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Showing NP-Card for Alanylclavam (NP0062167)

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Record Information
Version2.0
Created at2022-04-28 06:49:46 UTC
Updated at2022-04-28 06:49:46 UTC
NP-MRD IDNP0062167
Secondary Accession NumbersNone
Natural Product Identification
Common NameAlanylclavam
DescriptionAlanylclavam belongs to the class of organic compounds known as furanoid amino acids and derivatives. These are sugar amino acids containing a furan ring. Alanylclavam is found in Streptomyces clavuligerus NRRL 3585. Alanylclavam was first documented in 2008 (PMID: 18931110). Based on a literature review very few articles have been published on Alanylclavam.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0062167 (Alanylclavam)


  Mrv1652304282208492D          

 14 15  0  0  1  0            999 V2000
   -0.1477   -0.1073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1477   -0.9323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7310   -1.5156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6773   -0.9323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6773   -0.1073    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4620    0.1477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9469   -0.5198    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4620   -1.1872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7719   -0.5198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1844    0.1947    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7719    0.9092    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0094    0.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4219    0.9092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4219   -0.5198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  1  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  8  1  0  0  0  0
  7  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
M  END
Download

3D MOL for NP0062167 (Alanylclavam)

     RDKit          3D

 26 27  0  0  0  0  0  0  0  0999 V2000
    3.1320   -0.7337   -0.5484 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6609   -0.4083   -0.6058 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1692   -0.7790    0.7310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2424   -0.6293    1.1049 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7953    0.7417    1.0893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8098    0.7184    0.0936 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8895    0.9660   -0.7837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3951    1.9580   -1.3643 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1588   -0.5190   -0.7025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6585   -0.5652   -0.6125 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1090   -1.4187    0.3311 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6288    1.0010   -1.0059 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6429    1.5534   -1.5460 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7304    1.8651   -0.8096 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4544   -0.3502    0.3689 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2470   -1.7699   -0.5681 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2488   -1.0627   -1.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5016   -1.8331    1.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7794   -0.1574    1.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3531   -1.0773    2.1512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0739    1.5684    0.9771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2304    0.9215    2.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6173   -0.9386   -1.5957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6453   -0.7785    0.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1745   -0.5023   -1.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9576    2.2297    0.0985 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6 10  1  0
 10  9  1  0
  9  7  1  0
  7  8  2  0
 10 11  1  0
  2 12  1  0
 12 14  1  0
 12 13  2  0
 11  4  1  0
  7  6  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  6
  3 18  1  0
  3 19  1  0
  4 20  1  1
  5 21  1  0
  5 22  1  0
 10 25  1  6
  9 23  1  0
  9 24  1  0
 14 26  1  0
M  END
Download

3D SDF for NP0062167 (Alanylclavam)


  Mrv1652304282208492D          

 14 15  0  0  1  0            999 V2000
   -0.1477   -0.1073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1477   -0.9323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7310   -1.5156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6773   -0.9323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6773   -0.1073    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4620    0.1477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9469   -0.5198    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4620   -1.1872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7719   -0.5198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1844    0.1947    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7719    0.9092    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0094    0.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4219    0.9092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4219   -0.5198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  1  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  8  1  0  0  0  0
  7  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0062167

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@@H](C[C@H]1CN2[C@H](CC2=O)O1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H12N2O4/c9-5(8(12)13)1-4-3-10-6(11)2-7(10)14-4/h4-5,7H,1-3,9H2,(H,12,13)/t4-,5-,7-/m0/s1

> <INCHI_KEY>
KCAIYJDHLVYANU-VPLCAKHXSA-N

> <FORMULA>
C8H12N2O4

> <MOLECULAR_WEIGHT>
200.194

> <EXACT_MASS>
200.079706874

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
19.369368329106006

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-3-[(3S,5S)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptan-3-yl]propanoic acid

> <ALOGPS_LOGP>
-2.79

> <JCHEM_LOGP>
-3.7870231844202213

> <ALOGPS_LOGS>
0.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.708908505515385

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.897788835229429

> <JCHEM_PKA_STRONGEST_BASIC>
9.148727654093985

> <JCHEM_POLAR_SURFACE_AREA>
92.86

> <JCHEM_REFRACTIVITY>
44.527

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.01e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-amino-3-[(3S,5S)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptan-3-yl]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0062167 (Alanylclavam)

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PDB for NP0062167 (Alanylclavam)
HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -0.276  -0.200   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.276  -1.740   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.365  -2.829   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       1.264  -1.740   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       1.264  -0.200   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.729   0.276   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.634  -0.970   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.729  -2.216   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.174  -0.970   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.944   0.363   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       5.174   1.697   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       7.484   0.363   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.254   1.697   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       8.254  -0.970   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    8                                                  
CONECT    5    4    1    6                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7    4                                                       
CONECT    9    7   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

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3D PDB for NP0062167 (Alanylclavam)
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SMILES for NP0062167 (Alanylclavam)
N[C@@H](C[C@H]1CN2[C@H](CC2=O)O1)C(O)=O
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INCHI for NP0062167 (Alanylclavam)
InChI=1S/C8H12N2O4/c9-5(8(12)13)1-4-3-10-6(11)2-7(10)14-4/h4-5,7H,1-3,9H2,(H,12,13)/t4-,5-,7-/m0/s1
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View in JSmol
Synonyms
ValueSource
3-(7-oxo-1-Aza-4-oxabicyclo(3.2.0)hept-3-yl)alanineMeSH
Chemical FormulaC8H12N2O4
Average Mass200.1940 Da
Monoisotopic Mass200.07971 Da
IUPAC Name(2S)-2-amino-3-[(3S,5S)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptan-3-yl]propanoic acid
Traditional Name(2S)-2-amino-3-[(3S,5S)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptan-3-yl]propanoic acid
CAS Registry NumberNot Available
SMILES
N[C@@H](C[C@H]1CN2[C@H](CC2=O)O1)C(O)=O
InChI Identifier
InChI=1S/C8H12N2O4/c9-5(8(12)13)1-4-3-10-6(11)2-7(10)14-4/h4-5,7H,1-3,9H2,(H,12,13)/t4-,5-,7-/m0/s1
InChI KeyKCAIYJDHLVYANU-VPLCAKHXSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Streptomyces clavuligerusBacteria
Chemical Taxonomy
Description Belongs to the class of organic compounds known as furanoid amino acids and derivatives. These are sugar amino acids containing a furan ring.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbohydrates and carbohydrate conjugates  
Direct ParentFuranoid amino acids and derivatives  
Alternative Parents
Substituents
  • Furanoid amino acid
    • 

  • Alpha-amino acid
    • 

  • Alpha-amino acid or derivatives
    • 

  • L-alpha-amino acid
    • 

  • Clavam
    • 

  • Para-oxazepine
    • 

  • Beta-lactam
    • 

  • Tertiary carboxylic acid amide
    • 

  • Oxazolidine
    • 

  • Amino acid
    • 

  • Amino acid or derivatives
    • 

  • Azetidine
    • 

  • Carboxamide group
    • 

  • Lactam
    • 

  • Oxacycle
    • 

  • Azacycle
    • 

  • Organoheterocyclic compound
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organopnictogen compound
    • 

  • Carbonyl group
    • 

  • Organic nitrogen compound
    • 

  • Organic oxide
    • 

  • Amine
    • 

  • Primary amine
    • 

  • Organonitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Primary aliphatic amine
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.8ALOGPS
logP-3.8ChemAxon
logS0.4ALOGPS
pKa (Strongest Acidic)1.9ChemAxon
pKa (Strongest Basic)9.15ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area92.86 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity44.53 m³·mol⁻¹ChemAxon
Polarizability19.37 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00018492  
Chemspider ID168852  
KEGG Compound IDC17360  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound194618  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Zelyas NJ, Cai H, Kwong T, Jensen SE: Alanylclavam biosynthetic genes are clustered together with one group of clavulanic acid biosynthetic genes in Streptomyces clavuligerus. J Bacteriol. 2008 Dec;190(24):7957-65. doi: 10.1128/JB.00698-08. Epub 2008 Oct  17. [PubMed:18931110  ]