NP-MRD: Showing NP-Card for 1-Amino-1-cyclohexanecarboxylic acid (NP0002878)

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Record Information

Version

1.0

Created at

2020-11-23 19:42:38 UTC

Updated at

2021-08-12 19:52:24 UTC

NP-MRD ID

NP0002878

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-Amino-1-cyclohexanecarboxylic acid

Provided By

BMRB

Description

1-Aminocyclohexanecarboxylic acid, also known as 1-azanylcyclohexane-1-carboxylate, 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. It was first documented in 1983 (PMID: 6847699). Based on a literature review a significant number of articles have been published on 1-Aminocyclohexanecarboxylic acid (PMID: 17984079) (PMID: 3346675) (PMID: 24039017) (PMID: 18821748).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


     RDKit          2D

 23 23  0  0  0  0  0  0  0  0999 V2000
    1.7691   -1.2042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7285   -0.1239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9732    0.7133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0260    1.6960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3205    0.0539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1548   -1.3362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6464   -1.1774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2546    0.1937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3713    1.4061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1202    1.2473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6138   -2.1761    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2691   -1.2063    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5652    0.8911    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6699   -1.8733    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5702   -2.7775    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5437   -2.6739    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1023   -1.5384    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4993   -0.6434    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2952    1.2741    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7187    2.0654    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9560    2.8474    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0176    2.7438    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0395    1.5988    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  1
  3  4  2  0
  3  5  1  0
  2  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10  2  1  0
  1 11  1  0
  1 12  1  0
  5 13  1  0
  6 14  1  1
  6 15  1  0
  7 16  1  1
  7 17  1  0
  8 18  1  6
  8 19  1  0
  9 20  1  6
  9 21  1  0
 10 22  1  1
 10 23  1  0
M  END
> <DATABASE_ID>
NP0002878

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1(CCCCC1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H13NO2/c8-7(6(9)10)4-2-1-3-5-7/h1-5,8H2,(H,9,10)

> <INCHI_KEY>
WOXWUZCRWJWTRT-UHFFFAOYSA-N

> <FORMULA>
C7H13NO2

> <MOLECULAR_WEIGHT>
143.1836

> <EXACT_MASS>
143.094628665

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
15.07772667266025

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-aminocyclohexane-1-carboxylic acid

> <ALOGPS_LOGP>
-2.26

> <JCHEM_LOGP>
-1.3824455202126407

> <ALOGPS_LOGS>
-0.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.5651725232554874

> <JCHEM_PKA_STRONGEST_BASIC>
9.825359221511077

> <JCHEM_POLAR_SURFACE_AREA>
63.32000000000001

> <JCHEM_REFRACTIVITY>
37.0574

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.53e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-aminocyclohexane-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

View in JSmol

Synonyms

Value	Source
1-Azanylcyclohexane-1-carboxylic acid	ChEBI
alpha-Aminocyclohexanecarboxylic aicd	ChEBI
1-Azanylcyclohexane-1-carboxylate	Generator
a-Aminocyclohexanecarboxylic aicd	Generator
Α-aminocyclohexanecarboxylic aicd	Generator
1-Aminocyclohexanecarboxylate	Generator
1-Amino-1-cyclohexanecarboxylate	HMDB
1-Aminocyclohexane-1-carboxylic acid	HMDB
1-Aminocyclohexanecarboxylic acid, 14C-labeled	HMDB
1-Aminocyclohexanecarboxylic acid	ChEBI

Chemical Formula

C₇H₁₃NO₂

Average Mass

143.1836 Da

Monoisotopic Mass

143.09463 Da

IUPAC Name

1-aminocyclohexane-1-carboxylic acid

Traditional Name

1-aminocyclohexane-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

NC1(CCCCC1)C(O)=O

InChI Identifier

InChI=1S/C7H13NO2/c8-7(6(9)10)4-2-1-3-5-7/h1-5,8H2,(H,9,10)

InChI Key

WOXWUZCRWJWTRT-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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

Not Available

Substituents

Not Available

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	-2.3	ALOGPS
logP	-1.4	ChemAxon
logS	-0.5	ALOGPS
pKa (Strongest Acidic)	2.57	ChemAxon
pKa (Strongest Basic)	9.83	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	37.06 m³·mol⁻¹	ChemAxon
Polarizability	15.08 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

HMDB0243822

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

1325

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

1366

PDB ID

Not Available

ChEBI ID

86534

Good Scents ID

Not Available

References

General References

Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
Aoyagi M, Agranoff BW, Washburn LC, Smith QR: Blood-brain barrier transport of 1-aminocyclohexanecarboxylic acid, a nonmetabolizable amino acid for in vivo studies of brain transport. J Neurochem. 1988 Apr;50(4):1220-6. doi: 10.1111/j.1471-4159.1988.tb10596.x. [PubMed:3346675 ]
Lombardini JB, Sufrin JR: Chemotherapeutic potential of methionine analogue inhibitors of tumor-derived methionine adenosyltransferases. Biochem Pharmacol. 1983 Feb 1;32(3):489-95. doi: 10.1016/0006-2952(83)90528-2. [PubMed:6847699 ]
Akagawa K, Sen J, Kudo K: Peptide-catalyzed regio- and enantioselective reduction of alpha,beta,gamma,delta-unsaturated aldehydes. Angew Chem Int Ed Engl. 2013 Oct 25;52(44):11585-8. doi: 10.1002/anie.201305004. Epub 2013 Sep 5. [PubMed:24039017 ]
Long YQ, Xue T, Song YL, Liu ZL, Huang SX, Yu Q: Synthesis and utilization of chiral alpha-methylated alpha-amino acids with a carboxyalkyl side chain in the design of novel Grb2-SH2 peptide inhibitors free of phosphotyrosine. J Med Chem. 2008 Oct 23;51(20):6371-80. doi: 10.1021/jm800487r. Epub 2008 Sep 27. [PubMed:18821748 ]

Showing NP-Card for 1-Amino-1-cyclohexanecarboxylic acid (NP0002878)

MOL for NP0002878 (1-Amino-1-cyclohexanecarboxylic acid)

3D MOL for NP0002878 (1-Amino-1-cyclohexanecarboxylic acid)

3D SDF for NP0002878 (1-Amino-1-cyclohexanecarboxylic acid)

3D-SDF for NP0002878 (1-Amino-1-cyclohexanecarboxylic acid)

PDB for NP0002878 (1-Amino-1-cyclohexanecarboxylic acid)

3D PDB for NP0002878 (1-Amino-1-cyclohexanecarboxylic acid)

SMILES for NP0002878 (1-Amino-1-cyclohexanecarboxylic acid)

INCHI for NP0002878 (1-Amino-1-cyclohexanecarboxylic acid)

Structure for NP0002878 (1-Amino-1-cyclohexanecarboxylic acid)

3D Structure for NP0002878 (1-Amino-1-cyclohexanecarboxylic acid)