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Berberrubine

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 1c3fcdbb-9c2c-4751-a068-5bb45d0c3ad7
Taxonomy Alkaloids and derivatives > Protoberberine alkaloids and derivatives
IUPAC Name 17-methoxy-5,7-dioxa-13-azoniapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(13),2,4(8),9,14,16,18,20-octaen-16-ol
SMILES (Canonical) COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC5=C(C=C4CC3)OCO5)O
SMILES (Isomeric) COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC5=C(C=C4CC3)OCO5)O
InChI InChI=1S/C19H15NO4/c1-22-16-3-2-11-6-15-13-8-18-17(23-10-24-18)7-12(13)4-5-20(15)9-14(11)19(16)21/h2-3,6-9H,4-5,10H2,1H3/p+1
InChI Key GLYPKDKODVRYGP-UHFFFAOYSA-O
Popularity 58 references in papers

Physical and Chemical Properties

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Molecular Formula C19H16NO4+
Molecular Weight 322.30 g/mol
Exact Mass 322.10793299 g/mol
Topological Polar Surface Area (TPSA) 51.80 Ų
XlogP 3.30
Atomic LogP (AlogP) 2.79
H-Bond Acceptor 4
H-Bond Donor 1
Rotatable Bonds 1

Synonyms

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17388-19-1
Berberrubin
Beroline
ZZT5GBZ8KE
DTXSID90169675
Benzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium, 5,6-dihydro-9-hydroxy-10-methoxy-
Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium, 5,6-dihydro-9-hydroxy-10-methoxy-
9-Berberoline chloride
17-methoxy-5,7-dioxa-13-azoniapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(13),2,4(8),9,14,16,18,20-octaen-16-ol
17-methoxy-5,7-dioxa-13-azoniapentacyclo(11.8.0.02,10.04,8.015,20)henicosa-1(13),2,4(8),9,14,16,18,20-octaen-16-ol
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of Berberrubine

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7273 72.73%
Caco-2 + 0.9312 93.12%
Blood Brain Barrier + 0.6000 60.00%
Human oral bioavailability - 0.5286 52.86%
Subcellular localzation Mitochondria 0.5656 56.56%
OATP2B1 inhibitior - 0.8802 88.02%
OATP1B1 inhibitior + 0.8893 88.93%
OATP1B3 inhibitior + 0.9522 95.22%
MATE1 inhibitior - 0.8200 82.00%
OCT2 inhibitior - 0.6000 60.00%
BSEP inhibitior + 0.8423 84.23%
P-glycoprotein inhibitior - 0.5495 54.95%
P-glycoprotein substrate - 0.7327 73.27%
CYP3A4 substrate + 0.5651 56.51%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.7675 76.75%
CYP3A4 inhibition - 0.6196 61.96%
CYP2C9 inhibition - 0.8842 88.42%
CYP2C19 inhibition - 0.7033 70.33%
CYP2D6 inhibition + 0.8762 87.62%
CYP1A2 inhibition + 0.8578 85.78%
CYP2C8 inhibition + 0.4842 48.42%
CYP inhibitory promiscuity + 0.7911 79.11%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.4470 44.70%
Eye corrosion - 0.9875 98.75%
Eye irritation - 0.8896 88.96%
Skin irritation - 0.7661 76.61%
Skin corrosion - 0.9430 94.30%
Ames mutagenesis - 0.7200 72.00%
Human Ether-a-go-go-Related Gene inhibition - 0.8474 84.74%
Micronuclear + 0.6700 67.00%
Hepatotoxicity + 0.6125 61.25%
skin sensitisation - 0.8685 86.85%
Respiratory toxicity + 0.5444 54.44%
Reproductive toxicity + 0.7667 76.67%
Mitochondrial toxicity + 0.7625 76.25%
Nephrotoxicity - 0.6825 68.25%
Acute Oral Toxicity (c) III 0.6163 61.63%
Estrogen receptor binding + 0.9439 94.39%
Androgen receptor binding + 0.7981 79.81%
Thyroid receptor binding + 0.7198 71.98%
Glucocorticoid receptor binding + 0.8566 85.66%
Aromatase binding + 0.5208 52.08%
PPAR gamma + 0.8506 85.06%
Honey bee toxicity - 0.8743 87.43%
Biodegradation - 0.9250 92.50%
Crustacea aquatic toxicity + 0.5800 58.00%
Fish aquatic toxicity - 0.6919 69.19%

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
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.89% 91.11%
CHEMBL1951 P21397 Monoamine oxidase A 96.64% 91.49%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 94.79% 96.77%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.74% 95.56%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 91.37% 94.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 91.13% 94.45%
CHEMBL2581 P07339 Cathepsin D 90.14% 98.95%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 88.75% 92.62%
CHEMBL3192 Q9BY41 Histone deacetylase 8 88.59% 93.99%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 87.37% 89.62%
CHEMBL1293249 Q13887 Kruppel-like factor 5 86.92% 86.33%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 85.28% 96.09%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 83.85% 96.21%
CHEMBL5608 Q16288 NT-3 growth factor receptor 83.82% 95.89%
CHEMBL5311 P37023 Serine/threonine-protein kinase receptor R3 82.97% 82.67%
CHEMBL3060 Q9Y345 Glycine transporter 2 82.38% 99.17%
CHEMBL3438 Q05513 Protein kinase C zeta 81.99% 88.48%
CHEMBL4208 P20618 Proteasome component C5 81.97% 90.00%
CHEMBL1255126 O15151 Protein Mdm4 81.93% 90.20%
CHEMBL241 Q14432 Phosphodiesterase 3A 81.49% 92.94%
CHEMBL5339 Q5NUL3 G-protein coupled receptor 120 81.21% 95.78%
CHEMBL3401 O75469 Pregnane X receptor 81.21% 94.73%
CHEMBL1806 P11388 DNA topoisomerase II alpha 81.14% 89.00%
CHEMBL4895 P30530 Tyrosine-protein kinase receptor UFO 80.85% 90.95%
CHEMBL2056 P21728 Dopamine D1 receptor 80.28% 91.00%

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.
There are no matching plants.

Cross-Links

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PubChem 72704
NPASS NPC4669