HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Compound

Tylophorine

HCID 92114
New noteNew reactionRequest quotes
Print preview
Basic informationOverviewNames & identifiersPropertiesChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
482-20-2
Standard SMILES
COc1cc2c3c(c4cc(OC)c(OC)cc4c2cc1OC)CN1CCC[C@H]1C3
InChIKey
SSEUDFYBEOIWGF-AWEZNQCLSA-N
Molecular formula
C24H27NO4
Average molar mass
393.5 g/mol
Monoisotopic mass
393.19400834

Overview

Tylophorine is an organonitrogen heterocyclic compound and an organic heteropentacyclic compound.

Names & identifiers

Preferred name
Tylophorine
IUPAC
(13aS)-2,3,6,7-tetramethoxy-9,11,12,13,13a,14-hexahydrophenanthro[9,10-f]indolizine
English name
Tylophorine
Molecular formula
C24H27NO4
Molecular weight
393.48

Names & synonyms

Tylophorine482-20-2NSC-76387NSC-717335O41630Y8V3NSTP-0G012,3,6,7-Tetramethoxyphenanthro(9,10:6,7')indolizidine(13aS)-2,3,6,7-tetramethoxy-9,11,12,13,13a,14-hexahydrophenanthro[9,10-f]indolizine(S)-9,11,12,13,13a,14-Hexahydro-2,3,6,7-tetramethoxydibenzo(f,h)pyrrolo(1,2-b)isoquinoline(13aS)-2,3,6,7-tetramethoxy-9,11,12,13,13a,14-hexahydrophenanthro(9,10-f)indolizineRefChem:50680(13aR)-2,3,6,7-tetramethoxy-9,11,12,13,13a,14-hexahydrophenanthro(9,10-f)indolizine
Show more names
NSTP 0G01NSC 717335Tylophorine ( (+)-(S)-Tylophorine6,7,10,11-Tetramethoxy-2,3-trimethylene-1,2,3,4-tetrahydrodibenzo[f,h]isoquinoline9,11,12,13,13a,14-Hexahydro-2,3,6,7-tetramethoxydibenzo[f,h]pyrrolo[1,2-b]isoquinoline(S)-9,11,12,13,13a,14-Hexahydro-2,3,6,7-tetramethoxydibenzo(f,h)pyrrol o(1,2-b)isoquinoline
(+)-(S)-TylophorineTylophorin(+)-TylophorineUNII-O41630Y8V3Dibenzo[f,2-b]isoquinoline, 9,11,12,13,13a,14-hexahydro-2,3,6,7-tetramethoxy-, (S)-S(+)-TylophorineNSC 76387(S)-TYLOPHORINE

Database identifiers

CAS
482-20-2
PubChem CID
92114
DTXSID
DTXSID30964025
ChEMBL
CHEMBL250426、CHEMBL258137
ChEBI
CHEBI:9786
UNII
O41630Y8V3
Nikkaji
J1.826.262B

Properties

Computed structural properties

XLogP
4.7
Topological polar surface area
40.2 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
5
Rotatable bonds
4
Heavy atoms
29
Formal charge
0
Complexity
573

Physicochemical properties

Melting point
125 · 125-130 °C (decomp)
Boiling point
559.9 · 559.9±45.0 °C(Predicted)
alpha
23 · D23 +15° (c = 0.7 in chloroform); D21 +73° (c = 0.7 in chloroform)
Density
1.26 · 1.26±0.1 g/cm3(Predicted)
solubility
Chloroform (Slightly), Methanol (Slightly, Heated)
form
Solid
pka
7.63 · 7.63±0.20(Predicted)
color
Pale Yellow to Yellow
FDA UNII
41630 Y8V3 · O41630Y8V3

Chemistry & industry

Applications · 2 items

DescriptionTylophorine is an alkaloid first isolated in 1935 from plants of the genus Tylophora. Studies have demonstrated that this class of alkaloids, characterized by a phenanthroindolizidine skeleton, exhibits potent antitumor, anti-inflammatory, and antiviral activities. A representative tylophorine analogue, DCB-3503 (NSC-716802, 1), displayed an average GI₅₀ value of approximately 10⁻⁸ M against 59 human tumor cell lines in the National Cancer Institute (NCI) anticancer drug screening panel and also inhibited the proliferation of multidrug-resistant tumor cells. Tylocrebrine, another representative member of this class, advanced to Phase I clinical trials as a potential antitumor agent but was subsequently withdrawn because of severe neurotoxicity. Although extensive studies have investigated the antitumor mechanisms of tylophorine alkaloids, their direct molecular targets remain unclear.[1]

Uses(+)-(S)-Tylophorine is a a major alkaloid of Tylophora indica. (+)-(S)-Tylophorine is an immunosuppressant and inflammation inhibitor. (+)-(S)-Tylophorine showed antiproliferative activity and induction of apoptosis in tumor cells.

Additional notes

DefinitionChEBI: Tylophorine is an organonitrogen heterocyclic compound and an organic heteropentacyclic compound.

Related reactions

0 records
New reaction record

No reaction records under the current filter.

Compound notes

Loading…

On this pageBasic informationOverviewNames & identifiersPropertiesChemistry & industryRelated reactionsCompound notes
More actions
New noteNew reactionRequest quotes