MONOSODIUM 1,2-DIPALMITOYL-SN-GLYCERO-3-PHOSPHATE

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

Structure Search

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

Molecular Formula	Na
Molecular Weight	22.98976928
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C35H68O8P
Molecular Weight	647.8834
Charge	-1
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28529455

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

Primary Target	Pharmacology	Condition	Potency
G2/mitotic-specific cyclin B1 1 Target ID: CHEMBL2412 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28529455	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Breast cancer 432 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28529455	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Encapsulating nanoemulsions inside eLiposomes for ultrasonic drug delivery.	2012-10-16	22989347
Determination of liposome-buffer distribution coefficients of charged drugs by capillary electrophoresis frontal analysis.	2009-08	19621377
Catanionic vesicles formed with arginine-based surfactants and 1,2-dipalmitoyl-sn-glycero-3-phosphate monosodium salt.	2009-05-07	19402726
Role of phospholipase D2 in anti-apoptotic signaling through increased expressions of Bcl-2 and Bcl-xL.	2007-08-15	17541981

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:18:35 GMT 2025` Edited by `admin` on `Mon Mar 31 18:18:35 GMT 2025`
Record UNII	PB9252N8GT
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

1,2-DIHEXADECANOYL-SN-GLYCERO-3-PHOSPHATE (SODIUM SALT)

Preferred Name

English

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

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