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Details

Stereochemistry RACEMIC
Molecular Formula C14H22O4
Molecular Weight 254.3221
Optical Activity ( + / - )
Defined Stereocenters 4 / 4
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of PALITANTIN

SMILES

CCC\C=C\C=C\[C@@H]1C[C@@H](O)[C@@H](O)C(=O)[C@H]1CO

InChI

InChIKey=MPOXQBRZHHNMER-XZQMCIKJSA-N
InChI=1S/C14H22O4/c1-2-3-4-5-6-7-10-8-12(16)14(18)13(17)11(10)9-15/h4-7,10-12,14-16,18H,2-3,8-9H2,1H3/b5-4+,7-6+/t10-,11+,12-,14-/m1/s1

HIDE SMILES / InChI

Molecular Formula C14H22O4
Molecular Weight 254.3221
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 2
Optical Activity UNSPECIFIED

Palitantin is an antifungal and antiprotozoal compound used in biochemical research. Palitantin was first isolated as a metabolite of Penicillium palitaus by Birkinshaw and Raistrick in 1936. Palitantin possess moderate antimycobacterial activity.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Studies in the biochemistry of micro-organisms: Palitantin, C(14)H(22)O(4), a hitherto undescribed metabolic product of Penicillium palitans Westling.
1936 May
A structural relationship between frequentin and palitantin.
1952 May
Studies in the biosynthesis of fungal metabolites. The biosynthesis of palitantin.
1960 Oct
The effect of palitantin, a metabolite of Penicillium frequentans on Leishmania brasiliensis.
1970
Organocatalytic asymmetric robinson annulation of alpha,beta-unsaturated aldehydes: applications to the total synthesis of (+)-palitantin.
2007 Oct 26
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Leishmania brasiliensis five to eight day-old culture was used for testing. One ml contained 200,000 of organisms. The clear filtrate containing palitantin (0.1 ml) was suc- cessively applied on squares of chromato- graphic paper (1 cm ~) . The paper was then cut into pieces about 1 mm 2 and aseptically inserted into a tube containing 1 ml of Leish- mania brasiliensis culture. After 24 hours of cultivation at 28 C 0.2 ml was pipetted from each tube for the microscopic calculation of dead organisms per field. The pure compound affects Leishmania brasiliensis at concentrations of 50 to 100 ~g/ml.
Substance Class Chemical
Created
by admin
on Sat Dec 16 00:25:37 GMT 2023
Edited
by admin
on Sat Dec 16 00:25:37 GMT 2023
Record UNII
25M588OEZF
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PALITANTIN
MI  
Common Name English
REL-(2R,3S,5R,6R)-3-(1E,3E)-1,3-HEPTADIEN-1-YL-5,6-DIHYDROXY-2-(HYDROXYMETHYL)CYCLOHEXANONE
Common Name English
(±)-PALITANTIN
Common Name English
PALITANTIN [MI]
Common Name English
CYCLOHEXANONE, 3-(1E,3E)-1,3-HEPTADIENYL-5,6-DIHYDROXY-2-(HYDROXYMETHYL)-, (2R,3S,5R,6R)-REL-
Systematic Name English
NSC-246119
Code English
Code System Code Type Description
CAS
15265-28-8
Created by admin on Sat Dec 16 00:25:37 GMT 2023 , Edited by admin on Sat Dec 16 00:25:37 GMT 2023
PRIMARY
EPA CompTox
DTXSID601017488
Created by admin on Sat Dec 16 00:25:37 GMT 2023 , Edited by admin on Sat Dec 16 00:25:37 GMT 2023
PRIMARY
PUBCHEM
6438427
Created by admin on Sat Dec 16 00:25:37 GMT 2023 , Edited by admin on Sat Dec 16 00:25:37 GMT 2023
PRIMARY PUBCHEM
NSC
246119
Created by admin on Sat Dec 16 00:25:37 GMT 2023 , Edited by admin on Sat Dec 16 00:25:37 GMT 2023
PRIMARY
MERCK INDEX
m8358
Created by admin on Sat Dec 16 00:25:37 GMT 2023 , Edited by admin on Sat Dec 16 00:25:37 GMT 2023
PRIMARY Merck Index
MESH
C108794
Created by admin on Sat Dec 16 00:25:37 GMT 2023 , Edited by admin on Sat Dec 16 00:25:37 GMT 2023
PRIMARY
FDA UNII
25M588OEZF
Created by admin on Sat Dec 16 00:25:37 GMT 2023 , Edited by admin on Sat Dec 16 00:25:37 GMT 2023
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE