CALACTIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C29H40O9
Molecular Weight	532.6225
Optical Activity	UNSPECIFIED
Defined Stereocenters	13 / 13
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CC[C@]3([H])[C@]([H])(CC[C@]4(C)[C@H](CC[C@]34O)C5=CC(=O)OC5)[C@]1(C[C@@]6([H])O[C@@]7(O)[C@H](O)C[C@@H](C)O[C@@]7([H])O[C@]6([H])C2)C=O

InChI

InChIKey=OWPWFVVPBYFKBG-SXDHXEJRSA-N

InChI=1S/C29H40O9/c1-15-9-23(31)29(34)25(36-15)37-21-11-17-3-4-20-19(27(17,14-30)12-22(21)38-29)5-7-26(2)18(6-8-28(20,26)33)16-10-24(32)35-13-16/h10,14-15,17-23,25,31,33-34H,3-9,11-13H2,1-2H3/t15-,17+,18-,19+,20-,21-,22-,23-,25+,26-,27-,28+,29+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C29H40O9
Molecular Weight	532.6225
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	13 / 13
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22828439

Calactin and calotropin were the major cardenolides in Danaus plexippus reared on A. fruticosa or A. curassavica. It was discovered, that calactin could be potential anticancer compound that was supported for human leukemia cells. It was shown, that calactin decreased the expression of cell cycle regulatory proteins Cyclin B1, Cdk1, and Cdc25C was consistent with a G2/M phase arrest. Furthermore, calactin induced extracellular signal-regulated kinase (ERK) phosphorylation, activation of caspase-3, caspase-8, and caspase-9, and PARP cleavage.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
MAPK signaling pathway 26 Target ID: map04010 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22828439	Activator 1430

Conditions

Condition	Modality	Targets	Highest Phase	Product
Leukemia 87 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22828439	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
In vitro metabolism of the cardiotonic steroids gomphogenin and calactin.	1988 Jan	3347047
The small molecule calactin induces DNA damage and apoptosis in human leukemia cells.	2012 Sep	22828439

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

The growth inhibitory activity of the calactin was evaluated against human A549 and Hela cell lines. This compound showed the highest activity with IC50s values of (0.036 μM, A-549) and (0.083 μM, Hela)

Substance Class	Chemical Created by `admin` on `Sat Dec 16 09:52:45 GMT 2023` Edited by `admin` on `Sat Dec 16 09:52:45 GMT 2023`
Record UNII	6299V7SZXG
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CALACTIN

Common Name

English

PEKILOCERIN B

Common Name

English

POEKILOCERIN B

Common Name

English

PECILOCERIN B

Common Name

English

CARD-20(22)-ENOLIDE, 14-HYDROXY-19-OXO-2,3-(((2S,3S,4R,6R)-TETRAHYDRO-3,4-DIHYDROXY-6-METHYL-2H-PYRAN-3,2-DIYL)BIS(OXY))-, (2.ALPHA.,3.BETA.,5.ALPHA.)-

Systematic Name

English

POKILOCERIN B

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID80174192