HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
Huagongshe Open Program：[email protected]AI access: llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.7.9
  1. Home
  2. /Compound

(1R,4S,9Z,13S,13aR,20aR,21aR)-2,3,5,6,7,8,11,12,15,16,17,18,20a,21-Tetradecahydro-24-(9H-pyrido(3,4-b)indol-1-yl)-1,13-etheno-4,21a-methano-1H-azocino(1',2':1,5)pyrrolo(3,2-e)azacyclopentadecin-13(13aH)-ol

HCID 6509753
New noteNew reactionRequest quotesPrint preview
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
104196-68-1
Standard SMILES
O[C@]12C=C(c3nccc4c3[nH]c3ccccc34)[C@@H]3CCN(CCCC/C=C\CC1)C[C@@]31C[C@@H]3/C=C\CCCCN3[C@H]12
InChIKey
FUCSLKWLLSEMDQ-MKYGIPPKSA-N
Molecular formula
C36H44N4O
Average molar mass
548.8 g/mol
Monoisotopic mass
548.35151204

Overview

Manzamine A is an alkaloid of the class of beta-carbolines isolated from Haliclona and Acanthostrongylophora. It exhibits inhibitory activity against Glycogen Synthase Kinase-3 (EC 2.7.11.26). It has a role as an antineoplastic agent, an antimalarial, an anti-HSV-1 agent, an animal metabolite, a marine metabolite and an EC 2.7.11.26 (tau-protein kinase) inhibitor. It is an alkaloid, a member of isoquinolines and a member of beta-carbolines.

Names & identifiers

Preferred name
(1R,4S,9Z,13S,13aR,20aR,21aR)-2,3,5,6,7,8,11,12,15,16,17,18,20a,21-Tetradecahydro-24-(9H-pyrido(3,4-b)indol-1-yl)-1,13-etheno-4,21a-methano-1H-azocino(1',2':1,5)pyrrolo(3,2-e)azacyclopentadecin-13(13aH)-ol
IUPAC
(1R,2R,4R,5Z,12R,13S,16Z)-25-(9H-pyrido[3,4-b]indol-1-yl)-11,22-diazapentacyclo[11.11.2.12,22.02,12.04,11]heptacosa-5,16,25-trien-13-ol
English name
Manzamine a
Molecular formula
C36H44N4O
Molecular weight
548.76

Names & synonyms

Manzamine A104196-68-1DTXSID001098329CHEBI:66667(1R,2R,4R,5Z,12R,13S,16Z)-25-(9H-pyrido[3,4-b]indol-1-yl)-11,22-diazapentacyclo[11.11.2.12,22.02,12.04,11]heptacosa-5,16,25-trien-13-ol(4aR,7S,7aR,13Z,14aR,15aR,18Z)-5-(9H-beta-carbolin-1-yl)-4,4a,9,10,11,12,14a,15-octahydro-3H-7,2-oct[3]enoazocino[1',2':1,5]pyrrolo[2,3-i]isoquinolin-7(1H,7aH)-ol(1R,2R,4R,5Z,12R,13S,16Z)-25-(9H-pyrido(3,4-b)indol-1-yl)-11,22-diazapentacyclo(11.11.2.12,22.02,12.04,11)heptacosa-5,16,25-trien-13-ol(4aR,7S,7aR,13Z,14aR,15aR,18Z)-5-(9H-beta-carbolin-1-yl)-4,4a,9,10,11,12,14a,15-octahydro-3H-7,2-oct(3)enoazocino(1',2':1,5)pyrrolo(2,3-i)isoquinolin-7(1H,7aH)-olRefChem:393499DTXCID601530072(1R,2R,5Z,12R,13S,16Z)-25-(9H-pyrido(3,4-b)indol-1-yl)-11,22-diazapentacyclo(11.11.2.12,22.02,12.04,11)heptacosa-5,16,25-trien-13-ol;hydrochloride(1R,4S,9Z,13S,13aR,20aR,21aR)-2,3,5,6,7,8,11,12,15,16,17,18,20a,21-Tetradecahydro-24-(9H-pyrido(3,4-b)indol-1-yl)-1,13-etheno-4,21a-methano-1H-azocino(1',2':1,5)pyrrolo(3,2-e)azacyclopentadecin-13(13aH)-ol
Show more names
Keramamine A1,13-Etheno-4,21a-methano-1H-azocino[1',2':1,5]pyrrolo[3,2-e]azacyclopentadecin-13(13aH)-ol, 2,3,5,6,7,8,11,12,15,16,17,18,20a,21-tetradecahydro-24-(9H-pyrido[3,4-b]indol-1-yl)-, (1R,4S,9Z,13S,13aR,20aR,21aR)-
(1R,2R,5Z,12R,13S,16Z)-25-(9H-pyrido(3,4-b)indol-1-yl)-11,22-diazapentacyclo(11.11.2.12,22.02,12.04,11)heptacosa-5,16,25-trien-13-olCHEMBL403233MANZAMINECHEMBL326531SCHEMBL14377624BDBM50232478AKOS040748872HY-117025

Database identifiers

CAS
104196-68-1
PubChem CID
6509753
DTXSID
DTXSID001098329
ChEMBL
CHEMBL326531、CHEMBL403233
ChEBI
CHEBI:66667
EC Number
972-489-7
Nikkaji
J342.443J

Properties

Computed structural properties

XLogP
5.7
Topological polar surface area
55.4 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
4
Rotatable bonds
1
Heavy atoms
41
Formal charge
0
Complexity
1,050

Physicochemical properties

Melting point
240 · >240(disassembly)
Boiling point
756.6 · 756.6±60.0 °C(Predicted)
Density
1.26 · 1.26±0.1 g/cm3(Predicted)
storage temp.
-20 ° · -20°
solubility
Soluble in DMSO (up to 25 mg/ml).
form
Off white to yellow solid.
pka
13.58 · 13.58±0.40(Predicted)
color
Off-White to Pale Yellow
optical activity
5020 · +5020 (CHCl3)
Stability
1 year · Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302
Precautionary statements
264 · P264-P270-P301+P312-P330-P501

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Safety data

Signal word
Warning
Symbol(GHS)
GHS07
Hazard statements
H302
Precautionary statements
P264-P270-P301+P312-P330-P501

Chemistry & industry

Applications · 2 items

DescriptionManzamine A (104196-68-1) inhibits vacuolar ATPases and inhibits autophagy in pancreatic cancer cells1. Suppresses atherosclerosisin vivo2. Manzamine A displays neuritogenic activity3and suppresses tau hyperphosphorylation in human neuroblastoma cell lines4.

UsesManzamine A is a β-Carboline alkaloid with anti-inflammatory.

Additional notes

DefinitionChEBI: An alkaloid of the class of beta-carbolines isolated from Haliclona and Acanthostrongylophora. It exhibits inhibitory activity against Glycogen Synthase Kinase-3 (EC 2.7.11.26).

Suppliers

Loading…

Open inquiries

Loading…

Related reactions

0 records
New reaction record

No reaction records under the current filter.

Compound notes

Loading…

On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes