NP-MRD: Showing NP-Card for Alanylvaline (NP0136339)

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Record Information

Version

2.0

Created at

2022-05-12 15:12:00 UTC

Updated at

2022-05-12 15:12:00 UTC

NP-MRD ID

NP0136339

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Alanylvaline

Description

Alanylvaline, also known as AV or L-ala-L-val, belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. Alanylvaline is a very strong basic compound (based on its pKa). Alanylvaline was first documented in 2005 (PMID: 16113687). It is an incomplete breakdown product of protein digestion or protein catabolism (PMID: 18031357) (PMID: 15950528) (PMID: 19921840).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 28  0  0  0  0  0  0  0  0999 V2000
   -1.7051   -2.0686   -0.3097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9829   -0.6055   -0.2520 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7769    0.0777   -1.5981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1606    0.1296    0.7738 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2524    0.0314    0.5561 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0767    1.1652    0.3209 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4950    2.2891    0.3121 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5354    1.0653    0.0960 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8832    1.6764   -1.2486 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9639   -0.3107    0.1515 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5498   -0.3610    2.1060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6545   -0.7905    2.8710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8742   -0.3445    2.4955 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6597   -2.3696   -1.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5570   -2.6712    0.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8092   -2.3966    0.2200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0505   -0.4468    0.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9811   -0.4361   -2.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4895    1.1310   -1.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7138    0.0229   -2.1751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4423    1.2016    0.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7622   -0.8998    0.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0258    1.6113    0.9301 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1671    2.7541   -1.1105 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9900    1.6694   -1.9271 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7087    1.1376   -1.7576 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6916   -0.5193   -0.5582 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3152   -0.6007    1.0828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4602   -1.1417    2.5793 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
  4 11  1  0
 11 13  1  0
 11 12  2  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  1
  3 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  1
  5 22  1  0
  8 23  1  1
  9 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 13 29  1  0
M  END


  Mrv1652304062013212D          

 13 12  0  0  0  0            999 V2000
 2501.4333 2502.0498    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2501.4333 2501.2243    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2502.1562 2500.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.8689 2501.2367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.1562 2499.9997    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2501.4415 2499.5860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.8689 2499.5860    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2500.7186 2502.4613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.0039 2502.0498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.7186 2503.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.1480 2502.4613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.8628 2502.0498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.1480 2503.2868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  0  0  0
  1  8  1  0  0  0  0
  1 11  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0136339

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H16N2O3/c1-4(2)6(8(12)13)10-7(11)5(3)9/h4-6H,9H2,1-3H3,(H,10,11)(H,12,13)/t5-,6-/m0/s1

> <INCHI_KEY>
LIWMQSWFLXEGMA-WDSKDSINSA-N

> <FORMULA>
C8H16N2O3

> <MOLECULAR_WEIGHT>
188.227

> <EXACT_MASS>
188.116092383

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
19.35550647458459

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-[(2S)-2-aminopropanamido]-3-methylbutanoic acid

> <ALOGPS_LOGP>
-1.82

> <JCHEM_LOGP>
-2.4922657517320337

> <ALOGPS_LOGS>
-0.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.760018087599107

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8897681536658184

> <JCHEM_PKA_STRONGEST_BASIC>
8.388621131385031

> <JCHEM_POLAR_SURFACE_AREA>
92.42000000000002

> <JCHEM_REFRACTIVITY>
46.7903

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.37e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(2S)-2-aminopropanamido]-3-methylbutanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  C   UNK     0    4669.3424670.493   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    4669.3424668.952   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    4670.6924668.207   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    4672.0224668.975   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    4670.6924666.666   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    4669.3574665.894   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0    4672.0224665.894   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0    4668.0084671.261   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    4666.6744670.493   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    4668.0084672.802   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    4670.6764671.261   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0    4672.0114670.493   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    4670.6764672.802   0.000  0.00  0.00           O+0
CONECT    1    2    8   11                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    1    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    1   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

View in JSmol

Synonyms

Value	Source
AV	ChEBI
L-Ala-L-val	ChEBI
N-L-Alanyl-L-valine	ChEBI
a-V Dipeptide	HMDB
AV dipeptide	HMDB
Ala-val	HMDB
Alanine valine dipeptide	HMDB
Alanine-valine dipeptide	HMDB
Alanyl-valine	HMDB
L-Alanyl-L-valine	HMDB
N-Alanylvaline	HMDB
NSC 89603	HMDB
Alanylvaline	ChEBI

Chemical Formula

C₈H₁₆N₂O₃

Average Mass

188.2270 Da

Monoisotopic Mass

188.11609 Da

IUPAC Name

(2S)-2-[(2S)-2-aminopropanamido]-3-methylbutanoic acid

Traditional Name

(2S)-2-[(2S)-2-aminopropanamido]-3-methylbutanoic acid

CAS Registry Number

Not Available

SMILES

CC(C)[C@H](NC(=O)[C@H](C)N)C(O)=O

InChI Identifier

InChI=1S/C8H16N2O3/c1-4(2)6(8(12)13)10-7(11)5(3)9/h4-6H,9H2,1-3H3,(H,10,11)(H,12,13)/t5-,6-/m0/s1

InChI Key

LIWMQSWFLXEGMA-WDSKDSINSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Peptides

Alternative Parents

Substituents

Alpha peptide
N-acyl-alpha-amino acid
Valine or derivatives
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
Branched fatty acid
Methyl-branched fatty acid
Fatty acyl
Fatty acid
Amino acid or derivatives
Amino acid
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic oxide
Organic oxygen compound
Primary aliphatic amine
Amine
Organic nitrogen compound
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Primary amine
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dipeptide (CHEBI:73809 )

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	-1.8	ALOGPS
logP	-2.5	ChemAxon
logS	-0.54	ALOGPS
pKa (Strongest Acidic)	3.89	ChemAxon
pKa (Strongest Basic)	8.39	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	92.42 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	46.79 m³·mol⁻¹	ChemAxon
Polarizability	19.36 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

External Links

HMDB ID

HMDB0028700

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

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

96799

PDB ID

Not Available

ChEBI ID

73809

Good Scents ID

Not Available

References

General References

Cha MH, Kim KS, Suh D, Yoon Y: Effects of genetic polymorphism of uncoupling protein 2 on body fat and calorie restriction-induced changes. Hereditas. 2007 Nov;144(5):222-7. doi: 10.1111/j.2007.0018-0661.02005.x. [PubMed:18031357 ]
Nath M, Pokharia S, Eng G, Song X, Kumar A: New triorganotin (IV) derivatives of dipeptides as models for metal-protein interactions: synthesis, structural characterization and biological studies. Spectrochim Acta A Mol Biomol Spectrosc. 2006 Jan;63(1):66-75. doi: 10.1016/j.saa.2005.04.038. Epub 2005 Jun 9. [PubMed:15950528 ]
Chen L, Morris K, Laybourn A, Elias D, Hicks MR, Rodger A, Serpell L, Adams DJ: Self-assembly mechanism for a naphthalene-dipeptide leading to hydrogelation. Langmuir. 2010 Apr 6;26(7):5232-42. doi: 10.1021/la903694a. [PubMed:19921840 ]
Negri L, Lattanzi R, Giannini E, Colucci MA, Mignogna G, Barra D, Grohovaz F, Codazzi F, Kaiser A, Kreil G, Melchiorri P: Biological activities of Bv8 analogues. Br J Pharmacol. 2005 Nov;146(5):625-32. doi: 10.1038/sj.bjp.0706376. [PubMed:16113687 ]

Showing NP-Card for Alanylvaline (NP0136339)

MOL for NP0136339 (Alanylvaline)

3D MOL for NP0136339 (Alanylvaline)

3D SDF for NP0136339 (Alanylvaline)

3D-SDF for NP0136339 (Alanylvaline)

PDB for NP0136339 (Alanylvaline)

3D PDB for NP0136339 (Alanylvaline)

SMILES for NP0136339 (Alanylvaline)

INCHI for NP0136339 (Alanylvaline)

Structure for NP0136339 (Alanylvaline)

3D Structure for NP0136339 (Alanylvaline)