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Bicuculline

UUID 7dbe4248-15ad-44aa-8b0f-19c240d03966
Flow Object IDfo-a12c6574aa868d4c
Source EF 3.1
Context Environmental → Air → Ground level → Rural (<1000 people/square mile)
CAS Numbers 485-49-4
EC Numbers 207-619-7
prefLabel
Language Value Provenance
en Bicuculline
altLabel ⓘ
Language Value Provenance
en (6R)-6-[(5S)-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl]furo[3,4-e][1,3]benzodioxol-8(6H)-one
en Bicculine
en Bicucullin
en d-Bicuculline
en (+)-Bicuculline
en (6<em>R</em>)-6-[(5<em>S</em>)-5,6,7,8-Tetrahydro-6-methyl-1,3-dioxolo[4,5-<em>g</em>]isoquinolin-5-yl]furo[3,4-<em>e</em>]-1,3-benzodioxol-8(6<em>H</em>)-one
en 1,3-Dioxolo[4,5-<em>g</em>]isoquinoline, furo[3,4-<em>e</em>]-1,3-benzodioxol-8(6<em>H</em>)-one deriv.
en <em>d</em>-Bicuculline
en Bucuculline
en Furo[3,4-<em>e</em>]-1,3-benzodioxol-8(6<em>H</em>)-one, 6-(5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo[4,5-<em>g</em>]isoquinolin-5-yl)-, [<em>R</em>-(<em>R</em>*,<em>S</em>*)]-
en Furo[3,4-<em>e</em>]-1,3-benzodioxol-8(6<em>H</em>)-one, 6-[(5<em>S</em>)-5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo[4,5-<em>g</em>]isoquinolin-5-yl]-, (6<em>R</em>)-
en MeSH ID: D001640
en NSC 32192
Definitions
Language Value Provenance
en 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.
References
Shared Properties
Predicate Value
Formal charge 0
InChIKey IYGYMKDQCDOMRE-ZWKOTPCHSA-N
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
IUPAC name (6R)-6-[(5S)-6-methyl-7,8-dihydro-5H-[1,3]dioxol[4,5-g]isoquinolin-5-yl]-6H-furo[3,4-g][1,3]benzodioxol-8-one, (6R)-6-[(5S)-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6H-furo[3,4-g][1,3]benzodioxol-8-one
Molecular formula C20H17NO6
Molecular mass 367.357
Monoisotopic mass 367.10559
SMILES CN1CCC2=CC3=C(C=C2C1C4C5=C(C6=C(C=C5)OCO6)C(=O)O4)OCO3, CN1CCC2=CC3=C(C=C2[C@H]1[C@H]4C5=C(C6=C(C=C5)OCO6)C(=O)O4)OCO3, [H][C@@]1([C@]2([H])c3cc4c(cc3CCN2C)OCO4)OC(=O)c2c1ccc1c2OCO1

Source List References

List Version Source Flow UUID Source Flow Name
EF 3.1 7dbe4248-15ad-44aa-8b0f-19c240d03966 bicuculline

Concept Associations

Source List Source Flow Source Context Unit Match Type Conversion Provenance
EF 3.1 bicuculline Emissions/Emissions to air/Emissions to air, unspecified (long-term) kg exactMatch —

Consolidated Field Provenance

0 total PROV activity record(s) for this flow.

Field Change Count Latest Time Transformers Latest Comment
altLabel 1 — consensus_match group_key=bicuculline||dimension=Environmental > media=Air > indoor=Unknown; cas=485-49-4; added Common Chemistry CAS names as altLabel: (+)-Bicuculline, (6<em>R</em>)-6-[(5<em>S</em>)-5,6,7,8-Tetrahydro-6-methyl-1,3-dioxolo[4,5-<em>g</em>]isoquinolin-5-yl]furo[3,4-<em>e</em>]-1,3-benzodioxol-8(6<em>H</em>)-one, 1,3-Dioxolo[4,5-<em>g</em>]isoquinoline, furo[3,4-<em>e</em>]-1,3-benzodioxol-8(6<em>H</em>)-one deriv., <em>d</em>-Bicuculline, Bucuculline, Furo[3,4-<em>e</em>]-1,3-benzodioxol-8(6<em>H</em>)-one, 6-(5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo[4,5-<em>g</em>]isoquinolin-5-yl)-, [<em>R</em>-(<em>R</em>*,<em>S</em>*)]-, Furo[3,4-<em>e</em>]-1,3-benzodioxol-8(6<em>H</em>)-one, 6-[(5<em>S</em>)-5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo[4,5-<em>g</em>]isoquinolin-5-yl]-, (6<em>R</em>)-, MeSH ID: D001640, NSC 32192; object_uuid=fo-a12c6574aa868d4c
cas_match_labels 1 — consensus_match group_key=bicuculline||dimension=Environmental > media=Air > indoor=Unknown; group_sources=['chebi', 'ec_inventory', 'pubchem']; cas_sources={'485-49-4': ['chebi', 'ec_inventory', 'pubchem']}; assigned CAS labels from group consensus; object_uuid=fo-a12c6574aa868d4c: {'485-49-4': 'exactMatch'}

Context Attributes

AttributeValue
dimensionEnvironmental
mediaAir
strataGround level
population_densityRural (<1000 people/square mile)

Consensus Changes

Field Old Value New Value Comment
altLabel [{'@value': '(6R)-6-[(5S)-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl]furo[3,4-e][1,3]benzodioxol-8(6H)-one', '@language': 'en', 'source': {'prov:wasGeneratedBy': 'chebi_altlabels', 'prov:wasAttributedTo': 'consensus-flow-list', 'prov:hadPrimarySource': ['label:(6R)-6-[(5S)-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl]furo[3,4-e][1,3]benzodioxol-8(6H)-one', 'http://purl.obolibrary.org/obo/CHEBI_3092', 'EF 3.1'], 'prov:wasDerivedFrom': 'chebi synonym match'}}, {'@value': 'Bicculine', '@language': 'en', 'source': {'prov:wasGeneratedBy': 'chebi_altlabels', 'prov:wasAttributedTo': 'consensus-flow-list', 'prov:hadPrimarySource': ['label:Bicculine', 'http://purl.obolibrary.org/obo/CHEBI_3092', 'EF 3.1'], 'prov:wasDerivedFrom': 'chebi synonym match'}}, {'@value': 'Bicucullin', '@language': 'en', 'source': {'prov:wasGeneratedBy': 'chebi_altlabels', 'prov:wasAttributedTo': 'consensus-flow-list', 'prov:hadPrimarySource': ['label:Bicucullin', 'http://purl.obolibrary.org/obo/CHEBI_3092', 'EF 3.1'], 'prov:wasDerivedFrom': 'chebi synonym match'}}, {'@value': 'd-Bicuculline', '@language': 'en', 'source': {'prov:wasGeneratedBy': 'chebi_altlabels', 'prov:wasAttributedTo': 'consensus-flow-list', 'prov:hadPrimarySource': ['label:d-Bicuculline', 'http://purl.obolibrary.org/obo/CHEBI_3092', 'EF 3.1'], 'prov:wasDerivedFrom': 'chebi synonym match'}}] [{'@value': '(6R)-6-[(5S)-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl]furo[3,4-e][1,3]benzodioxol-8(6H)-one', '@language': 'en', 'source': {'prov:wasGeneratedBy': 'chebi_altlabels', 'prov:wasAttributedTo': 'consensus-flow-list', 'prov:hadPrimarySource': ['label:(6R)-6-[(5S)-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl]furo[3,4-e][1,3]benzodioxol-8(6H)-one', 'http://purl.obolibrary.org/obo/CHEBI_3092', 'EF 3.1'], 'prov:wasDerivedFrom': 'chebi synonym match'}}, {'@value': 'Bicculine', '@language': 'en', 'source': {'prov:wasGeneratedBy': 'chebi_altlabels', 'prov:wasAttributedTo': 'consensus-flow-list', 'prov:hadPrimarySource': ['label:Bicculine', 'http://purl.obolibrary.org/obo/CHEBI_3092', 'EF 3.1'], 'prov:wasDerivedFrom': 'chebi synonym match'}}, {'@value': 'Bicucullin', '@language': 'en', 'source': {'prov:wasGeneratedBy': 'chebi_altlabels', 'prov:wasAttributedTo': 'consensus-flow-list', 'prov:hadPrimarySource': ['label:Bicucullin', 'http://purl.obolibrary.org/obo/CHEBI_3092', 'EF 3.1'], 'prov:wasDerivedFrom': 'chebi synonym match'}}, {'@value': 'd-Bicuculline', '@language': 'en', 'source': {'prov:wasGeneratedBy': 'chebi_altlabels', 'prov:wasAttributedTo': 'consensus-flow-list', 'prov:hadPrimarySource': ['label:d-Bicuculline', 'http://purl.obolibrary.org/obo/CHEBI_3092', 'EF 3.1'], 'prov:wasDerivedFrom': 'chebi synonym match'}}, {'@value': '(+)-Bicuculline', '@language': 'en', 'source': {'prov:wasGeneratedBy': 'consensus_match', 'prov:wasAttributedTo': 'consensus-flow-list', 'prov:hadPrimarySource': ['CAS:485-49-4', 'https://commonchemistry.cas.org/detail?cas_rn=485-49-4'], 'prov:wasDerivedFrom': 'common chemistry CAS lookup'}}, {'@value': '(6<em>R</em>)-6-[(5<em>S</em>)-5,6,7,8-Tetrahydro-6-methyl-1,3-dioxolo[4,5-<em>g</em>]isoquinolin-5-yl]furo[3,4-<em>e</em>]-1,3-benzodioxol-8(6<em>H</em>)-one', '@language': 'en', 'source': {'prov:wasGeneratedBy': 'consensus_match', 'prov:wasAttributedTo': 'consensus-flow-list', 'prov:hadPrimarySource': ['CAS:485-49-4', 'https://commonchemistry.cas.org/detail?cas_rn=485-49-4'], 'prov:wasDerivedFrom': 'common chemistry CAS lookup'}}, {'@value': '1,3-Dioxolo[4,5-<em>g</em>]isoquinoline, furo[3,4-<em>e</em>]-1,3-benzodioxol-8(6<em>H</em>)-one deriv.', '@language': 'en', 'source': {'prov:wasGeneratedBy': 'consensus_match', 'prov:wasAttributedTo': 'consensus-flow-list', 'prov:hadPrimarySource': ['CAS:485-49-4', 'https://commonchemistry.cas.org/detail?cas_rn=485-49-4'], 'prov:wasDerivedFrom': 'common chemistry CAS lookup'}}, {'@value': '<em>d</em>-Bicuculline', '@language': 'en', 'source': {'prov:wasGeneratedBy': 'consensus_match', 'prov:wasAttributedTo': 'consensus-flow-list', 'prov:hadPrimarySource': ['CAS:485-49-4', 'https://commonchemistry.cas.org/detail?cas_rn=485-49-4'], 'prov:wasDerivedFrom': 'common chemistry CAS lookup'}}, {'@value': 'Bucuculline', '@language': 'en', 'source': {'prov:wasGeneratedBy': 'consensus_match', 'prov:wasAttributedTo': 'consensus-flow-list', 'prov:hadPrimarySource': ['CAS:485-49-4', 'https://commonchemistry.cas.org/detail?cas_rn=485-49-4'], 'prov:wasDerivedFrom': 'common chemistry CAS lookup'}}, {'@value': 'Furo[3,4-<em>e</em>]-1,3-benzodioxol-8(6<em>H</em>)-one, 6-(5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo[4,5-<em>g</em>]isoquinolin-5-yl)-, [<em>R</em>-(<em>R</em>*,<em>S</em>*)]-', '@language': 'en', 'source': {'prov:wasGeneratedBy': 'consensus_match', 'prov:wasAttributedTo': 'consensus-flow-list', 'prov:hadPrimarySource': ['CAS:485-49-4', 'https://commonchemistry.cas.org/detail?cas_rn=485-49-4'], 'prov:wasDerivedFrom': 'common chemistry CAS lookup'}}, {'@value': 'Furo[3,4-<em>e</em>]-1,3-benzodioxol-8(6<em>H</em>)-one, 6-[(5<em>S</em>)-5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo[4,5-<em>g</em>]isoquinolin-5-yl]-, (6<em>R</em>)-', '@language': 'en', 'source': {'prov:wasGeneratedBy': 'consensus_match', 'prov:wasAttributedTo': 'consensus-flow-list', 'prov:hadPrimarySource': ['CAS:485-49-4', 'https://commonchemistry.cas.org/detail?cas_rn=485-49-4'], 'prov:wasDerivedFrom': 'common chemistry CAS lookup'}}, {'@value': 'MeSH ID: D001640', '@language': 'en', 'source': {'prov:wasGeneratedBy': 'consensus_match', 'prov:wasAttributedTo': 'consensus-flow-list', 'prov:hadPrimarySource': ['CAS:485-49-4', 'https://commonchemistry.cas.org/detail?cas_rn=485-49-4'], 'prov:wasDerivedFrom': 'common chemistry CAS lookup'}}, {'@value': 'NSC 32192', '@language': 'en', 'source': {'prov:wasGeneratedBy': 'consensus_match', 'prov:wasAttributedTo': 'consensus-flow-list', 'prov:hadPrimarySource': ['CAS:485-49-4', 'https://commonchemistry.cas.org/detail?cas_rn=485-49-4'], 'prov:wasDerivedFrom': 'common chemistry CAS lookup'}}] group_key=bicuculline||dimension=Environmental > media=Air > indoor=Unknown; cas=485-49-4; added Common Chemistry CAS names as altLabel: (+)-Bicuculline, (6<em>R</em>)-6-[(5<em>S</em>)-5,6,7,8-Tetrahydro-6-methyl-1,3-dioxolo[4,5-<em>g</em>]isoquinolin-5-yl]furo[3,4-<em>e</em>]-1,3-benzodioxol-8(6<em>H</em>)-one, 1,3-Dioxolo[4,5-<em>g</em>]isoquinoline, furo[3,4-<em>e</em>]-1,3-benzodioxol-8(6<em>H</em>)-one deriv., <em>d</em>-Bicuculline, Bucuculline, Furo[3,4-<em>e</em>]-1,3-benzodioxol-8(6<em>H</em>)-one, 6-(5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo[4,5-<em>g</em>]isoquinolin-5-yl)-, [<em>R</em>-(<em>R</em>*,<em>S</em>*)]-, Furo[3,4-<em>e</em>]-1,3-benzodioxol-8(6<em>H</em>)-one, 6-[(5<em>S</em>)-5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo[4,5-<em>g</em>]isoquinolin-5-yl]-, (6<em>R</em>)-, MeSH ID: D001640, NSC 32192; object_uuid=fo-a12c6574aa868d4c
cas_match_labels None {'485-49-4': 'exactMatch'} group_key=bicuculline||dimension=Environmental > media=Air > indoor=Unknown; group_sources=['chebi', 'ec_inventory', 'pubchem']; cas_sources={'485-49-4': ['chebi', 'ec_inventory', 'pubchem']}; assigned CAS labels from group consensus; object_uuid=fo-a12c6574aa868d4c: {'485-49-4': 'exactMatch'}

PROV-O Consensus Activity Trail

No PROV-O consensus activities found for this flow.

Full Flow JSON

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    "strata": "Ground level",
    "population_density": "Rural (<1000 people/square mile)"
  },
  "general_comment": null,
  "synonyms": [],
  "unit": "kg",
  "lcia_methods": [],
  "source": "EF 3.1",
  "identifier": "7dbe4248-15ad-44aa-8b0f-19c240d03966",
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