methyl (1S,15R,17R,18S)-17-[(1S)-1-hydroxyethyl]-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4,6,8-tetraene-1-carboxylate

Details

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Internal ID 738c02eb-a310-471e-b1eb-27c278d201f8
Taxonomy Alkaloids and derivatives > Ibogan-type alkaloids
IUPAC Name methyl (1S,15R,17R,18S)-17-[(1S)-1-hydroxyethyl]-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4,6,8-tetraene-1-carboxylate
SMILES (Canonical) CC(C1CC2CC3(C1N(C2)CCC4=C3NC5=CC=CC=C45)C(=O)OC)O
SMILES (Isomeric) C[C@@H]([C@@H]1C[C@@H]2C[C@@]3([C@H]1N(C2)CCC4=C3NC5=CC=CC=C45)C(=O)OC)O
InChI InChI=1S/C21H26N2O3/c1-12(24)16-9-13-10-21(20(25)26-2)18-15(7-8-23(11-13)19(16)21)14-5-3-4-6-17(14)22-18/h3-6,12-13,16,19,22,24H,7-11H2,1-2H3/t12-,13+,16-,19-,21+/m0/s1
InChI Key VGDQBNXQAOYMPS-CFWLMFDNSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C21H26N2O3
Molecular Weight 354.40 g/mol
Exact Mass 354.19434270 g/mol
Topological Polar Surface Area (TPSA) 65.60 Ų
XlogP 2.40
Atomic LogP (AlogP) 2.23
H-Bond Acceptor 4
H-Bond Donor 2
Rotatable Bonds 2

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of methyl (1S,15R,17R,18S)-17-[(1S)-1-hydroxyethyl]-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4,6,8-tetraene-1-carboxylate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9211 92.11%
Caco-2 + 0.7749 77.49%
Blood Brain Barrier + 0.6000 60.00%
Human oral bioavailability - 0.7000 70.00%
Subcellular localzation Mitochondria 0.6324 63.24%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9278 92.78%
OATP1B3 inhibitior + 0.9382 93.82%
MATE1 inhibitior - 0.8800 88.00%
OCT2 inhibitior - 0.7000 70.00%
BSEP inhibitior - 0.5208 52.08%
P-glycoprotein inhibitior - 0.5190 51.90%
P-glycoprotein substrate + 0.8059 80.59%
CYP3A4 substrate + 0.7048 70.48%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate + 0.4401 44.01%
CYP3A4 inhibition + 0.5193 51.93%
CYP2C9 inhibition - 0.7887 78.87%
CYP2C19 inhibition - 0.8656 86.56%
CYP2D6 inhibition + 0.5305 53.05%
CYP1A2 inhibition - 0.7132 71.32%
CYP2C8 inhibition - 0.7789 77.89%
CYP inhibitory promiscuity - 0.8192 81.92%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.6985 69.85%
Eye corrosion - 0.9916 99.16%
Eye irritation - 0.9947 99.47%
Skin irritation - 0.8000 80.00%
Skin corrosion - 0.9502 95.02%
Ames mutagenesis - 0.7600 76.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6774 67.74%
Micronuclear + 0.5900 59.00%
Hepatotoxicity - 0.6727 67.27%
skin sensitisation - 0.8704 87.04%
Respiratory toxicity + 0.9000 90.00%
Reproductive toxicity + 0.9556 95.56%
Mitochondrial toxicity + 0.9875 98.75%
Nephrotoxicity - 0.8534 85.34%
Acute Oral Toxicity (c) II 0.4530 45.30%
Estrogen receptor binding + 0.6239 62.39%
Androgen receptor binding + 0.6178 61.78%
Thyroid receptor binding + 0.5881 58.81%
Glucocorticoid receptor binding + 0.6707 67.07%
Aromatase binding + 0.5225 52.25%
PPAR gamma - 0.5657 56.57%
Honey bee toxicity - 0.7756 77.56%
Biodegradation - 0.9250 92.50%
Crustacea aquatic toxicity - 0.6900 69.00%
Fish aquatic toxicity + 0.8691 86.91%

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 99.19% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.87% 91.11%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 98.17% 85.14%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 97.93% 94.45%
CHEMBL2581 P07339 Cathepsin D 96.82% 98.95%
CHEMBL2535 P11166 Glucose transporter 94.85% 98.75%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.70% 95.56%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 93.80% 94.08%
CHEMBL4302 P08183 P-glycoprotein 1 87.80% 92.98%
CHEMBL5028 O14672 ADAM10 87.71% 97.50%
CHEMBL3310 Q96DB2 Histone deacetylase 11 86.87% 88.56%
CHEMBL3137262 O60341 LSD1/CoREST complex 86.83% 97.09%
CHEMBL3430907 Q96GD4 Aurora kinase B/Inner centromere protein 86.56% 97.50%
CHEMBL255 P29275 Adenosine A2b receptor 85.13% 98.59%
CHEMBL4208 P20618 Proteasome component C5 84.97% 90.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 84.76% 99.23%
CHEMBL340 P08684 Cytochrome P450 3A4 82.89% 91.19%
CHEMBL1806 P11388 DNA topoisomerase II alpha 81.59% 89.00%
CHEMBL4073 P09237 Matrix metalloproteinase 7 81.44% 97.56%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.96% 95.89%

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.
Tabernaemontana calcarea
Tabernaemontana catharinensis
Tabernaemontana divaricata
Tabernaemontana mocquerysii

Cross-Links

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PubChem 102067253
LOTUS LTS0203342
wikiData Q105285732