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Details

Stereochemistry ABSOLUTE
Molecular Formula C35H68O8P.Na
Molecular Weight 670.8732
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MONOSODIUM 1,2-DIPALMITOYL-SN-GLYCERO-3-PHOSPHATE

SMILES

[Na+].CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)([O-])=O)OC(=O)CCCCCCCCCCCCCCC

InChI

InChIKey=BMBWFDPPCSTUSZ-MGDILKBHSA-M
InChI=1S/C35H69O8P.Na/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-34(36)41-31-33(32-42-44(38,39)40)43-35(37)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2;/h33H,3-32H2,1-2H3,(H2,38,39,40);/q;+1/p-1/t33-;/m1./s1

HIDE SMILES / InChI
1,2-Dipalmitoyl-sn-glycero-3-phosphate monosodium salt (Phosphatidic Acid, DPPA) is a bioactive phospholipid. Dipalmitoylphosphatidic acid (DPPA) is a minor phospholipid metabolite that is involved in lipid biosynthesis. DPPA has two palmitic acid moieties instead of AA and can convert to lyso-PA to increase Bcl-2 expression in Hela cells but not in B lymphoma cells. DPPA significantly inhibited tumor growth, cell proliferation and tumor angiogenesis. Furthermore, DPPA strongly arrested the G2/M transition and further inhibited cell cycle progression in MDA-MB-231 cells. cyclin B1 (CCNB1) was the DPPA target that regulated cellular proliferation in human TNBC. DPPA, as an anti-cancer drug, inhibited the expression of CCNB1 to arrest the G2/M transition in human TNBC.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Role of phospholipase D2 in anti-apoptotic signaling through increased expressions of Bcl-2 and Bcl-xL.
2007 Aug 15
Determination of liposome-buffer distribution coefficients of charged drugs by capillary electrophoresis frontal analysis.
2009 Aug
Catanionic vesicles formed with arginine-based surfactants and 1,2-dipalmitoyl-sn-glycero-3-phosphate monosodium salt.
2009 May 7
Patents

Sample Use Guides

Mice: Dipalmitoylphosphatidic acid (DPPA) (3 mg/kg) was injected every two days for two weeks beginning on the ninth day after the subcutaneous inoculation of 4T1 cells into the mouse mammary fat pad. At 9 days after the 4T1 cell injection or 7 days after the MDA-MB-231 cell injection, the mice received an intravenous tail injection of DPPA (3mg/kg body weight) .
Route of Administration: Intravenous
Dipalmitoylphosphatidic acid (DPPA) significantly inhibited the viability of the MDA-MB-231 cells at a concentration greater than 100uM (15% DMSO). Furthermore, the cells were treated with 100uM and 150uM DPPA, and DPPA markedly suppressed cell proliferation in a time-dependent manner.
Name Type Language
MONOSODIUM 1,2-DIPALMITOYL-SN-GLYCERO-3-PHOSPHATE
Common Name English
1,2-DIPALMITOYL-SN-GLYCERO-3-PHOSPHATE, MONOSODIUM SALT
Common Name English
1.2-DIPALMITOYL-SN-GLYCERO-3-PHOSPHATIDIC ACID, MONOSODIUM SALT (DPPA)
Common Name English
1.2-DIPALMITOYL-SN-GLYCERO-3-PHOSPHATIDIC ACID, MONOSODIUM SALT
Common Name English
1,2-DIHEXADECANOYL-SN-GLYCERO-3-PHOSPHATE (SODIUM SALT)
Common Name English
DPPA-NA, L-
Common Name English
HEXADECANOIC ACID, 1,1'-((1R)-1-((PHOSPHONOOXY)METHYL)-1,2-ETHANEDIYL) ESTER, SODIUM SALT (1:1)
Common Name English
1,2-DIPALMITOYL-SN-GLYCERO-3-PHOSPHATE (SODIUM SALT)
Common Name English
1,2-DIPALMITOYL-SN-GLYCERO-3-PHOSPHATE MONOSODIUM
Common Name English
DPPA-NA, R-
Common Name English
Code System Code Type Description
EVMPD
SUB22682
Created by admin on Fri Dec 15 16:05:03 GMT 2023 , Edited by admin on Fri Dec 15 16:05:03 GMT 2023
PRIMARY
PUBCHEM
46891879
Created by admin on Fri Dec 15 16:05:03 GMT 2023 , Edited by admin on Fri Dec 15 16:05:03 GMT 2023
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CAS
169051-60-9
Created by admin on Fri Dec 15 16:05:03 GMT 2023 , Edited by admin on Fri Dec 15 16:05:03 GMT 2023
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EPA CompTox
DTXSID20937581
Created by admin on Fri Dec 15 16:05:03 GMT 2023 , Edited by admin on Fri Dec 15 16:05:03 GMT 2023
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FDA UNII
PB9252N8GT
Created by admin on Fri Dec 15 16:05:03 GMT 2023 , Edited by admin on Fri Dec 15 16:05:03 GMT 2023
PRIMARY