berberine (CHEBI:16118)

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CHEBI:16118 - berberine

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ChEBI Name	berberine

ChEBI ID	CHEBI:16118

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:41098, CHEBI:13893, CHEBI:22753, CHEBI:3066

Supplier Information	ChemicalBook:CB2262877, eMolecules:537156

Download	Molfile XML SDF

more structures >>

Molfile

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Marvin 12190714143D

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Marvin 12190714143D

43 47 0 0 0 0 999 V2000

-0.5073 4.5542 0.7778 C 0 0 0 0 0 0 0 0 0 4 0 0

-2.2031 2.4522 0.0072 C 0 0 0 0 0 0 0 0 0 1 0 0

0.0137 3.2405 0.6254 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.8230 2.1614 0.2064 C 0 0 0 0 0 0 0 0 0 0 0 0

1.4521 3.0405 0.9179 C 0 0 0 0 0 0 0 0 0 5 0 0

1.9507 1.5721 0.8603 C 0 0 0 0 0 0 0 0 0 6 0 0

-0.2656 0.8462 0.0181 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.0578 -0.2252 -0.4741 C 0 0 0 0 0 0 0 0 0 13 0 0

1.5720 -0.6925 0.1754 C 0 0 0 0 0 0 0 0 0 8 0 0

0.7890 -1.7807 -0.2650 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.5769 -1.5419 -0.5422 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.4311 -2.6200 -0.8677 C 0 0 0 0 0 0 0 0 0 12 0 0

-0.9538 -3.9388 -0.8097 C 0 0 0 0 0 0 0 0 0 11 0 0

1.0504 0.5691 0.3307 N 0 3 0 0 0 0 0 0 0 7 0 0

-2.7011 3.7474 0.1622 C 0 0 0 0 0 0 0 0 0 2 0 0

-1.8697 4.7864 0.5357 C 0 0 0 0 0 0 0 0 0 3 0 0

1.2969 -3.0926 -0.4384 C 0 0 0 0 0 0 0 0 0 9 0 0

0.4036 -4.1855 -0.5308 C 0 0 0 0 0 0 0 0 0 10 0 0

0.7944 -5.3804 -0.3549 O 0 0 0 0 0 0 0 0 0 0 0 0

0.9393 -5.9542 0.8494 C 0 0 0 0 0 0 0 0 0 0 0 0

2.5398 -3.2989 -0.6046 O 0 0 0 0 0 0 0 0 0 0 0 0

3.1475 -3.0569 -1.7821 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.5876 5.8112 0.5875 O 0 0 0 0 0 0 0 0 0 0 0 0

-3.8557 4.1972 0.0173 O 0 0 0 0 0 0 0 0 0 0 0 0

-3.8517 5.5047 0.2688 C 0 0 0 0 0 0 0 0 0 0 0 0

0.0809 5.3408 1.0643 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.9073 1.7647 -0.2492 H 0 0 0 0 0 0 0 0 0 0 0 0

2.0249 3.6472 0.2098 H 0 0 0 0 0 0 0 0 0 0 0 0

1.6690 3.4397 1.9146 H 0 0 0 0 0 0 0 0 0 0 0 0

2.2265 1.2663 1.8764 H 0 0 0 0 0 0 0 0 0 0 0 0

2.8827 1.5742 0.2833 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.0166 -0.0943 -0.7882 H 0 0 0 0 0 0 0 0 0 0 0 0

2.5535 -0.8787 0.4129 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.4135 -2.4644 -1.1088 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.6023 -4.7149 -0.9664 H 0 0 0 0 0 0 0 0 0 0 0 0

1.3289 -6.9633 0.7198 H 0 0 0 0 0 0 0 0 0 0 0 0

1.6371 -5.4056 1.4886 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.0184 -6.0314 1.3728 H 0 0 0 0 0 0 0 0 0 0 0 0

4.2160 -3.2414 -1.6894 H 0 0 0 0 0 0 0 0 0 0 0 0

2.7615 -3.7117 -2.5700 H 0 0 0 0 0 0 0 0 0 0 0 0

3.0211 -2.0229 -2.1194 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.1787 6.0544 -0.6178 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.5310 5.7257 1.0960 H 0 0 0 0 0 0 0 0 0 0 0 0

1 16 4 0 0 0 0

1 3 4 0 0 0 0

15 2 4 0 0 0 0

2 4 4 0 0 0 0

5 3 1 0 0 0 0

3 4 4 0 0 0 0

4 7 1 0 0 0 0

5 6 1 0 0 0 0

14 6 1 0 0 0 0

14 9 4 0 0 0 0

14 7 4 0 0 0 0

7 8 4 0 0 0 0

8 11 4 0 0 0 0

10 9 4 0 0 0 0

10 17 4 0 0 0 0

10 11 4 0 0 0 0

11 12 4 0 0 0 0

12 13 4 0 0 0 0

13 18 4 0 0 0 0

18 17 4 0 0 0 0

23 25 1 0 0 0 0

23 16 1 0 0 0 0

25 24 1 0 0 0 0

24 15 1 0 0 0 0

16 15 4 0 0 0 0

17 21 1 0 0 0 0

18 19 1 0 0 0 0

20 19 1 0 0 0 0

21 22 1 0 0 0 0

1 26 1 0 0 0 0

2 27 1 0 0 0 0

5 28 1 0 0 0 0

5 29 1 0 0 0 0

6 30 1 0 0 0 0

6 31 1 0 0 0 0

8 32 1 0 0 0 0

9 33 1 0 0 0 0

12 34 1 0 0 0 0

13 35 1 0 0 0 0

20 36 1 0 0 0 0

20 37 1 0 0 0 0

20 38 1 0 0 0 0

22 39 1 0 0 0 0

22 40 1 0 0 0 0

22 41 1 0 0 0 0

25 42 1 0 0 0 0

25 43 1 0 0 0 0

M CHG 1 14 1

M APO 2 20 1 22 1

M STY 2 1 SUP 2 SUP

M SAL 1 4 20 36 37 38

M SBL 1 1 28

M SMT 1 Me

M SDS EXP 1 1

M SAL 2 4 22 39 40 41

M SBL 2 1 29

M SMT 2 Me

M SDS EXP 1 2

M END): 25 ms

reading 43 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

43 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

Script completed

Jmol script terminated

Molfile expand

Wikipedia	License
Iohexol, sold under the trade name Iodaque among others, is a contrast agent used for X-ray imaging. This includes when visualizing arteries, veins, ventricles of the brain, the urinary system, and joints, as well as during computed tomography (CT scan). It is given by mouth, injection into a vein, or into a body cavity. Side effects include vomiting, skin flushing, headache, itchiness, kidney problems, and low blood pressure. Less commonly allergic reactions or seizures may occur. Allergies to povidone-iodine or shellfish do not affect the risk of side effects more than other allergies. Use in the later part of pregnancy may cause hypothyroidism in the baby. Iohexol is an iodinated non-ionic radiocontrast agent. It is in the low osmolar family. Iohexol was approved for medical use in 1985. It is on the World Health Organization's List of Essential Medicines.
Read full article at Wikipedia

Formula

C20H18NO4

Net Charge

Average Mass

336.36126

Monoisotopic Mass

336.12303

InChI

InChI=1S/C20H18NO4/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/h3-4,7-10H,5-6,11H2,1-2H3/q+1

InChIKey

YBHILYKTIRIUTE-UHFFFAOYSA-N

SMILES

COc1ccc2cc3-c4cc5OCOc5cc4CC[n+]3cc2c1OC

Metabolite of Species	Details
Hydrastis canadensis (NCBI:txid13569)	Found in leaf (BTO:0000713). EtOH:H2O(50:50) extract of leaves See: PubMed
Coptis japonica (NCBI:txid3442)	Found in rhizome (BTO:0001181). See: PubMed
Homo sapiens (NCBI:txid9606)	Found in blood plasma (BTO:0000118). See: PubMed

Roles Classification
Chemical Role(s):	antioxidant A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.

Biological Role(s):	potassium channel blocker An agent that inhibits cell membrane glycoproteins that are selectively permeable to potassium ions. EC 1.1.1.21 (aldehyde reductase) inhibitor An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD+ or NADP+ acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21). EC 1.1.1.141 [15-hydroxyprostaglandin dehydrogenase (NAD(+))] inhibitor An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD+ or NADP+ acceptor) inhibitor that interferes with the action of 15-hydroxyprostaglandin dehydrogenase (NAD+) (EC 1.1.1.141). EC 1.13.11.52 (indoleamine 2,3-dioxygenase) inhibitor An EC 1.13.11.* (oxidoreductase acting on single donors and incorporating 2 atoms of oxygen) inhibitor that interferes with the action of indoleamine 2,3-dioxygenase (EC 1.13.11.52). EC 1.21.3.3 (reticuline oxidase) inhibitor An EC 1.21.3.* (oxidoreductase acting on X-H and Y-H to form an X-Y bond, with oxygen as acceptor) inhibitor that interferes with the action of reticuline oxidase (EC 1.21.3.3, previously EC 1.5.3.9). EC 2.1.1.116 [3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase] inhibitor An EC 2.1.1.* (methyltransferases) inhibitor that interferes with the action of 3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase (EC 2.1.1.116). EC 3.1.1.4 (phospholipase A2) inhibitor An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of phospholipase A2 (EC 3.1.1.4). EC 3.4.21.26 (prolyl oligopeptidase) inhibitor Any EC 3.4.21.* (serine endopeptidase) inhibitor that interferes with the action of prolyl oligopeptidase (EC 3.4.21.26). EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor An EC 3.4.14.* (dipeptidyl- and tripeptidyl-peptidases) inhibitor that specifically inhibits dipeptidyl peptidase-4 (EC 3.4.14.5). EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor An EC 3.1.3.* (phosphoric monoester hydrolase) inhibitor which interferes with the activity of the enzyme protein tyrosine phosphatases (PTPs), EC 3.1.3.48, involved in the removal of phosphate groups from phosphorylated tyrosine residues on proteins. EC 3.1.1.7 (acetylcholinesterase) inhibitor An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid. EC 3.1.1.8 (cholinesterase) inhibitor An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of cholinesterase (EC 3.1.1.8). EC 2.7.11.10 (IkappaB kinase) inhibitor An EC 2.7.11.* (protein-serine/threonine kinase) inhibitor that interferes with the action of IkappaB kinase (EC 2.7.11.10). EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor An EC 2.1.1.* (methyltransferases) inhibitor that interferes with the action of (S)-tetrahydroprotoberberine N-methyltransferase (EC 2.1.1.122). metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. (via alkaloid ) antifungal agent An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce. (via botanical anti-fungal agent ) plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. (via botanical anti-fungal agent ) antimicrobial agent A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. (via alkaloid antibiotic )

Application(s):	antilipemic drug A substance used to treat hyperlipidemia (an excess of lipids in the blood). hypoglycemic agent A drug which lowers the blood glucose level. antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms. geroprotector Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	berberine (CHEBI:16118) has role antilipemic drug (CHEBI:35679) berberine (CHEBI:16118) has role antineoplastic agent (CHEBI:35610) berberine (CHEBI:16118) has role antioxidant (CHEBI:22586) berberine (CHEBI:16118) has role EC 1.1.1.141 [15-hydroxyprostaglandin dehydrogenase (NAD⁺)] inhibitor (CHEBI:77108) berberine (CHEBI:16118) has role EC 1.1.1.21 (aldehyde reductase) inhibitor (CHEBI:48550) berberine (CHEBI:16118) has role EC 1.13.11.52 (indoleamine 2,3-dioxygenase) inhibitor (CHEBI:72854) berberine (CHEBI:16118) has role EC 1.21.3.3 (reticuline oxidase) inhibitor (CHEBI:77110) berberine (CHEBI:16118) has role EC 2.1.1.116 [3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase] inhibitor (CHEBI:77111) berberine (CHEBI:16118) has role EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor (CHEBI:77115) berberine (CHEBI:16118) has role EC 2.7.11.10 (IκB kinase) inhibitor (CHEBI:77113) berberine (CHEBI:16118) has role EC 3.1.1.4 (phospholipase A₂) inhibitor (CHEBI:50469) berberine (CHEBI:16118) has role EC 3.1.1.7 (acetylcholinesterase) inhibitor (CHEBI:38462) berberine (CHEBI:16118) has role EC 3.1.1.8 (cholinesterase) inhibitor (CHEBI:37733) berberine (CHEBI:16118) has role EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor (CHEBI:35608) berberine (CHEBI:16118) has role EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor (CHEBI:68612) berberine (CHEBI:16118) has role EC 3.4.21.26 (prolyl oligopeptidase) inhibitor (CHEBI:76779) berberine (CHEBI:16118) has role geroprotector (CHEBI:176497) berberine (CHEBI:16118) has role hypoglycemic agent (CHEBI:35526) berberine (CHEBI:16118) has role metabolite (CHEBI:25212) berberine (CHEBI:16118) has role potassium channel blocker (CHEBI:50509) berberine (CHEBI:16118) is a alkaloid antibiotic (CHEBI:86322) berberine (CHEBI:16118) is a berberine alkaloid (CHEBI:22754) berberine (CHEBI:16118) is a botanical anti-fungal agent (CHEBI:86494) berberine (CHEBI:16118) is a organic heteropentacyclic compound (CHEBI:38164)

IUPAC Name

9,10-dimethoxy-5,6-dihydro[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ium

Synonyms	Sources
5,6-dihydro-9,10-dimethoxy-1,3-benzodioxolo[5,6-a]benzo[g]quinolizinium	Alan Wood's Pesticides
7,8,13,13a-tetradehydro-9,10-dimethoxy-2,3-[methylenebis(oxy)]berbinium	IUPAC
9,10-dimethoxy-2,3-(methylenedioxy)-7,8,13,13a-tetradehydroberbinium	ChEBI
Berberin	ChemIDplus
Berberine	KEGG COMPOUND
BERBERINE	PDBeChem
berberine	UniProt
Umbellatine	KEGG COMPOUND

Manual Xrefs	Databases
2263	ChemSpider
BER	PDBeChem
berberine	Alan Wood's Pesticides
Berberine	Wikipedia
BERBERINE	MetaCyc
C00001819	KNApSAcK
C00757	KEGG COMPOUND
DB04115	DrugBank
FDB023165	FooDB
HMDB0003409	HMDB
LSM-6553	LINCS
View more database links

Registry Numbers	Types	Sources
2086-83-1	CAS Registry Number	KEGG COMPOUND
2086-83-1	CAS Registry Number	NIST Chemistry WebBook
2086-83-1	CAS Registry Number	ChemIDplus
3570374	Beilstein Registry Number	ChemIDplus

Citations

Last Modified

21 September 2021

CHEBI:16118 - berberine

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