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(1R,21S)-16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-2,4(8),9,15(20),16,18-hexaen-21-ol

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 d3a9c37a-12ee-48a2-80a7-643888d49a98
Taxonomy Alkaloids and derivatives > Protoberberine alkaloids and derivatives
IUPAC Name (1R,21S)-16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-2,4(8),9,15(20),16,18-hexaen-21-ol
SMILES (Canonical) COC1=C(C2=C(C=C1)C(C3C4=CC5=C(C=C4CCN3C2)OCO5)O)OC
SMILES (Isomeric) COC1=C(C2=C(C=C1)[C@@H]([C@H]3C4=CC5=C(C=C4CCN3C2)OCO5)O)OC
InChI InChI=1S/C20H21NO5/c1-23-15-4-3-12-14(20(15)24-2)9-21-6-5-11-7-16-17(26-10-25-16)8-13(11)18(21)19(12)22/h3-4,7-8,18-19,22H,5-6,9-10H2,1-2H3/t18-,19+/m1/s1
InChI Key FLSSXYPKPLFNLK-MOPGFXCFSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C20H21NO5
Molecular Weight 355.40 g/mol
Exact Mass 355.14197277 g/mol
Topological Polar Surface Area (TPSA) 60.40 Ų
XlogP 2.00
Atomic LogP (AlogP) 2.58
H-Bond Acceptor 6
H-Bond Donor 1
Rotatable Bonds 2

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (1R,21S)-16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-2,4(8),9,15(20),16,18-hexaen-21-ol

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.6659 66.59%
Caco-2 + 0.8331 83.31%
Blood Brain Barrier + 0.7250 72.50%
Human oral bioavailability - 0.7286 72.86%
Subcellular localzation Mitochondria 0.5288 52.88%
OATP2B1 inhibitior - 0.8664 86.64%
OATP1B1 inhibitior + 0.9541 95.41%
OATP1B3 inhibitior + 0.9377 93.77%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.5067 50.67%
BSEP inhibitior + 0.7788 77.88%
P-glycoprotein inhibitior - 0.4812 48.12%
P-glycoprotein substrate - 0.7172 71.72%
CYP3A4 substrate + 0.6133 61.33%
CYP2C9 substrate - 0.6063 60.63%
CYP2D6 substrate + 0.6929 69.29%
CYP3A4 inhibition + 0.6099 60.99%
CYP2C9 inhibition - 0.8670 86.70%
CYP2C19 inhibition + 0.8029 80.29%
CYP2D6 inhibition + 0.8195 81.95%
CYP1A2 inhibition + 0.8310 83.10%
CYP2C8 inhibition - 0.6404 64.04%
CYP inhibitory promiscuity + 0.7737 77.37%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5699 56.99%
Eye corrosion - 0.9893 98.93%
Eye irritation - 0.9709 97.09%
Skin irritation - 0.7795 77.95%
Skin corrosion - 0.9400 94.00%
Ames mutagenesis - 0.5100 51.00%
Human Ether-a-go-go-Related Gene inhibition - 0.3912 39.12%
Micronuclear + 0.5400 54.00%
Hepatotoxicity - 0.5750 57.50%
skin sensitisation - 0.8639 86.39%
Respiratory toxicity + 0.9000 90.00%
Reproductive toxicity + 0.8667 86.67%
Mitochondrial toxicity + 0.8750 87.50%
Nephrotoxicity - 0.6559 65.59%
Acute Oral Toxicity (c) III 0.5994 59.94%
Estrogen receptor binding + 0.6422 64.22%
Androgen receptor binding + 0.5477 54.77%
Thyroid receptor binding + 0.5570 55.70%
Glucocorticoid receptor binding + 0.6022 60.22%
Aromatase binding - 0.7031 70.31%
PPAR gamma + 0.6482 64.82%
Honey bee toxicity - 0.8673 86.73%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity + 0.5200 52.00%
Fish aquatic toxicity - 0.4401 44.01%

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 97.80% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 96.14% 94.45%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 95.34% 96.77%
CHEMBL1293249 Q13887 Kruppel-like factor 5 93.58% 86.33%
CHEMBL5608 Q16288 NT-3 growth factor receptor 91.49% 95.89%
CHEMBL3192 Q9BY41 Histone deacetylase 8 91.01% 93.99%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 89.76% 89.62%
CHEMBL2535 P11166 Glucose transporter 88.53% 98.75%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 88.32% 92.62%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 88.05% 95.56%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 87.86% 91.11%
CHEMBL5311 P37023 Serine/threonine-protein kinase receptor R3 87.53% 82.67%
CHEMBL2146302 O94925 Glutaminase kidney isoform, mitochondrial 86.70% 100.00%
CHEMBL2069156 Q14145 Kelch-like ECH-associated protein 1 86.70% 82.38%
CHEMBL2581 P07339 Cathepsin D 86.10% 98.95%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 85.87% 95.89%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 85.40% 85.14%
CHEMBL5697 Q9GZT9 Egl nine homolog 1 85.04% 93.40%
CHEMBL2056 P21728 Dopamine D1 receptor 83.95% 91.00%
CHEMBL4247 Q9UM73 ALK tyrosine kinase receptor 83.68% 96.86%
CHEMBL4895 P30530 Tyrosine-protein kinase receptor UFO 83.16% 90.95%
CHEMBL5339 Q5NUL3 G-protein coupled receptor 120 82.70% 95.78%
CHEMBL1994 P08235 Mineralocorticoid receptor 82.60% 100.00%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 82.01% 90.71%
CHEMBL1806 P11388 DNA topoisomerase II alpha 81.11% 89.00%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 80.98% 94.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 80.65% 97.09%
CHEMBL261 P00915 Carbonic anhydrase I 80.42% 96.76%

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 campulicarpa

Cross-Links

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PubChem 21587563
LOTUS LTS0151547
wikiData Q104997476