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Evodiamine

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

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Internal ID 4e84c263-8bc4-4b98-818b-0af05677f9e8
Taxonomy Organoheterocyclic compounds > Indoles and derivatives > Pyridoindoles > Beta carbolines
IUPAC Name (1S)-21-methyl-3,13,21-triazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,15,17,19-heptaen-14-one
SMILES (Canonical) CN1C2C3=C(CCN2C(=O)C4=CC=CC=C41)C5=CC=CC=C5N3
SMILES (Isomeric) CN1[C@@H]2C3=C(CCN2C(=O)C4=CC=CC=C41)C5=CC=CC=C5N3
InChI InChI=1S/C19H17N3O/c1-21-16-9-5-3-7-14(16)19(23)22-11-10-13-12-6-2-4-8-15(12)20-17(13)18(21)22/h2-9,18,20H,10-11H2,1H3/t18-/m0/s1
InChI Key TXDUTHBFYKGSAH-SFHVURJKSA-N
Popularity 658 references in papers

Physical and Chemical Properties

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Molecular Formula C19H17N3O
Molecular Weight 303.40 g/mol
Exact Mass 303.137162174 g/mol
Topological Polar Surface Area (TPSA) 39.30 Ų
XlogP 3.10
Atomic LogP (AlogP) 3.31
H-Bond Acceptor 2
H-Bond Donor 1
Rotatable Bonds 0

Synonyms

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518-17-2
d-Evodiamine
(+)-Evodiamine
Evodiamine, (+)-
CHEBI:4948
UNII-C01825BVNL
C01825BVNL
CHEMBL463165
(S)-14-methyl-8,13,13b,14-tetrahydroindolo[2',3':3,4]pyrido[2,1-b]quinazolin-5(7H)-one
(S)-14-methyl-7,8,13b,14-tetrahydroindolo[2',3':3,4]pyrido[2,1-b]quinazolin-5(13H)-one
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of Evodiamine

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9913 99.13%
Caco-2 + 0.9312 93.12%
Blood Brain Barrier + 0.9750 97.50%
Human oral bioavailability - 0.6571 65.71%
Subcellular localzation Mitochondria 0.6674 66.74%
OATP2B1 inhibitior - 0.7039 70.39%
OATP1B1 inhibitior + 0.8989 89.89%
OATP1B3 inhibitior + 0.9442 94.42%
MATE1 inhibitior - 0.7800 78.00%
OCT2 inhibitior + 0.7178 71.78%
BSEP inhibitior + 0.9054 90.54%
P-glycoprotein inhibitior - 0.6667 66.67%
P-glycoprotein substrate + 0.5000 50.00%
CYP3A4 substrate + 0.6541 65.41%
CYP2C9 substrate + 0.6141 61.41%
CYP2D6 substrate - 0.8158 81.58%
CYP3A4 inhibition + 0.5230 52.30%
CYP2C9 inhibition - 0.7938 79.38%
CYP2C19 inhibition - 0.7896 78.96%
CYP2D6 inhibition - 0.8397 83.97%
CYP1A2 inhibition + 0.8729 87.29%
CYP2C8 inhibition - 0.9001 90.01%
CYP inhibitory promiscuity + 0.5949 59.49%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.6931 69.31%
Eye corrosion - 0.9893 98.93%
Eye irritation - 0.9952 99.52%
Skin irritation - 0.8019 80.19%
Skin corrosion - 0.9486 94.86%
Ames mutagenesis + 0.5200 52.00%
Human Ether-a-go-go-Related Gene inhibition + 0.8088 80.88%
Micronuclear + 0.7600 76.00%
Hepatotoxicity - 0.5375 53.75%
skin sensitisation - 0.9153 91.53%
Respiratory toxicity + 0.9000 90.00%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.9125 91.25%
Nephrotoxicity - 0.6597 65.97%
Acute Oral Toxicity (c) II 0.5066 50.66%
Estrogen receptor binding + 0.9540 95.40%
Androgen receptor binding + 0.5962 59.62%
Thyroid receptor binding + 0.6681 66.81%
Glucocorticoid receptor binding + 0.6952 69.52%
Aromatase binding + 0.8427 84.27%
PPAR gamma + 0.6029 60.29%
Honey bee toxicity - 0.9342 93.42%
Biodegradation - 0.9250 92.50%
Crustacea aquatic toxicity + 0.6000 60.00%
Fish aquatic toxicity - 0.7726 77.26%

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
CHEMBL2581 P07339 Cathepsin D 97.91% 98.95%
CHEMBL1951 P21397 Monoamine oxidase A 97.62% 91.49%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 96.67% 95.56%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.87% 96.09%
CHEMBL2535 P11166 Glucose transporter 93.16% 98.75%
CHEMBL255 P29275 Adenosine A2b receptor 92.84% 98.59%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 91.14% 91.11%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 89.89% 99.23%
CHEMBL2095172 P14867 GABA-A receptor; alpha-1/beta-2/gamma-2 89.08% 92.67%
CHEMBL217 P14416 Dopamine D2 receptor 88.88% 95.62%
CHEMBL3310 Q96DB2 Histone deacetylase 11 87.47% 88.56%
CHEMBL4302 P08183 P-glycoprotein 1 87.23% 92.98%
CHEMBL3155 P34969 Serotonin 7 (5-HT7) receptor 86.73% 90.71%
CHEMBL5697 Q9GZT9 Egl nine homolog 1 86.69% 93.40%
CHEMBL3869 P50281 Matrix metalloproteinase 14 86.33% 93.10%
CHEMBL5103 Q969S8 Histone deacetylase 10 86.02% 90.08%
CHEMBL333 P08253 Matrix metalloproteinase-2 85.57% 96.31%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 84.48% 85.14%
CHEMBL2094127 P06493 Cyclin-dependent kinase 1/cyclin B 84.07% 96.00%
CHEMBL4208 P20618 Proteasome component C5 83.42% 90.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 83.20% 89.00%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 83.16% 95.83%
CHEMBL2378 P30307 Dual specificity phosphatase Cdc25C 82.99% 96.67%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 82.64% 82.69%
CHEMBL5409 Q8TDU6 G-protein coupled bile acid receptor 1 81.41% 93.65%
CHEMBL2140 P48775 Tryptophan 2,3-dioxygenase 81.05% 98.46%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.05% 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.
Dendrobium nobile
Hesperocyparis abramsiana
Phellodendron amurense
Phellodendron chinense
Spiranthera odoratissima
Tetradium ruticarpum
Vincetoxicum indicum var. indicum
Zanthoxylum rhetsa

Cross-Links

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PubChem 442088
NPASS NPC141612
ChEMBL CHEMBL463165
LOTUS LTS0199197
wikiData Q27894193