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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2006-05-22 15:12:47 UTC

Update Date

2023-02-21 17:16:35 UTC

HMDB ID

HMDB0003290

Secondary Accession Numbers

HMDB03290

Metabolite Identification

Common Name

Gulonic acid

Description

Gulonic acid, also known as gulonate, belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain. Gulonic acid 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 gulonic acid a potential biomarker for the consumption of these foods. Gulonic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Gulonic acid.

Structure

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


  Mrv1652305271900142D          

 13 12  0  0  1  0            999 V2000
   24.6507  -16.5953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9363  -18.6577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.3652  -18.6577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.2219  -16.5953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.7940  -17.8328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7930  -17.4202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5074  -18.6577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.6507  -17.4202    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   23.9363  -17.8328    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   25.3652  -17.8328    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   23.2219  -17.4202    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   26.0795  -17.4202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5074  -17.8328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  1  0  0  0
  9  2  1  1  0  0  0
 10  3  1  1  0  0  0
 11  4  1  6  0  0  0
  5 12  1  0  0  0  0
  6 13  1  0  0  0  0
  7 13  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003290

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H12O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-5,7-11H,1H2,(H,12,13)/t2-,3+,4-,5-/m1/s1

> <INCHI_KEY>
RGHNJXZEOKUKBD-KKQCNMDGSA-N

> <FORMULA>
C6H12O7

> <MOLECULAR_WEIGHT>
196.1553

> <EXACT_MASS>
196.058302738

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
17.160552515423085

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4S,5R)-2,3,4,5,6-pentahydroxyhexanoic acid

> <ALOGPS_LOGP>
-2.57

> <JCHEM_LOGP>
-3.4097443106666665

> <ALOGPS_LOGS>
-0.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.593710458724516

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.388205574321856

> <JCHEM_PKA_STRONGEST_BASIC>
-2.974220927705365

> <JCHEM_POLAR_SURFACE_AREA>
138.45000000000002

> <JCHEM_REFRACTIVITY>
38.27100000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.59e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gulonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      46.015 -30.978   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      44.681 -34.828   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      47.348 -34.828   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      43.348 -30.978   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      50.015 -33.288   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      40.680 -32.518   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      42.014 -34.828   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      46.015 -32.518   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      44.681 -33.288   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      47.348 -33.288   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      43.348 -32.518   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      48.682 -32.518   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      42.014 -33.288   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4   11                                                            
CONECT    5   12                                                            
CONECT    6   13                                                            
CONECT    7   13                                                            
CONECT    8    1    9   10                                                  
CONECT    9    2    8   11                                                  
CONECT   10    3    8   12                                                  
CONECT   11    4    9   13                                                  
CONECT   12    5   10                                                       
CONECT   13    6    7   11                                                  
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Gulonate	Generator
Gulonic acid, (L)-isomer	MeSH
Gulonic acid, ion (1-), (L)-isomer	MeSH
Gulonic acid, monosodium salt, (L)-isomer	MeSH
D-Gulonate	HMDB
D-Gulonic acid	HMDB
L-Gulonate	HMDB
L-Gulonic acid	HMDB

Chemical Formula

C₆H₁₂O₇

Average Molecular Weight

196.1553

Monoisotopic Molecular Weight

196.058302738

IUPAC Name

(2R,3R,4S,5R)-2,3,4,5,6-pentahydroxyhexanoic acid

Traditional Name

gulonic acid

CAS Registry Number

20246-53-1

SMILES

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

InChI Identifier

InChI=1S/C6H12O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-5,7-11H,1H2,(H,12,13)/t2-,3+,4-,5-/m1/s1

InChI Key

RGHNJXZEOKUKBD-KKQCNMDGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Medium-chain hydroxy acids and derivatives

Direct Parent

Medium-chain hydroxy acids and derivatives

Alternative Parents

Substituents

Medium-chain hydroxy acid
Medium-chain fatty acid
Beta-hydroxy acid
Hydroxy fatty acid
Alpha-hydroxy acid
Monosaccharide
Fatty acyl
Fatty acid
Secondary alcohol
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Primary alcohol
Alcohol
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

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	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	159 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-3.4	ChemAxon
logS	-0.09	ALOGPS
pKa (Strongest Acidic)	3.39	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	138.45 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	38.27 m³·mol⁻¹	ChemAxon
Polarizability	17.16 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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]+	144.165	31661259
DarkChem	[M-H]-	136.808	31661259
DeepCCS	[M+H]+	149.135	30932474
DeepCCS	[M-H]-	146.767	30932474
DeepCCS	[M-2H]-	180.007	30932474
DeepCCS	[M+Na]+	155.048	30932474
AllCCS	[M+H]+	143.9	32859911
AllCCS	[M+H-H2O]+	140.2	32859911
AllCCS	[M+NH4]+	147.3	32859911
AllCCS	[M+Na]+	148.3	32859911
AllCCS	[M-H]-	134.1	32859911
AllCCS	[M+Na-2H]-	135.2	32859911
AllCCS	[M+HCOO]-	136.5	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.	7.05 minutes	32390414
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.	0.91 minutes	32390414
Predicted by Siyang on May 30, 2022	10.9057 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	7.74 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	376.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	665.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	356.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	19.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	205.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	96.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	327.4 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	230.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	794.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	636.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	44.2 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	889.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	215.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	327.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	715.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	407.2 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	434.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Gulonic acid	OC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)C(O)=O	3328.4	Standard polar	33892256
Gulonic acid	OC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)C(O)=O	1773.7	Standard non polar	33892256
Gulonic acid	OC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)C(O)=O	1797.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Gulonic acid,1TMS,isomer #1	C[Si](C)(C)OC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)C(=O)O	1796.7	Semi standard non polar	33892256
Gulonic acid,1TMS,isomer #2	C[Si](C)(C)O[C@H](CO)[C@H](O)[C@@H](O)[C@@H](O)C(=O)O	1788.4	Semi standard non polar	33892256
Gulonic acid,1TMS,isomer #3	C[Si](C)(C)O[C@H]([C@@H](O)[C@@H](O)C(=O)O)[C@H](O)CO	1752.9	Semi standard non polar	33892256
Gulonic acid,1TMS,isomer #4	C[Si](C)(C)O[C@H]([C@@H](O)[C@H](O)CO)[C@@H](O)C(=O)O	1757.3	Semi standard non polar	33892256
Gulonic acid,1TMS,isomer #5	C[Si](C)(C)O[C@@H](C(=O)O)[C@H](O)[C@@H](O)[C@H](O)CO	1754.6	Semi standard non polar	33892256
Gulonic acid,1TMS,isomer #6	C[Si](C)(C)OC(=O)[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO	1778.3	Semi standard non polar	33892256
Gulonic acid,2TMS,isomer #1	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H](O)[C@@H](O)C(=O)O	1868.4	Semi standard non polar	33892256
Gulonic acid,2TMS,isomer #10	C[Si](C)(C)O[C@H]([C@@H](O[Si](C)(C)C)[C@@H](O)C(=O)O)[C@H](O)CO	1819.9	Semi standard non polar	33892256
Gulonic acid,2TMS,isomer #11	C[Si](C)(C)O[C@@H]([C@H](O)CO)[C@@H](O)[C@@H](O[Si](C)(C)C)C(=O)O	1830.8	Semi standard non polar	33892256
Gulonic acid,2TMS,isomer #12	C[Si](C)(C)OC(=O)[C@H](O)[C@H](O)[C@@H](O[Si](C)(C)C)[C@H](O)CO	1835.9	Semi standard non polar	33892256
Gulonic acid,2TMS,isomer #13	C[Si](C)(C)O[C@@H](C(=O)O)[C@H](O[Si](C)(C)C)[C@@H](O)[C@H](O)CO	1826.5	Semi standard non polar	33892256
Gulonic acid,2TMS,isomer #14	C[Si](C)(C)OC(=O)[C@H](O)[C@H](O[Si](C)(C)C)[C@@H](O)[C@H](O)CO	1825.1	Semi standard non polar	33892256
Gulonic acid,2TMS,isomer #15	C[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C)[C@H](O)[C@@H](O)[C@H](O)CO	1823.3	Semi standard non polar	33892256
Gulonic acid,2TMS,isomer #2	C[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H](O)C(=O)O	1836.6	Semi standard non polar	33892256
Gulonic acid,2TMS,isomer #3	C[Si](C)(C)OC[C@@H](O)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H](O)C(=O)O	1832.5	Semi standard non polar	33892256
Gulonic acid,2TMS,isomer #4	C[Si](C)(C)OC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O[Si](C)(C)C)C(=O)O	1851.7	Semi standard non polar	33892256
Gulonic acid,2TMS,isomer #5	C[Si](C)(C)OC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)C(=O)O[Si](C)(C)C	1857.7	Semi standard non polar	33892256
Gulonic acid,2TMS,isomer #6	C[Si](C)(C)O[C@H](CO)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H](O)C(=O)O	1849.6	Semi standard non polar	33892256
Gulonic acid,2TMS,isomer #7	C[Si](C)(C)O[C@H](CO)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H](O)C(=O)O	1840.6	Semi standard non polar	33892256
Gulonic acid,2TMS,isomer #8	C[Si](C)(C)O[C@H](CO)[C@H](O)[C@@H](O)[C@@H](O[Si](C)(C)C)C(=O)O	1849.4	Semi standard non polar	33892256
Gulonic acid,2TMS,isomer #9	C[Si](C)(C)OC(=O)[C@H](O)[C@H](O)[C@@H](O)[C@@H](CO)O[Si](C)(C)C	1850.8	Semi standard non polar	33892256
Gulonic acid,3TMS,isomer #1	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H](O)C(=O)O	1886.7	Semi standard non polar	33892256
Gulonic acid,3TMS,isomer #10	C[Si](C)(C)OC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1883.7	Semi standard non polar	33892256
Gulonic acid,3TMS,isomer #11	C[Si](C)(C)O[C@H]([C@@H](O[Si](C)(C)C)[C@@H](O)C(=O)O)[C@@H](CO)O[Si](C)(C)C	1885.0	Semi standard non polar	33892256
Gulonic acid,3TMS,isomer #12	C[Si](C)(C)O[C@H](CO)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H](O[Si](C)(C)C)C(=O)O	1903.9	Semi standard non polar	33892256
Gulonic acid,3TMS,isomer #13	C[Si](C)(C)OC(=O)[C@H](O)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H](CO)O[Si](C)(C)C	1895.8	Semi standard non polar	33892256
Gulonic acid,3TMS,isomer #14	C[Si](C)(C)O[C@H](CO)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O	1891.7	Semi standard non polar	33892256
Gulonic acid,3TMS,isomer #15	C[Si](C)(C)OC(=O)[C@H](O)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H](CO)O[Si](C)(C)C	1897.5	Semi standard non polar	33892256
Gulonic acid,3TMS,isomer #16	C[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C)[C@H](O)[C@@H](O)[C@@H](CO)O[Si](C)(C)C	1893.7	Semi standard non polar	33892256
Gulonic acid,3TMS,isomer #17	C[Si](C)(C)O[C@@H]([C@H](O)CO)[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O	1874.5	Semi standard non polar	33892256
Gulonic acid,3TMS,isomer #18	C[Si](C)(C)OC(=O)[C@H](O)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)CO	1878.4	Semi standard non polar	33892256
Gulonic acid,3TMS,isomer #19	C[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C)[C@H](O)[C@@H](O[Si](C)(C)C)[C@H](O)CO	1883.4	Semi standard non polar	33892256
Gulonic acid,3TMS,isomer #2	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H](O)C(=O)O	1890.1	Semi standard non polar	33892256
Gulonic acid,3TMS,isomer #20	C[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](O)[C@H](O)CO	1854.0	Semi standard non polar	33892256
Gulonic acid,3TMS,isomer #3	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H](O)[C@@H](O[Si](C)(C)C)C(=O)O	1909.4	Semi standard non polar	33892256
Gulonic acid,3TMS,isomer #4	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H](O)[C@@H](O)C(=O)O[Si](C)(C)C	1900.3	Semi standard non polar	33892256
Gulonic acid,3TMS,isomer #5	C[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H](O)C(=O)O	1884.4	Semi standard non polar	33892256
Gulonic acid,3TMS,isomer #6	C[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H](O[Si](C)(C)C)C(=O)O	1902.7	Semi standard non polar	33892256
Gulonic acid,3TMS,isomer #7	C[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H](O)C(=O)O[Si](C)(C)C	1898.4	Semi standard non polar	33892256
Gulonic acid,3TMS,isomer #8	C[Si](C)(C)OC[C@@H](O)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O	1883.2	Semi standard non polar	33892256
Gulonic acid,3TMS,isomer #9	C[Si](C)(C)OC[C@@H](O)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H](O)C(=O)O[Si](C)(C)C	1892.5	Semi standard non polar	33892256
Gulonic acid,4TMS,isomer #1	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H](O)C(=O)O	1919.5	Semi standard non polar	33892256
Gulonic acid,4TMS,isomer #10	C[Si](C)(C)OC[C@@H](O)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1926.6	Semi standard non polar	33892256
Gulonic acid,4TMS,isomer #11	C[Si](C)(C)O[C@@H]([C@@H](CO)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O	1919.4	Semi standard non polar	33892256
Gulonic acid,4TMS,isomer #12	C[Si](C)(C)OC(=O)[C@H](O)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H](CO)O[Si](C)(C)C	1938.2	Semi standard non polar	33892256
Gulonic acid,4TMS,isomer #13	C[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H](CO)O[Si](C)(C)C	1940.0	Semi standard non polar	33892256
Gulonic acid,4TMS,isomer #14	C[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H](CO)O[Si](C)(C)C	1931.9	Semi standard non polar	33892256
Gulonic acid,4TMS,isomer #15	C[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)CO	1922.1	Semi standard non polar	33892256
Gulonic acid,4TMS,isomer #2	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H](O[Si](C)(C)C)C(=O)O	1939.4	Semi standard non polar	33892256
Gulonic acid,4TMS,isomer #3	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H](O)C(=O)O[Si](C)(C)C	1948.7	Semi standard non polar	33892256
Gulonic acid,4TMS,isomer #4	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O	1931.8	Semi standard non polar	33892256
Gulonic acid,4TMS,isomer #5	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H](O)C(=O)O[Si](C)(C)C	1936.2	Semi standard non polar	33892256
Gulonic acid,4TMS,isomer #6	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H](O)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1945.3	Semi standard non polar	33892256
Gulonic acid,4TMS,isomer #7	C[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O	1928.6	Semi standard non polar	33892256
Gulonic acid,4TMS,isomer #8	C[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H](O)C(=O)O[Si](C)(C)C	1936.7	Semi standard non polar	33892256
Gulonic acid,4TMS,isomer #9	C[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1943.0	Semi standard non polar	33892256
Gulonic acid,5TMS,isomer #1	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O	1927.2	Semi standard non polar	33892256
Gulonic acid,5TMS,isomer #2	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H](O)C(=O)O[Si](C)(C)C	1942.2	Semi standard non polar	33892256
Gulonic acid,5TMS,isomer #3	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1935.7	Semi standard non polar	33892256
Gulonic acid,5TMS,isomer #4	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1931.0	Semi standard non polar	33892256
Gulonic acid,5TMS,isomer #5	C[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1910.7	Semi standard non polar	33892256
Gulonic acid,5TMS,isomer #6	C[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H](CO)O[Si](C)(C)C	1935.9	Semi standard non polar	33892256
Gulonic acid,6TMS,isomer #1	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1983.7	Semi standard non polar	33892256
Gulonic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)C(=O)O	2088.9	Semi standard non polar	33892256
Gulonic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H](CO)[C@H](O)[C@@H](O)[C@@H](O)C(=O)O	2075.2	Semi standard non polar	33892256
Gulonic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@H]([C@@H](O)[C@@H](O)C(=O)O)[C@H](O)CO	2032.4	Semi standard non polar	33892256
Gulonic acid,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@H]([C@@H](O)[C@H](O)CO)[C@@H](O)C(=O)O	2021.7	Semi standard non polar	33892256
Gulonic acid,1TBDMS,isomer #5	CC(C)(C)[Si](C)(C)O[C@@H](C(=O)O)[C@H](O)[C@@H](O)[C@H](O)CO	2056.9	Semi standard non polar	33892256
Gulonic acid,1TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC(=O)[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO	2063.9	Semi standard non polar	33892256
Gulonic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](O)[C@@H](O)C(=O)O	2316.2	Semi standard non polar	33892256
Gulonic acid,2TBDMS,isomer #10	CC(C)(C)[Si](C)(C)O[C@H]([C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O)[C@H](O)CO	2267.6	Semi standard non polar	33892256
Gulonic acid,2TBDMS,isomer #11	CC(C)(C)[Si](C)(C)O[C@@H]([C@H](O)CO)[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O	2303.5	Semi standard non polar	33892256
Gulonic acid,2TBDMS,isomer #12	CC(C)(C)[Si](C)(C)OC(=O)[C@H](O)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)CO	2304.4	Semi standard non polar	33892256
Gulonic acid,2TBDMS,isomer #13	CC(C)(C)[Si](C)(C)O[C@@H](C(=O)O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)CO	2284.7	Semi standard non polar	33892256
Gulonic acid,2TBDMS,isomer #14	CC(C)(C)[Si](C)(C)OC(=O)[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)CO	2293.5	Semi standard non polar	33892256
Gulonic acid,2TBDMS,isomer #15	CC(C)(C)[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](O)[C@H](O)CO	2298.2	Semi standard non polar	33892256
Gulonic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H](O)C(=O)O	2288.5	Semi standard non polar	33892256
Gulonic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O	2282.6	Semi standard non polar	33892256
Gulonic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O	2329.8	Semi standard non polar	33892256
Gulonic acid,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C	2319.3	Semi standard non polar	33892256
Gulonic acid,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)O[C@H](CO)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H](O)C(=O)O	2311.2	Semi standard non polar	33892256
Gulonic acid,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)O[C@H](CO)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O	2291.1	Semi standard non polar	33892256
Gulonic acid,2TBDMS,isomer #8	CC(C)(C)[Si](C)(C)O[C@H](CO)[C@H](O)[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O	2325.5	Semi standard non polar	33892256
Gulonic acid,2TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC(=O)[C@H](O)[C@H](O)[C@@H](O)[C@@H](CO)O[Si](C)(C)C(C)(C)C	2319.9	Semi standard non polar	33892256
Gulonic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H](O)C(=O)O	2520.2	Semi standard non polar	33892256
Gulonic acid,3TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2551.5	Semi standard non polar	33892256
Gulonic acid,3TBDMS,isomer #11	CC(C)(C)[Si](C)(C)O[C@H]([C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O)[C@@H](CO)O[Si](C)(C)C(C)(C)C	2532.1	Semi standard non polar	33892256
Gulonic acid,3TBDMS,isomer #12	CC(C)(C)[Si](C)(C)O[C@H](CO)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O	2578.3	Semi standard non polar	33892256
Gulonic acid,3TBDMS,isomer #13	CC(C)(C)[Si](C)(C)OC(=O)[C@H](O)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO)O[Si](C)(C)C(C)(C)C	2575.3	Semi standard non polar	33892256
Gulonic acid,3TBDMS,isomer #14	CC(C)(C)[Si](C)(C)O[C@H](CO)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O	2566.0	Semi standard non polar	33892256
Gulonic acid,3TBDMS,isomer #15	CC(C)(C)[Si](C)(C)OC(=O)[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H](CO)O[Si](C)(C)C(C)(C)C	2577.8	Semi standard non polar	33892256
Gulonic acid,3TBDMS,isomer #16	CC(C)(C)[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](O)[C@@H](CO)O[Si](C)(C)C(C)(C)C	2570.6	Semi standard non polar	33892256
Gulonic acid,3TBDMS,isomer #17	CC(C)(C)[Si](C)(C)O[C@@H]([C@H](O)CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O	2534.1	Semi standard non polar	33892256
Gulonic acid,3TBDMS,isomer #18	CC(C)(C)[Si](C)(C)OC(=O)[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)CO	2550.2	Semi standard non polar	33892256
Gulonic acid,3TBDMS,isomer #19	CC(C)(C)[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)CO	2555.9	Semi standard non polar	33892256
Gulonic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O	2532.8	Semi standard non polar	33892256
Gulonic acid,3TBDMS,isomer #20	CC(C)(C)[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)CO	2526.3	Semi standard non polar	33892256
Gulonic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O	2578.0	Semi standard non polar	33892256
Gulonic acid,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](O)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C	2559.8	Semi standard non polar	33892256
Gulonic acid,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O	2521.4	Semi standard non polar	33892256
Gulonic acid,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O	2586.8	Semi standard non polar	33892256
Gulonic acid,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C	2568.6	Semi standard non polar	33892256
Gulonic acid,3TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O	2562.1	Semi standard non polar	33892256
Gulonic acid,3TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C	2563.4	Semi standard non polar	33892256
Gulonic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O	2766.5	Semi standard non polar	33892256
Gulonic acid,4TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2773.7	Semi standard non polar	33892256
Gulonic acid,4TBDMS,isomer #11	CC(C)(C)[Si](C)(C)O[C@@H]([C@@H](CO)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O	2798.7	Semi standard non polar	33892256
Gulonic acid,4TBDMS,isomer #12	CC(C)(C)[Si](C)(C)OC(=O)[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO)O[Si](C)(C)C(C)(C)C	2799.5	Semi standard non polar	33892256
Gulonic acid,4TBDMS,isomer #13	CC(C)(C)[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO)O[Si](C)(C)C(C)(C)C	2790.9	Semi standard non polar	33892256
Gulonic acid,4TBDMS,isomer #14	CC(C)(C)[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H](CO)O[Si](C)(C)C(C)(C)C	2786.9	Semi standard non polar	33892256
Gulonic acid,4TBDMS,isomer #15	CC(C)(C)[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)CO	2762.0	Semi standard non polar	33892256
Gulonic acid,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O	2821.6	Semi standard non polar	33892256
Gulonic acid,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C	2802.6	Semi standard non polar	33892256
Gulonic acid,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O	2810.2	Semi standard non polar	33892256
Gulonic acid,4TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C	2802.1	Semi standard non polar	33892256
Gulonic acid,4TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2793.9	Semi standard non polar	33892256
Gulonic acid,4TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O	2803.2	Semi standard non polar	33892256
Gulonic acid,4TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C	2798.2	Semi standard non polar	33892256
Gulonic acid,4TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2792.2	Semi standard non polar	33892256
Gulonic acid,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O	3009.4	Semi standard non polar	33892256
Gulonic acid,5TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C	3005.2	Semi standard non polar	33892256
Gulonic acid,5TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2991.5	Semi standard non polar	33892256
Gulonic acid,5TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2988.2	Semi standard non polar	33892256
Gulonic acid,5TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2988.3	Semi standard non polar	33892256
Gulonic acid,5TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO)O[Si](C)(C)C(C)(C)C	2997.1	Semi standard non polar	33892256
Gulonic acid,6TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3213.8	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Endoplasmic reticulum

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Both	Normal	22411374	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

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

Not Available

METLIN ID

344

PubChem Compound

152304

PDB ID

Not Available

ChEBI ID

87753

Food Biomarker Ontology

Not Available

VMH ID

GULN

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

ASHWELL G, KANFER J, SMILEY JD, BURNS JJ: Metabolism of ascorbic acid and related uronic acids, aldonic acids, and pentoses. Ann N Y Acad Sci. 1961 Apr 21;92:105-14. [PubMed:13684759 ]
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 ]

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

Enzyme Details

2. Lambda-crystallin homolog

General function:: Involved in 3-hydroxyacyl-CoA dehydrogenase activity
Specific function:: Not Available
Gene Name:: CRYL1
Uniprot ID:: Q9Y2S2
Molecular weight:: 35418.91

Reactions

Gulonic acid + NAD → 3-Dehydro-L-gulonate + NADH	details
Gulonic acid + NAD → 3-Dehydro-L-gulonate + NADH + Hydrogen Ion	details

Showing metabocard for Gulonic acid (HMDB0003290)

MOL for HMDB0003290 (Gulonic acid)

3D MOL for HMDB0003290 (Gulonic acid)

3D SDF for HMDB0003290 (Gulonic acid)

3D-SDF for HMDB0003290 (Gulonic acid)

PDB for HMDB0003290 (Gulonic acid)

3D PDB for HMDB0003290 (Gulonic acid)

SMILES for HMDB0003290 (Gulonic acid)

INCHI for HMDB0003290 (Gulonic acid)

Structure for HMDB0003290 (Gulonic acid)

3D Structure for HMDB0003290 (Gulonic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

Reactions

Reactions