NP-MRD: Showing NP-Card for 2-[(2-amino-1-hydroxy-3-methylbutylidene)amino]-3-hydroxy-4-{7-oxo-4-oxa-1-azabicyclo[3.2.0]heptan-3-yl}butanoic acid (NP0252641)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-07 16:13:18 UTC

Updated at

2022-09-07 16:13:18 UTC

NP-MRD ID

NP0252641

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(2-amino-1-hydroxy-3-methylbutylidene)amino]-3-hydroxy-4-{7-oxo-4-oxa-1-azabicyclo[3.2.0]heptan-3-yl}butanoic acid

Description

Valclavam belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. 2-[(2-amino-1-hydroxy-3-methylbutylidene)amino]-3-hydroxy-4-{7-oxo-4-oxa-1-azabicyclo[3.2.0]heptan-3-yl}butanoic acid was first documented in 1987 (PMID: 3304182). Based on a literature review very few articles have been published on Valclavam (PMID: 9245367).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309072218132D          

 23 24  0  0  0  0            999 V2000
   -1.4709   -2.4082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7564   -1.9957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7564   -1.1707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0419   -2.4082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0419   -3.2332    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6725   -1.9957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6725   -1.1707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3870   -2.4082    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1015   -1.9957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1015   -1.1707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3870   -0.7582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8159   -0.7582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8159   -2.4082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8159   -3.2332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5304   -1.9957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2449   -2.4082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9986   -2.0727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5506   -2.6857    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2651   -3.0982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0620   -2.8847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8526   -3.8127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1381   -3.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3311   -3.2287    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  4  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 18 22  1  0  0  0  0
 22 23  1  0  0  0  0
 16 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0252641

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(N)C(O)=NC(C(O)CC1CN2C(CC2=O)O1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H23N3O6/c1-6(2)11(15)13(20)16-12(14(21)22)8(18)3-7-5-17-9(19)4-10(17)23-7/h6-8,10-12,18H,3-5,15H2,1-2H3,(H,16,20)(H,21,22)

> <INCHI_KEY>
YCGXMNQNHBKSKZ-UHFFFAOYSA-N

> <FORMULA>
C14H23N3O6

> <MOLECULAR_WEIGHT>
329.353

> <EXACT_MASS>
329.158685473

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
33.349135641010236

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(2-amino-1-hydroxy-3-methylbutylidene)amino]-3-hydroxy-4-{7-oxo-4-oxa-1-azabicyclo[3.2.0]heptan-3-yl}butanoic acid

> <JCHEM_LOGP>
-3.547502279850661

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
4.047918560968092

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1966542043416952

> <JCHEM_PKA_STRONGEST_BASIC>
9.680572472271484

> <JCHEM_POLAR_SURFACE_AREA>
145.68

> <JCHEM_REFRACTIVITY>
77.3042

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-[(2-amino-1-hydroxy-3-methylbutylidene)amino]-3-hydroxy-4-{7-oxo-4-oxa-1-azabicyclo[3.2.0]heptan-3-yl}butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.746  -4.495   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.412  -3.725   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.412  -2.185   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.078  -4.495   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -0.078  -6.035   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       1.255  -3.725   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.255  -2.185   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0       2.589  -4.495   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       3.923  -3.725   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.923  -2.185   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.589  -1.415   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       5.256  -1.415   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.256  -4.495   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.256  -6.035   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.590  -3.725   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.924  -4.495   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.331  -3.869   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      10.361  -5.013   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      11.695  -5.783   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      13.182  -5.385   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      10.925  -7.117   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.591  -6.347   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.085  -6.027   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                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    9   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   23                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   22                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   18   23                                                  
CONECT   23   22   16                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₂₃N₃O₆

Average Mass

329.3530 Da

Monoisotopic Mass

329.15869 Da

IUPAC Name

2-[(2-amino-1-hydroxy-3-methylbutylidene)amino]-3-hydroxy-4-{7-oxo-4-oxa-1-azabicyclo[3.2.0]heptan-3-yl}butanoic acid

Traditional Name

2-[(2-amino-1-hydroxy-3-methylbutylidene)amino]-3-hydroxy-4-{7-oxo-4-oxa-1-azabicyclo[3.2.0]heptan-3-yl}butanoic acid

CAS Registry Number

Not Available

SMILES

CC(C)C(N)C(O)=NC(C(O)CC1CN2C(CC2=O)O1)C(O)=O

InChI Identifier

InChI=1S/C14H23N3O6/c1-6(2)11(15)13(20)16-12(14(21)22)8(18)3-7-5-17-9(19)4-10(17)23-7/h6-8,10-12,18H,3-5,15H2,1-2H3,(H,16,20)(H,21,22)

InChI Key

YCGXMNQNHBKSKZ-UHFFFAOYSA-N

Experimental Spectra

Not Available

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 dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
Valine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Alpha-amino acid or derivatives
Clavam
Para-oxazepine
Beta-hydroxy acid
Branched fatty acid
Heterocyclic fatty acid
Hydroxy fatty acid
Short-chain hydroxy acid
Fatty amide
Hydroxy acid
N-acyl-amine
Fatty acyl
Fatty acid
Oxazolidine
Tertiary carboxylic acid amide
Beta-lactam
Secondary carboxylic acid amide
Secondary alcohol
Amino acid or derivatives
Azetidine
Amino acid
Lactam
Carboxamide group
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Azacycle
Carboxylic acid
Oxacycle
Organonitrogen compound
Carbonyl group
Primary aliphatic amine
Organooxygen compound
Organic oxide
Organic oxygen compound
Amine
Organopnictogen compound
Hydrocarbon derivative
Organic nitrogen compound
Primary amine
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	ChemAxon
pKa (Strongest Acidic)	3.2	ChemAxon
pKa (Strongest Basic)	9.68	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	145.68 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	77.3 m³·mol⁻¹	ChemAxon
Polarizability	33.35 Å³	ChemAxon
Number of Rings	2	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

112707

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

126919

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Miller AF, Egan LA, Townsend CA: Measurement of the degree of coupled isotopic enrichment of different positions in an antibiotic peptide by NMR. J Magn Reson. 1997 Mar;125(1):120-31. doi: 10.1006/jmre.1997.1107. [PubMed:9245367 ]
Rohl F, Rabenhorst J, Zahner H: Biological properties and mode of action of clavams. Arch Microbiol. 1987 May;147(4):315-20. doi: 10.1007/BF00406126. [PubMed:3304182 ]
LOTUS database [Link]

Showing NP-Card for 2-[(2-amino-1-hydroxy-3-methylbutylidene)amino]-3-hydroxy-4-{7-oxo-4-oxa-1-azabicyclo[3.2.0]heptan-3-yl}butanoic acid (NP0252641)

MOL for NP0252641 (2-[(2-amino-1-hydroxy-3-methylbutylidene)amino]-3-hydroxy-4-{7-oxo-4-oxa-1-azabicyclo[3.2.0]heptan-3-yl}butanoic acid)

3D MOL for NP0252641 (2-[(2-amino-1-hydroxy-3-methylbutylidene)amino]-3-hydroxy-4-{7-oxo-4-oxa-1-azabicyclo[3.2.0]heptan-3-yl}butanoic acid)

3D SDF for NP0252641 (2-[(2-amino-1-hydroxy-3-methylbutylidene)amino]-3-hydroxy-4-{7-oxo-4-oxa-1-azabicyclo[3.2.0]heptan-3-yl}butanoic acid)

3D-SDF for NP0252641 (2-[(2-amino-1-hydroxy-3-methylbutylidene)amino]-3-hydroxy-4-{7-oxo-4-oxa-1-azabicyclo[3.2.0]heptan-3-yl}butanoic acid)

PDB for NP0252641 (2-[(2-amino-1-hydroxy-3-methylbutylidene)amino]-3-hydroxy-4-{7-oxo-4-oxa-1-azabicyclo[3.2.0]heptan-3-yl}butanoic acid)

3D PDB for NP0252641 (2-[(2-amino-1-hydroxy-3-methylbutylidene)amino]-3-hydroxy-4-{7-oxo-4-oxa-1-azabicyclo[3.2.0]heptan-3-yl}butanoic acid)

SMILES for NP0252641 (2-[(2-amino-1-hydroxy-3-methylbutylidene)amino]-3-hydroxy-4-{7-oxo-4-oxa-1-azabicyclo[3.2.0]heptan-3-yl}butanoic acid)

INCHI for NP0252641 (2-[(2-amino-1-hydroxy-3-methylbutylidene)amino]-3-hydroxy-4-{7-oxo-4-oxa-1-azabicyclo[3.2.0]heptan-3-yl}butanoic acid)

Structure for NP0252641 (2-[(2-amino-1-hydroxy-3-methylbutylidene)amino]-3-hydroxy-4-{7-oxo-4-oxa-1-azabicyclo[3.2.0]heptan-3-yl}butanoic acid)

3D Structure for NP0252641 (2-[(2-amino-1-hydroxy-3-methylbutylidene)amino]-3-hydroxy-4-{7-oxo-4-oxa-1-azabicyclo[3.2.0]heptan-3-yl}butanoic acid)