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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-12 21:33:03 UTC

Update Date

2023-02-21 17:16:42 UTC

HMDB ID

HMDB0003466

Secondary Accession Numbers

HMDB03466

Metabolite Identification

Common Name

L-Gulonolactone

Description

L-Gulonolactone belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. L-Gulonolactone exists in all living species, ranging from bacteria to plants to humans. L-Gulonolactone has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make L-gulonolactone a potential biomarker for the consumption of these foods. L-Gulonolactone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on L-Gulonolactone.

Structure

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


  Mrv1652309182018542D          

 13 13  0  0  0  0            999 V2000
10000.718610000.5377    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.432810000.1248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.718610001.3634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.149210000.5377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.2108 9998.6765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4175 9998.6845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.880710000.3808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.6360 9999.5943    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.331310000.6189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.663910000.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9188 9999.3493    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.7438 9999.3493    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.998710000.1339    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  1  0  0  0
  2  4  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 10  1  0  0  0  0
  9 13  1  0  0  0  0
  1 13  1  0  0  0  0
 13  8  1  1  0  0  0
 12  5  1  6  0  0  0
 11  6  1  6  0  0  0
 10  7  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003466

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]1(OC(=O)[C@@H](O)[C@H]1O)[C@@H](O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C6H10O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2-5,7-10H,1H2/t2-,3+,4-,5+/m0/s1

> <INCHI_KEY>
SXZYCXMUPBBULW-SKNVOMKLSA-N

> <FORMULA>
C6H10O6

> <MOLECULAR_WEIGHT>
178.14

> <EXACT_MASS>
178.047738052

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
15.465415844188865

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,4R,5R)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-one

> <ALOGPS_LOGP>
-2.05

> <JCHEM_LOGP>
-2.745273186

> <ALOGPS_LOGS>
0.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.172871312116015

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.623539809865173

> <JCHEM_PKA_STRONGEST_BASIC>
-2.974938008499871

> <JCHEM_POLAR_SURFACE_AREA>
107.22

> <JCHEM_REFRACTIVITY>
34.7788

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.37e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-gulonolactone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-SEP-20         0                                  
HETATM    1  C   UNK     0    8668.0088667.670   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8669.3418666.900   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8668.0088669.212   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8670.6798667.670   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8667.0608664.196   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8663.7138664.211   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8662.7118667.377   0.000  0.00  0.00           O+0
HETATM    8  H   UNK     0    8667.8548665.909   0.000  0.00  0.00           H+0
HETATM    9  O   UNK     0    8665.4188667.822   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0    8664.1738666.917   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8664.6488665.452   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8666.1888665.452   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8666.6648666.917   0.000  0.00  0.00           C+0
CONECT    1    2    3   13                                                  
CONECT    2    1    4                                                       
CONECT    3    1                                                            
CONECT    4    2                                                            
CONECT    5   12                                                            
CONECT    6   11                                                            
CONECT    7   10                                                            
CONECT    8   13                                                            
CONECT    9   10   13                                                       
CONECT   10   11    9    7                                                  
CONECT   11   10   12    6                                                  
CONECT   12   11   13    5                                                  
CONECT   13   12    9    1    8                                             
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
gamma-Gulonolactone	ChEBI
L-Gulonic acid gamma-lactone	ChEBI
L-Gulono-gamma-lactone	ChEBI
g-Gulonolactone	Generator
Γ-gulonolactone	Generator
L-Gulonate g-lactone	Generator
L-Gulonate gamma-lactone	Generator
L-Gulonate γ-lactone	Generator
L-Gulonic acid g-lactone	Generator
L-Gulonic acid γ-lactone	Generator
L-Gulono-g-lactone	Generator
L-Gulono-γ-lactone	Generator
L-(+)-gulono-1,4-Lactone	HMDB
L-Gulono-1,4-lactone	HMDB
Reduced ascorbate	HMDB
Reduced ascorbic acid	HMDB
Gulonolactone, (L)-isomer	MeSH, HMDB
Gulonolactone	MeSH, HMDB
Gulonolactone, (D)-isomer	MeSH, HMDB
Dihydroascorbic acid	HMDB
L-(+)-Gulonic acid gamma-lactone	HMDB
L-(+)-Gulonic acid γ-lactone	HMDB
L-Gulonolactone	HMDB

Chemical Formula

C₆H₁₀O₆

Average Molecular Weight

178.14

Monoisotopic Molecular Weight

178.047738052

IUPAC Name

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

Traditional Name

L-gulonolactone

CAS Registry Number

1128-23-0

SMILES

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

InChI Identifier

InChI=1S/C6H10O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2-5,7-10H,1H2/t2-,3+,4-,5+/m0/s1

InChI Key

SXZYCXMUPBBULW-SKNVOMKLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Gamma butyrolactone
Tetrahydrofuran
Secondary alcohol
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

gulonolactone (CHEBI:17587 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 19212411)
Saliva (PMID: 22308371)

Excreta

Biofluid or Excreta

Feces (PMID: 24029555)

Source

Endogenous

Endogenous (HMDB: HMDB0003466)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Prostate cancer (HMDB: HMDB0003466)

Metabolic pathway

Ascorbate Biosynthesis (PathBank: SMP0063817)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	-2.571	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	130.7	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000357

Predicted Molecular Properties

Property	Value	Source
Water Solubility	637 g/L	ALOGPS
logP	-2	ALOGPS
logP	-2.7	ChemAxon
logS	0.55	ALOGPS
pKa (Strongest Acidic)	11.62	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	34.78 m³·mol⁻¹	ChemAxon
Polarizability	15.47 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
DarkChem	[M+H]+	140.416	31661259
DarkChem	[M-H]-	132.851	31661259
DeepCCS	[M+H]+	139.658	30932474
DeepCCS	[M-H]-	137.262	30932474
DeepCCS	[M-2H]-	171.343	30932474
DeepCCS	[M+Na]+	145.914	30932474
AllCCS	[M+H]+	139.8	32859911
AllCCS	[M+H-H2O]+	135.7	32859911
AllCCS	[M+NH4]+	143.6	32859911
AllCCS	[M+Na]+	144.7	32859911
AllCCS	[M-H]-	130.8	32859911
AllCCS	[M+Na-2H]-	131.8	32859911
AllCCS	[M+HCOO]-	132.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.69 minutes	32390414
Predicted by Siyang on May 30, 2022	10.5705 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.76 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	260.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	774.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	347.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	32.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	194.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	86.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	297.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	253.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	749.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	639.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	48.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	938.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	209.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	271.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	712.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	292.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	365.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
L-Gulonolactone	[H][C@@]1(OC(=O)[C@@H](O)[C@H]1O)[C@@H](O)CO	3095.0	Standard polar	33892256
L-Gulonolactone	[H][C@@]1(OC(=O)[C@@H](O)[C@H]1O)[C@@H](O)CO	1960.5	Standard non polar	33892256
L-Gulonolactone	[H][C@@]1(OC(=O)[C@@H](O)[C@H]1O)[C@@H](O)CO	1675.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
L-Gulonolactone,1TMS,isomer #1	C[Si](C)(C)O[C@@H]1C(=O)O[C@H]([C@@H](O)CO)[C@@H]1O	1745.9	Semi standard non polar	33892256
L-Gulonolactone,1TMS,isomer #2	C[Si](C)(C)O[C@@H]1[C@H](O)C(=O)O[C@@H]1[C@@H](O)CO	1726.0	Semi standard non polar	33892256
L-Gulonolactone,1TMS,isomer #3	C[Si](C)(C)O[C@@H](CO)[C@H]1OC(=O)[C@@H](O)[C@H]1O	1707.1	Semi standard non polar	33892256
L-Gulonolactone,1TMS,isomer #4	C[Si](C)(C)OC[C@H](O)[C@H]1OC(=O)[C@@H](O)[C@H]1O	1701.8	Semi standard non polar	33892256
L-Gulonolactone,2TMS,isomer #1	C[Si](C)(C)O[C@@H](CO)[C@H]1OC(=O)[C@@H](O[Si](C)(C)C)[C@H]1O	1829.0	Semi standard non polar	33892256
L-Gulonolactone,2TMS,isomer #2	C[Si](C)(C)OC[C@H](O)[C@H]1OC(=O)[C@@H](O[Si](C)(C)C)[C@H]1O	1856.2	Semi standard non polar	33892256
L-Gulonolactone,2TMS,isomer #3	C[Si](C)(C)O[C@@H]1C(=O)O[C@H]([C@@H](O)CO)[C@@H]1O[Si](C)(C)C	1819.7	Semi standard non polar	33892256
L-Gulonolactone,2TMS,isomer #4	C[Si](C)(C)O[C@@H](CO)[C@H]1OC(=O)[C@@H](O)[C@H]1O[Si](C)(C)C	1808.2	Semi standard non polar	33892256
L-Gulonolactone,2TMS,isomer #5	C[Si](C)(C)OC[C@H](O)[C@H]1OC(=O)[C@@H](O)[C@H]1O[Si](C)(C)C	1826.7	Semi standard non polar	33892256
L-Gulonolactone,2TMS,isomer #6	C[Si](C)(C)OC[C@H](O[Si](C)(C)C)[C@H]1OC(=O)[C@@H](O)[C@H]1O	1772.4	Semi standard non polar	33892256
L-Gulonolactone,3TMS,isomer #1	C[Si](C)(C)OC[C@H](O[Si](C)(C)C)[C@H]1OC(=O)[C@@H](O[Si](C)(C)C)[C@H]1O	1916.7	Semi standard non polar	33892256
L-Gulonolactone,3TMS,isomer #2	C[Si](C)(C)O[C@@H]1C(=O)O[C@H]([C@H](CO)O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	1891.4	Semi standard non polar	33892256
L-Gulonolactone,3TMS,isomer #3	C[Si](C)(C)OC[C@H](O)[C@H]1OC(=O)[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	1916.5	Semi standard non polar	33892256
L-Gulonolactone,3TMS,isomer #4	C[Si](C)(C)OC[C@H](O[Si](C)(C)C)[C@H]1OC(=O)[C@@H](O)[C@H]1O[Si](C)(C)C	1880.4	Semi standard non polar	33892256
L-Gulonolactone,4TMS,isomer #1	C[Si](C)(C)OC[C@H](O[Si](C)(C)C)[C@H]1OC(=O)[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	1929.0	Semi standard non polar	33892256
L-Gulonolactone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1C(=O)O[C@H]([C@@H](O)CO)[C@@H]1O	1988.5	Semi standard non polar	33892256
L-Gulonolactone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)C(=O)O[C@@H]1[C@@H](O)CO	1970.2	Semi standard non polar	33892256
L-Gulonolactone,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H](CO)[C@H]1OC(=O)[C@@H](O)[C@H]1O	1949.8	Semi standard non polar	33892256
L-Gulonolactone,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC[C@H](O)[C@H]1OC(=O)[C@@H](O)[C@H]1O	1949.5	Semi standard non polar	33892256
L-Gulonolactone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H](CO)[C@H]1OC(=O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	2280.1	Semi standard non polar	33892256
L-Gulonolactone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H](O)[C@H]1OC(=O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	2300.1	Semi standard non polar	33892256
L-Gulonolactone,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1C(=O)O[C@H]([C@@H](O)CO)[C@@H]1O[Si](C)(C)C(C)(C)C	2260.9	Semi standard non polar	33892256
L-Gulonolactone,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H](CO)[C@H]1OC(=O)[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	2269.9	Semi standard non polar	33892256
L-Gulonolactone,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC[C@H](O)[C@H]1OC(=O)[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	2273.9	Semi standard non polar	33892256
L-Gulonolactone,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@@H](O)[C@H]1O	2239.3	Semi standard non polar	33892256
L-Gulonolactone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1OC(=O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	2559.1	Semi standard non polar	33892256
L-Gulonolactone,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1C(=O)O[C@H]([C@H](CO)O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	2555.0	Semi standard non polar	33892256
L-Gulonolactone,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H](O)[C@H]1OC(=O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	2568.4	Semi standard non polar	33892256
L-Gulonolactone,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@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	2542.3	Semi standard non polar	33892256
L-Gulonolactone,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@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	2792.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - L-Gulonolactone GC-MS (4 TMS)	splash10-0gc0-2961000000-10e3ffe56d1491c35d8a	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - L-Gulonolactone GC-MS (Non-derivatized)	splash10-0gc0-2961000000-10e3ffe56d1491c35d8a	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - L-Gulonolactone GC-EI-TOF (Non-derivatized)	splash10-0fr2-0930000000-725e277ca1152a7fbc98	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Gulonolactone GC-MS (Non-derivatized) - 70eV, Positive	splash10-08fr-9400000000-615dd94b06b3e5e78526	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Gulonolactone GC-MS (4 TMS) - 70eV, Positive	splash10-0pk9-5359600000-e93f868058ca84374468	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Gulonolactone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Gulonolactone 40V, Negative-QTOF	splash10-0a4i-9000000000-ec8c949182af76945e86	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Gulonolactone 20V, Negative-QTOF	splash10-0a4i-9000000000-7a0472476f07853a992b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Gulonolactone 10V, Negative-QTOF	splash10-0a70-9300000000-74777b41198e9cd46262	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Gulonolactone 20V, Positive-QTOF	splash10-06ds-9000000000-2d40464867d71e6c1135	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Gulonolactone 10V, Positive-QTOF	splash10-01b9-9400000000-d5de17e2c0c42a02efc0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Gulonolactone 40V, Positive-QTOF	splash10-052f-9000000000-0435329cc0eb001898fa	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Gulonolactone 10V, Positive-QTOF	splash10-01t9-1900000000-f47818211aa007edc5f4	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Gulonolactone 20V, Positive-QTOF	splash10-03di-5900000000-c7c9eb2eaa1f91ac9951	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Gulonolactone 40V, Positive-QTOF	splash10-0a4i-9100000000-072c615a4ace0aca930a	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Gulonolactone 10V, Negative-QTOF	splash10-00or-3900000000-5f8e27814cf4a835d41a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Gulonolactone 20V, Negative-QTOF	splash10-0ar0-6900000000-9a9aef2bcc37f743beab	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Gulonolactone 40V, Negative-QTOF	splash10-0596-9100000000-4892df7d8d2a53c17d7f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Gulonolactone 10V, Negative-QTOF	splash10-0a4i-9300000000-cd9f8103b846d70baac0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Gulonolactone 20V, Negative-QTOF	splash10-0a4l-9000000000-650b3c2ec9303d9b2a96	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Gulonolactone 40V, Negative-QTOF	splash10-0006-9000000000-232c502ee9a5b93d5a17	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Gulonolactone 10V, Positive-QTOF	splash10-03fu-1900000000-a9b5237063a8327d87cd	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Gulonolactone 20V, Positive-QTOF	splash10-0296-9500000000-aadb547d81673dce1915	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Gulonolactone 40V, Positive-QTOF	splash10-08mm-9100000000-0a3f8e5a08a10aa888eb	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	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

Not Available

Biospecimen Locations

Blood
Feces
Saliva

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24029555	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.5 (0.0-1.0) uM	Adult (>18 years old)	Both	Prostate Cancer	19212411	details

Associated Disorders and Diseases

Disease References

Prostate cancer

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 ]

Associated OMIM IDs

176807 (Prostate cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

L-gulonolactone oxidase

METLIN ID

Not Available

PubChem Compound

439373

PDB ID

Not Available

ChEBI ID

17587

Food Biomarker Ontology

Not Available

VMH ID

GULLAC

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Wolucka BA, Communi D: Mycobacterium tuberculosis possesses a functional enzyme for the synthesis of vitamin C, L-gulono-1,4-lactone dehydrogenase. FEBS J. 2006 Oct;273(19):4435-45. Epub 2006 Sep 5. [PubMed:16956367 ]
Steinberg JG, Delliaux S, Jammes Y: Reliability of different blood indices to explore the oxidative stress in response to maximal cycling and static exercises. Clin Physiol Funct Imaging. 2006 Mar;26(2):106-12. [PubMed:16494601 ]

Enzymes

Enzyme Details

1. Regucalcin

General function:: Involved in calcium ion binding
Specific function:: Gluconolactonase with low activity towards other sugar lactones, including gulonolactone and galactonolactone. Can also hydrolyze diisopropyl phosphorofluoridate and phenylacetate (in vitro). Calcium-binding protein. Modulates Ca(2+) signaling, and Ca(2+)-dependent cellular processes and enzyme activities (By similarity).
Gene Name:: RGN
Uniprot ID:: Q15493
Molecular weight:: 33252.53

Reactions

L-Gulonolactone + Water → Gulonic acid	details

Showing metabocard for L-Gulonolactone (HMDB0003466)

MOL for HMDB0003466 (L-Gulonolactone)

3D MOL for HMDB0003466 (L-Gulonolactone)

3D SDF for HMDB0003466 (L-Gulonolactone)

3D-SDF for HMDB0003466 (L-Gulonolactone)

PDB for HMDB0003466 (L-Gulonolactone)

3D PDB for HMDB0003466 (L-Gulonolactone)

SMILES for HMDB0003466 (L-Gulonolactone)

INCHI for HMDB0003466 (L-Gulonolactone)

Structure for HMDB0003466 (L-Gulonolactone)

3D Structure for HMDB0003466 (L-Gulonolactone)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions