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Showing NP-Card for ahba (NP0288369)

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Record Information
Version2.0
Created at2022-09-09 18:02:39 UTC
Updated at2022-09-09 18:02:40 UTC
NP-MRD IDNP0288369
Secondary Accession NumbersNone
Natural Product Identification
Common Nameahba
Description ahba is found in Streptomyces hygroscopicus. ahba was first documented in 1991 (PMID: 1672686).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0288369 (ahba)


  Mrv1533004261501542D          

 11 11  0  0  0  0            999 V2000
    0.7145    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  2  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
M  END
Download

3D MOL for NP0288369 (ahba)

     RDKit          3D

 18 18  0  0  0  0  0  0  0  0999 V2000
    2.5836   -0.5667    0.7800 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3495   -0.0882    0.2759 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2563    1.1970   -0.2243 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0415    1.6461   -0.7124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0204    2.9419   -1.2082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0590    0.7985   -0.6906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9870   -0.4840   -0.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1443   -1.3738   -0.1746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2683   -1.0548   -0.5906 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0083   -2.6674    0.3400 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2353   -0.9057    0.2830 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2244   -1.1350    0.1960 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8306   -0.3303    1.7591 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1348    1.8480   -0.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2623    3.6766   -0.5353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9935    1.1554   -1.0703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2402   -2.7621    1.3282 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3273   -1.8952    0.6734 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7 11  2  0
  7  8  1  0
  8 10  1  0
  8  9  2  0
 11  2  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  5 15  1  0
  6 16  1  0
 11 18  1  0
 10 17  1  0
M  END
Download

3D SDF for NP0288369 (ahba)


  Mrv1533004261501542D          

 11 11  0  0  0  0            999 V2000
    0.7145    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  2  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0288369

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=CC(O)=CC(=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H7NO3/c8-5-1-4(7(10)11)2-6(9)3-5/h1-3,9H,8H2,(H,10,11)

> <INCHI_KEY>
QPEJHSFTZVMSJH-UHFFFAOYSA-N

> <FORMULA>
C7H7NO3

> <MOLECULAR_WEIGHT>
153.137

> <EXACT_MASS>
153.042593089

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
14.366845282436488

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-amino-5-hydroxybenzoic acid

> <ALOGPS_LOGP>
0.63

> <JCHEM_LOGP>
0.3433315981790158

> <ALOGPS_LOGS>
-1.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.837091791614577

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.5635039260538965

> <JCHEM_PKA_STRONGEST_BASIC>
2.8404757965657614

> <JCHEM_POLAR_SURFACE_AREA>
83.55

> <JCHEM_REFRACTIVITY>
39.99550000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.21e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
AHBA

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0288369 (ahba)

Download
PDB for NP0288369 (ahba)
HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  N   UNK     0       1.334   3.850   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7    2                                                       
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

Download
3D PDB for NP0288369 (ahba)
Download
SMILES for NP0288369 (ahba)
NC1=CC(O)=CC(=C1)C(O)=O
Download
INCHI for NP0288369 (ahba)
InChI=1S/C7H7NO3/c8-5-1-4(7(10)11)2-6(9)3-5/h1-3,9H,8H2,(H,10,11)
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View in JSmol
Synonyms
ValueSource
3-AhbaChEBI
AHBAChEBI
3-Amino-5-hydroxybenzoateGenerator
Chemical FormulaC7H7NO3
Average Mass153.1370 Da
Monoisotopic Mass153.04259 Da
IUPAC Name3-amino-5-hydroxybenzoic acid
Traditional NameAHBA
CAS Registry NumberNot Available
SMILES
NC1=CC(O)=CC(=C1)C(O)=O
InChI Identifier
InChI=1S/C7H7NO3/c8-5-1-4(7(10)11)2-6(9)3-5/h1-3,9H,8H2,(H,10,11)
InChI KeyQPEJHSFTZVMSJH-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Streptomyces hygroscopicusLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassBenzene and substituted derivatives  
Sub ClassBenzoic acids and derivatives  
Direct ParentHydroxybenzoic acid derivatives  
Alternative Parents
Substituents
  • Aminobenzoic acid
    • 

  • Aminobenzoic acid or derivatives
    • 

  • Hydroxybenzoic acid
    • 

  • Benzoic acid
    • 

  • M-aminophenol
    • 

  • Aminophenol
    • 

  • Aniline or substituted anilines
    • 

  • Benzoyl
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • Amino acid or derivatives
    • 

  • Amino acid
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Amine
    • 

  • Organonitrogen compound
    • 

  • Organooxygen compound
    • 

  • Primary amine
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Organic nitrogen compound
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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
logP0.63ALOGPS
logP0.34ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)4.56ChemAxon
pKa (Strongest Basic)2.84ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.55 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity40 m³·mol⁻¹ChemAxon
Polarizability14.37 ųChemAxon
Number of Rings1ChemAxon
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 IDNot Available
Chemspider IDNot Available
KEGG Compound IDC12107  
BioCyc IDCPD-10231  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound127115  
PDB IDNot Available
ChEBI ID29507  
Good Scents IDNot Available
References
General References
  1. Arakawa K, Muller R, Mahmud T, Yu TW, Floss HG: Characterization of the early stage aminoshikimate pathway in the formation of 3-amino-5-hydroxybenzoic acid: the RifN protein specifically converts kanosamine into kanosamine 6-phosphate. J Am Chem Soc. 2002 Sep 11;124(36):10644-5. doi: 10.1021/ja0206339. [PubMed:12207505  ] 
  2. Yu TW, Muller R, Muller M, Zhang X, Draeger G, Kim CG, Leistner E, Floss HG: Mutational analysis and reconstituted expression of the biosynthetic genes involved in the formation of 3-amino-5-hydroxybenzoic acid, the starter unit of rifamycin biosynthesis in amycolatopsis Mediterranei S699. J Biol Chem. 2001 Apr 20;276(16):12546-55. doi: 10.1074/jbc.M009667200. Epub 2001 Jan 18. [PubMed:11278540  ] 
  3. Staley AL, Rinehart KL: Biosynthesis of the streptovaricins: 3-amino-5-hydroxybenzoic acid as a precursor to the meta-C7N unit. J Antibiot (Tokyo). 1991 Feb;44(2):218-24. doi: 10.7164/antibiotics.44.218. [PubMed:1672686  ] 
  4. Chamberland S, Gruschow S, Sherman DH, Williams RM: Synthesis of potential early-stage intermediates in the biosynthesis of FR900482 and mitomycin C. Org Lett. 2009 Feb 19;11(4):791-4. doi: 10.1021/ol802631c. [PubMed:19161340  ] 
  5. Floss HG, Yu TW, Arakawa K: The biosynthesis of 3-amino-5-hydroxybenzoic acid (AHBA), the precursor of mC7N units in ansamycin and mitomycin antibiotics: a review. J Antibiot (Tokyo). 2011 Jan;64(1):35-44. doi: 10.1038/ja.2010.139. Epub 2010 Nov 17. [PubMed:21081954  ] 
  6. LOTUS database [Link]