NP-MRD: Showing NP-Card for 3-(3,4-dihydroxy-5-oxooxolan-2-yl)-2-hydroxypropanoic acid (NP0151221)

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Record Information

Version

2.0

Created at

2022-09-02 07:30:35 UTC

Updated at

2022-09-02 07:30:35 UTC

NP-MRD ID

NP0151221

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(3,4-dihydroxy-5-oxooxolan-2-yl)-2-hydroxypropanoic acid

Description

3-(3,4-Dihydroxy-5-oxooxolan-2-yl)-2-hydroxypropanoic acid 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. 3-(3,4-dihydroxy-5-oxooxolan-2-yl)-2-hydroxypropanoic acid is found in Cereus repandus. 3-(3,4-Dihydroxy-5-oxooxolan-2-yl)-2-hydroxypropanoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241508042D          

 14 14  0  0  0  0            999 V2000
   -0.8612    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    3.5893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    3.5893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0151221

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(CC1OC(=O)C(O)C1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H10O7/c8-2(6(11)12)1-3-4(9)5(10)7(13)14-3/h2-5,8-10H,1H2,(H,11,12)

> <INCHI_KEY>
FHTUHRLYAPRFEZ-UHFFFAOYSA-N

> <FORMULA>
C7H10O7

> <MOLECULAR_WEIGHT>
206.15

> <EXACT_MASS>
206.042652662

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
17.65876218219629

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(3,4-dihydroxy-5-oxooxolan-2-yl)-2-hydroxypropanoic acid

> <ALOGPS_LOGP>
-2.06

> <JCHEM_LOGP>
-2.365038909

> <ALOGPS_LOGS>
-0.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.641558010364164

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2431241213899136

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7020385512225173

> <JCHEM_POLAR_SURFACE_AREA>
124.29

> <JCHEM_REFRACTIVITY>
39.51160000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.65e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(3,4-dihydroxy-5-oxooxolan-2-yl)-2-hydroxypropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  O   UNK     0      -1.608   3.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.274   4.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.306   1.175   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.735  -1.536   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.615  -1.536   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.651   1.651   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.274   5.930   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.608   6.700   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       1.060   6.700   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    4   11                                                  
CONECT   11   10                                                            
CONECT   12    2   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol

Synonyms

Value	Source
3-(3,4-Dihydroxy-5-oxooxolan-2-yl)-2-hydroxypropanoate	Generator

Chemical Formula

C₇H₁₀O₇

Average Mass

206.1500 Da

Monoisotopic Mass

206.04265 Da

IUPAC Name

3-(3,4-dihydroxy-5-oxooxolan-2-yl)-2-hydroxypropanoic acid

Traditional Name

3-(3,4-dihydroxy-5-oxooxolan-2-yl)-2-hydroxypropanoic acid

CAS Registry Number

Not Available

SMILES

OC(CC1OC(=O)C(O)C1O)C(O)=O

InChI Identifier

InChI=1S/C7H10O7/c8-2(6(11)12)1-3-4(9)5(10)7(13)14-3/h2-5,8-10H,1H2,(H,11,12)

InChI Key

FHTUHRLYAPRFEZ-UHFFFAOYSA-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
Cereus repandus	LOTUS Database	35616633

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

Sugar acid
Alpha-hydroxy acid
Dicarboxylic acid or derivatives
Gamma butyrolactone
Hydroxy acid
Monosaccharide
Tetrahydrofuran
Secondary alcohol
Lactone
Carboxylic acid ester
Carboxylic acid derivative
Carboxylic acid
Organoheterocyclic compound
Oxacycle
Carbonyl group
Alcohol
Organic oxide
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	-2.1	ALOGPS
logP	-2.4	ChemAxon
logS	-0.1	ALOGPS
pKa (Strongest Acidic)	3.24	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	124.29 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	39.51 m³·mol⁻¹	ChemAxon
Polarizability	17.66 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

130020481

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-(3,4-dihydroxy-5-oxooxolan-2-yl)-2-hydroxypropanoic acid (NP0151221)

MOL for NP0151221 (3-(3,4-dihydroxy-5-oxooxolan-2-yl)-2-hydroxypropanoic acid)

3D MOL for NP0151221 (3-(3,4-dihydroxy-5-oxooxolan-2-yl)-2-hydroxypropanoic acid)

3D SDF for NP0151221 (3-(3,4-dihydroxy-5-oxooxolan-2-yl)-2-hydroxypropanoic acid)

3D-SDF for NP0151221 (3-(3,4-dihydroxy-5-oxooxolan-2-yl)-2-hydroxypropanoic acid)

PDB for NP0151221 (3-(3,4-dihydroxy-5-oxooxolan-2-yl)-2-hydroxypropanoic acid)

3D PDB for NP0151221 (3-(3,4-dihydroxy-5-oxooxolan-2-yl)-2-hydroxypropanoic acid)

SMILES for NP0151221 (3-(3,4-dihydroxy-5-oxooxolan-2-yl)-2-hydroxypropanoic acid)

INCHI for NP0151221 (3-(3,4-dihydroxy-5-oxooxolan-2-yl)-2-hydroxypropanoic acid)

Structure for NP0151221 (3-(3,4-dihydroxy-5-oxooxolan-2-yl)-2-hydroxypropanoic acid)

3D Structure for NP0151221 (3-(3,4-dihydroxy-5-oxooxolan-2-yl)-2-hydroxypropanoic acid)