Usambarine

Details

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Internal ID b4e3665b-fc87-4a46-b06b-696640b40a8b
Taxonomy Alkaloids and derivatives > Harmala alkaloids
IUPAC Name (2S,3R,12bS)-3-ethenyl-2-[[(1S)-2-methyl-1,3,4,9-tetrahydropyrido[3,4-b]indol-1-yl]methyl]-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine
SMILES (Canonical) CN1CCC2=C(C1CC3CC4C5=C(CCN4CC3C=C)C6=CC=CC=C6N5)NC7=CC=CC=C27
SMILES (Isomeric) CN1CCC2=C([C@@H]1C[C@H]3C[C@H]4C5=C(CCN4C[C@@H]3C=C)C6=CC=CC=C6N5)NC7=CC=CC=C27
InChI InChI=1S/C30H34N4/c1-3-19-18-34-15-13-24-22-9-5-7-11-26(22)32-30(24)28(34)17-20(19)16-27-29-23(12-14-33(27)2)21-8-4-6-10-25(21)31-29/h3-11,19-20,27-28,31-32H,1,12-18H2,2H3/t19-,20-,27-,28-/m0/s1
InChI Key JICXOAIUPFUZPK-DXBSEXLMSA-N
Popularity 6 references in papers

Physical and Chemical Properties

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Molecular Formula C30H34N4
Molecular Weight 450.60 g/mol
Exact Mass 450.27834710 g/mol
Topological Polar Surface Area (TPSA) 38.10 Ų
XlogP 5.40
Atomic LogP (AlogP) 5.99
H-Bond Acceptor 2
H-Bond Donor 2
Rotatable Bonds 3

Synonyms

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35226-29-0
CHEBI:9911
CHEMBL1214432
C09250
(2S,3R,12bS)-3-ethenyl-2-[[(1S)-2-methyl-1,3,4,9-tetrahydropyrido[3,4-b]indol-1-yl]methyl]-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine
AC1L9CA8
DTXSID20331742
Q27108513
(2S,3R,12bS)-2-[[(1S)-2-methyl-1,3,4,9-tetrahydropyrido[3,4-b]indol-1-yl]methyl]-3-vinyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine

2D Structure

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2D Structure of Usambarine

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9794 97.94%
Caco-2 - 0.5378 53.78%
Blood Brain Barrier + 0.8750 87.50%
Human oral bioavailability - 0.6857 68.57%
Subcellular localzation Nucleus 0.3714 37.14%
OATP2B1 inhibitior - 0.8584 85.84%
OATP1B1 inhibitior + 0.8679 86.79%
OATP1B3 inhibitior + 0.9423 94.23%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior + 0.6000 60.00%
BSEP inhibitior + 0.9878 98.78%
P-glycoprotein inhibitior + 0.9213 92.13%
P-glycoprotein substrate + 0.6568 65.68%
CYP3A4 substrate + 0.6849 68.49%
CYP2C9 substrate + 0.6000 60.00%
CYP2D6 substrate + 0.7148 71.48%
CYP3A4 inhibition - 0.7412 74.12%
CYP2C9 inhibition - 0.9040 90.40%
CYP2C19 inhibition - 0.7877 78.77%
CYP2D6 inhibition + 0.5000 50.00%
CYP1A2 inhibition - 0.5330 53.30%
CYP2C8 inhibition - 0.7016 70.16%
CYP inhibitory promiscuity + 0.5291 52.91%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.7276 72.76%
Eye corrosion - 0.9921 99.21%
Eye irritation - 0.9717 97.17%
Skin irritation - 0.6628 66.28%
Skin corrosion - 0.9022 90.22%
Ames mutagenesis - 0.5837 58.37%
Human Ether-a-go-go-Related Gene inhibition + 0.9532 95.32%
Micronuclear + 0.5500 55.00%
Hepatotoxicity + 0.5125 51.25%
skin sensitisation - 0.8869 88.69%
Respiratory toxicity + 0.8889 88.89%
Reproductive toxicity + 0.9222 92.22%
Mitochondrial toxicity + 0.9625 96.25%
Nephrotoxicity + 0.4840 48.40%
Acute Oral Toxicity (c) III 0.5978 59.78%
Estrogen receptor binding + 0.8165 81.65%
Androgen receptor binding + 0.8066 80.66%
Thyroid receptor binding + 0.5577 55.77%
Glucocorticoid receptor binding + 0.5884 58.84%
Aromatase binding - 0.5645 56.45%
PPAR gamma + 0.5849 58.49%
Honey bee toxicity - 0.7710 77.10%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity + 0.6100 61.00%
Fish aquatic toxicity + 0.9828 98.28%

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
CHEMBL240 Q12809 HERG 99.55% 89.76%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.39% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 96.20% 95.56%
CHEMBL5697 Q9GZT9 Egl nine homolog 1 94.73% 93.40%
CHEMBL3192 Q9BY41 Histone deacetylase 8 92.86% 93.99%
CHEMBL3227 P41594 Metabotropic glutamate receptor 5 91.97% 96.42%
CHEMBL2581 P07339 Cathepsin D 90.42% 98.95%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 87.14% 91.11%
CHEMBL3902 P09211 Glutathione S-transferase Pi 85.05% 93.81%
CHEMBL255 P29275 Adenosine A2b receptor 84.95% 98.59%
CHEMBL3310 Q96DB2 Histone deacetylase 11 84.90% 88.56%
CHEMBL253 P34972 Cannabinoid CB2 receptor 84.82% 97.25%
CHEMBL3137262 O60341 LSD1/CoREST complex 84.77% 97.09%
CHEMBL333 P08253 Matrix metalloproteinase-2 82.94% 96.31%
CHEMBL1951 P21397 Monoamine oxidase A 82.28% 91.49%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 82.08% 94.45%
CHEMBL321 P14780 Matrix metalloproteinase 9 80.89% 92.12%
CHEMBL3155 P34969 Serotonin 7 (5-HT7) receptor 80.58% 90.71%

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.
Strychnos usambarensis
Strychnos usambarensis
Zanthoxylum usambarense

Cross-Links

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PubChem 442121
NPASS NPC229173
ChEMBL CHEMBL1214432
LOTUS LTS0118878
wikiData Q27108513