CAS 485-49-4|Bicuculline|bicuculline|(10R)-10-[(5S)-6-methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3,5,11-trioxatricyclo[7.3.0.0<sup>2</sup>,<sup>6</sup>]dodeca-1(9),2(6),7-trien-12-on...

General Information

Structure

Molecular Formula

C₂₀H₁₇NO₆

Molecular Mass

367.35208

Exact Mass

367.10558727

Charge

InChI

InChI=1S/C20H17NO6/c1-21-5-4-10-6-14-15(25-8-24-14)7-12(10)17(21)18-11-2-3-13-19(26-9-23-13)16(11)20(22)27-18/h2-3,6-7,17-18H,4-5,8-9H2,1H3/t17-,18+/m0/s1

InChIKey

IYGYMKDQCDOMRE-ZWKOTPCHSA-N

Canonic Smiles

CN1CCc2c([C@H]1[C@@H]1OC(=O)c3c1ccc1c3OCO1)cc1c(c2)OCO1

Isomeric Smiles

O=C1O[C@H](c2c1c1OCOc1cc2)[C@@H]1c2cc3OCOc3cc2CCN1C

Calculated Properties

JChem

LogD (pH = 7.4)

2.60

LogD (pH = 5.5)

1.48

Log P

2.68

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

6.67

Polar Surface Area

66.46

Polarizability

36.69

Molar Refractivity

93.45

LOG S

-4.20

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

Synonyms

Bicuculline(+)-BicucullineNSC 32192(6R)-6-[(5S)-5,6,7,8-Tetrahydro-6-methyl-1,3-dioxolo[4,5-g]lisoquinolin-5-yl]furo[3,4-e]-1,3-benzodioxol-8(6H)-oned-Bicucullined-Bicucullined-BicucullineBicculinebicucullineBicucullineBicucullin

IUPAC Traditional name

bicuculline (10R)-10-[(5S)-6-methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3,5,11-trioxatricyclo[7.3.0.0²,⁶]dodeca-1(9),2(6),7-trien-12-one (10R)-10-[(5S)-6-methyl-2H,5H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3,5,11-trioxatricyclo[7.3.0.0^{2,6}]dodeca-1(9),2(6),7-trien-12-one

IUPAC name

(10R)-10-[(5S)-6-methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3,5,11-trioxatricyclo[7.3.0.0²,⁶]dodeca-1(9),2(6),7-trien-12-one (10R)-10-[(5S)-6-methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3,5,11-trioxatricyclo[7.3.0.0²,⁶]dodeca-1(9),2(6),7-trien-12-one

Names and Identifiers

Registration numbers

Wikipedia Title

Bicuculline

Chemspider ID

9820

Unique Ingredient Identifier

IUPHAR ligand ID

CHEBI ID

PubChem CID

CAS Number

CHEMBL

PubChem SID

KNApSAcK Database

SureChEMBL Database

BRENDA Database

UniProt Database

PubMed Citation Links

30858801275797702994974329137474

CompTox Database

DTXSID3042687

BRENDA Ligand Database

169874

MetaboLights Database

MTBLS379MTBLS2096MTBLS4820

Beilstein Number

98786

ACToR Database

485-49-4

ArrayExpress (Gene Expression Altlas)

Protein Data Bank

KEGG ID

BKMS React Database

Registration numbers

Properties

Safety Information

MSDS Link

Download link

Refrigerator

Product Information

Download link

Alkaloid from many Corydalis spp. and several Fumaria spp. (opt. rotn. of isolates not recorded in some cases). Also isol. from Adlumia fungosa (Adlumia cirrhosa) (Fumariaceae, Papaveraceae)

Mimics epilepsy.

Utilised in the in vitro study of epilepsy.

Pharmacology Properties

GABA(A)-receptor antagonist

Properties

Related Proteins

PDB Bank

6HUK

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

Wikipedia

Bicuculline

TRC

B382500

Alkaloid naturally occurring in the d-form. Shows GABA antagonist activity.

ChEBI

CHEBI:3092

A benzylisoquinoline alkaloid that is 6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinoline which is substituted at the 5-pro-S position by a (6R)-8-oxo-6,8-dihydrofuro[3,4-e][1,3]benzodioxol-6-yl group. A light-sensitive competitive antagonist of GABAA receptors. It was originally identified in 1932 in plant alkaloid extracts and has been isolated from Dicentra cucullaria, Adlumia fungosa, Fumariaceae, and several Corydalis species.

Molecule Details

References

PubChem Literature

From Data Sources

• Curtis, et al.: Nature, 226, 1222 (1970)

• Avoli, M., et al.: J. Physiol. Pharmacol., 75, 526 (1970)

• Chebib, M., et al.: Clin. Exp. Pharmacol. Physiol., 26, 927 (1970)

• 1. Manske, Can. J. Res. 7:265, 1932

• 2. Khawaled R, Bruening-Wright A, Adelman JP, Maylie J (1999) Bicuculline block of small-conductance calcium-activated potassium channels. Pflugers Arch 438: 314-321

References

Bioactivity

PubChem BioAssay

Bioactivity

Data Source

Academic Data

Commercial Catalog

Names and Identifiers

Synonyms

IUPAC Traditional name

IUPAC name

Registration numbers

Wikipedia Title

Bicuculline

Chemspider ID

9820

Unique Ingredient Identifier

IUPHAR ligand ID

CHEBI ID

PubChem CID

CAS Number

CHEMBL

PubChem SID

KNApSAcK Database

SureChEMBL Database

BRENDA Database

UniProt Database

PubMed Citation Links

30858801275797702994974329137474

CompTox Database

DTXSID3042687

BRENDA Ligand Database

169874

MetaboLights Database

MTBLS379MTBLS2096MTBLS4820

Beilstein Number

98786

ACToR Database

485-49-4

ArrayExpress (Gene Expression Altlas)

Protein Data Bank

KEGG ID

BKMS React Database

Related Proteins

Molecule Details

B382500

Alkaloid naturally occurring in the d-form. Shows GABA antagonist activity.

ChEBI

CHEBI:3092

References

PubChem Literature

From Data Sources

• Curtis, et al.: Nature, 226, 1222 (1970)

• Avoli, M., et al.: J. Physiol. Pharmacol., 75, 526 (1970)

• Chebib, M., et al.: Clin. Exp. Pharmacol. Physiol., 26, 927 (1970)

• 1. Manske, Can. J. Res. 7:265, 1932

• 2. Khawaled R, Bruening-Wright A, Adelman JP, Maylie J (1999) Bicuculline block of small-conductance calcium-activated potassium channels. Pflugers Arch 438: 314-321

Bioactivity

PubChem BioAssay

Properties

Safety Information

MSDS Link

Download link

Refrigerator

Product Information

Download link

Alkaloid from many Corydalis spp. and several Fumaria spp. (opt. rotn. of isolates not recorded in some cases). Also isol. from Adlumia fungosa (Adlumia cirrhosa) (Fumariaceae, Papaveraceae)

Mimics epilepsy.

Utilised in the in vitro study of epilepsy.

Pharmacology Properties

GABA(A)-receptor antagonist

Molecule

ID:130533