NP-MRD: Showing NP-Card for Betalamic acid (NP0045469)

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Record Information

Version

2.0

Created at

2022-03-17 19:20:30 UTC

Updated at

2022-03-17 19:20:30 UTC

NP-MRD ID

NP0045469

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Betalamic acid

Description

Betalamic acid, also known as betalamate, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Betalamic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Betalamic acid has been detected, but not quantified in, a few different foods, such as common beets, red beetroots, and root vegetables. Betalamic acid is found in Amanita muscaria, Amaranthus mangostanus , Atriplex hortensis, Basella rubra , Beta valgaris, Celosia argentea var.cristata (L.) Kuntze , Celosia argentea var.plumosa (Burvenich) Voss , Celosia cristata , Chenopodium quinoa , Glottiphylum longum, Gomphrena globosa , Mirabilis jalapa , Opuntia elatior, Portulaca grandiflora , Rivina humilis , Schlumbergera x buckleyi and Spinacia oleracea . This could make betalamic acid a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241220052D          

 15 15  0  0  0  0            999 V2000
    2.1248    0.2001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0446   -0.6011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3228   -1.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6813   -0.6011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0397   -1.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7615   -0.6011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7615    0.2001    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0397    0.6011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0397    1.4030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7615    1.8040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4030   -1.8040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4030   -1.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1248   -0.6011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6813    0.2001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6813    1.8040    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  2  0  0  0  0
  4  5  1  0  0  0  0
  4 14  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 12  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 14  2  0  0  0  0
  9 10  1  0  0  0  0
  9 15  2  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045469

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1C\C(=C\C=O)C=C(N1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H9NO5/c11-2-1-5-3-6(8(12)13)10-7(4-5)9(14)15/h1-3,7,10H,4H2,(H,12,13)(H,14,15)/b5-1+

> <INCHI_KEY>
YQDKULBMDMPFLH-ORCRQEGFSA-N

> <FORMULA>
C9H9NO5

> <MOLECULAR_WEIGHT>
211.1715

> <EXACT_MASS>
211.048072403

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
19.03711146530265

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4Z)-4-(2-oxoethylidene)-1,2,3,4-tetrahydropyridine-2,6-dicarboxylic acid

> <ALOGPS_LOGP>
0.53

> <JCHEM_LOGP>
-0.9358051243333332

> <ALOGPS_LOGS>
-1.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.155163588475271

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4254683422539434

> <JCHEM_PKA_STRONGEST_BASIC>
-0.013612267174621828

> <JCHEM_POLAR_SURFACE_AREA>
103.70000000000002

> <JCHEM_REFRACTIVITY>
50.78000000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.72e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4Z)-4-(2-oxoethylidene)-2,3-dihydro-1H-pyridine-2,6-dicarboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       3.966   0.374   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.817  -1.122   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.469  -1.870   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.272  -1.122   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.074  -1.870   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.421  -1.122   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -1.421   0.374   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -0.074   1.122   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.074   2.619   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.421   3.367   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -2.619  -3.367   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.619  -1.870   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.966  -1.122   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.272   0.374   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.272   3.367   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   14                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10   15                                                  
CONECT   10    9                                                            
CONECT   11   12                                                            
CONECT   12    6   11   13                                                  
CONECT   13   12                                                            
CONECT   14    4    8                                                       
CONECT   15    9                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol

Synonyms

Value	Source
Betalamate	Generator
1,2,3,4-Tetrahydro-4-(oxoethylidene)-2,6-pyridinedicarboxylic acid	HMDB
Betalanic acid	HMDB
(4Z)-4-(2-Oxoethylidene)-1,2,3,4-tetrahydropyridine-2,6-dicarboxylate	Generator

Chemical Formula

C₉H₉NO₅

Average Mass

211.1715 Da

Monoisotopic Mass

211.04807 Da

IUPAC Name

(4Z)-4-(2-oxoethylidene)-1,2,3,4-tetrahydropyridine-2,6-dicarboxylic acid

Traditional Name

(4Z)-4-(2-oxoethylidene)-2,3-dihydro-1H-pyridine-2,6-dicarboxylic acid

CAS Registry Number

18766-66-0

SMILES

OC(=O)C1C\C(=C\C=O)C=C(N1)C(O)=O

InChI Identifier

InChI=1S/C9H9NO5/c11-2-1-5-3-6(8(12)13)10-7(4-5)9(14)15/h1-3,7,10H,4H2,(H,12,13)(H,14,15)/b5-1+

InChI Key

YQDKULBMDMPFLH-ORCRQEGFSA-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
Amanita muscaria	LOTUS Database	35616633
Amaranthus mangostanus	Plant	KNApSAcK
Atriplex hortensis	LOTUS Database	35616633
Basella alba	Plant	KNApSAcK
Beta valgaris	Plant	KNApSAcK
Beta vulgaris	FooDB	KNAPSACK
Celosia argentea var.cristata (L.) Kuntze	Plant	KNApSAcK
Celosia argentea var.plumosa (Burvenich) Voss	Plant	KNApSAcK
Celosia cristata	Plant	KNApSAcK
Chenopodium quinoa	Plant	KNApSAcK
Glottiphyllum longum	-	KNApSAcK
Gomphrena globosa	Plant	KNApSAcK
Mirabilis jalapa	Plant	KNApSAcK
Opuntia elatior	Plant	KNApSAcK
Portulaca grandiflora	Plant	KNApSAcK
Rivina humilis	Plant	KNApSAcK
Schlumbergera x buckleyi	Plant	KNApSAcK
Spinacia oleracea	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids

Alternative Parents

Substituents

Alpha-amino acid
Tetrahydropyridine
Dicarboxylic acid or derivatives
Hydropyridine
Alpha,beta-unsaturated aldehyde
Enal
Amino acid
Carboxylic acid
Secondary aliphatic amine
Azacycle
Organoheterocyclic compound
Secondary amine
Enamine
Aldehyde
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Amine
Organic oxygen compound
Organic nitrogen compound
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	0.53	ALOGPS
logP	-0.94	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	3.43	ChemAxon
pKa (Strongest Basic)	-0.014	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	103.7 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	50.78 m³·mol⁻¹	ChemAxon
Polarizability	19.04 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

HMDB0029842

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB001057

KNApSAcK ID

C00001582

Chemspider ID

Not Available

KEGG Compound ID

C08538

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6123097

PDB ID

Not Available

ChEBI ID

27483

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Betalamic acid (NP0045469)

MOL for NP0045469 (Betalamic acid)

3D MOL for NP0045469 (Betalamic acid)

3D SDF for NP0045469 (Betalamic acid)

3D-SDF for NP0045469 (Betalamic acid)

PDB for NP0045469 (Betalamic acid)

3D PDB for NP0045469 (Betalamic acid)

SMILES for NP0045469 (Betalamic acid)

INCHI for NP0045469 (Betalamic acid)

Structure for NP0045469 (Betalamic acid)

3D Structure for NP0045469 (Betalamic acid)