NP-MRD: Showing NP-Card for Glucoheptonic acid (NP0084063)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-29 04:54:56 UTC

Updated at

2022-04-29 04:54:56 UTC

NP-MRD ID

NP0084063

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Glucoheptonic acid

Description

2,3,4,5,6,7-Hexahydroxyheptanoic acid, also known as (2xi)-D-glycero-D-gulo-heptonic acid or (2xi)-D-gluco-heptonate, belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group. An unspecified mixture of (2R)- and 2(S)-D-gluco-heptonic acid. Glucoheptonic acid is found in Pogostemon cablin and Triticum aestivum . 2,3,4,5,6,7-Hexahydroxyheptanoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 28  0  0  0  0  0  0  0  0999 V2000
    4.3008   -1.7205   -1.1476 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4641   -0.7792   -1.1288 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9745    0.4900   -1.4306 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0239   -0.9789   -0.8097 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8415   -2.3256   -0.5612 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6875   -0.1075    0.3524 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4994   -0.4416    1.4473 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2596   -0.2294    0.8120 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0960    0.6686    1.8773 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7456    0.1100   -0.2364 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6025    1.4024   -0.7230 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1233   -0.0107    0.3803 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3487   -1.2844    0.8951 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2124    0.2720   -0.6274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4428    0.2117    0.0133 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4648    1.0312   -0.7243 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4587   -0.6388   -1.7022 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2434   -2.5339    0.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9366    0.9390    0.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1315    0.0744    2.2168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0290   -1.2377    1.2084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1862    1.5261    1.4699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7246   -0.5680   -1.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2230    2.0432   -0.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2467    0.7059    1.2234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7974   -1.8147    0.2029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2216   -0.4659   -1.4451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1226    1.2860   -1.0694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4142   -0.5647    0.6234 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 12  1  0
 12 13  1  0
 12 10  1  0
 10 11  1  0
 10  8  1  0
  8  9  1  0
  8  6  1  0
  6  7  1  0
  6  4  1  0
  4  5  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
 15 29  1  0
 14 27  1  0
 14 28  1  0
 12 25  1  1
 13 26  1  0
 10 23  1  6
 11 24  1  0
  8 21  1  1
  9 22  1  0
  6 19  1  6
  7 20  1  0
  4 17  1  6
  5 18  1  0
  3 16  1  0
M  END


  Mrv1652306071803372D          

 15 14  0  0  1  0            999 V2000
   -3.2151   -0.1547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006    0.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -0.1547    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7862   -0.9797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    0.2578    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0717    1.0828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.1547    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3572   -0.9797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    0.2578    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3572    1.0828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.9797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    0.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006   -0.1547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    1.0828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  0  0  0  0
  3  4  1  6  0  0  0
  5  3  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0084063

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H14O8/c8-1-2(9)3(10)4(11)5(12)6(13)7(14)15/h2-6,8-13H,1H2,(H,14,15)/t2-,3-,4+,5-,6?/m1/s1

> <INCHI_KEY>
KWMLJOLKUYYJFJ-GASJEMHNSA-N

> <FORMULA>
C7H14O8

> <MOLECULAR_WEIGHT>
226.181

> <EXACT_MASS>
226.068867411

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
19.73535589342621

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,4S,5R,6R)-2,3,4,5,6,7-hexahydroxyheptanoic acid

> <ALOGPS_LOGP>
-2.62

> <JCHEM_LOGP>
-4.040079252666667

> <ALOGPS_LOGS>
-0.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.467210588266337

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.384685145485425

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9742118640167448

> <JCHEM_POLAR_SURFACE_AREA>
158.68

> <JCHEM_REFRACTIVITY>
44.2335

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.33e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2xi)-D-gluco-heptonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-JUN-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JUN-18         0                                  
HETATM    1  O   UNK     0      -6.002  -0.289   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.668   0.481   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.334  -0.289   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -3.334  -1.829   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.001   0.481   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.001   2.021   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.667  -0.289   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.667  -1.829   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.667   0.481   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.667   2.021   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.001  -0.289   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.001  -1.829   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.334   0.481   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.668  -0.289   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       3.334   2.021   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

View in JSmol

Synonyms

Value	Source
(2XI)-D-glycero-D-gulo-heptonic acid	ChEBI
(2XI)-D-glycero-D-ido-heptonic acid	ChEBI
(2XI)-D-glycero-D-gulo-heptonate	Generator
(2XI)-D-glycero-D-ido-heptonate	Generator
2,3,4,5,6,7-Hexahydroxyheptanoate	Generator
(2XI)-D-gluco-heptonate	HMDB

Chemical Formula

C₇H₁₄O₈

Average Mass

226.1810 Da

Monoisotopic Mass

226.06887 Da

IUPAC Name

(3R,4S,5R,6R)-2,3,4,5,6,7-hexahydroxyheptanoic acid

Traditional Name

(2xi)-D-gluco-heptonic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C7H14O8/c8-1-2(9)3(10)4(11)5(12)6(13)7(14)15/h2-6,8-13H,1H2,(H,14,15)/t2-,3-,4+,5-,6?/m1/s1

InChI Key

KWMLJOLKUYYJFJ-GASJEMHNSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
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, 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	¹³C NMR Spectrum (1D, 126 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, 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	¹³C NMR Spectrum (1D, 176 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, 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
Pogostemon cablin	LOTUS Database	35616633
Triticum aestivum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Sugar acids and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:59201 )
carbohydrate acid (CHEBI:59201 )

Physical Properties

State

Not Available

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
logP	-2.6	ALOGPS
logP	-4	ChemAxon
logS	-0.23	ALOGPS
pKa (Strongest Acidic)	3.38	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	158.68 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	44.23 m³·mol⁻¹	ChemAxon
Polarizability	19.74 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

HMDB0240292

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

55750

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

61888

PDB ID

Not Available

ChEBI ID

59201

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Glucoheptonic acid (NP0084063)

MOL for NP0084063 (Glucoheptonic acid)

3D MOL for NP0084063 (Glucoheptonic acid)

3D SDF for NP0084063 (Glucoheptonic acid)

3D-SDF for NP0084063 (Glucoheptonic acid)

PDB for NP0084063 (Glucoheptonic acid)

3D PDB for NP0084063 (Glucoheptonic acid)

SMILES for NP0084063 (Glucoheptonic acid)

INCHI for NP0084063 (Glucoheptonic acid)

Structure for NP0084063 (Glucoheptonic acid)

3D Structure for NP0084063 (Glucoheptonic acid)