Page last updated: 2024-12-06

1-carboxyglutamic acid

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Description

1-carboxyglutamic acid (Gla) is an unusual amino acid that is found in proteins involved in blood coagulation, bone metabolism, and other biological processes. It is synthesized by a post-translational modification of glutamic acid residues in proteins, catalyzed by a specific enzyme called gamma-glutamyl carboxylase. This enzyme requires vitamin K as a cofactor. The carboxylation of glutamic acid residues is essential for the function of these proteins, as it allows them to bind calcium ions. Calcium binding is crucial for the activity of these proteins, such as the coagulation factors, which require calcium to interact with phospholipid membranes and other proteins involved in the clotting cascade. Gla is also found in proteins involved in bone metabolism, where it plays a role in regulating calcium deposition and bone formation. The study of Gla and its role in protein function is important for understanding a variety of physiological processes, as well as for developing therapeutic strategies for diseases related to blood coagulation, bone metabolism, and other Gla-dependent functions. For example, Gla is a target for anticoagulant drugs, such as warfarin, which inhibit the synthesis of Gla-containing proteins. The study of Gla is also important for understanding the role of vitamin K in health and disease. Vitamin K deficiency can lead to impaired synthesis of Gla-containing proteins, which can result in bleeding disorders.'

1-Carboxyglutamic Acid: Found in various tissues, particularly in four blood-clotting proteins including prothrombin, in kidney protein, in bone protein, and in the protein present in various ectopic calcifications. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID40772
SCHEMBL ID148584
MeSH IDM0023166

Synonyms (39)

Synonym
gamma-carboxyglutamate
gamma-carboxy-dl-glutamic acid, >=99.0%
53445-96-8
3-aminopropane-1,1,3-tricarboxylic acid
56271-99-9
3-amino-1,1,3-propanetricarboxylic cid
einecs 260-087-8
gamma-carboxyglutamic acid, dl-
(1)-3-aminopropane-1,1,3-tricarboxylic acid
1k3cgy068s ,
unii-1k3cgy068s
FT-0640370
FT-0640929
1,1,3-propanetricarboxylic acid, 3-amino-
1-carboxyglutamic acid
(s)-3-aminopropane-1,1,3-tricarboxylic acid
3-amino-1,1,3-propanetricarboxylic acid
1,1,3-propanetricarboxylicacid, 3-amino-
SCHEMBL148584
h-dl-gla-oh
dl-.gamma.-carboxyglutamic acid
(+/-)-3-amino-1,1,3-propanetricarboxylic acid
.gamma.-carboxyglutamic acid, dl-
1,1,3-propanetricarboxylic acid, 3-amino-, (+/-)-
gamma-carboxy-dl-glutamic acid
gamma-carboxyglutaminsaure
h-gamma-carboxy-dl-glu-oh
h-g-carboxy-dl-glu-oh
mfcd00065488
h--carboxy-dl-glu-oh
Q2823245
dl-gamma-carboxyglutamic acid
CS-0201745
DTXSID50872037
FT-0775227
h-d-gla-oh
HY-W141955
1,1,3-propanetricarboxylic acid, 3-amino-, (r)-
gamma -carboxy-dl-glutamic acid

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" The increased urinary Gla-excretion was found for both phylloquinone and menaquinone-4, but not for menaquinone-8, which questions the bioavailability of higher menaquinones for extrahepatic tissues."( Nutritional vitamin K-intake and urinary gamma-carboxyglutamate excretion in the rat.
Craciun, AM; Groenen-van Dooren, MM; Vermeer, C, 1997
)
0.3
" Among these, MK7 is the most efficient in terms of bioavailability and biological effect."( Carboxylative efficacy of trans and cis MK7 and comparison with other vitamin K isomers.
Cirilli, I; Dludla, PV; Kaesler, N; Marcheggiani, F; Orlando, P; Silvestri, S; Tiano, L, 2022
)
0.72

Dosage Studied

ExcerptRelevanceReference
"204 Chinese postmenopausal women with osteoporosis from 3 hospitals in Beijing and Shanghai were randomly divided into 2 groups of 102 women: RLX group (RLX of the dosage of 60 mg/day was given for 12 months) and placebo group."( [Effect of raloxifene hydrochloride on bone mineral density, bone metabolism and serum lipids in Chinese postmenopausal women with osteoporosis].
Chen, XP; Diez-Perez, A; Ekangaki, A; Harpe, K; Huang, QR; Li, HL; Liu, H; Liu, JL; Liu, YJ; Lu, JH; Qin, YJ; Wei, DL; Zhang, Y; Zhang, ZL; Zheng, YM; Zhu, HM, 2004
)
0.32
"RLX of the dosage of 60 mg/day for 12 months significantly increases the lumbar spine and total hip bone BMD, significantly decreases bone turnover and has favorable effects on serum lipids in Chinese postmenopausal women with osteoporosis."( [Effect of raloxifene hydrochloride on bone mineral density, bone metabolism and serum lipids in Chinese postmenopausal women with osteoporosis].
Chen, XP; Diez-Perez, A; Ekangaki, A; Harpe, K; Huang, QR; Li, HL; Liu, H; Liu, JL; Liu, YJ; Lu, JH; Qin, YJ; Wei, DL; Zhang, Y; Zhang, ZL; Zheng, YM; Zhu, HM, 2004
)
0.32
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (633)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990287 (45.34)18.7374
1990's190 (30.02)18.2507
2000's109 (17.22)29.6817
2010's42 (6.64)24.3611
2020's5 (0.79)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 7.72

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index7.72 (24.57)
Research Supply Index6.50 (2.92)
Research Growth Index4.22 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (7.72)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials8 (1.23%)5.53%
Reviews62 (9.49%)6.00%
Case Studies9 (1.38%)4.05%
Observational0 (0.00%)0.25%
Other574 (87.90%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]