NP-MRD: Showing NP-Card for (2S,3S,4S)-2-(carboxycyclopropyl)glycine (NP0084845)

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Record Information

Version

2.0

Created at

2022-04-29 05:28:33 UTC

Updated at

2022-04-29 05:28:33 UTC

NP-MRD ID

NP0084845

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2S,3S,4S)-2-(carboxycyclopropyl)glycine

Description

(2S,1'S,2'S)-2-(carboxycyclopropyl)glycine, also known as L-CCG-ii or alpha-(carboxycyclopropyl)glycine, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. (2S,3S,4S)-2-(carboxycyclopropyl)glycine is found in Blighia sapida and Ephedra altissima . (2S,3S,4S)-2-(carboxycyclopropyl)glycine was first documented in 2009 (PMID: 19637276). Based on a literature review a small amount of articles have been published on (2S,1'S,2'S)-2-(carboxycyclopropyl)glycine (PMID: 21584239) (PMID: 20826132).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292207282D          

 12 12  0  0  1  0            999 V2000
    1.3651   -1.0632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3651   -0.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0796    0.1743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6507    0.1743    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1743    0.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2382    0.8888    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0350    1.1023    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2382    1.7138    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4763    2.1263    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9526    2.1263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9526    2.9513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6671    1.7138    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
  4  2  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  6  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0084845

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(C[C@@H]1C(O)=O)[C@H](N)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H9NO4/c7-4(6(10)11)2-1-3(2)5(8)9/h2-4H,1,7H2,(H,8,9)(H,10,11)/t2-,3-,4-/m0/s1

> <INCHI_KEY>
GZOVEPYOCJWRFC-HZLVTQRSSA-N

> <FORMULA>
C6H9NO4

> <MOLECULAR_WEIGHT>
159.141

> <EXACT_MASS>
159.053157774

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
14.469208620854264

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S)-2-[(S)-amino(carboxy)methyl]cyclopropane-1-carboxylic acid

> <ALOGPS_LOGP>
-3.49

> <JCHEM_LOGP>
-3.246514280206225

> <ALOGPS_LOGS>
-0.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.120840058672924

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8009104205836288

> <JCHEM_PKA_STRONGEST_BASIC>
9.584625380472678

> <JCHEM_POLAR_SURFACE_AREA>
100.62

> <JCHEM_REFRACTIVITY>
33.930600000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.28e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S)-2-[(S)-amino(carboxy)methyl]cyclopropane-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  O   UNK     0       2.548  -1.985   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.548  -0.445   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.882   0.325   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.215   0.325   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.325   0.325   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.445   1.659   0.000  0.00  0.00           C+0
HETATM    7  H   UNK     0       1.932   2.058   0.000  0.00  0.00           H+0
HETATM    8  C   UNK     0       0.445   3.199   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -0.889   3.969   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       1.778   3.969   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.778   5.509   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       3.112   3.199   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4    6                                                       
CONECT    6    5    4    7    8                                             
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol

Synonyms

Value	Source
L-2-(Carboxypropyl)glycine	MeSH
L-CCG-II	MeSH
(alpha-Carboxycyclopropyl)glycine, (1S-(1alpha(r*),2alpha))-isomer	MeSH
2-(Carboxycyclopropyl)glycine	MeSH
L-CCG III	MeSH
(alpha-Carboxycyclopropyl)glycine, (1R-(1alpha(s*),2alpha))-isomer	MeSH
(alpha-Carboxycyclopropyl)glycine, (1R-(1alpha(s*),2beta))-isomer	MeSH
3,4-Cyclopropylglutamate	MeSH
L-CCG-I	MeSH
alpha-(Carboxycyclopropyl)glycine	MeSH
(alpha-Carboxycyclopropyl)glycine	MeSH
(alpha-Carboxycyclopropyl)glycine, (1S-(1alpha(r*),2beta))-isomer	MeSH
CCPG	MeSH

Chemical Formula

C₆H₉NO₄

Average Mass

159.1410 Da

Monoisotopic Mass

159.05316 Da

IUPAC Name

(1S,2S)-2-[(S)-amino(carboxy)methyl]cyclopropane-1-carboxylic acid

Traditional Name

(1S,2S)-2-[(S)-amino(carboxy)methyl]cyclopropane-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]1(C[C@@H]1C(O)=O)[C@H](N)C(O)=O

InChI Identifier

InChI=1S/C6H9NO4/c7-4(6(10)11)2-1-3(2)5(8)9/h2-4H,1,7H2,(H,8,9)(H,10,11)/t2-,3-,4-/m0/s1

InChI Key

GZOVEPYOCJWRFC-HZLVTQRSSA-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
Blighia sapida	Plant	KNApSAcK
Ephedra altissima	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-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

L-alpha-amino acids

Alternative Parents

Substituents

L-alpha-amino acid
Cyclopropanecarboxylic acid
Cyclopropanecarboxylic acid or derivatives
Dicarboxylic acid or derivatives
Amino acid
Carboxylic acid
Amine
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	-3.5	ALOGPS
logP	-3.2	ChemAxon
logS	-0.28	ALOGPS
pKa (Strongest Acidic)	1.8	ChemAxon
pKa (Strongest Basic)	9.58	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	100.62 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	33.93 m³·mol⁻¹	ChemAxon
Polarizability	14.47 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

C00054453

Chemspider ID

4470505

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5310956

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Del Valle-Mojica LM, Ayala-Marin YM, Ortiz-Sanchez CM, Torres-Hernandez BA, Abdalla-Mukhaimer S, Ortiz JG: Selective Interactions of Valeriana officinalis Extracts and Valerenic Acid with [H]Glutamate Binding to Rat Synaptic Membranes. Evid Based Complement Alternat Med. 2011;2011:403591. doi: 10.1155/2011/403591. Epub 2011 Apr 26. [PubMed:21584239 ]
Lennon SM, Rivero G, Matharu A, Howson PA, Jane DE, Roberts PJ, Kelly E: Metabotropic glutamate receptor mGlu2 is resistant to homologous agonist-induced desensitization but undergoes protein kinase C-mediated heterologous desensitization. Eur J Pharmacol. 2010 Dec 15;649(1-3):29-37. doi: 10.1016/j.ejphar.2010.08.038. Epub 2010 Sep 15. [PubMed:20826132 ]
Wostrack M, Dietrich D: Involvement of Group II mGluRs in mossy fiber LTD. Synapse. 2009 Dec;63(12):1060-8. doi: 10.1002/syn.20692. [PubMed:19637276 ]

Showing NP-Card for (2S,3S,4S)-2-(carboxycyclopropyl)glycine (NP0084845)

MOL for NP0084845 ((2S,3S,4S)-2-(carboxycyclopropyl)glycine)

3D MOL for NP0084845 ((2S,3S,4S)-2-(carboxycyclopropyl)glycine)

3D SDF for NP0084845 ((2S,3S,4S)-2-(carboxycyclopropyl)glycine)

3D-SDF for NP0084845 ((2S,3S,4S)-2-(carboxycyclopropyl)glycine)

PDB for NP0084845 ((2S,3S,4S)-2-(carboxycyclopropyl)glycine)

3D PDB for NP0084845 ((2S,3S,4S)-2-(carboxycyclopropyl)glycine)

SMILES for NP0084845 ((2S,3S,4S)-2-(carboxycyclopropyl)glycine)

INCHI for NP0084845 ((2S,3S,4S)-2-(carboxycyclopropyl)glycine)

Structure for NP0084845 ((2S,3S,4S)-2-(carboxycyclopropyl)glycine)

3D Structure for NP0084845 ((2S,3S,4S)-2-(carboxycyclopropyl)glycine)