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Berberrubine chloride

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 61ff5058-7b06-406a-a500-7efdd5d2b9ec
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;chloride
SMILES (Canonical) COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC5=C(C=C4CC3)OCO5)O.[Cl-]
SMILES (Isomeric) COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC5=C(C=C4CC3)OCO5)O.[Cl-]
InChI InChI=1S/C19H15NO4.ClH/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;1H
InChI Key GYFSYEVKFOOLFZ-UHFFFAOYSA-N
Popularity 56 references in papers

Physical and Chemical Properties

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Molecular Formula C19H16ClNO4
Molecular Weight 357.80 g/mol
Exact Mass 357.0767857 g/mol
Topological Polar Surface Area (TPSA) 51.80 Ų
XlogP 0.00
Atomic LogP (AlogP) -0.20
H-Bond Acceptor 4
H-Bond Donor 1
Rotatable Bonds 1

Synonyms

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RefChem:565201
Berberrubine chloride
15401-69-1
9-hydroxy-10-methoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium chloride
Berberrubine (chloride)
Beroline 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;chloride
NSC96347
Benzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium, 5,6-dihydro-9-hydroxy-10-methoxy-, chloride
9-Hydroxy-10-methoxy-5,6-dihydro-[1,3]dioxolo-[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium chloride
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 chloride

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8646 86.46%
Caco-2 + 0.9312 93.12%
Blood Brain Barrier + 0.6250 62.50%
Human oral bioavailability - 0.5286 52.86%
Subcellular localzation Mitochondria 0.4016 40.16%
OATP2B1 inhibitior - 0.8802 88.02%
OATP1B1 inhibitior + 0.8941 89.41%
OATP1B3 inhibitior + 0.9502 95.02%
MATE1 inhibitior - 0.8400 84.00%
OCT2 inhibitior - 0.5750 57.50%
BSEP inhibitior + 0.8423 84.23%
P-glycoprotein inhibitior - 0.5495 54.95%
P-glycoprotein substrate - 0.6799 67.99%
CYP3A4 substrate + 0.5641 56.41%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8086 80.86%
CYP3A4 inhibition - 0.5509 55.09%
CYP2C9 inhibition - 0.8414 84.14%
CYP2C19 inhibition - 0.6090 60.90%
CYP2D6 inhibition + 0.7846 78.46%
CYP1A2 inhibition + 0.8217 82.17%
CYP2C8 inhibition + 0.5335 53.35%
CYP inhibitory promiscuity + 0.8005 80.05%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.8518 85.18%
Carcinogenicity (trinary) Non-required 0.4234 42.34%
Eye corrosion - 0.9846 98.46%
Eye irritation - 0.8896 88.96%
Skin irritation - 0.7666 76.66%
Skin corrosion - 0.9321 93.21%
Ames mutagenesis - 0.6900 69.00%
Human Ether-a-go-go-Related Gene inhibition - 0.8474 84.74%
Micronuclear + 0.6600 66.00%
Hepatotoxicity + 0.6000 60.00%
skin sensitisation - 0.8535 85.35%
Respiratory toxicity + 0.5444 54.44%
Reproductive toxicity + 0.8111 81.11%
Mitochondrial toxicity + 0.7750 77.50%
Nephrotoxicity - 0.7246 72.46%
Acute Oral Toxicity (c) III 0.6269 62.69%
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 - 0.8718 87.18%
Biodegradation - 0.9250 92.50%
Crustacea aquatic toxicity + 0.6100 61.00%
Fish aquatic toxicity - 0.5892 58.92%

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 98.25% 91.11%
CHEMBL1951 P21397 Monoamine oxidase A 96.91% 91.49%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 94.64% 96.77%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 91.37% 94.00%
CHEMBL2581 P07339 Cathepsin D 91.21% 98.95%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 90.03% 94.45%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 89.00% 92.62%
CHEMBL3192 Q9BY41 Histone deacetylase 8 88.97% 93.99%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 88.11% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 88.07% 95.56%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 87.49% 89.62%
CHEMBL1293249 Q13887 Kruppel-like factor 5 87.41% 86.33%
CHEMBL5311 P37023 Serine/threonine-protein kinase receptor R3 85.23% 82.67%
CHEMBL1806 P11388 DNA topoisomerase II alpha 84.85% 89.00%
CHEMBL4208 P20618 Proteasome component C5 83.80% 90.00%
CHEMBL2094127 P06493 Cyclin-dependent kinase 1/cyclin B 82.83% 96.00%
CHEMBL4895 P30530 Tyrosine-protein kinase receptor UFO 82.53% 90.95%
CHEMBL5608 Q16288 NT-3 growth factor receptor 82.00% 95.89%
CHEMBL1255126 O15151 Protein Mdm4 81.91% 90.20%
CHEMBL2056 P21728 Dopamine D1 receptor 81.55% 91.00%
CHEMBL3401 O75469 Pregnane X receptor 81.42% 94.73%
CHEMBL5747 Q92793 CREB-binding protein 81.41% 95.12%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 81.11% 96.21%
CHEMBL241 Q14432 Phosphodiesterase 3A 80.95% 92.94%
CHEMBL5339 Q5NUL3 G-protein coupled receptor 120 80.39% 95.78%

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 72703
NPASS NPC306669
ChEMBL CHEMBL1223099