NP-MRD: Showing NP-Card for Ascorbalamic acid (NP0084758)

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Record Information

Version

2.0

Created at

2022-04-29 05:25:09 UTC

Updated at

2022-04-29 05:25:09 UTC

NP-MRD ID

NP0084758

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ascorbalamic acid

Description

Ascorbalamic acid, also known as ascorbalamate, belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Ascorbalamic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Ascorbalamic acid has been detected, but not quantified in, brassicas. Ascorbalamic acid is found in Brassica oleracea . This could make ascorbalamic acid a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 32  0  0  0  0  0  0  0  0999 V2000
    3.5613    1.5736   -2.2504 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4406    1.4664   -1.0018 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9766    2.4685   -0.2234 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7654    0.3391   -0.3599 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4951    0.7795    0.3829 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7462   -0.5181    0.4216 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2473   -1.3228    1.4261 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7312   -0.3664    0.5754 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9786    0.1985    1.8258 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3938   -1.5637    0.5136 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6943   -1.3505    0.1500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8418    0.0517   -0.3340 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5022    0.1612   -1.5514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3759    0.4911   -0.4569 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3234    1.8277   -0.0701 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1317   -1.1338   -0.8751 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4191   -2.0952   -1.5695 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2532   -0.6325   -1.2720 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6370    2.3489    0.5195 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4375   -0.1172    0.4037 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9933    1.5580   -0.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8178    1.1206    1.3702 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7085   -2.1607    1.4825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0972   -0.4770    2.5390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3763   -1.5721    1.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9795   -2.0879   -0.6556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3505    0.6500    0.4627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2134    0.8520   -1.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0123    0.3103   -1.4729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1976    2.2618   -0.0216 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4374   -3.0607   -1.2288 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  8  1  0
  8  9  1  1
  8 14  1  0
 14 15  1  0
  8  6  1  0
  6  7  1  1
  6  5  1  0
  5  4  1  0
  4 18  1  0
 18 16  2  0
 16 17  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
 14 12  1  0
 16  6  1  0
 13 28  1  0
 12 27  1  1
 11 25  1  0
 11 26  1  0
  9 24  1  0
 14 29  1  6
 15 30  1  0
  7 23  1  0
  5 21  1  0
  5 22  1  0
  4 20  1  1
 17 31  1  0
  3 19  1  0
M  END


  Mrv0541 05061304552D          

 18 19  0  0  0  0            999 V2000
   -0.6568    1.2495    0.0000 C   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
   -1.3191    1.7414    0.0000 C   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
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1063    1.4947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2310    2.5146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0157    1.7274    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
   -1.0559    2.5233    0.0000 N   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
    2.0198    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7136    2.0531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2863    0.6895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2609    3.1770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7966    1.9704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1787    1.6095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  4  1  0  0  0  0
  6  3  1  0  0  0  0
  8  1  1  0  0  0  0
  8  7  1  0  0  0  0
  9  5  1  0  0  0  0
  9  8  1  0  0  0  0
 10  3  1  0  0  0  0
 10  7  2  0  0  0  0
 11  4  1  0  0  0  0
 12  5  1  0  0  0  0
 13  6  2  0  0  0  0
 14  6  1  0  0  0  0
 15  7  1  0  0  0  0
 16  8  1  0  0  0  0
 17  9  1  0  0  0  0
 18  2  1  0  0  0  0
 18  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0084758

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1COC(O)(C1O)C1(O)CC(N=C1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H13NO8/c11-4-2-18-9(17,5(4)12)8(16)1-3(6(13)14)10-7(8)15/h3-5,11-12,16-17H,1-2H2,(H,10,15)(H,13,14)

> <INCHI_KEY>
FLVJBXHFHKVHJN-UHFFFAOYSA-N

> <FORMULA>
C9H13NO8

> <MOLECULAR_WEIGHT>
263.2014

> <EXACT_MASS>
263.064116397

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
22.62762495679913

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,5-dihydroxy-4-(2,3,4-trihydroxyoxolan-2-yl)-3,4-dihydro-2H-pyrrole-2-carboxylic acid

> <ALOGPS_LOGP>
-2.51

> <JCHEM_LOGP>
-2.547054878

> <ALOGPS_LOGS>
-0.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.067282740733736

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.201214932567862

> <JCHEM_PKA_STRONGEST_BASIC>
-0.435019075803568

> <JCHEM_POLAR_SURFACE_AREA>
160.04

> <JCHEM_REFRACTIVITY>
52.1598

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.84e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,5-dihydroxy-4-(2,3,4-trihydroxyoxolan-2-yl)-2,3-dihydropyrrole-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -1.226   2.332   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.462   3.251   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.932   2.790   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.431   4.694   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.029   3.224   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -1.971   4.710   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0       2.735  -1.536   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       3.770   1.651   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -5.065   3.832   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -4.268   1.287   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       0.487   5.930   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       1.487   3.678   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.200   3.004   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -0.186   1.175   0.000  0.00  0.00           O+0
CONECT    1    3    8                                                       
CONECT    2    4   18                                                       
CONECT    3    1    6   10                                                  
CONECT    4    2    5   11                                                  
CONECT    5    4    9   12                                                  
CONECT    6    3   13   14                                                  
CONECT    7    8   10   15                                                  
CONECT    8    1    7    9   16                                             
CONECT    9    5    8   17   18                                             
CONECT   10    3    7                                                       
CONECT   11    4                                                            
CONECT   12    5                                                            
CONECT   13    6                                                            
CONECT   14    6                                                            
CONECT   15    7                                                            
CONECT   16    8                                                            
CONECT   17    9                                                            
CONECT   18    2    9                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Value	Source
Ascorbalamate	Generator
4,5-Dihydroxy-4-(2,3,4-trihydroxyoxolan-2-yl)-3,4-dihydro-2H-pyrrole-2-carboxylate	Generator

Chemical Formula

C₉H₁₃NO₈

Average Mass

263.2014 Da

Monoisotopic Mass

263.06412 Da

IUPAC Name

4,5-dihydroxy-4-(2,3,4-trihydroxyoxolan-2-yl)-3,4-dihydro-2H-pyrrole-2-carboxylic acid

Traditional Name

4,5-dihydroxy-4-(2,3,4-trihydroxyoxolan-2-yl)-2,3-dihydropyrrole-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

OC1COC(O)(C1O)C1(O)CC(N=C1O)C(O)=O

InChI Identifier

InChI=1S/C9H13NO8/c11-4-2-18-9(17,5(4)12)8(16)1-3(6(13)14)10-7(8)15/h3-5,11-12,16-17H,1-2H2,(H,10,15)(H,13,14)

InChI Key

FLVJBXHFHKVHJN-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, 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
Brassica oleracea	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Proline and derivatives

Alternative Parents

Substituents

Proline or derivatives
Pentose monosaccharide
Oxoproline
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
Monosaccharide
Pyrrolidone
2-pyrrolidone
Pyrrolidine
Tertiary alcohol
Tetrahydrofuran
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Hemiacetal
Lactam
Azacycle
Oxacycle
Organoheterocyclic compound
Carboxylic acid
Polyol
Monocarboxylic acid or derivatives
Alcohol
Organonitrogen compound
Organic nitrogen compound
Organooxygen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
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	-2.5	ALOGPS
logP	-2.5	ChemAxon
logS	-0.16	ALOGPS
pKa (Strongest Acidic)	3.2	ChemAxon
pKa (Strongest Basic)	-0.44	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	160.04 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	52.16 m³·mol⁻¹	ChemAxon
Polarizability	22.63 Å³	ChemAxon
Number of Rings	2	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

HMDB0029944

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB001222

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

71437684

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Ascorbalamic acid (NP0084758)

MOL for NP0084758 (Ascorbalamic acid)

3D MOL for NP0084758 (Ascorbalamic acid)

3D SDF for NP0084758 (Ascorbalamic acid)

3D-SDF for NP0084758 (Ascorbalamic acid)

PDB for NP0084758 (Ascorbalamic acid)

3D PDB for NP0084758 (Ascorbalamic acid)

SMILES for NP0084758 (Ascorbalamic acid)

INCHI for NP0084758 (Ascorbalamic acid)

Structure for NP0084758 (Ascorbalamic acid)

3D Structure for NP0084758 (Ascorbalamic acid)