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Dihydroberberine

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 0962fedc-e5ab-482e-92f7-34674dca4c32
Taxonomy Alkaloids and derivatives > Protoberberine alkaloids and derivatives
IUPAC Name 16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(21),2,4(8),9,15(20),16,18-heptaene
SMILES (Canonical) COC1=C(C2=C(C=C1)C=C3C4=CC5=C(C=C4CCN3C2)OCO5)OC
SMILES (Isomeric) COC1=C(C2=C(C=C1)C=C3C4=CC5=C(C=C4CCN3C2)OCO5)OC
InChI InChI=1S/C20H19NO4/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2/h3-4,7-9H,5-6,10-11H2,1-2H3
InChI Key FZAGOOYMTPGPGF-UHFFFAOYSA-N
Popularity 75 references in papers

Physical and Chemical Properties

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Molecular Formula C20H19NO4
Molecular Weight 337.40 g/mol
Exact Mass 337.13140809 g/mol
Topological Polar Surface Area (TPSA) 40.20 Ų
XlogP 3.50
Atomic LogP (AlogP) 3.30
H-Bond Acceptor 5
H-Bond Donor 0
Rotatable Bonds 2

Synonyms

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483-15-8
Dihydroberbine
Dihydroumbellatine
9,10-Dimethoxy-6,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinoline
Lambertine
7,8-Dihydroberberine
Berberine, dihydro-
NSC 331264
BRN 0344128
9,10-Dimethoxy-2,3-(methylenedioxy)-13,13a-didehydroberbine
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of Dihydroberberine

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9526 95.26%
Caco-2 + 0.9332 93.32%
Blood Brain Barrier + 0.6750 67.50%
Human oral bioavailability - 0.5143 51.43%
Subcellular localzation Mitochondria 0.6284 62.84%
OATP2B1 inhibitior - 0.8791 87.91%
OATP1B1 inhibitior + 0.9462 94.62%
OATP1B3 inhibitior + 0.9415 94.15%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.5098 50.98%
BSEP inhibitior + 0.7918 79.18%
P-glycoprotein inhibitior + 0.6243 62.43%
P-glycoprotein substrate - 0.6600 66.00%
CYP3A4 substrate + 0.6063 60.63%
CYP2C9 substrate - 0.6000 60.00%
CYP2D6 substrate + 0.6187 61.87%
CYP3A4 inhibition + 0.7378 73.78%
CYP2C9 inhibition - 0.8779 87.79%
CYP2C19 inhibition + 0.5065 50.65%
CYP2D6 inhibition + 0.8627 86.27%
CYP1A2 inhibition + 0.8143 81.43%
CYP2C8 inhibition - 0.6330 63.30%
CYP inhibitory promiscuity + 0.8761 87.61%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.4650 46.50%
Eye corrosion - 0.9855 98.55%
Eye irritation - 0.9147 91.47%
Skin irritation - 0.7673 76.73%
Skin corrosion - 0.9329 93.29%
Ames mutagenesis + 0.5100 51.00%
Human Ether-a-go-go-Related Gene inhibition - 0.3746 37.46%
Micronuclear + 0.5200 52.00%
Hepatotoxicity - 0.5591 55.91%
skin sensitisation - 0.8253 82.53%
Respiratory toxicity + 0.8333 83.33%
Reproductive toxicity + 0.8444 84.44%
Mitochondrial toxicity + 0.8500 85.00%
Nephrotoxicity + 0.5465 54.65%
Acute Oral Toxicity (c) III 0.6225 62.25%
Estrogen receptor binding + 0.8506 85.06%
Androgen receptor binding + 0.6354 63.54%
Thyroid receptor binding + 0.6708 67.08%
Glucocorticoid receptor binding + 0.7713 77.13%
Aromatase binding - 0.5665 56.65%
PPAR gamma + 0.5940 59.40%
Honey bee toxicity - 0.8673 86.73%
Biodegradation - 0.9750 97.50%
Crustacea aquatic toxicity + 0.6000 60.00%
Fish aquatic toxicity + 0.8940 89.40%

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
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 97.19% 96.77%
CHEMBL5697 Q9GZT9 Egl nine homolog 1 96.09% 93.40%
CHEMBL5747 Q92793 CREB-binding protein 95.28% 95.12%
CHEMBL1293249 Q13887 Kruppel-like factor 5 94.93% 86.33%
CHEMBL1951 P21397 Monoamine oxidase A 93.82% 91.49%
CHEMBL5311 P37023 Serine/threonine-protein kinase receptor R3 93.03% 82.67%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 93.01% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 91.87% 91.11%
CHEMBL2581 P07339 Cathepsin D 91.69% 98.95%
CHEMBL3192 Q9BY41 Histone deacetylase 8 90.82% 93.99%
CHEMBL2535 P11166 Glucose transporter 90.05% 98.75%
CHEMBL4208 P20618 Proteasome component C5 88.22% 90.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 87.84% 95.56%
CHEMBL2146302 O94925 Glutaminase kidney isoform, mitochondrial 87.17% 100.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 86.85% 95.89%
CHEMBL5339 Q5NUL3 G-protein coupled receptor 120 86.41% 95.78%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 85.97% 94.00%
CHEMBL261 P00915 Carbonic anhydrase I 85.25% 96.76%
CHEMBL4247 Q9UM73 ALK tyrosine kinase receptor 83.88% 96.86%
CHEMBL4895 P30530 Tyrosine-protein kinase receptor UFO 83.02% 90.95%
CHEMBL2056 P21728 Dopamine D1 receptor 83.01% 91.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 82.92% 94.45%
CHEMBL2069156 Q14145 Kelch-like ECH-associated protein 1 82.45% 82.38%
CHEMBL2047 Q96RI1 Bile acid receptor FXR 82.22% 96.10%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 82.08% 89.62%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 81.10% 92.62%
CHEMBL3746 P80365 11-beta-hydroxysteroid dehydrogenase 2 80.99% 94.78%
CHEMBL2781 P19634 Sodium/hydrogen exchanger 1 80.31% 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.
Chelidonium majus
Thalictrum foliolosum

Cross-Links

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PubChem 10217
NPASS NPC93593
LOTUS LTS0007586
wikiData Q72466426