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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:14:28 UTC

HMDB ID

HMDB0000044

Secondary Accession Numbers

HMDB00044
HMDB0014273
HMDB0029945
HMDB14273
HMDB29945

Metabolite Identification

Common Name

Ascorbic acid

Description

Ascorbic acid is found naturally in citrus fruits and many vegetables and is an essential nutrient in human diets. It is necessary to maintain connective tissue and bone. The biologically active form of ascorbic acid is vitamin C. Vitamin C is a water soluble vitamin. Primates (including humans) and a few other species in all divisions of the animal kingdom, notably the guinea pig, have lost the ability to synthesize ascorbic acid and must obtain it in their food. Vitamin C functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant (PubChem). Ascorbic acid is an electron donor for enzymes involved in collagen hydroxylation, biosynthesis of carnitine and norepinephrine, tyrosine metabolism, and amidation of peptide hormones. Ascrobic acid (vitamin C) deficiency causes scurvy. The amount of vitamin C necessary to prevent scurvy may not be adequate to maintain optimal health. The ability of vitamin C to donate electrons also makes it a potent water-soluble antioxidant that readily scavenges free radicals such as molecular oxygen, superoxide, hydroxyl radical, and hypochlorous acid. In this setting, several mechanisms could account for a link between vitamin C and heart disease. One is the relation between LDL oxidation and vitamins C and E. Vitamin C in vitro can recycle vitamin E, which can donate electrons to prevent LDL oxidation in vitro. As the lipid-phase vitamin E is oxidized, it can be regenerated by aqueous vitamin C. Other possibilities are that vitamin C could decrease cholesterol by mechanisms not well characterized, or could improve vasodilatation and vascular reactivity, perhaps by decreasing the interactions of nitric oxide with oxidants (PMID: 10799361 ). Moreover, ascorbic acid is found to be associated with hyperoxalemia, which is an inborn error of metabolism. Ascorbic acid is also a microbial metabolite produced by Ketogulonicigenium (PMID: 15785002 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 03-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-20         0                                  
HETATM    1  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      -1.675  -3.616   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       1.675  -3.616   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.246  -0.905   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.711  -0.429   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.770  -2.370   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.770  -2.370   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -5.247  -0.135   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -3.913  -0.905   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.580  -0.135   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.580   1.405   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.246  -0.905   0.000  0.00  0.00           C+0
HETATM   13  H   UNK     0      -2.335  -1.994   0.000  0.00  0.00           H+0
CONECT    1    4   12                                                       
CONECT    2    7                                                            
CONECT    3    6                                                            
CONECT    4    1    5    6                                                  
CONECT    5    4                                                            
CONECT    6    3    4    7                                                  
CONECT    7    2    6   12                                                  
CONECT    8    9                                                            
CONECT    9    8   10                                                       
CONECT   10    9   12   11                                                  
CONECT   11   10                                                            
CONECT   12    1    7   10   13                                             
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Acide ascorbique	ChEBI
Acido ascorbico	ChEBI
Acidum ascorbicum	ChEBI
Acidum ascorbinicum	ChEBI
Ascoltin	ChEBI
Ascorbicap	ChEBI
Ascorbinsaeure	ChEBI
e 300	ChEBI
e-300	ChEBI
e300	ChEBI
L-(+)-Ascorbic acid	ChEBI
L-Ascorbate	ChEBI
Vitamin C	ChEBI
Monodehydroascorbate radical	Kegg
Ascorbate radical	Kegg
Semidehydroascorbic acid	Kegg
ASCOR	Kegg
L-(+)-Ascorbate	Generator
L-Ascorbic acid	Generator
Monodehydroascorbic acid radical	Generator
Ascorbic acid radical	Generator
Semidehydroascorbate	Generator
Ascorbate	Generator
Ascorbic acid, monosodium salt	MeSH
Ferrous ascorbate	MeSH
L Ascorbic acid	MeSH
Magnesium di L ascorbate	MeSH
Magnorbin	MeSH
Sodium ascorbate	MeSH
Acid, L-ascorbic	MeSH
Ascorbate, magnesium	MeSH
Acid, ascorbic	MeSH
Ascorbate, ferrous	MeSH
Ascorbate, sodium	MeSH
Hybrin	MeSH
Magnesium ascorbate	MeSH
Magnesium ascorbicum	MeSH
Magnesium di-L-ascorbate	MeSH
Di-L-ascorbate, magnesium	MeSH
(+)-Ascorbate	HMDB
(+)-Ascorbic acid	HMDB
(+)-Sodium L-ascorbate	HMDB
3-keto-L-Gulofuranolactone	HMDB
3-oxo-L-Gulofuranolactone	HMDB
Adenex	HMDB
Allercorb	HMDB
Antiscorbic vitamin	HMDB
Antiscorbutic vitamin	HMDB
arco-Cee	HMDB
Ascor-b.i.d.	HMDB
Ascorb	HMDB
Ascorbajen	HMDB
Ascorbicab	HMDB
Ascorbicin	HMDB
Ascorbin	HMDB
Ascorbutina	HMDB
Ascorin	HMDB
Ascorteal	HMDB
Ascorvit	HMDB
C-Level	HMDB
C-Long	HMDB
C-Quin	HMDB
C-Span	HMDB
C-Vimin	HMDB
Cantan	HMDB
Cantaxin	HMDB
Catavin C	HMDB
Ce lent	HMDB
Ce-mi-lin	HMDB
Ce-vi-sol	HMDB
Cebicure	HMDB
Cebid	HMDB
Cebion	HMDB
Cebione	HMDB
Cecon	HMDB
Cee-caps TD	HMDB
Cee-vite	HMDB
Cegiolan	HMDB
Ceglion	HMDB
Ceklin	HMDB
Celaskon	HMDB
Celin	HMDB
Cell C	HMDB
Cemagyl	HMDB
Cemill	HMDB
Cenetone	HMDB
Cenolate	HMDB
Cereon	HMDB
Cergona	HMDB
Cescorbat	HMDB
Cetamid	HMDB
Cetane	HMDB
Cetane-caps TC	HMDB
Cetane-caps TD	HMDB
Cetebe	HMDB
Cetemican	HMDB
Cevalin	HMDB
Cevatine	HMDB
Cevex	HMDB
Cevi-bid	HMDB
Cevimin	HMDB
Cevital	HMDB
Cevitamate	HMDB
Cevitamic acid	HMDB
Cevitamin	HMDB
Cevitan	HMDB
Cevitex	HMDB
Cewin	HMDB
Chewcee	HMDB
Ciamin	HMDB
Cipca	HMDB
Citriscorb	HMDB
Citrovit	HMDB
Colascor	HMDB
Concemin	HMDB
Davitamon C	HMDB
Dora-C-500	HMDB
Duoscorb	HMDB
gamma-Lactone L-threo-hex-2-enonate	HMDB
gamma-Lactone L-threo-hex-2-enonic acid	HMDB
HiCee	HMDB
ido-C	HMDB
Juvamine	HMDB
Kangbingfeng	HMDB
Kyselina askorbova	HMDB
L(+)-Ascorbate	HMDB
L(+)-Ascorbic acid	HMDB
L-3-Ketothreohexuronic acid lactone	HMDB
L-Lyxoascorbate	HMDB
L-Lyxoascorbic acid	HMDB
L-threo-Ascorbic acid	HMDB
L-Xyloascorbate	HMDB
L-Xyloascorbic acid	HMDB
Laroscorbine	HMDB
Lemascorb	HMDB
Liqui-cee	HMDB
Meri-c	HMDB
Natrascorb	HMDB
Natrascorb injectable	HMDB
Planavit C	HMDB
Proscorbin	HMDB
Redoxon	HMDB
Ribena	HMDB
Ronotec 100	HMDB
Rontex 100	HMDB
Roscorbic	HMDB
Rovimix C	HMDB
Scorbacid	HMDB
Scorbu C	HMDB
Scorbu-C	HMDB
Secorbate	HMDB
Sodascorbate	HMDB
Suncoat VC 40	HMDB
Testascorbic	HMDB
VASC	HMDB
Vicelat	HMDB
Vicin	HMDB
Vicomin C	HMDB
Viforcit	HMDB
Viscorin	HMDB
Viscorin 100m	HMDB
Vitace	HMDB
Vitacee	HMDB
Vitacimin	HMDB
Vitacin	HMDB
Vitamisin	HMDB
Vitascorbol	HMDB
Xitix	HMDB
ASCORBIC ACID	ChEBI

Chemical Formula

C₆H₈O₆

Average Molecular Weight

176.1241

Monoisotopic Molecular Weight

176.032087988

IUPAC Name

(5R)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxy-2,5-dihydrofuran-2-one

Traditional Name

vitamin C

CAS Registry Number

50-81-7

SMILES

[H][C@@]1(OC(=O)C(O)=C1O)[C@@H](O)CO

InChI Identifier

InChI=1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2/t2-,5+/m0/s1

InChI Key

CIWBSHSKHKDKBQ-JLAZNSOCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dihydrofurans

Sub Class

Furanones

Direct Parent

Butenolides

Alternative Parents

Substituents

2-furanone
Vinylogous acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
1,2-diol
Carboxylic acid ester
Enediol
Secondary alcohol
Lactone
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Primary alcohol
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

ascorbic acid (CHEBI:29073 )
Water-soluble vitamins (C00072 )

Ontology

Not Available

Adipose tissue (HMDB: HMDB0000044)

Epithelium

Epidermis (HMDB: HMDB0000044)

Eye Lens (HMDB: HMDB0000044)

Muscle tissue

Skeletal muscle (HMDB: HMDB0000044)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 15640471)
Breast milk (PMID: 24027187)
Cerebrospinal Fluid (CSF) (PMID: 1503069)
Cellular Cytoplasm (HMDB: HMDB0000044)
Amniotic Fluid (PMID: 16139832)
Saliva (PMID: 12097436)

Organ substructure

Adrenal cortex (HMDB: HMDB0000044)
Adrenal medulla (HMDB: HMDB0000044)

Organ

Cell

Hematocyte

Platelet (HMDB: HMDB0000044)

Excreta

Biofluid or Excreta

Urine (PMID: 2026685)

Cellular substructure

Cytoplasm (HMDB: HMDB0000044)
Extracellular (HMDB: HMDB0000044)

Source

Exogenous

Exogenous (HMDB: HMDB0000044)

Food

Beverage

Fermented beverage

Grape wine (FooDB: FOOD00612)

Vegetable

Cabbage

Broccoli (FooDB: FOOD00034)

Leaf vegetable

Lettuce (FooDB: FOOD00095)

Vegetables (HMDB: HMDB0000044)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Fruit

Fruits (HMDB: HMDB0000044)

Berry

Nanking cherry (FooDB: FOOD00885)

Process

Naturally occurring process

Biological process

Biochemical pathway

Disease pathway

The Oncogenic Action of Succinate (PathBank: SMP0002292)
Tyrosinemia, Transient, of the Newborn (PathBank: SMP0120779)
Aromatic L-Aminoacid Decarboxylase Deficiency (PathBank: SMP0120457)
Tyrosine Hydroxylase Deficiency (PathBank: SMP0120562)
Hawkinsinuria (PathBank: SMP0120711)
Tyrosinemia Type I (PathBank: SMP0120729)
Alkaptonuria (PathBank: SMP0120453)
Dopamine beta-Hydroxylase Deficiency (PathBank: SMP0120563)
Refsum Disease (PathBank: SMP0120749)
Monoamine Oxidase-A Deficiency (MAO-A) (PathBank: SMP0120817)
The Oncogenic Action of Fumarate (PathBank: SMP0002295)

Metabolic pathway

Oxidation of Branched-Chain Fatty Acids (PathBank: SMP0087255)
Phytanic Acid Peroxisomal Oxidation (PathBank: SMP0087312)
Tyrosine Metabolism (PathBank: SMP0087328)
Carnitine Synthesis (PathBank: SMP0087187)
Ascorbate Metabolism (PathBank: SMP0012446)
Catecholamine Biosynthesis (PathBank: SMP0063606)
Flavonoid Biosynthesis (PathBank: SMP0012021)
Flavone and Flavonol Biosynthesis (PathBank: SMP0012025)
Xanthophyll Cycle (PathBank: SMP0012035)
Gibberellin Biosynthesis I (Early C-3 Hydroxylation) (PathBank: SMP0012069)
Gibberellin Biosynthesis II (Early C-13 Hydroxylation) (PathBank: SMP0012070)
Gibberellin Biosynthesis III (Non C-3, Non C-13 Hydroxylation) (PathBank: SMP0012071)
Ascorbate Biosynthesis (PathBank: SMP0063817)

Drug action pathway

Disulfiram Action Pathway (PathBank: SMP0000429)

Role

Industrial application

Pharmaceutical industry

Biomarker

Meningitis (MarkerDB: MDB00000023)
Hyperoxalemia (MarkerDB: MDB00000023)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	191 °C	PhysProp
Boiling Point	552.67 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	400 mg/mL at 40 °C	MERCK INDEX (1996)
LogP	-1.85	AVDEEF,A (1997)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Astarita_neg	126.7	30932474
[M-H]-	Not Available	128.9	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001791

Predicted Molecular Properties

Property	Value	Source
Water Solubility	245 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-1.9	ChemAxon
logS	0.14	ALOGPS
pKa (Strongest Acidic)	4.36	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	37.03 m³·mol⁻¹	ChemAxon
Polarizability	14.93 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	138.212	32859911
AllCCS	[M-H]-	129.8	32859911
DeepCCS	[M+H]+	139.092	30932474
DeepCCS	[M-H]-	137.017	30932474
DeepCCS	[M-2H]-	170.607	30932474
DeepCCS	[M+Na]+	145.005	30932474
AllCCS	[M+H]+	138.2	32859911
AllCCS	[M+H-H2O]+	134.0	32859911
AllCCS	[M+NH4]+	142.1	32859911
AllCCS	[M+Na]+	143.3	32859911
AllCCS	[M-H]-	129.8	32859911
AllCCS	[M+Na-2H]-	130.8	32859911
AllCCS	[M+HCOO]-	131.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ascorbic acid	[H][C@@]1(OC(=O)C(O)=C1O)[C@@H](O)CO	3155.3	Standard polar	33892256
Ascorbic acid	[H][C@@]1(OC(=O)C(O)=C1O)[C@@H](O)CO	1812.7	Standard non polar	33892256
Ascorbic acid	[H][C@@]1(OC(=O)C(O)=C1O)[C@@H](O)CO	1558.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ascorbic acid,1TMS,isomer #1	C[Si](C)(C)OC1=C(O)[C@@H]([C@@H](O)CO)OC1=O	1685.6	Semi standard non polar	33892256
Ascorbic acid,1TMS,isomer #2	C[Si](C)(C)OC1=C(O)C(=O)O[C@@H]1[C@@H](O)CO	1709.6	Semi standard non polar	33892256
Ascorbic acid,1TMS,isomer #3	C[Si](C)(C)O[C@@H](CO)[C@H]1OC(=O)C(O)=C1O	1711.3	Semi standard non polar	33892256
Ascorbic acid,1TMS,isomer #4	C[Si](C)(C)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O	1710.9	Semi standard non polar	33892256
Ascorbic acid,2TMS,isomer #1	C[Si](C)(C)OC1=C(O[Si](C)(C)C)[C@@H]([C@@H](O)CO)OC1=O	1774.1	Semi standard non polar	33892256
Ascorbic acid,2TMS,isomer #2	C[Si](C)(C)OC1=C(O)[C@@H]([C@H](CO)O[Si](C)(C)C)OC1=O	1768.0	Semi standard non polar	33892256
Ascorbic acid,2TMS,isomer #3	C[Si](C)(C)OC[C@H](O)[C@H]1OC(=O)C(O[Si](C)(C)C)=C1O	1753.1	Semi standard non polar	33892256
Ascorbic acid,2TMS,isomer #4	C[Si](C)(C)OC1=C(O)C(=O)O[C@@H]1[C@H](CO)O[Si](C)(C)C	1804.2	Semi standard non polar	33892256
Ascorbic acid,2TMS,isomer #5	C[Si](C)(C)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O[Si](C)(C)C	1792.7	Semi standard non polar	33892256
Ascorbic acid,2TMS,isomer #6	C[Si](C)(C)OC[C@H](O[Si](C)(C)C)[C@H]1OC(=O)C(O)=C1O	1754.2	Semi standard non polar	33892256
Ascorbic acid,3TMS,isomer #1	C[Si](C)(C)OC1=C(O[Si](C)(C)C)[C@@H]([C@H](CO)O[Si](C)(C)C)OC1=O	1909.6	Semi standard non polar	33892256
Ascorbic acid,3TMS,isomer #2	C[Si](C)(C)OC[C@H](O)[C@H]1OC(=O)C(O[Si](C)(C)C)=C1O[Si](C)(C)C	1899.2	Semi standard non polar	33892256
Ascorbic acid,3TMS,isomer #3	C[Si](C)(C)OC[C@H](O[Si](C)(C)C)[C@H]1OC(=O)C(O[Si](C)(C)C)=C1O	1841.3	Semi standard non polar	33892256
Ascorbic acid,3TMS,isomer #4	C[Si](C)(C)OC[C@H](O[Si](C)(C)C)[C@H]1OC(=O)C(O)=C1O[Si](C)(C)C	1900.4	Semi standard non polar	33892256
Ascorbic acid,4TMS,isomer #1	C[Si](C)(C)OC[C@H](O[Si](C)(C)C)[C@H]1OC(=O)C(O[Si](C)(C)C)=C1O[Si](C)(C)C	1998.4	Semi standard non polar	33892256
Ascorbic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C(O)[C@@H]([C@@H](O)CO)OC1=O	1967.8	Semi standard non polar	33892256
Ascorbic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=C(O)C(=O)O[C@@H]1[C@@H](O)CO	1985.9	Semi standard non polar	33892256
Ascorbic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H](CO)[C@H]1OC(=O)C(O)=C1O	1982.4	Semi standard non polar	33892256
Ascorbic acid,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O	1976.6	Semi standard non polar	33892256
Ascorbic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C(O[Si](C)(C)C(C)(C)C)[C@@H]([C@@H](O)CO)OC1=O	2299.6	Semi standard non polar	33892256
Ascorbic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=C(O)[C@@H]([C@H](CO)O[Si](C)(C)C(C)(C)C)OC1=O	2273.6	Semi standard non polar	33892256
Ascorbic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H](O)[C@H]1OC(=O)C(O[Si](C)(C)C(C)(C)C)=C1O	2271.3	Semi standard non polar	33892256
Ascorbic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=C(O)C(=O)O[C@@H]1[C@H](CO)O[Si](C)(C)C(C)(C)C	2309.1	Semi standard non polar	33892256
Ascorbic acid,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O[Si](C)(C)C(C)(C)C	2297.4	Semi standard non polar	33892256
Ascorbic acid,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1OC(=O)C(O)=C1O	2253.9	Semi standard non polar	33892256
Ascorbic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C(O[Si](C)(C)C(C)(C)C)[C@@H]([C@H](CO)O[Si](C)(C)C(C)(C)C)OC1=O	2620.4	Semi standard non polar	33892256
Ascorbic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H](O)[C@H]1OC(=O)C(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	2615.5	Semi standard non polar	33892256
Ascorbic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1OC(=O)C(O[Si](C)(C)C(C)(C)C)=C1O	2540.3	Semi standard non polar	33892256
Ascorbic acid,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1OC(=O)C(O)=C1O[Si](C)(C)C(C)(C)C	2575.1	Semi standard non polar	33892256
Ascorbic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1OC(=O)C(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	2867.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Ascorbic acid EI-B (Non-derivatized)	splash10-004i-4900000000-e99089fd55560fb70cfe	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ascorbic acid GC-EI-TOF (Non-derivatized)	splash10-0002-0912000000-baa8cffda0478e1bc197	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ascorbic acid GC-EI-TOF (Non-derivatized)	splash10-00di-9400000000-8ff8f48bfa2dd4fd3cf5	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ascorbic acid GC-EI-TOF (Non-derivatized)	splash10-00di-9400000000-c1dc72c6cbc49fbf3454	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ascorbic acid GC-EI-TOF (Non-derivatized)	splash10-00di-9400000000-b207f4024993c5a74769	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ascorbic acid GC-EI-TOF (Non-derivatized)	splash10-0002-0911000000-9af0c08e85e0c51a25c4	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ascorbic acid EI-B (Non-derivatized)	splash10-004i-4900000000-e99089fd55560fb70cfe	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ascorbic acid GC-EI-TOF (Non-derivatized)	splash10-0002-0912000000-baa8cffda0478e1bc197	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ascorbic acid GC-EI-TOF (Non-derivatized)	splash10-00di-9400000000-8ff8f48bfa2dd4fd3cf5	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ascorbic acid GC-EI-TOF (Non-derivatized)	splash10-00di-9400000000-c1dc72c6cbc49fbf3454	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ascorbic acid GC-EI-TOF (Non-derivatized)	splash10-00di-9400000000-b207f4024993c5a74769	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ascorbic acid GC-EI-TOF (Non-derivatized)	splash10-0002-0911000000-9af0c08e85e0c51a25c4	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ascorbic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0560-9700000000-ab53eee999ee7fee672d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ascorbic acid GC-MS (4 TMS) - 70eV, Positive	splash10-0kkj-9357500000-5c2c439f726b729dd50d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ascorbic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ascorbic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ascorbic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ascorbic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ascorbic acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ascorbic acid GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ascorbic acid GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ascorbic acid GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ascorbic acid GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ascorbic acid GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ascorbic acid GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ascorbic acid NA , positive-QTOF	splash10-0002-9300000000-d8c8254ad1dd4de2674c	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ascorbic acid LC-ESI-QTOF 35V, positive-QTOF	splash10-004i-1900000000-da5bc92501d37735007f	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ascorbic acid NA , positive-QTOF	splash10-0006-0900000000-b653774b8718c29fe97a	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ascorbic acid LC-ESI-QFT , negative-QTOF	splash10-000i-9200000000-5d1ea04ef6404f5ecf7c	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ascorbic acid LC-ESI-QTOF 35V, negative-QTOF	splash10-000i-9000000000-0371d7191fa8a89176f3	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ascorbic acid QqQ 6V, negative-QTOF	splash10-004i-0900000000-76825c62319d5f4cbed9	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ascorbic acid QqQ 10V, negative-QTOF	splash10-016r-2900000000-700d5d6247efb36c48d7	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ascorbic acid QqQ 13V, negative-QTOF	splash10-014i-8900000000-4d76fc951d56a75a025e	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ascorbic acid QqQ 16V, negative-QTOF	splash10-05tr-9300000000-0967cf71e141f71c2e00	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ascorbic acid QqQ 20V, negative-QTOF	splash10-052r-9100000000-2bca6a943255612f1e7d	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ascorbic acid n/a 12V, negative-QTOF	splash10-000i-9000000000-804b40cc657a43d298fb	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ascorbic acid n/a 12V, negative-QTOF	splash10-0a4i-9000000000-cad0cc415c906a783cfc	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ascorbic acid n/a 12V, negative-QTOF	splash10-0a4r-9000000000-f79a7dfc866621b3c926	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ascorbic acid Orbitrap 2V, negative-QTOF	splash10-004i-0900000000-707796161cd4fae98f67	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ascorbic acid Orbitrap 2V, negative-QTOF	splash10-004i-0900000000-035a78987127cc9f23f5	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ascorbic acid Orbitrap 2V, negative-QTOF	splash10-004i-0900000000-dac785ef05051971e946	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ascorbic acid Orbitrap 3V, negative-QTOF	splash10-00or-1900000000-a91dc1a29cb724a17811	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ascorbic acid Orbitrap 4V, negative-QTOF	splash10-016r-3900000000-78f1f46067d2459f17c7	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ascorbic acid Orbitrap 5V, negative-QTOF	splash10-014i-6900000000-8044f242bb90f54a595a	2020-07-22	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ascorbic acid 10V, Positive-QTOF	splash10-0kdi-2900000000-f05a720e6e6361c97e5f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ascorbic acid 20V, Positive-QTOF	splash10-0bvl-5900000000-6ca3f37a74403d8495c9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ascorbic acid 40V, Positive-QTOF	splash10-0a4i-9100000000-5625440c512f60760fdf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ascorbic acid 10V, Negative-QTOF	splash10-0o90-2900000000-b7c897849334927f5bf5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ascorbic acid 20V, Negative-QTOF	splash10-0bvi-4900000000-1f1fa10e7e06a79c028a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ascorbic acid 40V, Negative-QTOF	splash10-08fu-9300000000-b98375c0cd3a54b61ef7	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Amniotic Fluid
Blood
Breast Milk
Cellular Cytoplasm
Cerebrospinal Fluid (CSF)
Saliva
Urine

Tissue Locations

Adipose Tissue
Adrenal Cortex
Adrenal Medulla
Bladder
Brain
Epidermis
Erythrocyte
Eye Lens
Fibroblasts
Heart
Intestine
Leukocyte
Liver
Lung
Neuron
Ovary
Placenta
Platelet
Prostate
Skeletal Muscle
Spleen
Testis

Pathways

Name	SMPDB/PathBank	KEGG
Tyrosine metabolism	Not Available
Carnitine Synthesis		Not Available
Aromatic L-Aminoacid Decarboxylase Deficiency		Not Available
Tyrosine hydroxylase deficiency		Not Available
Phytanic Acid Peroxisomal Oxidation		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Amniotic Fluid	Detected and Quantified	20.4 +/- 12.21 uM	Adult (>18 years old)	Both	Normal	16139832	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	88.6 (21.0 - 171.0) uM	Children (1-13 years old)	Not Specified	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	60.8 +/- 15.9 uM	Adult (>18 years old)	Not Specified	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	51.0 (11.0 - 125.0) uM	Newborn (0-30 days old)	Not Specified	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	36.0 +/- 18.0 uM	Adult (>18 years old)	Both	Normal	15640471	details
Blood	Detected and Quantified	63.0 (11.0-114.0) uM	Adult (>18 years old)	Both	Normal	The Merck Manual,...	details
Blood	Detected and Quantified	8.19 uM	Adult (>18 years old)	Both	Normal	19248870	details
Blood	Detected and Quantified	48.829 +/- 23.847 uM	Adult (>18 years old)	Both	Normal	16755268	details
Blood	Detected and Quantified	9.06 uM	Adult (>18 years old)	Both	Normal	19248870	details
Blood	Detected and Quantified	35.4-80.1 uM	Adult (>18 years old)	Female	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	22.2 (14.0-40.0) uM	Adult (>18 years old)	Both	Normal	16522902	details
Blood	Detected and Quantified	27.0 (11.1-49.7) uM	Adult (>18 years old)	Male	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	50.9 (35.4-80.1) uM	Adult (>18 years old)	Female	Normal	Geigy Scientific ...	details
Breast Milk	Detected and Quantified	96.6 +/- 52.5 uM	Adult (>18 years old)	Female	Normal	24027187	details
Cellular Cytoplasm	Detected and Quantified	68.0 +/- 43.0 uM	Adult (>18 years old)	Female	Normal	Geigy Scientific ...	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	68.0 (17.0-119.0) uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	163.8 +/- 21 uM	Adult (>18 years old)	Not Specified	Normal	11978879	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	133 +/- 58.8 uM	Adult (>18 years old)	Not Specified	Normal	1503069	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	164.0 (143.0-185.0) uM	Adult (>18 years old)	Both	Normal	11978879	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	144.0 (36.2-251.0) uM	Adult (>18 years old)	Both	Normal	11805243	details
Saliva	Detected and Quantified	0.687 +/- 0.097 uM	Adult (>18 years old)	Male	Normal	17623524	details
Saliva	Detected and Quantified	0.641 +/- 0.074 uM	Adult (>18 years old)	Female	Normal	17623524	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	12097436	details
Saliva	Detected and Quantified	8.009 +/- 3.959 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	32.5 (4.6-78) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	1.70-22.72 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	David F. Putnam C...	details
Urine	Detected and Quantified	17.0 +/- 2.5 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	Geigy Scientific ...	details
Urine	Detected and Quantified	63.6 +/-142.9 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	2026685	details
Urine	Detected and Quantified	38.971 +/- 42.478 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	0.512 +/-0.058 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16139832	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21736852	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21736852	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	39.0 +/- 92.7 uM	Adult (>18 years old)	Both	Hyperoxalemia	15353324	details
Blood	Detected and Quantified	6.5 +/- 18.6 uM	Adult (>18 years old)	Both	Hyperoxalemia	15353324	details
Blood	Detected and Quantified	82.57 +/- 36.71 uM	Adult (>18 years old)	Both	Canavan disease	16139832	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	53.8 (45.8-61.8) uM	Children (1-13 years old)	Both	Brain injury	11978879	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	11.9 (0.0-24) uM	Adult (>18 years old)	Both	Meningitis	11805243	details
Saliva	Detected and Quantified	0.505 +/- 0.102 uM	Adult (>18 years old)	Male	Oral cancer	17623524	details
Saliva	Detected and Quantified	0.443 +/- 0.085 uM	Adult (>18 years old)	Female	Oral cancer	17623524	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details
Urine	Detected and Quantified	30.234 +/- 47.075 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details

Associated Disorders and Diseases

Disease References

Hyperoxalemia
Ogawa Y, Machida N, Jahana M, Gakiya M, Chinen Y, Oda M, Morozumi M, Sugaya K: Major factors modulating the serum oxalic acid level in hemodialysis patients. Front Biosci. 2004 Sep 1;9:2901-8. [PubMed:15353324 ]
Canavan disease
Tavazzi B, Lazzarino G, Leone P, Amorini AM, Bellia F, Janson CG, Di Pietro V, Ceccarelli L, Donzelli S, Francis JS, Giardina B: Simultaneous high performance liquid chromatographic separation of purines, pyrimidines, N-acetylated amino acids, and dicarboxylic acids for the chemical diagnosis of inborn errors of metabolism. Clin Biochem. 2005 Nov;38(11):997-1008. Epub 2005 Sep 1. [PubMed:16139832 ]
Traumatic brain injury
Bayir H, Kagan VE, Tyurina YY, Tyurin V, Ruppel RA, Adelson PD, Graham SH, Janesko K, Clark RS, Kochanek PM: Assessment of antioxidant reserves and oxidative stress in cerebrospinal fluid after severe traumatic brain injury in infants and children. Pediatr Res. 2002 May;51(5):571-8. [PubMed:11978879 ]
Meningitis
Kastenbauer S, Koedel U, Becker BF, Pfister HW: Oxidative stress in bacterial meningitis in humans. Neurology. 2002 Jan 22;58(2):186-91. [PubMed:11805243 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

271900 (Canavan disease)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

DB00126

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001224

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C01041

BioCyc ID

ASCORBATE

BiGG ID

Not Available

Wikipedia Link

Ascorbic_Acid

METLIN ID

Not Available

PubChem Compound

54670067

PDB ID

Not Available

ChEBI ID

29073

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000023

Good Scents ID

rw1006281

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. [PubMed:2026685 ]
Jacobsson L, Lindgarde F, Manthorpe R, Akesson B: Fatty acid composition of adipose tissue and serum micronutrients in relation to common rheumatic complaints in Swedish adults 50-70 years old. Scand J Rheumatol. 1992;21(4):171-7. [PubMed:1529283 ]
Bayir H, Kagan VE, Tyurina YY, Tyurin V, Ruppel RA, Adelson PD, Graham SH, Janesko K, Clark RS, Kochanek PM: Assessment of antioxidant reserves and oxidative stress in cerebrospinal fluid after severe traumatic brain injury in infants and children. Pediatr Res. 2002 May;51(5):571-8. [PubMed:11978879 ]
Luck MR, Jeyaseelan I, Scholes RA: Ascorbic acid and fertility. Biol Reprod. 1995 Feb;52(2):262-6. [PubMed:7711198 ]
Sotiriou S, Gispert S, Cheng J, Wang Y, Chen A, Hoogstraten-Miller S, Miller GF, Kwon O, Levine M, Guttentag SH, Nussbaum RL: Ascorbic-acid transporter Slc23a1 is essential for vitamin C transport into the brain and for perinatal survival. Nat Med. 2002 May;8(5):514-7. [PubMed:11984597 ]
Wolters M, Hickstein M, Flintermann A, Tewes U, Hahn A: Cognitive performance in relation to vitamin status in healthy elderly German women-the effect of 6-month multivitamin supplementation. Prev Med. 2005 Jul;41(1):253-9. Epub 2005 Jan 6. [PubMed:15917019 ]
Chiplonkar SA, Agte VV, Tarwadi KV, Paknikar KM, Diwate UP: Micronutrient deficiencies as predisposing factors for hypertension in lacto-vegetarian Indian adults. J Am Coll Nutr. 2004 Jun;23(3):239-47. [PubMed:15190049 ]
Dudek H, Farbiszewski R, Rydzewska M, Michno T, Kozlowski A: [Concentration of glutathione (GSH), ascorbic acid (vitamin C) and substances reacting with thiobarbituric acid (TBA-rs) in single human brain metastases]. Wiad Lek. 2005;58(7-8):379-81. [PubMed:16425787 ]
Berndt SI, Carter HB, Landis PK, Hallfrisch J, Rohrmann S, Metter EJ, Platz EA: Prediagnostic plasma vitamin C levels and the subsequent risk of prostate cancer. Nutrition. 2005 Jun;21(6):686-90. [PubMed:15925292 ]
Atanasova BD, Li AC, Bjarnason I, Tzatchev KN, Simpson RJ: Duodenal ascorbate and ferric reductase in human iron deficiency. Am J Clin Nutr. 2005 Jan;81(1):130-3. [PubMed:15640471 ]
Huang J, May JM: Ascorbic acid protects SH-SY5Y neuroblastoma cells from apoptosis and death induced by beta-amyloid. Brain Res. 2006 Jun 30;1097(1):52-8. Epub 2006 May 24. [PubMed:16725131 ]
Kastenbauer S, Koedel U, Becker BF, Pfister HW: Oxidative stress in bacterial meningitis in humans. Neurology. 2002 Jan 22;58(2):186-91. [PubMed:11805243 ]
Hino K, Murakami Y, Nagai A, Kitase A, Hara Y, Furutani T, Ren F, Yamaguchi Y, Yutoku K, Yamashita S, Okuda M, Okita M, Okita K: Alpha-tocopherol [corrected] and ascorbic acid attenuates the ribavirin [corrected] induced decrease of eicosapentaenoic acid in erythrocyte membrane in chronic hepatitis C patients. J Gastroenterol Hepatol. 2006 Aug;21(8):1269-75. [PubMed:16872308 ]
Kodama M, Inoue F, Kodama T, Kodama M: Intraperitoneal administration of ascorbic acid delays the turnover of 3H-labelled cortisol in the plasma of an ODS rat, but not in the Wistar rat. Evidence in support of the cardinal role of vitamin C in the progression of glucocorticoid synthesis. In Vivo. 1996 Jan-Feb;10(1):97-102. [PubMed:8726814 ]
Trommer H, Bottcher R, Poppl A, Hoentsch J, Wartewig S, Neubert RH: Role of ascorbic acid in stratum corneum lipid models exposed to UV irradiation. Pharm Res. 2002 Jul;19(7):982-90. [PubMed:12180551 ]
Grunewald RA: Ascorbic acid in the brain. Brain Res Brain Res Rev. 1993 Jan-Apr;18(1):123-33. [PubMed:8467348 ]
Close GL, Ashton T, Cable T, Doran D, Holloway C, McArdle F, MacLaren DP: Ascorbic acid supplementation does not attenuate post-exercise muscle soreness following muscle-damaging exercise but may delay the recovery process. Br J Nutr. 2006 May;95(5):976-81. [PubMed:16611389 ]
Li C, Chen Y, Wang Q: [Whole bladder wall laser irradiation to prevent bladder cancer recurrence with intravesical HpD and ascorbic acid]. Zhonghua Zhong Liu Za Zhi. 1997 Nov;19(6):463-5. [PubMed:10920885 ]
Wannamethee SG, Lowe GD, Rumley A, Bruckdorfer KR, Whincup PH: Associations of vitamin C status, fruit and vegetable intakes, and markers of inflammation and hemostasis. Am J Clin Nutr. 2006 Mar;83(3):567-74; quiz 726-7. [PubMed:16522902 ]
Padayatty SJ, Levine M: Vitamin C and myocardial infarction: the heart of the matter. Am J Clin Nutr. 2000 May;71(5):1027-8. [PubMed:10799361 ]
Englard S, Seifter S: The biochemical functions of ascorbic acid. Annu Rev Nutr. 1986;6:365-406. [PubMed:3015170 ]
Proctor P: Similar functions of uric acid and ascorbate in man? Nature. 1970 Nov 28;228(5274):868. [PubMed:5477017 ]
Meister A: Glutathione-ascorbic acid antioxidant system in animals. J Biol Chem. 1994 Apr 1;269(13):9397-400. [PubMed:8144521 ]
Banhegyi G, Mandl J: The hepatic glycogenoreticular system. Pathol Oncol Res. 2001;7(2):107-10. [PubMed:11458272 ]
Padayatty SJ, Katz A, Wang Y, Eck P, Kwon O, Lee JH, Chen S, Corpe C, Dutta A, Dutta SK, Levine M: Vitamin C as an antioxidant: evaluation of its role in disease prevention. J Am Coll Nutr. 2003 Feb;22(1):18-35. [PubMed:12569111 ]
Korcok J, Dixon SJ, Lo TC, Wilson JX: Differential effects of glucose on dehydroascorbic acid transport and intracellular ascorbate accumulation in astrocytes and skeletal myocytes. Brain Res. 2003 Dec 12;993(1-2):201-7. [PubMed:14642847 ]
Sugisawa T, Miyazaki T, Hoshino T: Microbial production of L-ascorbic acid from D-sorbitol, L-sorbose, L-gulose, and L-sorbosone by Ketogulonicigenium vulgare DSM 4025. Biosci Biotechnol Biochem. 2005 Mar;69(3):659-62. doi: 10.1271/bbb.69.659. [PubMed:15785002 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Only showing the first 10 proteins. There are 29 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Peptidyl-glycine alpha-amidating monooxygenase

General function:: Involved in monooxygenase activity
Specific function:: Bifunctional enzyme that catalyzes 2 sequential steps in C-terminal alpha-amidation of peptides. The monooxygenase part produces an unstable peptidyl(2-hydroxyglycine) intermediate that is dismutated to glyoxylate and the corresponding desglycine peptide amide by the lyase part. C-terminal amidation of peptides such as neuropeptides is essential for full biological activity.
Gene Name:: PAM
Uniprot ID:: P19021
Molecular weight:: 108402.425

Reactions

Peptidylglycine + Ascorbic acid + Oxygen → peptidyl(2-hydroxyglycine) + Dehydroascorbic acid + Water	details

References

Romero I, Teresa Sanchez-Ballesta M, Maldonado R, Isabel Escribano M, Merodio C: Anthocyanin, antioxidant activity and stress-induced gene expression in high CO2-treated table grapes stored at low temperature. J Plant Physiol. 2008;165(5):522-30. Epub 2007 Jun 13. [PubMed:17570561 ]
Floryszak-Wieczorek J, Milczarek G, Arasimowicz M, Ciszewski A: Do nitric oxide donors mimic endogenous NO-related response in plants? Planta. 2006 Nov;224(6):1363-72. Epub 2006 Jun 14. [PubMed:16773376 ]
Crespo A, Marti MA, Roitberg AE, Amzel LM, Estrin DA: The catalytic mechanism of peptidylglycine alpha-hydroxylating monooxygenase investigated by computer simulation. J Am Chem Soc. 2006 Oct 4;128(39):12817-28. [PubMed:17002377 ]

Enzyme Details

2. Dopamine beta-hydroxylase

General function:: Involved in monooxygenase activity
Specific function:: Conversion of dopamine to noradrenaline.
Gene Name:: DBH
Uniprot ID:: P09172
Molecular weight:: 69064.45

Reactions

Dopamine + Ascorbic acid + Oxygen → Norepinephrine + Dehydroascorbic acid + Water	details
Dopamine + Ascorbic acid + Oxygen → Norepinephrine + Dehydroascorbic acid + Water	details

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Suzuki E, Kurata T, Shibata M, Mori M, Arakawa N: Activities of D- and L-xyloascorbic acid and D- and L-araboascorbic acid as a cofactor for dopamine beta-hydroxylase reaction. J Nutr Sci Vitaminol (Tokyo). 1997 Oct;43(5):491-6. [PubMed:9505234 ]
Pettingill TM, Strange RW, Blackburn NJ: Carbonmonoxy dopamine beta-hydroxylase. Structural characterization by Fourier transform infrared, fluorescence, and x-ray absorption spectroscopy. J Biol Chem. 1991 Sep 15;266(26):16996-7003. [PubMed:1894598 ]
Feng J, Shi J, Sirimanne SR, Mounier-Lee CE, May SW: Kinetic and stereochemical studies on novel inactivators of C-terminal amidation. Biochem J. 2000 Sep 1;350 Pt 2:521-30. [PubMed:10947967 ]

Enzyme Details

3. Phytanoyl-CoA dioxygenase, peroxisomal

General function:: Involved in electron carrier activity
Specific function:: Converts phytanoyl-CoA to 2-hydroxyphytanoyl-CoA.
Gene Name:: PHYH
Uniprot ID:: O14832
Molecular weight:: 38538.065

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Enzyme Details

4. Prolyl 4-hydroxylase subunit alpha-2

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the post-translational formation of 4-hydroxyproline in -Xaa-Pro-Gly- sequences in collagens and other proteins.
Gene Name:: P4HA2
Uniprot ID:: O15460
Molecular weight:: 60632.19

Enzyme Details

5. Prolyl 4-hydroxylase subunit alpha-1

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the post-translational formation of 4-hydroxyproline in -Xaa-Pro-Gly- sequences in collagens and other proteins.
Gene Name:: P4HA1
Uniprot ID:: P13674
Molecular weight:: 60966.645

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Enzyme Details

6. Lactase-phlorizin hydrolase

General function:: Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:: LPH splits lactose in the small intestine.
Gene Name:: LCT
Uniprot ID:: P09848
Molecular weight:: 218584.77

References

Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Enzyme Details

7. Gamma-butyrobetaine dioxygenase

General function:: Involved in iron ion binding
Specific function:: Catalyzes the formation of L-carnitine from gamma-butyrobetaine.
Gene Name:: BBOX1
Uniprot ID:: O75936
Molecular weight:: 44714.6

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Dunn WA, Rettura G, Seifter E, Englard S: Carnitine biosynthesis from gamma-butyrobetaine and from exogenous protein-bound 6-N-trimethyl-L-lysine by the perfused guinea pig liver. Effect of ascorbate deficiency on the in situ activity of gamma-butyrobetaine hydroxylase. J Biol Chem. 1984 Sep 10;259(17):10764-70. [PubMed:6432788 ]
Vaz FM, van Gool S, Ofman R, IJlst L, Wanders RJ: Carnitine biosynthesis. Purification of gamma-butyrobetaine hydroxylase from rat liver. Adv Exp Med Biol. 1999;466:117-24. [PubMed:10709635 ]
Rebouche CJ: Ascorbic acid and carnitine biosynthesis. Am J Clin Nutr. 1991 Dec;54(6 Suppl):1147S-1152S. [PubMed:1962562 ]

Enzyme Details

8. Procollagen-lysine,2-oxoglutarate 5-dioxygenase 1

General function:: Involved in oxidoreductase activity
Specific function:: Forms hydroxylysine residues in -Xaa-Lys-Gly- sequences in collagens. These hydroxylysines serve as sites of attachment for carbohydrate units and are essential for the stability of the intermolecular collagen cross-links.
Gene Name:: PLOD1
Uniprot ID:: Q02809
Molecular weight:: 83549.55

References

Myllyla R, Majamaa K, Gunzler V, Hanauske-Abel HM, Kivirikko KI: Ascorbate is consumed stoichiometrically in the uncoupled reactions catalyzed by prolyl 4-hydroxylase and lysyl hydroxylase. J Biol Chem. 1984 May 10;259(9):5403-5. [PubMed:6325436 ]
Salavoura K, Valari M, Kolialexi A, Mavrou A, Kitsiou S: A case of Ehlers Danlos syndrome type VI. Genet Couns. 2006;17(3):291-4. [PubMed:17100196 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

9. Procollagen-lysine,2-oxoglutarate 5-dioxygenase 2

General function:: Involved in oxidoreductase activity
Specific function:: Forms hydroxylysine residues in -Xaa-Lys-Gly- sequences in collagens. These hydroxylysines serve as sites of attachment for carbohydrate units and are essential for the stability of the intermolecular collagen cross-links.
Gene Name:: PLOD2
Uniprot ID:: O00469
Molecular weight:: 84685.07

References

Myllyla R, Majamaa K, Gunzler V, Hanauske-Abel HM, Kivirikko KI: Ascorbate is consumed stoichiometrically in the uncoupled reactions catalyzed by prolyl 4-hydroxylase and lysyl hydroxylase. J Biol Chem. 1984 May 10;259(9):5403-5. [PubMed:6325436 ]
Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Enzyme Details

10. Procollagen-lysine,2-oxoglutarate 5-dioxygenase 3

General function:: Involved in oxidoreductase activity
Specific function:: Forms hydroxylysine residues in -Xaa-Lys-Gly- sequences in collagens. These hydroxylysines serve as sites of attachment for carbohydrate units and are essential for the stability of the intermolecular collagen cross-links.
Gene Name:: PLOD3
Uniprot ID:: O60568
Molecular weight:: 84784.505

References

Myllyla R, Majamaa K, Gunzler V, Hanauske-Abel HM, Kivirikko KI: Ascorbate is consumed stoichiometrically in the uncoupled reactions catalyzed by prolyl 4-hydroxylase and lysyl hydroxylase. J Biol Chem. 1984 May 10;259(9):5403-5. [PubMed:6325436 ]
Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Only showing the first 10 proteins. There are 29 proteins in total.

Show all enzymes and transporters

Showing metabocard for Ascorbic acid (HMDB0000044)

MOL for HMDB0000044 (Ascorbic acid)

3D MOL for HMDB0000044 (Ascorbic acid)

3D SDF for HMDB0000044 (Ascorbic acid)

3D-SDF for HMDB0000044 (Ascorbic acid)

PDB for HMDB0000044 (Ascorbic acid)

3D PDB for HMDB0000044 (Ascorbic acid)

SMILES for HMDB0000044 (Ascorbic acid)

INCHI for HMDB0000044 (Ascorbic acid)

Structure for HMDB0000044 (Ascorbic acid)

3D Structure for HMDB0000044 (Ascorbic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

References

Reactions

References

References

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