Cheilanthifoline

Details

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Internal ID 0286cf9d-3310-4207-bd2e-54e63a24e0c9
Taxonomy Alkaloids and derivatives > Protoberberine alkaloids and derivatives
IUPAC Name (13S)-16-methoxy-5,7-dioxa-1-azapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-3(11),4(8),9,14,16,18-hexaen-17-ol
SMILES (Canonical) COC1=C(C=C2CCN3CC4=C(CC3C2=C1)C=CC5=C4OCO5)O
SMILES (Isomeric) COC1=C(C=C2CCN3CC4=C(C[C@H]3C2=C1)C=CC5=C4OCO5)O
InChI InChI=1S/C19H19NO4/c1-22-18-8-13-12(7-16(18)21)4-5-20-9-14-11(6-15(13)20)2-3-17-19(14)24-10-23-17/h2-3,7-8,15,21H,4-6,9-10H2,1H3/t15-/m0/s1
InChI Key MKRKFSHHTKVRAR-HNNXBMFYSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C19H19NO4
Molecular Weight 325.40 g/mol
Exact Mass 325.13140809 g/mol
Topological Polar Surface Area (TPSA) 51.20 Ų
XlogP 2.80
Atomic LogP (AlogP) 2.79
H-Bond Acceptor 5
H-Bond Donor 1
Rotatable Bonds 1

Synonyms

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AKOS040760322
FS-7170
CS-0032418

2D Structure

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2D Structure of Cheilanthifoline

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9085 90.85%
Caco-2 + 0.8490 84.90%
Blood Brain Barrier + 0.8250 82.50%
Human oral bioavailability - 0.8286 82.86%
Subcellular localzation Mitochondria 0.6169 61.69%
OATP2B1 inhibitior - 0.8617 86.17%
OATP1B1 inhibitior + 0.9217 92.17%
OATP1B3 inhibitior + 0.9484 94.84%
MATE1 inhibitior - 0.8600 86.00%
OCT2 inhibitior - 0.5500 55.00%
BSEP inhibitior + 0.7054 70.54%
P-glycoprotein inhibitior - 0.6435 64.35%
P-glycoprotein substrate - 0.6227 62.27%
CYP3A4 substrate + 0.5992 59.92%
CYP2C9 substrate - 0.6106 61.06%
CYP2D6 substrate + 0.6924 69.24%
CYP3A4 inhibition + 0.6831 68.31%
CYP2C9 inhibition - 0.8963 89.63%
CYP2C19 inhibition + 0.8566 85.66%
CYP2D6 inhibition + 0.9062 90.62%
CYP1A2 inhibition + 0.9283 92.83%
CYP2C8 inhibition - 0.6079 60.79%
CYP inhibitory promiscuity + 0.6338 63.38%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.5434 54.34%
Eye corrosion - 0.9887 98.87%
Eye irritation - 0.9167 91.67%
Skin irritation - 0.7540 75.40%
Skin corrosion - 0.9442 94.42%
Ames mutagenesis - 0.5700 57.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6764 67.64%
Micronuclear + 0.6100 61.00%
Hepatotoxicity - 0.7000 70.00%
skin sensitisation - 0.8627 86.27%
Respiratory toxicity + 0.9111 91.11%
Reproductive toxicity + 0.8556 85.56%
Mitochondrial toxicity + 0.9125 91.25%
Nephrotoxicity + 0.5205 52.05%
Acute Oral Toxicity (c) III 0.5475 54.75%
Estrogen receptor binding + 0.5919 59.19%
Androgen receptor binding - 0.4817 48.17%
Thyroid receptor binding + 0.5470 54.70%
Glucocorticoid receptor binding + 0.6851 68.51%
Aromatase binding - 0.6183 61.83%
PPAR gamma + 0.5709 57.09%
Honey bee toxicity - 0.8006 80.06%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity + 0.6451 64.51%
Fish aquatic toxicity + 0.7002 70.02%

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 98.66% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.87% 91.11%
CHEMBL5697 Q9GZT9 Egl nine homolog 1 96.32% 93.40%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 94.65% 94.45%
CHEMBL2041 P07949 Tyrosine-protein kinase receptor RET 93.72% 91.79%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 93.59% 95.56%
CHEMBL1293249 Q13887 Kruppel-like factor 5 93.02% 86.33%
CHEMBL5311 P37023 Serine/threonine-protein kinase receptor R3 92.87% 82.67%
CHEMBL217 P14416 Dopamine D2 receptor 92.10% 95.62%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 91.90% 85.14%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 90.73% 89.62%
CHEMBL2581 P07339 Cathepsin D 90.72% 98.95%
CHEMBL5608 Q16288 NT-3 growth factor receptor 90.13% 95.89%
CHEMBL3438 Q05513 Protein kinase C zeta 89.29% 88.48%
CHEMBL241 Q14432 Phosphodiesterase 3A 89.18% 92.94%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 87.57% 95.89%
CHEMBL2535 P11166 Glucose transporter 86.61% 98.75%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 86.60% 92.62%
CHEMBL2069156 Q14145 Kelch-like ECH-associated protein 1 86.59% 82.38%
CHEMBL2056 P21728 Dopamine D1 receptor 86.58% 91.00%
CHEMBL4895 P30530 Tyrosine-protein kinase receptor UFO 86.56% 90.95%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 86.19% 96.77%
CHEMBL4247 Q9UM73 ALK tyrosine kinase receptor 85.75% 96.86%
CHEMBL5747 Q92793 CREB-binding protein 82.53% 95.12%
CHEMBL261 P00915 Carbonic anhydrase I 82.09% 96.76%
CHEMBL4208 P20618 Proteasome component C5 82.04% 90.00%
CHEMBL5339 Q5NUL3 G-protein coupled receptor 120 81.85% 95.78%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 81.44% 94.00%
CHEMBL1994 P08235 Mineralocorticoid receptor 81.30% 100.00%
CHEMBL2781 P19634 Sodium/hydrogen exchanger 1 81.06% 90.24%

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.
Corydalis saxicola
Dactylicapnos torulosa
Fumaria judaica
Fumaria parviflora
Fumaria vaillantii
Menispermum dauricum
Papaver macrostomum

Cross-Links

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PubChem 101277425
LOTUS LTS0255684
wikiData Q105166168