NP-MRD: Showing NP-Card for 2-[(4-amino-4-carboxy-1-hydroxybutylidene)amino]-3-methylidenepentanoic acid (NP0264534)

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Record Information

Version

2.0

Created at

2022-09-08 08:05:44 UTC

Updated at

2022-09-08 08:05:44 UTC

NP-MRD ID

NP0264534

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(4-amino-4-carboxy-1-hydroxybutylidene)amino]-3-methylidenepentanoic acid

Description

2-[(4-Amino-4-carboxy-1-hydroxybutylidene)amino]-3-methylidenepentanoic acid belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. 2-[(4-amino-4-carboxy-1-hydroxybutylidene)amino]-3-methylidenepentanoic acid is found in Philadelphus coronarius. 2-[(4-Amino-4-carboxy-1-hydroxybutylidene)amino]-3-methylidenepentanoic acid is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 35  0  0  0  0  0  0  0  0999 V2000
    2.3209   -0.7673   -1.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7256   -0.3526    0.0153 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0314   -0.8107    0.4748 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1251    0.2050    0.5307 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7912    0.4679    0.8163 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5427    0.6579    0.0572 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6814    0.0906    0.4496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7524   -0.6238    1.4980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8854    0.3312   -0.3672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0651   -0.4264    0.2589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3195   -0.2171   -0.5302 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1466   -0.6952   -1.9041 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3902   -1.0164    0.1145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9841   -1.9264   -0.5144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7187   -0.7346    1.4263 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3650    1.7299    1.2173 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8501    2.8219    0.7818 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4424    1.8865    2.0526 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9325   -1.4085   -1.8290 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3629   -0.4677   -1.6231 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9500   -1.2192    1.5316 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3706   -1.7308   -0.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9094    1.1391   -0.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0126   -0.2779   -0.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5450    0.3710    1.5419 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4886   -0.1533    1.7112 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6239    1.2396   -0.7906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0733    1.4096   -0.3869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8011   -0.0905   -1.4009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2380   -0.0597    1.2820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8352   -1.5082    0.3225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5561    0.8558   -0.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6068   -0.0188   -2.4692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6248   -1.5937   -1.8622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7506    0.2096    1.8128 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0395    2.6835    2.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 15  1  0
 13 14  2  0
  5 16  1  0
 16 18  1  0
 16 17  2  0
  4 23  1  0
  4 24  1  0
  4 25  1  0
  3 21  1  0
  3 22  1  0
  1 19  1  0
  1 20  1  0
  5 26  1  1
  6 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  6
 12 33  1  0
 12 34  1  0
 15 35  1  0
 18 36  1  0
M  END


  Mrv1533004171518582D          

 18 17  0  0  0  0            999 V2000
    4.2355    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    3.2704    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2368    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513    4.0954    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    1.6204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    1.6204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  5 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0264534

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(=C)C(NC(=O)CCC(N)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H18N2O5/c1-3-6(2)9(11(17)18)13-8(14)5-4-7(12)10(15)16/h7,9H,2-5,12H2,1H3,(H,13,14)(H,15,16)(H,17,18)

> <INCHI_KEY>
VMFRAEJIZGHFMQ-UHFFFAOYSA-N

> <FORMULA>
C11H18N2O5

> <MOLECULAR_WEIGHT>
258.274

> <EXACT_MASS>
258.121571688

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
25.67946654540251

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(4-amino-4-carboxybutanamido)-3-methylidenepentanoic acid

> <ALOGPS_LOGP>
-2.77

> <JCHEM_LOGP>
-2.742515007425696

> <ALOGPS_LOGS>
-1.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.9253374183293475

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.9278281754089908

> <JCHEM_PKA_STRONGEST_BASIC>
9.311984969776539

> <JCHEM_POLAR_SURFACE_AREA>
129.72

> <JCHEM_REFRACTIVITY>
61.88220000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.15e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(4-amino-4-carboxybutanamido)-3-methylidenepentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       7.906   6.105   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.240   5.335   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.574   6.105   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.574   7.645   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.907   5.335   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      13.241   6.105   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      14.575   5.335   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      14.575   3.795   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      15.908   6.105   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.242   5.335   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.576   6.105   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      18.576   7.645   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      19.909   5.335   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      21.243   6.105   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      19.909   3.795   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      11.907   3.795   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      13.241   3.025   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      10.574   3.025   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   16                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    5   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

View in JSmol

Synonyms

Value	Source
2-[(4-Amino-4-carboxy-1-hydroxybutylidene)amino]-3-methylidenepentanoate	Generator

Chemical Formula

C₁₁H₁₈N₂O₅

Average Mass

258.2740 Da

Monoisotopic Mass

258.12157 Da

IUPAC Name

2-(4-amino-4-carboxybutanamido)-3-methylidenepentanoic acid

Traditional Name

2-(4-amino-4-carboxybutanamido)-3-methylidenepentanoic acid

CAS Registry Number

Not Available

SMILES

CCC(=C)C(NC(=O)CCC(N)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C11H18N2O5/c1-3-6(2)9(11(17)18)13-8(14)5-4-7(12)10(15)16/h7,9H,2-5,12H2,1H3,(H,13,14)(H,15,16)(H,17,18)

InChI Key

VMFRAEJIZGHFMQ-UHFFFAOYSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Philadelphus coronarius	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic 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	-2.8	ALOGPS
logP	-2.7	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	1.93	ChemAxon
pKa (Strongest Basic)	9.31	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	129.72 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	61.88 m³·mol⁻¹	ChemAxon
Polarizability	25.68 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

Not Available

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-[(4-amino-4-carboxy-1-hydroxybutylidene)amino]-3-methylidenepentanoic acid (NP0264534)

MOL for NP0264534 (2-[(4-amino-4-carboxy-1-hydroxybutylidene)amino]-3-methylidenepentanoic acid)

3D MOL for NP0264534 (2-[(4-amino-4-carboxy-1-hydroxybutylidene)amino]-3-methylidenepentanoic acid)

3D SDF for NP0264534 (2-[(4-amino-4-carboxy-1-hydroxybutylidene)amino]-3-methylidenepentanoic acid)

3D-SDF for NP0264534 (2-[(4-amino-4-carboxy-1-hydroxybutylidene)amino]-3-methylidenepentanoic acid)

PDB for NP0264534 (2-[(4-amino-4-carboxy-1-hydroxybutylidene)amino]-3-methylidenepentanoic acid)

3D PDB for NP0264534 (2-[(4-amino-4-carboxy-1-hydroxybutylidene)amino]-3-methylidenepentanoic acid)

SMILES for NP0264534 (2-[(4-amino-4-carboxy-1-hydroxybutylidene)amino]-3-methylidenepentanoic acid)

INCHI for NP0264534 (2-[(4-amino-4-carboxy-1-hydroxybutylidene)amino]-3-methylidenepentanoic acid)

Structure for NP0264534 (2-[(4-amino-4-carboxy-1-hydroxybutylidene)amino]-3-methylidenepentanoic acid)

3D Structure for NP0264534 (2-[(4-amino-4-carboxy-1-hydroxybutylidene)amino]-3-methylidenepentanoic acid)