dioleoylphosphatidic acid profile

dioleoyl phosphatidic acid : A phosphatidic acid in which the phosphatidyl acyl groups are both oleoyl. [CHeBI]

ID Source	ID
PubMed CID	9547172
SCHEMBL ID	3817083
CHEBI ID	60427
MeSH ID	M0113774

ID Source

PubMed CID

9547172

SCHEMBL ID

3817083

CHEBI ID

60427

MeSH ID

M0113774

Synonyms (14)

Synonym
dioleoyl phosphatidic acid
dioleoylphosphatidic acid
CHEBI:60427 ,
pa(18:1(9z)/18:1(9z))[u]
pa(18:1/18:1)[u]
1,2-dioleoylglycerol-3-phosphate
3-(phosphonooxy)propane-1,2-diyl (9z,9'z)bis-octadec-9-enoate
EPITOPE ID:136905
gtpl5512
[1-[(z)-octadec-9-enoyl]oxy-3-phosphonooxypropan-2-yl] (z)-octadec-9-enoate
SCHEMBL3817083
[2-[(z)-octadec-9-enoyl]oxy-3-phosphonooxypropyl] (z)-octadec-9-enoate
Q27077072
pa 18:1_18:1

Synonym

dioleoyl phosphatidic acid

dioleoylphosphatidic acid

CHEBI:60427 ,

pa(18:1(9z)/18:1(9z))[u]

pa(18:1/18:1)[u]

1,2-dioleoylglycerol-3-phosphate

3-(phosphonooxy)propane-1,2-diyl (9z,9'z)bis-octadec-9-enoate

EPITOPE ID:136905

gtpl5512

[1-[(z)-octadec-9-enoyl]oxy-3-phosphonooxypropan-2-yl] (z)-octadec-9-enoate

SCHEMBL3817083

[2-[(z)-octadec-9-enoyl]oxy-3-phosphonooxypropyl] (z)-octadec-9-enoate

Q27077072

pa 18:1_18:1

Class	Description
1,2-bis(octadec-9-enoyl)phosphatidic acid	A phosphatidic acid (36:2) in which both acyl groups are specified as octadec-9-enoyl.

Class

Description

1,2-bis(octadec-9-enoyl)phosphatidic acid

A phosphatidic acid (36:2) in which both acyl groups are specified as octadec-9-enoyl.

Assay ID	Title	Year	Journal	Article
AID1345173	Human GPR63 (Class A Orphans)	2003	Cellular signalling, Apr, Volume: 15, Issue:4 ISSN: 0898-6568	Sphingosine 1-phosphate and dioleoylphosphatidic acid are low affinity agonists for the orphan receptor GPR63.

Assay ID

Title

Year

Journal

Article

AID1345173

Human GPR63 (Class A Orphans)

2003

Cellular signalling, Apr, Volume: 15, Issue:4
ISSN: 0898-6568

Sphingosine 1-phosphate and dioleoylphosphatidic acid are low affinity agonists for the orphan receptor GPR63.

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	13 (22.41)	18.7374
1990's	18 (31.03)	18.2507
2000's	20 (34.48)	29.6817
2010's	5 (8.62)	24.3611
2020's	2 (3.45)	2.80

Timeframe

Studies, This Drug (%)

All Drugs %

pre-1990

13 (22.41)

18.7374

1990's

18 (31.03)

18.2507

2000's

20 (34.48)

29.6817

2010's

5 (8.62)

24.3611

2020's

2 (3.45)

2.80

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	59 (100.00%)	84.16%

Publication Type

This drug (%)

All Drugs (%)

Trials

0 (0.00%)

5.53%

Reviews

0 (0.00%)

6.00%

Case Studies

0 (0.00%)

4.05%

Observational

0 (0.00%)

0.25%

Other

59 (100.00%)

84.16%

Substance	Studies	Classes	Roles	First Year	Last Year	Average Age	Relationship Strength	Trials	pre-1990	1990's	2000's	2010's	post-2020
dihydrosphingosine 1-phosphate	1	sphingoid 1-phosphate	mouse metabolite	2003	2003	21.0	low	0	0	0	1	0	0
sphingosine 1-phosphate	1	sphingoid 1-phosphate	mouse metabolite; signalling molecule; sphingosine-1-phosphate receptor agonist; T-cell proliferation inhibitor; vasodilator agent	2003	2003	21.0	low	0	0	0	1	0	0

Substance

Studies

Classes

Roles

First Year

Last Year

Average Age

Relationship Strength

Trials

pre-1990

1990's

2000's

2010's

post-2020

dihydrosphingosine 1-phosphate

sphingoid 1-phosphate

mouse metabolite

2003

21.0

low

sphingosine 1-phosphate

sphingoid 1-phosphate

mouse metabolite;
signalling molecule;
sphingosine-1-phosphate receptor agonist;
T-cell proliferation inhibitor;
vasodilator agent

2003

21.0

low

Substance	Studies	Classes	Roles	First Year	Last Year	Average Age	Relationship Strength	pre-1990	1990's	2000's	2010's	post-2020
ethylene glycol	1	ethanediol; glycol	metabolite; mouse metabolite; solvent; toxin	1986	1986	38.0	low	1	0	0	0	0
benzyl alcohol	1	benzyl alcohols	antioxidant; fragrance; metabolite; solvent	1986	1986	38.0	low	1	0	0	0	0
glycine	1	alpha-amino acid; amino acid zwitterion; proteinogenic amino acid; serine family amino acid	EC 2.1.2.1 (glycine hydroxymethyltransferase) inhibitor; fundamental metabolite; hepatoprotective agent; micronutrient; neurotransmitter; NMDA receptor agonist; nutraceutical	2003	2003	21.0	low	0	0	1	0	0
hydrogen	1	elemental hydrogen; elemental molecule; gas molecular entity	antioxidant; electron donor; food packaging gas; fuel; human metabolite	1995	1995	29.0	low	0	1	0	0	0
dihydroxyphenylalanine	1	hydroxyphenylalanine; non-proteinogenic alpha-amino acid; tyrosine derivative	human metabolite	2003	2003	21.0	low	0	0	1	0	0
phosphorylcholine	1	phosphocholines	allergen; epitope; hapten; human metabolite; mouse metabolite	2000	2000	24.0	low	0	1	0	0	0
putrescine	1	alkane-alpha,omega-diamine	antioxidant; fundamental metabolite	2020	2020	4.0	low	0	0	0	1	0
sarcosine	1	N-alkylglycine zwitterion; N-alkylglycine; N-methyl-amino acid; N-methylglycines	Escherichia coli metabolite; glycine receptor agonist; glycine transporter 1 inhibitor; human metabolite; mouse metabolite	2003	2003	21.0	low	0	0	1	0	0
dipalmitoylphosphatidic acid	2	phosphatidic acid		1990	1990	34.0	low	0	2	0	0	0
carbonyl cyanide p-trifluoromethoxyphenylhydrazone	1	aromatic ether; hydrazone; nitrile; organofluorine compound	ATP synthase inhibitor; geroprotector; ionophore	1999	1999	25.0	low	0	1	0	0	0
isoproterenol	1	catechols; secondary alcohol; secondary amino compound	beta-adrenergic agonist; bronchodilator agent; cardiotonic drug; sympathomimetic agent	2008	2008	16.0	low	0	0	1	0	0
tetracaine	1	benzoate ester; tertiary amino compound	local anaesthetic	1995	1995	29.0	low	0	1	0	0	0
carbachol	1	ammonium salt; carbamate ester	cardiotonic drug; miotic; muscarinic agonist; nicotinic acetylcholine receptor agonist; non-narcotic analgesic	1995	1995	29.0	low	0	1	0	0	0
alanine	1	alanine zwitterion; alanine; L-alpha-amino acid; proteinogenic amino acid; pyruvate family amino acid	EC 4.3.1.15 (diaminopropionate ammonia-lyase) inhibitor; fundamental metabolite	2003	2003	21.0	low	0	0	1	0	0
edetic acid	1	ethylenediamine derivative; polyamino carboxylic acid; tetracarboxylic acid	anticoagulant; antidote; chelator; copper chelator; geroprotector	1990	1990	34.0	low	0	1	0	0	0
1,2-dipalmitoylphosphatidylcholine	1			2009	2009	15.0	low	0	0	1	0	0
egtazic acid	3	diether; tertiary amino compound; tetracarboxylic acid	chelator	1984	1992	35.3	low	1	2	0	0	0
tryptophan	1	erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid; tryptophan zwitterion; tryptophan	antidepressant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite	2007	2007	17.0	low	0	0	1	0	0
4-toluic acid	1	methylbenzoic acid		2003	2003	21.0	low	0	0	1	0	0
isoxazoles	1	isoxazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene		2008	2008	16.0	low	0	0	1	0	0
methoxyhydroxyphenylglycol	1	methoxybenzenes; phenols		1985	1985	39.0	low	1	0	0	0	0
fluorescein-5-isothiocyanate	1	fluorescein isothiocyanate		2003	2003	21.0	low	0	0	1	0	0
terbium	1	f-block element atom; lanthanoid atom		1990	1990	34.0	low	0	1	0	0	0
cadmium	1	cadmium molecular entity; zinc group element atom		1984	1984	40.0	low	1	0	0	0	0
cerium	1	f-block element atom; lanthanoid atom		1990	1990	34.0	low	0	1	0	0	0
europium	1	f-block element atom; lanthanoid atom		1990	1990	34.0	low	0	1	0	0	0
hafnium	1	titanium group element atom		2021	2021	3.0	low	0	0	0	0	1
zirconium	1	titanium group element atom		2019	2019	5.0	low	0	0	0	1	0
calcium phosphate, dibasic, anhydrous	2	calcium phosphate		1988	1992	34.0	low	1	1	0	0	0
calcium phosphate, monobasic, anhydrous	2	calcium phosphate	fertilizer	1988	1992	34.0	low	1	1	0	0	0
tricalcium phosphate	4	calcium phosphate		1988	2016	22.0	low	1	1	0	2	0
deuterium	2	dihydrogen		1991	1995	31.0	low	0	2	0	0	0
ozone	1	elemental molecule; gas molecular entity; reactive oxygen species; triatomic oxygen	antiseptic drug; disinfectant; electrophilic reagent; greenhouse gas; mutagen; oxidising agent; tracer	2020	2020	4.0	low	0	0	0	1	0
tetradecanoylphorbol acetate	1	acetate ester; diester; phorbol ester; tertiary alpha-hydroxy ketone; tetradecanoate ester	antineoplastic agent; apoptosis inducer; carcinogenic agent; mitogen; plant metabolite; protein kinase C agonist; reactive oxygen species generator	1992	1992	32.0	low	0	1	0	0	0
etoposide	1	beta-D-glucoside; furonaphthodioxole; organic heterotetracyclic compound	antineoplastic agent; DNA synthesis inhibitor	2007	2007	17.0	low	0	0	1	0	0
acridine orange	1	aminoacridines; aromatic amine; tertiary amino compound	fluorochrome; histological dye	2016	2016	8.0	low	0	0	0	1	0
1,2-distearoyllecithin	1			1996	1996	28.0	low	0	1	0	0	0
dicetylphosphate	2	dialkyl phosphate		1988	1992	34.0	low	1	1	0	0	0
piperazine-n,n'-bis(2-ethanesulfonic acid)	1	PIPES		2004	2004	20.0	low	0	0	1	0	0
1-palmitoyl-lysophosphatidic acid	1	2-lysophosphatidic acid		1984	1984	40.0	low	1	0	0	0	0
3,4-dihydroxyphenylglycol	1	catechols; tetrol	metabolite; mouse metabolite	1985	1985	39.0	low	1	0	0	0	0
dimyristoylphosphatidic acid	1	phosphatidic acid		1990	1990	34.0	low	0	1	0	0	0
4-methylhippuric acid	1	N-acylglycine	metabolite	2003	2003	21.0	low	0	0	1	0	0
1,2-bis(2-aminophenoxy)ethane-n,n,n',n'-tetraacetic acid	1	polyamino carboxylic acid; tetracarboxylic acid	chelator	1992	1992	32.0	low	0	1	0	0	0
3-(trifluoromethyl)-3-(3-iodophenyl)diazirine	2			1992	2006	25.0	low	0	1	1	0	0
nitrosylprotoheme	1			2007	2007	17.0	low	0	0	1	0	0
glycerophosphoinositol 4,5-bisphosphate	2			2007	2008	16.5	low	0	0	2	0	0
1,2-dilauroylphosphatidic acid	2			1984	1990	37.0	high	1	1	0	0	0
singlet oxygen	1	chalcogen; monoatomic oxygen; nonmetal atom	macronutrient	2021	2021	3.0	low	0	0	0	0	1
calcium pyrophosphate	2			1988	1992	34.0	low	1	1	0	0	0
dihydrosphingosine 1-phosphate	1	sphingoid 1-phosphate	mouse metabolite	2003	2003	21.0	low	0	0	1	0	0
tempo	1	aminoxyls; piperidines	catalyst; ferroptosis inhibitor; radical scavenger	2000	2000	24.0	low	0	1	0	0	0
sodium dodecyl sulfate	1	organic sodium salt	detergent; protein denaturant	2003	2003	21.0	low	0	0	1	0	0
sphingosine	1	sphing-4-enine	human metabolite; mouse metabolite	2003	2003	21.0	low	0	0	1	0	0
1-monooleoyl-rac-glycerol	2	1-acylglycerol 18:1; monooleoylglycerol	plant metabolite	2001	2005	21.0	low	0	0	2	0	0
sphingosine 1-phosphate	1	sphingoid 1-phosphate	mouse metabolite; signalling molecule; sphingosine-1-phosphate receptor agonist; T-cell proliferation inhibitor; vasodilator agent	2003	2003	21.0	low	0	0	1	0	0
lysophosphatidic acid	4	1-acyl-sn-glycerol 3-phosphate		1992	2008	21.5	low	0	1	3	0	0
lysophosphatidylcholines	1	1-O-acyl-sn-glycero-3-phosphocholine		2000	2000	24.0	low	0	1	0	0	0
1,2-oleoylphosphatidylcholine	21	phosphatidylcholine(1+)		1985	2012	26.5	medium	4	10	6	1	0
dimyristoylphosphatidylcholine	1	1,2-diacyl-sn-glycero-3-phosphocholine; phosphatidylcholine 28:0; tetradecanoate ester	antigen; mouse metabolite	2009	2009	15.0	low	0	0	1	0	0
phosphorus	2	monoatomic phosphorus; nonmetal atom; pnictogen	macronutrient	1984	1991	36.5	low	1	1	0	0	0
1,2-dielaidoylphosphatidylethanolamine	2			1992	1992	32.0	low	0	2	0	0	0
1-palmitoyl-2-oleoylphosphatidylcholine	1			2009	2009	15.0	low	0	0	1	0	0
1,2-dioleoyloxy-3-(trimethylammonium)propane	1			2012	2012	12.0	low	0	0	0	1	0
dioleoyl phosphatidylethanolamine	2	phosphatidylethanolamine		2005	2009	17.0	low	0	0	2	0	0
1,2-dioleoylphosphatidylserine	7	phosphatidylserine(18:1/18:1)	mouse metabolite	1991	2008	23.9	low	0	4	3	0	0
erucylphosphocholine	1			2000	2000	24.0	low	0	1	0	0	0
dipalmitoleoylphosphatidylethanolamine	1			2004	2004	20.0	medium	0	0	1	0	0
mocetinostat	1	aminopyrimidine; benzamides; pyridines; secondary amino compound; secondary carboxamide; substituted aniline	antineoplastic agent; apoptosis inducer; autophagy inducer; cardioprotective agent; EC 3.5.1.98 (histone deacetylase) inhibitor; hepatotoxic agent	2007	2007	17.0	low	0	0	1	0	0
tetramethylrhodamine	1	xanthene dye		2008	2008	16.0	low	0	0	1	0	0
alpha-synuclein	2			2008	2017	11.5	low	0	0	1	1	0
calcimycin	3	benzoxazole		1984	1987	38.7	low	3	0	0	0	0
cytochrome c-t	1			2007	2007	17.0	low	0	0	1	0	0
phosphatidylcholines	26	1,2-diacyl-sn-glycero-3-phosphocholine		1985	2012	26.8	medium	5	13	7	1	0
1-palmitoyl-2-(6-(n-(7-nitrobenz)-2-oxa-1,3-diazol-4-yl)aminocaproyl)phosphatidylcholine	1	1,2-diacyl-sn-glycero-3-phosphocholine(1+)	fluorescent probe	2008	2008	16.0	low	0	0	1	0	0
glycolipids	2			1992	2009	23.5	low	0	1	1	0	0
vpc32183	1			2008	2008	16.0	low	0	0	1	0	0
1,2-dioleoyl-sn-glycero-3-phosphoglycerol	4	1,2-diacyl-sn-glycero-3-phospho-(1'-sn-glycerol)		1987	2008	24.5	low	1	1	2	0	0
heme	1			2007	2007	17.0	low	0	0	1	0	0
novobiocin	1	carbamate ester; ether; hexoside; hydroxycoumarin; monocarboxylic acid amide; monosaccharide derivative; phenols	antibacterial agent; antimicrobial agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; Escherichia coli metabolite; hepatoprotective agent	1990	1990	34.0	low	0	1	0	0	0
transforming growth factor beta	1			2003	2003	21.0	low	0	0	1	0	0
okadaic acid	1	ketal		2001	2001	23.0	low	0	0	1	0	0
arsenazo iii	2			1985	1986	38.5	low	2	0	0	0	0

Substance

Studies

Classes

Roles

First Year

Last Year

Average Age

Relationship Strength

Trials

pre-1990

1990's

2000's

2010's

post-2020

ethylene glycol

ethanediol;
glycol

metabolite;
mouse metabolite;
solvent;
toxin

1986

38.0

low

benzyl alcohol

benzyl alcohols

antioxidant;
fragrance;
metabolite;
solvent

1986

38.0

low

glycine

alpha-amino acid;
amino acid zwitterion;
proteinogenic amino acid;
serine family amino acid

EC 2.1.2.1 (glycine hydroxymethyltransferase) inhibitor;
fundamental metabolite;
hepatoprotective agent;
micronutrient;
neurotransmitter;
NMDA receptor agonist;
nutraceutical

2003

21.0

low

hydrogen

elemental hydrogen;
elemental molecule;
gas molecular entity

antioxidant;
electron donor;
food packaging gas;
fuel;
human metabolite

1995

29.0

low

dihydroxyphenylalanine

hydroxyphenylalanine;
non-proteinogenic alpha-amino acid;
tyrosine derivative

human metabolite

2003

21.0

low

phosphorylcholine

phosphocholines

allergen;
epitope;
hapten;
human metabolite;
mouse metabolite

2000

24.0

low

putrescine

alkane-alpha,omega-diamine

antioxidant;
fundamental metabolite

2020

4.0

low

sarcosine

N-alkylglycine zwitterion;
N-alkylglycine;
N-methyl-amino acid;
N-methylglycines

Escherichia coli metabolite;
glycine receptor agonist;
glycine transporter 1 inhibitor;
human metabolite;
mouse metabolite

2003

21.0

low

dipalmitoylphosphatidic acid

phosphatidic acid

1990

34.0

low

carbonyl cyanide p-trifluoromethoxyphenylhydrazone

aromatic ether;
hydrazone;
nitrile;
organofluorine compound

ATP synthase inhibitor;
geroprotector;
ionophore

1999

25.0

low

isoproterenol

catechols;
secondary alcohol;
secondary amino compound

beta-adrenergic agonist;
bronchodilator agent;
cardiotonic drug;
sympathomimetic agent

2008

16.0

low

tetracaine

benzoate ester;
tertiary amino compound

local anaesthetic

1995

29.0

low

carbachol

ammonium salt;
carbamate ester

cardiotonic drug;
miotic;
muscarinic agonist;
nicotinic acetylcholine receptor agonist;
non-narcotic analgesic

1995

29.0

low

alanine

alanine zwitterion;
alanine;
L-alpha-amino acid;
proteinogenic amino acid;
pyruvate family amino acid

EC 4.3.1.15 (diaminopropionate ammonia-lyase) inhibitor;
fundamental metabolite

2003

21.0

low

edetic acid

ethylenediamine derivative;
polyamino carboxylic acid;
tetracarboxylic acid

anticoagulant;
antidote;
chelator;
copper chelator;
geroprotector

1990

34.0

low

1,2-dipalmitoylphosphatidylcholine

2009

15.0

low

egtazic acid

diether;
tertiary amino compound;
tetracarboxylic acid

chelator

1984

1992

35.3

low

tryptophan

erythrose 4-phosphate/phosphoenolpyruvate family amino acid;
L-alpha-amino acid zwitterion;
L-alpha-amino acid;
proteinogenic amino acid;
tryptophan zwitterion;
tryptophan

antidepressant;
Escherichia coli metabolite;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
plant metabolite;
Saccharomyces cerevisiae metabolite

2007

17.0

low

4-toluic acid

methylbenzoic acid

2003

21.0

low

isoxazoles

isoxazoles;
mancude organic heteromonocyclic parent;
monocyclic heteroarene

2008

16.0

low

methoxyhydroxyphenylglycol

methoxybenzenes;
phenols

1985

39.0

low

fluorescein-5-isothiocyanate

fluorescein isothiocyanate

2003

21.0

low

terbium

f-block element atom;
lanthanoid atom

1990

34.0

low

cadmium

cadmium molecular entity;
zinc group element atom

1984

40.0

low

cerium

f-block element atom;
lanthanoid atom

1990

34.0

low

europium

f-block element atom;
lanthanoid atom

1990

34.0

low

hafnium

titanium group element atom

2021

3.0

low

zirconium

titanium group element atom

2019

5.0

low

calcium phosphate, dibasic, anhydrous

calcium phosphate

1988

1992

34.0

low

calcium phosphate, monobasic, anhydrous

calcium phosphate

fertilizer

1988

1992

34.0

low

tricalcium phosphate

calcium phosphate

1988

2016

22.0

low

deuterium

dihydrogen

1991

1995

31.0

low

ozone

elemental molecule;
gas molecular entity;
reactive oxygen species;
triatomic oxygen

antiseptic drug;
disinfectant;
electrophilic reagent;
greenhouse gas;
mutagen;
oxidising agent;
tracer

2020

4.0

low

tetradecanoylphorbol acetate

acetate ester;
diester;
phorbol ester;
tertiary alpha-hydroxy ketone;
tetradecanoate ester

antineoplastic agent;
apoptosis inducer;
carcinogenic agent;
mitogen;
plant metabolite;
protein kinase C agonist;
reactive oxygen species generator

1992

32.0

low

etoposide

beta-D-glucoside;
furonaphthodioxole;
organic heterotetracyclic compound

antineoplastic agent;
DNA synthesis inhibitor

2007

17.0

low

acridine orange

aminoacridines;
aromatic amine;
tertiary amino compound

fluorochrome;
histological dye

2016

8.0

low

1,2-distearoyllecithin

1996

28.0

low

dicetylphosphate

dialkyl phosphate

1988

1992

34.0

low

piperazine-n,n'-bis(2-ethanesulfonic acid)

PIPES

2004

20.0

low

1-palmitoyl-lysophosphatidic acid

2-lysophosphatidic acid

1984

40.0

low

3,4-dihydroxyphenylglycol

catechols;
tetrol

metabolite;
mouse metabolite

1985

39.0

low

dimyristoylphosphatidic acid

phosphatidic acid

1990

34.0

low

4-methylhippuric acid

N-acylglycine

metabolite

2003

21.0

low

1,2-bis(2-aminophenoxy)ethane-n,n,n',n'-tetraacetic acid

polyamino carboxylic acid;
tetracarboxylic acid

chelator

1992

32.0

low

3-(trifluoromethyl)-3-(3-iodophenyl)diazirine

1992

2006

25.0

low

nitrosylprotoheme

2007

17.0

low

glycerophosphoinositol 4,5-bisphosphate

2007

2008

16.5

low

1,2-dilauroylphosphatidic acid

1984

1990

37.0

high

singlet oxygen

chalcogen;
monoatomic oxygen;
nonmetal atom

macronutrient

2021

3.0

low

calcium pyrophosphate

1988

1992

34.0

low

dihydrosphingosine 1-phosphate

sphingoid 1-phosphate

mouse metabolite

2003

21.0

low

tempo

aminoxyls;
piperidines

catalyst;
ferroptosis inhibitor;
radical scavenger

2000

24.0

low

sodium dodecyl sulfate

organic sodium salt

detergent;
protein denaturant

2003

21.0

low

sphingosine

sphing-4-enine

human metabolite;
mouse metabolite

2003

21.0

low

1-monooleoyl-rac-glycerol

1-acylglycerol 18:1;
monooleoylglycerol

plant metabolite

2001

2005

21.0

low

sphingosine 1-phosphate

sphingoid 1-phosphate

mouse metabolite;
signalling molecule;
sphingosine-1-phosphate receptor agonist;
T-cell proliferation inhibitor;
vasodilator agent

2003

21.0

low

lysophosphatidic acid

1-acyl-sn-glycerol 3-phosphate

1992

2008

21.5

low

lysophosphatidylcholines

1-O-acyl-sn-glycero-3-phosphocholine

2000

24.0

low

1,2-oleoylphosphatidylcholine

phosphatidylcholine(1+)

1985

2012

26.5

medium

dimyristoylphosphatidylcholine

1,2-diacyl-sn-glycero-3-phosphocholine;
phosphatidylcholine 28:0;
tetradecanoate ester

antigen;
mouse metabolite

2009

15.0

low

phosphorus

monoatomic phosphorus;
nonmetal atom;
pnictogen

macronutrient

1984

1991

36.5

low

1,2-dielaidoylphosphatidylethanolamine

1992

32.0

low

1-palmitoyl-2-oleoylphosphatidylcholine

2009

15.0

low

1,2-dioleoyloxy-3-(trimethylammonium)propane

2012

12.0

low

dioleoyl phosphatidylethanolamine

phosphatidylethanolamine

2005

2009

17.0

low

1,2-dioleoylphosphatidylserine

phosphatidylserine(18:1/18:1)

mouse metabolite

1991

2008

23.9

low

erucylphosphocholine

2000

24.0

low

dipalmitoleoylphosphatidylethanolamine

2004

20.0

medium

mocetinostat

aminopyrimidine;
benzamides;
pyridines;
secondary amino compound;
secondary carboxamide;
substituted aniline

antineoplastic agent;
apoptosis inducer;
autophagy inducer;
cardioprotective agent;
EC 3.5.1.98 (histone deacetylase) inhibitor;
hepatotoxic agent

2007

17.0

low

tetramethylrhodamine

xanthene dye

2008

16.0

low

alpha-synuclein

2008

2017

11.5

low

calcimycin

benzoxazole

1984

1987

38.7

low

cytochrome c-t

2007

17.0

low

phosphatidylcholines

1,2-diacyl-sn-glycero-3-phosphocholine

1985

2012

26.8

medium

1-palmitoyl-2-(6-(n-(7-nitrobenz)-2-oxa-1,3-diazol-4-yl)aminocaproyl)phosphatidylcholine

1,2-diacyl-sn-glycero-3-phosphocholine(1+)

fluorescent probe

2008

16.0

low

glycolipids

1992

2009

23.5

low

vpc32183

2008

16.0

low

1,2-dioleoyl-sn-glycero-3-phosphoglycerol

1,2-diacyl-sn-glycero-3-phospho-(1'-sn-glycerol)

1987

2008

24.5

low

heme

2007

17.0

low

novobiocin

carbamate ester;
ether;
hexoside;
hydroxycoumarin;
monocarboxylic acid amide;
monosaccharide derivative;
phenols

antibacterial agent;
antimicrobial agent;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor;
Escherichia coli metabolite;
hepatoprotective agent

1990

34.0

low

transforming growth factor beta

2003

21.0

low

okadaic acid

ketal

2001

23.0

low

arsenazo iii

1985

1986

38.5

low

Condition	Studies	First Year	Last Year	Average Age	Relationship Strength	2000's	2010's	post-2020
Benign Neoplasms	3	2012	2021	6.7	medium	0	2	1
Breast Cancer	1	2019	2019	5.0	low	0	1	0
Breast Neoplasms	1	2019	2019	5.0	low	0	1	0
Experimental Neoplasms	1	2021	2021	3.0	low	0	0	1
Glial Cell Tumors	1	2008	2008	16.0	low	1	0	0
Glioma	1	2008	2008	16.0	low	1	0	0
Idiopathic Parkinson Disease	1	2008	2008	16.0	low	1	0	0
Inflammation	1	2001	2001	23.0	low	1	0	0
Innate Inflammatory Response	1	2001	2001	23.0	low	1	0	0
Leukemia, Acute Monocytic	1	2001	2001	23.0	low	1	0	0
Leukemia, Monocytic, Acute	1	2001	2001	23.0	low	1	0	0
Neoplasms	3	2012	2021	6.7	medium	0	2	1
Parkinson Disease	1	2008	2008	16.0	low	1	0	0

Condition

Indicated

Studies

First Year

Last Year

Average Age

Relationship Strength

Trials

pre-1990

1990's

2000's

2010's