Protoberberine alkaloids and derivatives

Description:

Alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton.

Ancestors:

Organic compounds ⮕ Alkaloids and derivatives ⮕ Protoberberine alkaloids and derivatives

Palmatrubine
- ≥98%
- Derived from green cow bile
Cas Number: 16176-68-4

Formula: C₂₀H₂₀NO₄ Molecular Weight: 338.38

IUPAC Name: 2,3,10-trimethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium-9-ol

SMILES: COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC(=C(C=C4CC3)OC)OC)O

InChIKey: QBUIDYLGKMWNEA-UHFFFAOYSA-O

InChI: InChI=1S/C20H19NO4/c1-23-17-5-4-12-8-16-14-10-19(25-3)18(24-2)9-13(14)6-7-21(16)11-15(12)20(17)22/h4-5,8-11H,6-7H2,1-3H3/p+1

Synonyms: 9-Hydroxy-2,3,10-trimethoxy-5,6-dihydroisoquinolino[3,2-a]isoquinolin-7-ium
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Discretamine
Cas Number: 605-34-5 Compound CID: 22955

Formula: C₁₉H₂₁NO₄ Molecular Weight: 327.4

IUPAC Name: 3,10-dimethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline-2,9-diol

SMILES: COC1=C(C2=C(CC3C4=CC(=C(C=C4CCN3C2)OC)O)C=C1)O

InChIKey: KNWVMRVOBAFFMH-UHFFFAOYSA-N

InChI: InChI=1S/C19H21NO4/c1-23-17-4-3-11-7-15-13-9-16(21)18(24-2)8-12(13)5-6-20(15)10-14(11)19(17)22/h3-4,8-9,15,21-22H,5-7,10H2,1-2H3

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Corydalmine
- ≥95%
Cas Number: 30413-84-4 Compound CID: 161665

Formula: C₂₀H₂₃NO₄ Molecular Weight: 341.4

IUPAC Name: (13aS)-2,3,9-trimethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinolin-10-ol

SMILES: COC1=C(C=C2C3CC4=C(CN3CCC2=C1)C(=C(C=C4)O)OC)OC

InChIKey: DIHXHTWYVOYYDC-INIZCTEOSA-N

InChI: InChI=1S/C20H23NO4/c1-23-18-9-13-6-7-21-11-15-12(4-5-17(22)20(15)25-3)8-16(21)14(13)10-19(18)24-2/h4-5,9-10,16,22H,6-8,11H2,1-3H3/t16-/m0/s1
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Pseudopalmatine
- ≥98%
Cas Number: 19716-66-6 Compound CID: 644002

Formula: C₂₁H₂₂NO₄+ Molecular Weight: 352.4

IUPAC Name: 2,3,10,11-tetramethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium

SMILES: COC1=C(C=C2C(=C1)CC[N+]3=CC4=CC(=C(C=C4C=C23)OC)OC)OC

InChIKey: CLFBXKHKECKSQM-UHFFFAOYSA-N

InChI: InChI=1S/C21H22NO4/c1-23-18-8-13-5-6-22-12-15-10-20(25-3)19(24-2)9-14(15)7-17(22)16(13)11-21(18)26-4/h7-12H,5-6H2,1-4H3/q+1
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Jatrorrhizine Hydrochloride
- ≥94%
Cas Number: 960383-96-4 Compound CID: 21115138

Formula: C₂₀H₂₁ClNO₄+ Molecular Weight: 374.8

IUPAC Name: 2,9,10-trimethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium-3-ol;hydrochloride

SMILES: COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC(=C(C=C4CC3)O)OC)OC.Cl

InChIKey: JKMUUZMCSNHBAX-UHFFFAOYSA-O

InChI: InChI=1S/C20H19NO4.ClH/c1-23-18-5-4-12-8-16-14-10-19(24-2)17(22)9-13(14)6-7-21(16)11-15(12)20(18)25-3;/h4-5,8-11H,6-7H2,1-3H3;1H/p+1
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Coptisine
- ≥98%
Cas Number: 3486-66-6 Compound CID: 72322

Formula: C₁₉H₁₄NO₄•1/2H₂SO₄ Molecular Weight: 369.32

IUPAC Name: 5,7,17,19-tetraoxa-13-azoniahexacyclo[11.11.0.02,10.04,8.015,23.016,20]tetracosa-1(13),2,4(8),9,14,16(20),21,23-octaene

SMILES: C1C[N+]2=C(C=C3C=CC4=C(C3=C2)OCO4)C5=CC6=C(C=C51)OCO6

InChIKey: XYHOBCMEDLZUMP-UHFFFAOYSA-N

InChI: InChI=1S/C19H14NO4/c1-2-16-19(24-10-21-16)14-8-20-4-3-12-6-17-18(23-9-22-17)7-13(12)15(20)5-11(1)14/h1-2,5-8H,3-4,9-10H2/q+1
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(R)-(+)-Corypalmine
- ≥98%
Cas Number: 13063-54-2

Formula: C₂₀H₂₃NO₄ Molecular Weight: 341.4

IUPAC Name: (13aR)-2,9,10-trimethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinolin-3-ol

SMILES: COC1=C(C2=C(CC3C4=CC(=C(C=C4CCN3C2)O)OC)C=C1)OC

InChIKey: BMCZTYDZHNTKPR-MRXNPFEDSA-N

InChI: InChI=1S/C20H23NO4/c1-23-18-5-4-12-8-16-14-10-19(24-2)17(22)9-13(14)6-7-21(16)11-15(12)20(18)25-3/h4-5,9-10,16,22H,6-8,11H2,1-3H3/t16-/m1/s1
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Tetrahydroepiberberine
- ≥99%
Cas Number: 38853-67-7 Compound CID: 5321317

Formula: C₂₀H₂₁NO₄ Molecular Weight: 339.39

IUPAC Name: 16,17-dimethoxy-5,7-dioxa-1-azapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-3(11),4(8),9,14,16,18-hexaene

SMILES: COC1=C(C=C2C3CC4=C(CN3CCC2=C1)C5=C(C=C4)OCO5)OC

InChIKey: UWEHVAXMSWXKRW-UHFFFAOYSA-N

InChI: InChI=1S/C20H21NO4/c1-22-18-8-13-5-6-21-10-15-12(3-4-17-20(15)25-11-24-17)7-16(21)14(13)9-19(18)23-2/h3-4,8-9,16H,5-7,10-11H2,1-2H3

Synonyms: C17898 | 16,17-dimethoxy-5,7-dioxa-1-azapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-3(11),4(8),9,14,16,18-hexaene | ...
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13-Methylberberine chloride
- ≥99%
Cas Number: 54260-72-9 Compound CID: 148670

Formula: C₂₁H₂₀ClNO₄ Molecular Weight: 385.84

IUPAC Name: 16,17-dimethoxy-21-methyl-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;chloride

SMILES: CC1=C2C=CC(=C(C2=C[N+]3=C1C4=CC5=C(C=C4CC3)OCO5)OC)OC.[Cl-]

InChIKey: MLEFNGNLISNJEQ-UHFFFAOYSA-M

InChI: InChI=1S/C21H20NO4.ClH/c1-12-14-4-5-17(23-2)21(24-3)16(14)10-22-7-6-13-8-18-19(26-11-25-18)9-15(13)20(12)22;/h4-5,8-10H,6-7,11H2,1-3H3;1H/q+1;/p-1

Synonyms: 16,17-dimethoxy-21-methyl-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-...
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Dihydroberberine
- ≥98%
Cas Number: 483-15-8 EC Number: 683-111-2 Compound CID: 10217

Formula: C₂₀H₁₉NO₄ Molecular Weight: 337.37

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: COC1=C(C2=C(C=C1)C=C3C4=CC5=C(C=C4CCN3C2)OCO5)OC

InChIKey: FZAGOOYMTPGPGF-UHFFFAOYSA-N

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

Synonyms: BERBINE, 13,13a-DIDEHYDRO-9,10-DIMETHOXY-2,3-(METHYLENEDIOXY)- | Dihydroberberine | Dihydroberberine/dihydroumbellati...
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Coptisine Sulfate
- ≥99%
Cas Number: 1198398-71-8 Compound CID: 72322

Formula: C₁₉H₁₄NO₄+ Molecular Weight: 320.3

IUPAC Name: 5,7,17,19-tetraoxa-13-azoniahexacyclo[11.11.0.02,10.04,8.015,23.016,20]tetracosa-1(13),2,4(8),9,14,16(20),21,23-octaene

SMILES: C1C[N+]2=C(C=C3C=CC4=C(C3=C2)OCO4)C5=CC6=C(C=C51)OCO6

InChIKey: XYHOBCMEDLZUMP-UHFFFAOYSA-N

InChI: InChI=1S/C19H14NO4/c1-2-16-19(24-10-21-16)14-8-20-4-3-12-6-17-18(23-9-22-17)7-13(12)15(20)5-11(1)14/h1-2,5-8H,3-4,9-10H2/q+1

Synonyms: 6,7-Dihydro[1,3]dioxolo[4,5-G][1,3]dioxolo[7,8]isoquino[3,2-A]isoquinolin-5-Ium | 3-Hydroxy-3-methylbutene | 1198398-...
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Epiberberine chloride
- ≥99%
Cas Number: 889665-86-5 Compound CID: 71467079

Formula: C₂₀H₁₈ClNO₄ Molecular Weight: 336.363545

IUPAC Name: 16,17-dimethoxy-5,7-dioxa-1-azoniapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-1(13),2,4(8),9,11,14,16,18-octaene;chloride

SMILES: COC1=C(C=C2C(=C1)CC[N+]3=C2C=C4C=CC5=C(C4=C3)OCO5)OC.[Cl-]

InChIKey: DGRBIBRPLDAHJH-UHFFFAOYSA-M

InChI: InChI=1S/C20H18NO4.ClH/c1-22-18-8-13-5-6-21-10-15-12(3-4-17-20(15)25-11-24-17)7-16(21)14(13)9-19(18)23-2;/h3-4,7-10H,5-6,11H2,1-2H3;1H/q+1;/p-1

Synonyms: UNII-ND559X5J59 | Epiberberine chloride | ND559X5J59 | AKOS032944990 | E80794 | HY-N0226A | 16,17-dimethoxy-5,7-dioxa...
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