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Cephaeline

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 c9700693-2cd7-4f71-9f3e-fb8773c5136c
Taxonomy Alkaloids and derivatives > Emetine alkaloids
IUPAC Name (1R)-1-[[(2S,3R,11bS)-3-ethyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizin-2-yl]methyl]-7-methoxy-1,2,3,4-tetrahydroisoquinolin-6-ol
SMILES (Canonical) CCC1CN2CCC3=CC(=C(C=C3C2CC1CC4C5=CC(=C(C=C5CCN4)O)OC)OC)OC
SMILES (Isomeric) CC[C@H]1CN2CCC3=CC(=C(C=C3[C@@H]2C[C@@H]1C[C@@H]4C5=CC(=C(C=C5CCN4)O)OC)OC)OC
InChI InChI=1S/C28H38N2O4/c1-5-17-16-30-9-7-19-13-27(33-3)28(34-4)15-22(19)24(30)11-20(17)10-23-21-14-26(32-2)25(31)12-18(21)6-8-29-23/h12-15,17,20,23-24,29,31H,5-11,16H2,1-4H3/t17-,20-,23+,24-/m0/s1
InChI Key DTGZHCFJNDAHEN-OZEXIGSWSA-N
Popularity 268 references in papers

Physical and Chemical Properties

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Molecular Formula C28H38N2O4
Molecular Weight 466.60 g/mol
Exact Mass 466.28315770 g/mol
Topological Polar Surface Area (TPSA) 63.20 Ų
XlogP 4.40
Atomic LogP (AlogP) 4.64
H-Bond Acceptor 6
H-Bond Donor 2
Rotatable Bonds 6

Synonyms

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483-17-0
Cephaelin
Cepheline
Dihydropsychotrine
7',10,11-Trimethoxyemetan-6'-ol
CHEBI:3533
(1R)-1-[[(2S,3R,11bS)-3-ethyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizin-2-yl]methyl]-7-methoxy-1,2,3,4-tetrahydroisoquinolin-6-ol
UNII-QA971541A1
EINECS 207-591-6
QA971541A1
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of Cephaeline

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8812 88.12%
Caco-2 - 0.5196 51.96%
Blood Brain Barrier + 0.5250 52.50%
Human oral bioavailability - 0.7000 70.00%
Subcellular localzation Mitochondria 0.4750 47.50%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8774 87.74%
OATP1B3 inhibitior + 0.9321 93.21%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.6500 65.00%
BSEP inhibitior + 0.9816 98.16%
P-glycoprotein inhibitior - 0.5919 59.19%
P-glycoprotein substrate + 0.9343 93.43%
CYP3A4 substrate + 0.6419 64.19%
CYP2C9 substrate - 0.6168 61.68%
CYP2D6 substrate + 0.7873 78.73%
CYP3A4 inhibition - 0.9017 90.17%
CYP2C9 inhibition - 0.9464 94.64%
CYP2C19 inhibition - 0.9300 93.00%
CYP2D6 inhibition - 0.8368 83.68%
CYP1A2 inhibition - 0.9397 93.97%
CYP2C8 inhibition + 0.4622 46.22%
CYP inhibitory promiscuity - 0.9488 94.88%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.7143 71.43%
Eye corrosion - 0.9895 98.95%
Eye irritation - 0.9753 97.53%
Skin irritation - 0.7443 74.43%
Skin corrosion - 0.9356 93.56%
Ames mutagenesis - 0.9000 90.00%
Human Ether-a-go-go-Related Gene inhibition + 0.9749 97.49%
Micronuclear + 0.5600 56.00%
Hepatotoxicity - 0.7000 70.00%
skin sensitisation - 0.8874 88.74%
Respiratory toxicity + 0.6889 68.89%
Reproductive toxicity + 0.8111 81.11%
Mitochondrial toxicity + 0.8750 87.50%
Nephrotoxicity - 0.7133 71.33%
Acute Oral Toxicity (c) III 0.6079 60.79%
Estrogen receptor binding + 0.8505 85.05%
Androgen receptor binding + 0.8361 83.61%
Thyroid receptor binding + 0.7715 77.15%
Glucocorticoid receptor binding + 0.8349 83.49%
Aromatase binding + 0.5912 59.12%
PPAR gamma + 0.6030 60.30%
Honey bee toxicity - 0.8180 81.80%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity + 0.5151 51.51%
Fish aquatic toxicity - 0.3890 38.90%

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 99.23% 96.09%
CHEMBL241 Q14432 Phosphodiesterase 3A 97.66% 92.94%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 96.13% 85.14%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 94.75% 91.11%
CHEMBL3192 Q9BY41 Histone deacetylase 8 94.35% 93.99%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 93.76% 94.45%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.38% 97.09%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 93.00% 97.21%
CHEMBL2581 P07339 Cathepsin D 91.49% 98.95%
CHEMBL1293249 Q13887 Kruppel-like factor 5 91.34% 86.33%
CHEMBL253 P34972 Cannabinoid CB2 receptor 87.83% 97.25%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 86.79% 89.62%
CHEMBL5469 Q14289 Protein tyrosine kinase 2 beta 86.62% 91.03%
CHEMBL2041 P07949 Tyrosine-protein kinase receptor RET 85.92% 91.79%
CHEMBL2069156 Q14145 Kelch-like ECH-associated protein 1 84.44% 82.38%
CHEMBL3060 Q9Y345 Glycine transporter 2 84.36% 99.17%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 84.03% 95.89%
CHEMBL217 P14416 Dopamine D2 receptor 83.63% 95.62%
CHEMBL2781 P19634 Sodium/hydrogen exchanger 1 83.42% 90.24%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 83.09% 94.00%
CHEMBL2535 P11166 Glucose transporter 83.05% 98.75%
CHEMBL3438 Q05513 Protein kinase C zeta 82.60% 88.48%
CHEMBL5608 Q16288 NT-3 growth factor receptor 82.53% 95.89%
CHEMBL213 P08588 Beta-1 adrenergic receptor 82.24% 95.56%
CHEMBL228 P31645 Serotonin transporter 81.18% 95.51%
CHEMBL5747 Q92793 CREB-binding protein 81.08% 95.12%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 80.90% 96.95%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 80.48% 92.62%
CHEMBL1744525 P43490 Nicotinamide phosphoribosyltransferase 80.33% 96.25%

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.
Alangium longiflorum
Carapichea ipecacuanha
Carapichea klugii
Dorstenia contrajerva
Pogonopus tubulosus

Cross-Links

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PubChem 442195
NPASS NPC284183
LOTUS LTS0009460
wikiData Q5063249