NP-MRD: Showing NP-Card for (3s,4r,5s,6r,7r)-1,3,4,5,6,7,8-heptahydroxyoctan-2-one (NP0215784)

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Record Information

Version

2.0

Created at

2022-09-05 15:30:47 UTC

Updated at

2022-09-05 15:30:47 UTC

NP-MRD ID

NP0215784

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,4r,5s,6r,7r)-1,3,4,5,6,7,8-heptahydroxyoctan-2-one

Description

D-glycero-d-ido-octulose belongs to the class of organic compounds known as octoses. These are monosaccharide compounds in which the sugar moiety is an octose (8 carbon atoms). (3s,4r,5s,6r,7r)-1,3,4,5,6,7,8-heptahydroxyoctan-2-one is found in Craterostigma plantagineum. (3s,4r,5s,6r,7r)-1,3,4,5,6,7,8-heptahydroxyoctan-2-one was first documented in 2016 (PMID: 32480496). Based on a literature review very few articles have been published on d-glycero-d-ido-octulose.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 31  0  0  0  0  0  0  0  0999 V2000
   -3.9646   -0.9771   -0.5238 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1966   -0.0554   -0.3024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7492    1.3162   -0.4267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0904    1.2648   -0.7861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8063   -0.3611    0.0643 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6369   -1.7425    0.0859 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8170    0.1851   -0.9361 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1399   -0.4115   -2.1673 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5934   -0.2154   -0.6294 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3996    0.2555   -1.6577 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1190    0.2500    0.6717 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2085    1.6349    0.7998 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4151   -0.4585    0.9951 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7900   -0.1921    2.3362 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5746   -0.0326    0.1251 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6690   -0.8146    0.5874 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2018    1.9495   -1.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7087    1.8181    0.5787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2388    0.5347   -1.4520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6291    0.0026    1.0903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2925   -2.1241   -0.5511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8596    1.2603   -1.0723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0768   -1.3908   -2.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6753   -1.3254   -0.6599 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4844   -0.3766   -2.4125 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4321   -0.0450    1.5296 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6318    2.0709    0.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3245   -1.5551    0.9217 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2576   -0.8311    2.8939 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8592    1.0152    0.2383 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4535   -0.3712   -0.9268 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5204   -0.2777    0.5118 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 13  1  0
 13 14  1  0
 13 11  1  0
 11 12  1  0
 11  9  1  0
  9 10  1  0
  9  7  1  0
  7  8  1  0
  7  5  1  0
  5  6  1  0
  5  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  1  0
 16 32  1  0
 15 30  1  0
 15 31  1  0
 13 28  1  1
 14 29  1  0
 11 26  1  1
 12 27  1  0
  9 24  1  1
 10 25  1  0
  7 22  1  6
  8 23  1  0
  5 20  1  1
  6 21  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  0
M  END


  Mrv1652309052217302D          

 16 15  0  0  1  0            999 V2000
    3.7125    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4270    3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1414    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8559    3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5704    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2849    3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  2  5  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  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0215784

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H16O8/c9-1-3(11)5(13)7(15)8(16)6(14)4(12)2-10/h3,5-11,13-16H,1-2H2/t3-,5-,6-,7+,8+/m1/s1

> <INCHI_KEY>
KSHYQYHHIKNYAY-KYEGTCRESA-N

> <FORMULA>
C8H16O8

> <MOLECULAR_WEIGHT>
240.208

> <EXACT_MASS>
240.084517475

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
21.768693334250017

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,4R,5S,6R,7R)-1,3,4,5,6,7,8-heptahydroxyoctan-2-one

> <JCHEM_LOGP>
-4.527701776

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.949971202455146

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.973150468989369

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9742118570300082

> <JCHEM_POLAR_SURFACE_AREA>
158.68

> <JCHEM_REFRACTIVITY>
49.486799999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4R,5S,6R,7R)-1,3,4,5,6,7,8-heptahydroxyoctan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  O   UNK     0       6.930   2.461   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.596   4.771   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.263   4.001   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       8.264   6.311   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       9.597   2.461   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      10.931   6.311   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      12.265   2.461   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      13.598   4.771   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      13.598   6.311   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      16.266   4.771   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    2    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   16                                                       
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₈H₁₆O₈

Average Mass

240.2080 Da

Monoisotopic Mass

240.08452 Da

IUPAC Name

(3S,4R,5S,6R,7R)-1,3,4,5,6,7,8-heptahydroxyoctan-2-one

Traditional Name

(3S,4R,5S,6R,7R)-1,3,4,5,6,7,8-heptahydroxyoctan-2-one

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C8H16O8/c9-1-3(11)5(13)7(15)8(16)6(14)4(12)2-10/h3,5-11,13-16H,1-2H2/t3-,5-,6-,7+,8+/m1/s1

InChI Key

KSHYQYHHIKNYAY-KYEGTCRESA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Craterostigma plantagineum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as octoses. These are monosaccharide compounds in which the sugar moiety is an octose (8 carbon atoms).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Octoses

Alternative Parents

Substituents

Octose monosaccharide
Beta-hydroxy ketone
Acyloin
Alpha-hydroxy ketone
Secondary alcohol
Ketone
1,2-diol
Polyol
Organic oxide
Hydrocarbon derivative
Primary alcohol
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

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	-4.5	ChemAxon
pKa (Strongest Acidic)	8.97	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	158.68 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	49.49 m³·mol⁻¹	ChemAxon
Polarizability	21.77 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

8529702

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10354250

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang Q, Bartels D: Physiological factors determine the accumulation of D-glycero-D-ido-octulose (D-g-D-i-oct) in the desiccation tolerant resurrection plant Craterostigma plantagineum. Funct Plant Biol. 2016 Jul;43(7):684-694. doi: 10.1071/FP15278. [PubMed:32480496 ]
LOTUS database [Link]

Showing NP-Card for (3s,4r,5s,6r,7r)-1,3,4,5,6,7,8-heptahydroxyoctan-2-one (NP0215784)

MOL for NP0215784 ((3s,4r,5s,6r,7r)-1,3,4,5,6,7,8-heptahydroxyoctan-2-one)

3D MOL for NP0215784 ((3s,4r,5s,6r,7r)-1,3,4,5,6,7,8-heptahydroxyoctan-2-one)

3D SDF for NP0215784 ((3s,4r,5s,6r,7r)-1,3,4,5,6,7,8-heptahydroxyoctan-2-one)

3D-SDF for NP0215784 ((3s,4r,5s,6r,7r)-1,3,4,5,6,7,8-heptahydroxyoctan-2-one)

PDB for NP0215784 ((3s,4r,5s,6r,7r)-1,3,4,5,6,7,8-heptahydroxyoctan-2-one)

3D PDB for NP0215784 ((3s,4r,5s,6r,7r)-1,3,4,5,6,7,8-heptahydroxyoctan-2-one)

SMILES for NP0215784 ((3s,4r,5s,6r,7r)-1,3,4,5,6,7,8-heptahydroxyoctan-2-one)

INCHI for NP0215784 ((3s,4r,5s,6r,7r)-1,3,4,5,6,7,8-heptahydroxyoctan-2-one)

Structure for NP0215784 ((3s,4r,5s,6r,7r)-1,3,4,5,6,7,8-heptahydroxyoctan-2-one)

3D Structure for NP0215784 ((3s,4r,5s,6r,7r)-1,3,4,5,6,7,8-heptahydroxyoctan-2-one)