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Details

Stereochemistry RACEMIC
Molecular Formula C3H9O6P
Molecular Weight 172.0737
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GLYCERYL 1-PHOSPHATE

SMILES

OCC(O)COP(O)(O)=O

InChI

InChIKey=AWUCVROLDVIAJX-UHFFFAOYSA-N
InChI=1S/C3H9O6P/c4-1-3(5)2-9-10(6,7)8/h3-5H,1-2H2,(H2,6,7,8)

HIDE SMILES / InChI
Molecular Formula C3H9O6P
Molecular Weight 172.0737
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment: description was created based on several sources, including: DOI: 10.1042/bj0280143 DOI: 10.1042/bj0280152 http://www.wikidoc.org/index.php/Glycerol_3-phosphate

Synthetic glycerophosphates have been known for many years and have been prepared in several ways. The acid may exist in two isomeric forms, alpha and beta. The L-a-acid is the naturally occurring form; the b-acid, present in hydrolyzates of lecithins from natural sources, arises from migration of the phosphoryl group from the a-carbon atom. Dehydrogenation of L-glycerol 3-phosphate produces Dihydroxyacetone phosphate and is part of the entry of glycerol (sourced from triglycerides) into the glycolytic pathway.

CNS Activity

Originator

Grimbert, L.|Bailly, O.
4
Curator's Comment: alpha-glycerophosphoric acid has long been known as a component of the lecithins and cephalins and may in a sense be looked on as a monoglyceride, the situation is much more favorable. Because of its great stability it has been possible for several workers to separate it from various phosphatides and free it from its accompanying beta-isomer. http://www.jbc.org/content/128/2/491.short

Approval Year

1921
1468
Targets

Targets

Primary TargetPharmacologyConditionPotency
Substrate
661
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Approved
8583
KABIVEN

Approved Use

It is indicated as a source of calories, protein, electrolytes and essential fatty acids for adult patients requiring parenteral nutrition when oral or enteral nutrition is not possible, insufficient, or contraindicated.

Launch Date

2014
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2.87 mM
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21986180/
80 mmol single, intravenous
dose: 80 mmol
route of administration: Intravenous
experiment type: SINGLE
co-administered:
PHOSPHATE ION serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
38.7 mM × h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21986180/
80 mmol single, intravenous
dose: 80 mmol
route of administration: Intravenous
experiment type: SINGLE
co-administered:
PHOSPHATE ION serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.06 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21986180/
80 mmol single, intravenous
dose: 80 mmol
route of administration: Intravenous
experiment type: SINGLE
co-administered:
PHOSPHATE ION serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
PubMed

PubMed

TitleDatePubMed
[IN VITRO EFFECT OF ALPHA GLYCEROPHOSPHATE ON RELEASE OF NON-ESTERIFIED FATTY ACIDS FROM ADIPOSE TISSUE].
1965-06
[Pharmacology of glycerophosphoric acid. II. Differences in the biological action of the alpha and beta isomers in combination with thiamine or cocarboxylase].
1955-12-01
alpha-Glycerophosphoric acid and brain metabolism.
1936-01
Patents

Patents

IT 460219
4

Sample Use Guides

In Vivo Use Guide
19 to 38 mL/kg/day. The maximum infusion rate is 2.6 mL/kg/hour. Recommended infusion period is 12 to 24 hours.
Route of Administration: Intravenous
In Vitro Use Guide
Maximal ATP production in the presence of Ca2+ (200 nM) is obtained at 10 mM L-glycerol 3-phosphate in intact mitochondria from pancreatic B-cells.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:34:59 GMT 2025
Edited
by admin
on Mon Mar 31 17:34:59 GMT 2025
Record UNII
9NTI6P3O4X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NSC-9231
Preferred Name English
GLYCERYL 1-PHOSPHATE
Common Name English
DL-GLYCEROL 1-PHOSPHATE
Common Name English
1,2,3-PROPANETRIOL, 1-(DIHYDROGEN PHOSPHATE)
Common Name English
GLYCERYL 1-PHOSPHORIC ACID
Common Name English
DL-.ALPHA.-GLYCEROPHOSPHORIC ACID
Common Name English
GLYCEROPHOSPHORIC ACID [MI]
Common Name English
GLYCEROL 1-PHOSPHATE
Common Name English
DL-.ALPHA.-GLYCERYL PHOSPHATE
Common Name English
DL-.ALPHA.-GLYCEROPHOSPHATE
Common Name English
1-GLYCEROPHOSPHATE
Common Name English
GLYCEROL, 1-(DIHYDROGEN PHOSPHATE)
Common Name English
DL-.ALPHA.-GLYCEROL PHOSPHATE
Common Name English
GLYCEROL 3-PHOSPHATE
Common Name English
3-GLYCEROPHOSPHATE
Common Name English
1-GLYCEROPHOSPHORIC ACID
Common Name English
DL-GLYCEROL 3-PHOSPHATE
Common Name English
Code System Code Type Description
ECHA (EC/EINECS)
200-307-1
Created by admin on Mon Mar 31 17:34:59 GMT 2025 , Edited by admin on Mon Mar 31 17:34:59 GMT 2025
PRIMARY
FDA UNII
9NTI6P3O4X
Created by admin on Mon Mar 31 17:34:59 GMT 2025 , Edited by admin on Mon Mar 31 17:34:59 GMT 2025
PRIMARY
EPA CompTox
DTXSID6023105
Created by admin on Mon Mar 31 17:34:59 GMT 2025 , Edited by admin on Mon Mar 31 17:34:59 GMT 2025
PRIMARY
MERCK INDEX
m5792
Created by admin on Mon Mar 31 17:34:59 GMT 2025 , Edited by admin on Mon Mar 31 17:34:59 GMT 2025
PRIMARY Merck Index
NSC
9231
Created by admin on Mon Mar 31 17:34:59 GMT 2025 , Edited by admin on Mon Mar 31 17:34:59 GMT 2025
PRIMARY
MESH
C029620
Created by admin on Mon Mar 31 17:34:59 GMT 2025 , Edited by admin on Mon Mar 31 17:34:59 GMT 2025
PRIMARY
WIKIPEDIA
GLYCEROL 3-PHOSPHATE
Created by admin on Mon Mar 31 17:34:59 GMT 2025 , Edited by admin on Mon Mar 31 17:34:59 GMT 2025
PRIMARY
CHEBI
14336
Created by admin on Mon Mar 31 17:34:59 GMT 2025 , Edited by admin on Mon Mar 31 17:34:59 GMT 2025
PRIMARY
PUBCHEM
754
Created by admin on Mon Mar 31 17:34:59 GMT 2025 , Edited by admin on Mon Mar 31 17:34:59 GMT 2025
PRIMARY
CHEBI
231935
Created by admin on Mon Mar 31 17:34:59 GMT 2025 , Edited by admin on Mon Mar 31 17:34:59 GMT 2025
PRIMARY
CAS
57-03-4
Created by admin on Mon Mar 31 17:34:59 GMT 2025 , Edited by admin on Mon Mar 31 17:34:59 GMT 2025
PRIMARY
Related Record Type Details
Structure of MAGNESIUM 1-GLYCEROPHOSPHATE
SALT/SOLVATE -> PARENT
Structure of FERRIC 1-GLYCEROPHOSPHATE
SALT/SOLVATE -> PARENT
Structure of POTASSIUM 1-GLYCEROPHOSPHATE TRIHYDRATE
SALT/SOLVATE -> PARENT
Structure of CALCIUM 1-GLYCEROPHOSPHATE
SALT/SOLVATE -> PARENT
Structure of SODIUM 1-GLYCEROPHOSPHATE
SALT/SOLVATE -> PARENT
Structure of MANGANESE RAC-GLYCERYL-1-PHOSPHATE
SALT/SOLVATE -> PARENT
Structure of POTASSIUM 1-GLYCEROPHOSPHATE
SALT/SOLVATE -> PARENT
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