NP-MRD: Showing NP-Card for Gulonic acid (NP0001130)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2006-05-22 15:12:47 UTC

Updated at

2021-06-29 00:47:43 UTC

NP-MRD ID

NP0001130

Secondary Accession Numbers

None

Natural Product 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.It is a gulonic acid having D-configuration.

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>
NP0001130

> <DATABASE_NAME>
NP-MRD

> <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

Synonyms

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

Chemical Formula

C₆H₁₂O₇

Average Mass

196.1553 Da

Monoisotopic Mass

196.05830 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Annona squamosa	KNApSAcK Database	22123792
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Centella asiatica	LOTUS Database	35616633
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Lotus burttii	LOTUS Database	35616633
Lotus corniculatus	LOTUS Database	35616633
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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

Physical Properties

State

Solid

Experimental 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

Predicted 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

External Links

HMDB ID

HMDB0003290

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

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 ]
Liu L, Chen Y, Yu S, Chen J, Zhou J: Simultaneous transformation of five vectors in Gluconobacter oxydans. Plasmid. 2021 Jul 10;117:102588. doi: 10.1016/j.plasmid.2021.102588. [PubMed:34256060 ]
Chen Y, Zhou J, Chen J: [Progress in vitamin C biosynthesis related dehydrogenases]. Sheng Wu Gong Cheng Xue Bao. 2021 Jun 25;37(6):1827-1844. doi: 10.13345/j.cjb.200449. [PubMed:34227279 ]
Sun X, Wang J, Song S, Yang Z, Duan Y, Lai J: [Metabolomics study on the newborns of pregnant women with gestational diabetes]. Wei Sheng Yan Jiu. 2021 May;50(3):466-471. doi: 10.19813/j.cnki.weishengyanjiu.2021.03.020. [PubMed:34074370 ]
Chen Y, Liu L, Yu S, Li J, Zhou J, Chen J: Identification of Gradient Promoters of Gluconobacter oxydans and Their Applications in the Biosynthesis of 2-Keto-L-Gulonic Acid. Front Bioeng Biotechnol. 2021 Apr 9;9:673844. doi: 10.3389/fbioe.2021.673844. eCollection 2021. [PubMed:33898410 ]
Luo Z, Yu S, Zeng W, Zhou J: Comparative analysis of the chemical and biochemical synthesis of keto acids. Biotechnol Adv. 2021 Mar-Apr;47:107706. doi: 10.1016/j.biotechadv.2021.107706. Epub 2021 Feb 4. [PubMed:33548455 ]
Yang W, Sun H, Dong D, Ma S, Mandlaa, Wang Z, Xu H: Enhanced 2-keto-L-gulonic acid production by a mixed culture of Ketogulonicigenium vulgare and Bacillus megaterium using three-stage temperature control strategy. Braz J Microbiol. 2021 Mar;52(1):257-265. doi: 10.1007/s42770-020-00396-w. Epub 2020 Nov 4. [PubMed:33145708 ]
Zeng W, Wang P, Li N, Li J, Chen J, Zhou J: Production of 2-keto-L-gulonic acid by metabolically engineered Escherichia coli. Bioresour Technol. 2020 Dec;318:124069. doi: 10.1016/j.biortech.2020.124069. Epub 2020 Sep 3. [PubMed:32916460 ]
Duan Y, Xiong D, Wang Y, Li H, Dong H, Zhang J: Toxic effects of ammonia and thermal stress on the intestinal microbiota and transcriptomic and metabolomic responses of Litopenaeus vannamei. Sci Total Environ. 2021 Feb 1;754:141867. doi: 10.1016/j.scitotenv.2020.141867. Epub 2020 Aug 21. [PubMed:32898779 ]
Fang J, Wan H, Zeng W, Li J, Chen J, Zhou J: Transcriptome Analysis of Gluconobacter oxydans WSH-003 Exposed to Elevated 2-Keto-L-Gulonic Acid Reveals the Responses to Osmotic and Oxidative Stress. Appl Biochem Biotechnol. 2021 Jan;193(1):128-141. doi: 10.1007/s12010-020-03405-8. Epub 2020 Aug 22. [PubMed:32827065 ]

Showing NP-Card for Gulonic acid (NP0001130)

MOL for NP0001130 (Gulonic acid)

3D MOL for NP0001130 (Gulonic acid)

3D SDF for NP0001130 (Gulonic acid)

3D-SDF for NP0001130 (Gulonic acid)

PDB for NP0001130 (Gulonic acid)

3D PDB for NP0001130 (Gulonic acid)

SMILES for NP0001130 (Gulonic acid)

INCHI for NP0001130 (Gulonic acid)

Structure for NP0001130 (Gulonic acid)

3D Structure for NP0001130 (Gulonic acid)