NP-MRD: Showing NP-Card for D-Manno-2-heptulose (NP0044896)

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Record Information

Version

2.0

Created at

2022-03-10 18:45:59 UTC

Updated at

2022-03-10 22:19:58 UTC

NP-MRD ID

NP0044896

Secondary Accession Numbers

None

Natural Product Identification

Common Name

D-Manno-2-heptulose

Description

D-Manno-2-heptulose, also called 1,3,4,5,6,7-Hexahydroxyheptan-2-one or mannoheptulose, belongs to the class of organic compounds known as heptoses. Heptoses are monosaccharides with seven carbon atoms in their structure. D-manno-2-heptulose is one of the few naturally occurring heptoses found primarily in alfalfa, avocados, and primrose (PMID: 31293606 ). D-manno-2-heptulose is also found in cannabis plants (PMID: 6991645 ). Though the carbohydrate is thought to be produced during photosynthesis, the precise biological pathway for the synthesis of mannoheptulose is still unknown. Like other sugars, it is transported in the plant through the phloem. Because it inhibits glycolysis in vitro, it has been investigated as a novel nutraceutical for weight management in dogs. However, while it is suggested that mannoheptulose affects the energy balance of adult dogs, research is still inconclusive regarding the significance of the alteration of energy expenditure in dogs (PMID: 26479244 , PMID: 26656105 , PMID: 28444793 ).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652303192000263D          

 14 13  0  0  0  0            999 V2000
   -2.7576   -0.5550    0.4867 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2129   -0.7643   -0.2904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2321    0.2890   -0.6651 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5991    0.1919    0.6482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9808    1.0294   -0.2837 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3979    0.9541    0.2806 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1831    0.0972   -0.0213 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9959   -1.0875    0.0766 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4021   -1.2975    0.2715 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0699   -0.4924   -1.7946 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1015    0.3459    1.7370 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2038    1.7898    0.8471 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0948    1.7908    1.3911 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4562   -0.7036   -1.1173 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  1  8  1  0  0  0  0
  2  4  1  0  0  0  0
  2  9  1  0  0  0  0
  3  5  1  0  0  0  0
  3 10  1  0  0  0  0
  4  6  1  0  0  0  0
  4 11  2  0  0  0  0
  5  7  1  0  0  0  0
  5 12  1  0  0  0  0
  6  7  1  0  0  0  0
  6 13  1  0  0  0  0
  7 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0044896

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H14O7/c8-1-3(10)5(12)7(14)6(13)4(11)2-9/h3,5-10,12-14H,1-2H2/t3-,5+,6-,7+/m0/s1

> <INCHI_KEY>
HSNZZMHEPUFJNZ-HTPUFBNKSA-N

> <FORMULA>
C7H14O7

> <MOLECULAR_WEIGHT>
210.182

> <EXACT_MASS>
210.073952791

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
18.98736083737949

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,4R,5R,6S)-1,3,4,5,6,7-hexahydroxyheptan-2-one

> <ALOGPS_LOGP>
-2.38

> <JCHEM_LOGP>
-3.8973668339999996

> <ALOGPS_LOGS>
0.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.265927956358581

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.913410871547823

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9742199929740236

> <JCHEM_POLAR_SURFACE_AREA>
138.45

> <JCHEM_REFRACTIVITY>
43.5243

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.27e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,4R,5R,6S)-1,3,4,5,6,7-hexahydroxyheptan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-MAR-20         0                                  
HETATM    1  C   UNK     0      -2.758  -0.555   0.487  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.213  -0.764  -0.290  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.232   0.289  -0.665  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.599   0.192   0.648  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.981   1.029  -0.284  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.398   0.954   0.281  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.183   0.097  -0.021  0.00  0.00           C+0
HETATM    8  O   UNK     0      -3.996  -1.087   0.077  0.00  0.00           O+0
HETATM    9  O   UNK     0       4.402  -1.298   0.272  0.00  0.00           O+0
HETATM   10  O   UNK     0      -2.070  -0.492  -1.795  0.00  0.00           O+0
HETATM   11  O   UNK     0       3.102   0.346   1.737  0.00  0.00           O+0
HETATM   12  O   UNK     0      -1.204   1.790   0.847  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.095   1.791   1.391  0.00  0.00           O+0
HETATM   14  O   UNK     0       0.456  -0.704  -1.117  0.00  0.00           O+0
CONECT    1    3    8                                                       
CONECT    2    4    9                                                       
CONECT    3    1    5   10                                                  
CONECT    4    2    6   11                                                  
CONECT    5    3    7   12                                                  
CONECT    6    4    7   13                                                  
CONECT    7    5    6   14                                                  
CONECT    8    1                                                            
CONECT    9    2                                                            
CONECT   10    3                                                            
CONECT   11    4                                                            
CONECT   12    5                                                            
CONECT   13    6                                                            
CONECT   14    7                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₇H₁₄O₇

Average Mass

210.1820 Da

Monoisotopic Mass

210.07395 Da

IUPAC Name

(3R,4R,5R,6S)-1,3,4,5,6,7-hexahydroxyheptan-2-one

Traditional Name

(3R,4R,5R,6S)-1,3,4,5,6,7-hexahydroxyheptan-2-one

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C7H14O7/c8-1-3(10)5(12)7(14)6(13)4(11)2-9/h3,5-10,12-14H,1-2H2/t3-,5+,6-,7+/m0/s1

InChI Key

HSNZZMHEPUFJNZ-HTPUFBNKSA-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
Cannabis sativa	NULL	Not Available
Persea americana	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Classification

Not classified

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	-2.4	ALOGPS
logP	-3.9	ChemAxon
logS	0.03	ALOGPS
pKa (Strongest Acidic)	8.91	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	138.45 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	43.52 m³·mol⁻¹	ChemAxon
Polarizability	18.99 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25791640

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for D-Manno-2-heptulose (NP0044896)

MOL for NP0044896 (D-Manno-2-heptulose)

3D MOL for NP0044896 (D-Manno-2-heptulose)

3D SDF for NP0044896 (D-Manno-2-heptulose)

3D-SDF for NP0044896 (D-Manno-2-heptulose)

PDB for NP0044896 (D-Manno-2-heptulose)

3D PDB for NP0044896 (D-Manno-2-heptulose)

SMILES for NP0044896 (D-Manno-2-heptulose)

INCHI for NP0044896 (D-Manno-2-heptulose)

Structure for NP0044896 (D-Manno-2-heptulose)

3D Structure for NP0044896 (D-Manno-2-heptulose)