Showing Compound L-Norleucine (FDB022699)

Record Information

Version

1.0

Creation date

2011-09-21 00:18:09 UTC

Update date

2019-11-26 03:21:05 UTC

Primary ID

FDB022699

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

L-Norleucine

Description

An unnatural amino acid that is used experimentally to study protein structure and function. It is structurally similar to methionine, however it does not contain sulfur. Aminocaproic acid works as an antifibrinolytic. It is a derivative of the amino acid lysine. It binds reversibly to the kringle domain of plasminogen and blocks the binding of plasminogen to fibrin and its activation to plasmin. [HMDB]

CAS Number

327-57-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(S)-2-Aminohexanoic acid	ChEBI
2-Aminocaproic acid	ChEBI
2-Aminohexanoic acid	ChEBI
alpha-Aminocaproic acid	ChEBI
Caprine	ChEBI
Glycoleucine	ChEBI
L(+)-Norleucine	ChEBI
L-(+)-Norleucine	ChEBI
L-2-Aminohexanoate	ChEBI
L-2-Aminohexanoic acid	ChEBI
L-Aminohexanoate	ChEBI
L-Aminohexanoic acid	ChEBI
Nle	ChEBI
Norleucine	ChEBI
(S)-2-Aminohexanoate	Generator
2-Aminocaproate	Generator
2-Aminohexanoate	Generator
a-Aminocaproate	Generator
a-Aminocaproic acid	Generator
alpha-Aminocaproate	Generator
Α-aminocaproate	Generator
Α-aminocaproic acid	Generator
(S)-2-amino-Hexanoate	HMDB
(S)-2-amino-Hexanoic acid	HMDB
(S)-Aminohexanoate	HMDB
(S)-Aminohexanoic acid	HMDB
(S)-Norleucine	HMDB
L-Isomer norleucine	MeSH, HMDB
Norleucine, L isomer	MeSH, HMDB
Norleucine, L-isomer	MeSH, HMDB
2S-Amino-hexanoate	Generator, HMDB
L-Norleucine	hmdb
α-aminocaproate	Generator
α-aminocaproic acid	Generator

Predicted Properties

Property	Value	Source
Water Solubility	89.2 g/L	ALOGPS
logP	-1.7	ALOGPS
logP	-1.4	ChemAxon
logS	-0.17	ALOGPS
pKa (Strongest Acidic)	2.79	ChemAxon
pKa (Strongest Basic)	9.53	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	4	ChemAxon
Refractivity	34.22 m³·mol⁻¹	ChemAxon
Polarizability	14.46 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C6H13NO2

IUPAC name

(2S)-2-aminohexanoic acid

InChI Identifier

InChI=1S/C6H13NO2/c1-2-3-4-5(7)6(8)9/h5H,2-4,7H2,1H3,(H,8,9)/t5-/m0/s1

InChI Key

LRQKBLKVPFOOQJ-YFKPBYRVSA-N

Isomeric SMILES

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

Average Molecular Weight

131.1729

Monoisotopic Molecular Weight

131.094628665

Classification

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
Medium-chain fatty acid
Amino fatty acid
Fatty acid
Fatty acyl
Amino acid
Monocarboxylic acid or derivatives
Carboxylic acid
Organic oxide
Organopnictogen compound
Organic oxygen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Organic nitrogen compound
Amine
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid (CHEBI:18347 )
2-aminohexanoic acid (CHEBI:18347 )
Amino fatty acids (C01933 )
Amino fatty acids (LMFA01100042 )

Ontology

Disposition

Source:

Endogenous

Biological location:

Organ and components:

Testicle

Cell and elements:

Element:

Platelet

Biofluid and excreta:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	L-Norleucine, 2 TMS, GC-MS Spectrum	splash10-0a4i-0900000000-b9e660e9ed085e0a2756	Spectrum
GC-MS	L-Norleucine, 2 TMS, GC-MS Spectrum	splash10-0a4i-0900000000-363d31fc4a3b15b97b49	Spectrum
GC-MS	L-Norleucine, non-derivatized, GC-MS Spectrum	splash10-000i-9200000000-786e1c364f918e406c7f	Spectrum
GC-MS	L-Norleucine, non-derivatized, GC-MS Spectrum	splash10-0a4i-0900000000-7c99693c3cc849290ecd	Spectrum
GC-MS	L-Norleucine, 2 TMS, GC-MS Spectrum	splash10-05fr-8900000000-3cf84aa3585ea0262b9a	Spectrum
GC-MS	L-Norleucine, 1 TMS, GC-MS Spectrum	splash10-000i-9200000000-d5ef9dd4b8be3c55a58f	Spectrum
GC-MS	L-Norleucine, 2 TMS, GC-MS Spectrum	splash10-0a4i-0900000000-df2e472e3bd858c871d0	Spectrum
GC-MS	L-Norleucine, 3 TMS, GC-MS Spectrum	splash10-001i-0391000000-a01428088011045cef83	Spectrum
GC-MS	L-Norleucine, non-derivatized, GC-MS Spectrum	splash10-000i-9100000000-1fddf89f6ec7f4b5cfbe	Spectrum
GC-MS	L-Norleucine, non-derivatized, GC-MS Spectrum	splash10-0a4i-0910000000-5eb6c8571ebbad86fac9	Spectrum
GC-MS	L-Norleucine, non-derivatized, GC-MS Spectrum	splash10-0a4i-0900000000-b9e660e9ed085e0a2756	Spectrum
GC-MS	L-Norleucine, non-derivatized, GC-MS Spectrum	splash10-0a4i-0900000000-363d31fc4a3b15b97b49	Spectrum
GC-MS	L-Norleucine, non-derivatized, GC-MS Spectrum	splash10-000i-9200000000-786e1c364f918e406c7f	Spectrum
GC-MS	L-Norleucine, non-derivatized, GC-MS Spectrum	splash10-05fr-8900000000-3cf84aa3585ea0262b9a	Spectrum
GC-MS	L-Norleucine, non-derivatized, GC-MS Spectrum	splash10-0a4i-0900000000-df2e472e3bd858c871d0	Spectrum
GC-MS	L-Norleucine, non-derivatized, GC-MS Spectrum	splash10-001i-0391000000-a01428088011045cef83	Spectrum
GC-MS	L-Norleucine, non-derivatized, GC-MS Spectrum	splash10-000i-9200000000-d5ef9dd4b8be3c55a58f	Spectrum
Predicted GC-MS	L-Norleucine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00bl-9000000000-201d4196a590a77910e6	Spectrum
Predicted GC-MS	L-Norleucine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00dl-9400000000-10c311ca7a06deeb972a	Spectrum
Predicted GC-MS	L-Norleucine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Norleucine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-9100000000-b124c751376d5dfa51a5	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00ku-9000000000-734efe7e83b2a5a46f00	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0006-9000000000-ac9b87f3b366d1310113	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-001i-0900000000-6cc58ea175a3d1492868	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-001i-0900000000-95aa6e4bfc4283439983	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-004i-3900000000-b75779678a92cd599f0c	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0019-9800000000-ee386f888d7ea62be255	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-000i-9000000000-93d53170f5b18b6e157c	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-00kr-9000000000-8abbc9ef83fc8fdd973c	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0006-9000000000-39712cf46e67bc1458fb	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-0006-9000000000-219a42048a733f3d5a23	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-000i-9000000000-2d321cebc7950b90d6b1	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-00kr-9200000000-916e946734d7c51678df	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-001i-0900000000-bc56a19fa8c09e226543	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001i-0900000000-6cc58ea175a3d1492868	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001i-0900000000-95aa6e4bfc4283439983	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-3900000000-b75779678a92cd599f0c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-001i-0900000000-bc56a19fa8c09e226543	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , negative	splash10-001i-0900000000-092c22a76d9d673f6ef9	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0019-9600000000-d20978980da1f4122a43	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-9000000000-e402468856ebe93f5632	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9000000000-323f487cfafb31db8c07	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-1900000000-87cdc1a1d627629c2d67	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-6900000000-7bd938134b1765555ef2	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9000000000-721ed018b3aaa7a7d07d	2016-09-12	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum