Berberine

C20H18NO4+ — CID 2353

IUPAC16,17-dimethoxy-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-octaene
SMILESCOC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC5=C(C=C4CC3)OCO5)OC
InChIInChI=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
InChIKeyYBHILYKTIRIUTE-UHFFFAOYSA-N
MW336.40 g/mol
LogP3.60
Rot. Bonds2

About Berberine

Berberine (PubChem CID 2353) has the molecular formula C20H18NO4+ and a molecular weight of 336.40 g/mol. Its IUPAC name is 16,17-dimethoxy-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-octaene.

Molecular Properties

Compound NameBerberine
PubChem CID2353
Molecular FormulaC20H18NO4+
Molecular Weight336.40 g/mol
Exact Mass336.12
IUPAC Name16,17-dimethoxy-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-octaene
SMILESCOC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC5=C(C=C4CC3)OCO5)OC
InChIInChI=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
InChIKeyYBHILYKTIRIUTE-UHFFFAOYSA-N
XLogP3.60
TPSA40.80 Ų
H-Bond Donors
H-Bond Acceptors4
Rotatable Bonds2
Heavy Atoms25
Complexity488

Lipinski Rule of Five

Passes Rule of Five

RuleValue
MW ≤ 500336.40
LogP ≤ 53.60
H-Bond Donors ≤ 50
H-Bond Acceptors ≤ 104

Computed Properties (RDKit)

Structural Alerts{'alert_name': 'quaternary_nitrogen_1', 'substructure': 'N/A'}

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Related Compounds

Papaverine
CID 4680
Coptisine
CID 72322
Sanguinarine
CID 5154
Papaverine Hydrochloride
CID 6084
Berberine chloride
CID 12456
Ethaverine
CID 3280
Ethaverine Hydrochloride
CID 5702159
Sanguinarine chloride
CID 68635
Berberine, sulfate
CID 5351462
Chelerythrine
CID 2703
Palmatine
CID 19009
Columbamine
CID 72310

Frequently Asked Questions

What is the IUPAC name of Berberine?
The IUPAC name of Berberine (CID 2353) is 16,17-dimethoxy-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-octaene.
What is the SMILES notation for Berberine?
The canonical SMILES for Berberine is COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC5=C(C=C4CC3)OCO5)OC.
What is the InChIKey of Berberine?
The InChIKey is YBHILYKTIRIUTE-UHFFFAOYSA-N. The full InChI is 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.
What are the key properties of Berberine?
Berberine has a molecular weight of 336.40 g/mol, XLogP of 3.60, 2 rotatable bonds, 0 hydrogen bond donors, and 4 hydrogen bond acceptors.
Where does this data come from?
All data for Berberine is sourced from PubChem (CID 2353), the world's largest open chemistry database maintained by the National Library of Medicine (NIH).