NXWOVTFFSA-N
Popularity 459 references in papers

Physical and Chemical Properties

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Molecular Formula C20H26N2O
Molecular Weight 310.40 g/mol
Exact Mass 310.204513457 g/mol
Topological Polar Surface Area (TPSA) 28.30 Ų
XlogP 3.90
Atomic LogP (AlogP) 3.94
H-Bond Acceptor 2
H-Bond Donor 1
Rotatable Bonds 2

Synonyms

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10-Methoxyibogamine
CHEMBL222287
83-74-9
(-)-Ibogaine
Ibogamine, 12-methoxy-
CHEBI:5852
AC1L9C9B
NSC-249764
12-methoxy-Ibogamine
SCHEMBL21333266
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of 10-Methoxyibogamine

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9961 99.61%
Caco-2 + 0.9061 90.61%
Blood Brain Barrier + 0.9038 90.38%
Human oral bioavailability - 0.6571 65.71%
Subcellular localzation Mitochondria 0.6131 61.31%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8861 88.61%
OATP1B3 inhibitior + 0.9406 94.06%
MATE1 inhibitior - 0.8600 86.00%
OCT2 inhibitior + 0.7000 70.00%
BSEP inhibitior + 0.8817 88.17%
P-glycoprotein inhibitior - 0.6182 61.82%
P-glycoprotein substrate + 0.7511 75.11%
CYP3A4 substrate + 0.6008 60.08%
CYP2C9 substrate - 0.8153 81.53%
CYP2D6 substrate + 0.6832 68.32%
CYP3A4 inhibition + 0.5000 50.00%
CYP2C9 inhibition - 0.8569 85.69%
CYP2C19 inhibition - 0.8795 87.95%
CYP2D6 inhibition + 0.9006 90.06%
CYP1A2 inhibition + 0.6874 68.74%
CYP2C8 inhibition - 0.6719 67.19%
CYP inhibitory promiscuity + 0.6572 65.72%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.7349 73.49%
Eye corrosion - 0.9907 99.07%
Eye irritation - 0.9800 98.00%
Skin irritation - 0.7349 73.49%
Skin corrosion - 0.9218 92.18%
Ames mutagenesis - 0.7000 70.00%
Human Ether-a-go-go-Related Gene inhibition + 0.9442 94.42%
Micronuclear + 0.5800 58.00%
Hepatotoxicity + 0.5250 52.50%
skin sensitisation - 0.8880 88.80%
Respiratory toxicity + 0.8556 85.56%
Reproductive toxicity + 0.8889 88.89%
Mitochondrial toxicity + 0.9125 91.25%
Nephrotoxicity - 0.9185 91.85%
Acute Oral Toxicity (c) II 0.7459 74.59%
Estrogen receptor binding + 0.6674 66.74%
Androgen receptor binding + 0.7100 71.00%
Thyroid receptor binding - 0.5000 50.00%
Glucocorticoid receptor binding - 0.4831 48.31%
Aromatase binding + 0.5569 55.69%
PPAR gamma - 0.6596 65.96%
Honey bee toxicity - 0.8633 86.33%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity + 0.6100 61.00%
Fish aquatic toxicity + 0.7939 79.39%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
CHEMBL4105907 Q5BJF2 Sigma intracellular receptor 2 90.4 nM
Ki
via Super-PRED
CHEMBL287 Q99720 Sigma opioid receptor 8554 nM
Ki
PMID: 20521771

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.78% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.62% 91.11%
CHEMBL3137262 O60341 LSD1/CoREST complex 96.44% 97.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 95.76% 94.45%
CHEMBL241 Q14432 Phosphodiesterase 3A 95.26% 92.94%
CHEMBL255 P29275 Adenosine A2b receptor 94.37% 98.59%
CHEMBL1907 P15144 Aminopeptidase N 94.22% 93.31%
CHEMBL3192 Q9BY41 Histone deacetylase 8 93.28% 93.99%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.56% 95.56%
CHEMBL5697 Q9GZT9 Egl nine homolog 1 89.72% 93.40%
CHEMBL5608 Q16288 NT-3 growth factor receptor 89.19% 95.89%
CHEMBL2581 P07339 Cathepsin D 89.07% 98.95%
CHEMBL4208 P20618 Proteasome component C5 88.47% 90.00%
CHEMBL5747 Q92793 CREB-binding protein 87.94% 95.12%
CHEMBL205 P00918 Carbonic anhydrase II 86.83% 98.44%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 85.05% 92.62%
CHEMBL2535 P11166 Glucose transporter 84.26% 98.75%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 84.07% 94.00%
CHEMBL240 Q12809 HERG 83.80% 89.76%
CHEMBL2146302 O94925 Glutaminase kidney isoform, mitochondrial 82.65% 100.00%
CHEMBL2288 Q13526 Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 80.76% 91.71%

Plants that contains it

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Cross-Links

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PubChem 442108
NPASS NPC329793
ChEMBL CHEMBL222287
LOTUS LTS0186031
wikiData Q105033042