NP-MRD: Showing NP-Card for N-(3-Carboxy-3-hydroxypropyl)-4-[(carboxymethyl)amino]-L-allothreonine (NP0084993)

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Record Information

Version

2.0

Created at

2022-04-29 05:35:16 UTC

Updated at

2022-04-29 05:35:16 UTC

NP-MRD ID

NP0084993

Secondary Accession Numbers

None

Natural Product Identification

Common Name

N-(3-Carboxy-3-hydroxypropyl)-4-[(carboxymethyl)amino]-L-allothreonine

Description

Distichonic acid A, also known as distichonate a, belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom. Distichonic acid A is a very strong basic compound (based on its pKa). Outside of the human body, Distichonic acid A has been detected, but not quantified in, barley and cereals and cereal products. N-(3-Carboxy-3-hydroxypropyl)-4-[(carboxymethyl)amino]-L-allothreonine is found in Hordeum vulgare . This could make distichonic acid a a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 37  0  0  0  0  0  0  0  0999 V2000
    6.6402   -0.9227    0.0699 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7055   -0.2122   -0.1932 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9587    1.1953   -0.3769 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2577   -0.5816   -0.3691 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4366   -0.0968    0.6971 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2123    0.4412    0.1748 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1719   -0.4563   -0.3214 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5881   -1.5231   -1.1400 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0529   -0.6729    0.4700 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3009   -0.8943   -0.2477 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7734    0.2841   -0.9748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9129    0.9196   -0.1832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1703    0.1278   -0.1712 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9282   -0.0199   -1.2802 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8926    0.1739    1.0848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2926    0.4710    2.1754 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2466   -0.0633    1.2344 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0993   -1.9167    1.2941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0285   -1.9306    2.5302 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3886   -3.1255    0.6090 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8445    1.5958   -0.4410 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3055   -1.7300   -0.1900 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9062   -0.2979   -1.3174 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5289   -0.3963    1.6336 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4646    1.2795   -0.5221 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7610    1.0100    1.0505 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7234    0.2110   -1.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0516   -2.1302   -0.4500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2221    0.1957    1.1814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9563   -1.2988    0.4141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1879   -0.0787   -1.9316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0343    1.0761   -1.0929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6183    1.3168    0.7927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1733    1.8334   -0.8370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7253   -1.0431   -0.1381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6100    0.3121   -2.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8270   -0.3903    0.4642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0914   -3.2162   -0.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 17  1  0
 15 16  2  0
  9 18  1  0
 18 20  1  0
 18 19  2  0
  8 28  1  0
  7 27  1  6
  6 25  1  0
  6 26  1  0
  5 24  1  0
  4 22  1  0
  4 23  1  0
  3 21  1  0
  9 29  1  1
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  1
 14 36  1  0
 17 37  1  0
 20 38  1  0
M  END


  Mrv0541 05061310372D          

 20 19  0  0  0  0            999 V2000
    9.4283    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1427    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   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
    7.2849    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8572    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1427    3.3809    0.0000 O   0  0  0  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
    2.9980    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5717    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8572    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    3.7934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    3.7934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  5  1  1  0  0  0  0
  6  3  1  0  0  0  0
  7  4  1  0  0  0  0
  8  6  1  0  0  0  0
  9  5  1  0  0  0  0
 10  8  1  0  0  0  0
 11  3  1  0  0  0  0
 11  4  1  0  0  0  0
 12  2  1  0  0  0  0
 12  8  1  0  0  0  0
 13  5  1  0  0  0  0
 14  6  1  0  0  0  0
 15  7  2  0  0  0  0
 16  7  1  0  0  0  0
 17  9  2  0  0  0  0
 18  9  1  0  0  0  0
 19 10  2  0  0  0  0
 20 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0084993

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(CNCC(O)=O)C(NCCC(O)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H18N2O8/c13-5(9(17)18)1-2-12-8(10(19)20)6(14)3-11-4-7(15)16/h5-6,8,11-14H,1-4H2,(H,15,16)(H,17,18)(H,19,20)

> <INCHI_KEY>
SEATYFZPTMHEIW-UHFFFAOYSA-N

> <FORMULA>
C10H18N2O8

> <MOLECULAR_WEIGHT>
294.2585

> <EXACT_MASS>
294.106315562

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
27.1138594388019

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(3-carboxy-3-hydroxypropyl)amino]-4-[(carboxymethyl)amino]-3-hydroxybutanoic acid

> <ALOGPS_LOGP>
-2.69

> <JCHEM_LOGP>
-8.00046332621347

> <ALOGPS_LOGS>
-1.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
1.843216710758711

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.1019616880478416

> <JCHEM_PKA_STRONGEST_BASIC>
10.20797454412454

> <JCHEM_POLAR_SURFACE_AREA>
176.42

> <JCHEM_REFRACTIVITY>
62.282399999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.34e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(3-carboxy-3-hydroxypropyl)amino]-4-[(carboxymethyl)amino]-3-hydroxybutanoic 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      17.599   4.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      16.266   4.771   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      18.933   4.771   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.598   4.771   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      20.267   4.001   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.598   6.311   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       9.597   4.001   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0      14.932   4.001   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0      18.933   6.311   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      12.265   2.461   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       5.596   4.771   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       6.930   2.461   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      21.601   4.771   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      20.267   2.461   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      14.932   7.081   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      12.265   7.081   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1   12                                                       
CONECT    3    6   11                                                       
CONECT    4    7   11                                                       
CONECT    5    1    9   13                                                  
CONECT    6    3    8   14                                                  
CONECT    7    4   15   16                                                  
CONECT    8    6   10   12                                                  
CONECT    9    5   17   18                                                  
CONECT   10    8   19   20                                                  
CONECT   11    3    4                                                       
CONECT   12    2    8                                                       
CONECT   13    5                                                            
CONECT   14    6                                                            
CONECT   15    7                                                            
CONECT   16    7                                                            
CONECT   17    9                                                            
CONECT   18    9                                                            
CONECT   19   10                                                            
CONECT   20   10                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   38    0
END

View in JSmol

Synonyms

Value	Source
Distichonate a	Generator
2'-Distichonic acid a	HMDB
2'-Epi-distichonic acid a	HMDB
N-(3-Carboxy-3-hydroxypropyl)-4-[(carboxymethyl)amino]-L-allothreonine	HMDB
2-[(3-Carboxy-3-hydroxypropyl)amino]-4-[(carboxymethyl)amino]-3-hydroxybutanoate	Generator

Chemical Formula

C₁₀H₁₈N₂O₈

Average Mass

294.2585 Da

Monoisotopic Mass

294.10632 Da

IUPAC Name

2-[(3-carboxy-3-hydroxypropyl)amino]-4-[(carboxymethyl)amino]-3-hydroxybutanoic acid

Traditional Name

2-[(3-carboxy-3-hydroxypropyl)amino]-4-[(carboxymethyl)amino]-3-hydroxybutanoic acid

CAS Registry Number

Not Available

SMILES

OC(CNCC(O)=O)C(NCCC(O)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C10H18N2O8/c13-5(9(17)18)1-2-12-8(10(19)20)6(14)3-11-4-7(15)16/h5-6,8,11-14H,1-4H2,(H,15,16)(H,17,18)(H,19,20)

InChI Key

SEATYFZPTMHEIW-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
Hordeum vulgare	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Gamma amino acids and derivatives

Alternative Parents

Substituents

Gamma amino acid or derivatives
Alpha-amino acid
Alpha-amino acid or derivatives
Tricarboxylic acid or derivatives
Amino fatty acid
Beta-hydroxy acid
Hydroxy fatty acid
Alpha-hydroxy acid
Hydroxy acid
Monosaccharide
Fatty acyl
1,3-aminoalcohol
Secondary alcohol
1,2-aminoalcohol
Amino acid
Secondary amine
Secondary aliphatic amine
Carboxylic acid
Organonitrogen compound
Carbonyl group
Organic oxide
Organopnictogen compound
Amine
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
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	-2.7	ALOGPS
logP	-8	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	1.1	ChemAxon
pKa (Strongest Basic)	10.21	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	176.42 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	62.28 m³·mol⁻¹	ChemAxon
Polarizability	27.11 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0038752

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB018164

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

85405750

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for N-(3-Carboxy-3-hydroxypropyl)-4-[(carboxymethyl)amino]-L-allothreonine (NP0084993)

MOL for NP0084993 (N-(3-Carboxy-3-hydroxypropyl)-4-[(carboxymethyl)amino]-L-allothreonine)

3D MOL for NP0084993 (N-(3-Carboxy-3-hydroxypropyl)-4-[(carboxymethyl)amino]-L-allothreonine)

3D SDF for NP0084993 (N-(3-Carboxy-3-hydroxypropyl)-4-[(carboxymethyl)amino]-L-allothreonine)

3D-SDF for NP0084993 (N-(3-Carboxy-3-hydroxypropyl)-4-[(carboxymethyl)amino]-L-allothreonine)

PDB for NP0084993 (N-(3-Carboxy-3-hydroxypropyl)-4-[(carboxymethyl)amino]-L-allothreonine)

3D PDB for NP0084993 (N-(3-Carboxy-3-hydroxypropyl)-4-[(carboxymethyl)amino]-L-allothreonine)

SMILES for NP0084993 (N-(3-Carboxy-3-hydroxypropyl)-4-[(carboxymethyl)amino]-L-allothreonine)

INCHI for NP0084993 (N-(3-Carboxy-3-hydroxypropyl)-4-[(carboxymethyl)amino]-L-allothreonine)

Structure for NP0084993 (N-(3-Carboxy-3-hydroxypropyl)-4-[(carboxymethyl)amino]-L-allothreonine)

3D Structure for NP0084993 (N-(3-Carboxy-3-hydroxypropyl)-4-[(carboxymethyl)amino]-L-allothreonine)