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Showing NP-Card for 1(2h)-phthalazinone hydrazone (NP0146103)

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Record Information
Version2.0
Created at2022-09-02 01:26:05 UTC
Updated at2022-09-02 01:26:05 UTC
NP-MRD IDNP0146103
Secondary Accession NumbersNone
Natural Product Identification
Common Name1(2h)-phthalazinone hydrazone
DescriptionHydralazine, also known as hidralazina or hypophthalin, belongs to the class of organic compounds known as phthalazines. Phthalazines are compounds containing a phthalazine moiety, which consists of a benzene ring fused to a pyridazine, forming a 2,3-benzodiazine skeleton. The 1-hydrazino derivative of phthalazine; a direct-acting vasodilator that is used as an antihypertensive agent. 1(2h)-phthalazinone hydrazone is found in Achillea nobilis and Achillea pseudopectinata. 1(2h)-phthalazinone hydrazone was first documented in 1975 (PMID: 808562). Hydralazine is a very strong basic compound (based on its pKa) (PMID: 20687078).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0146103 (1(2h)-phthalazinone hydrazone)

1275
  Mrv0541 02231215222D          

 12 13  0  0  0  0            999 V2000
    2.6954   -0.7582    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0094    0.4298    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0094    1.2219    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0094   -1.1543    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3813    0.4298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3813    1.2219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6954    0.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0893    0.0063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0893    1.6454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8070    0.4133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6954    1.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8070    1.2384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  2  7  2  0  0  0  0
  3 11  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  2  0  0  0  0
  6  9  2  0  0  0  0
  6 11  1  0  0  0  0
  8 10  1  0  0  0  0
  9 12  1  0  0  0  0
 10 12  2  0  0  0  0
M  END
Download

3D MOL for NP0146103 (1(2h)-phthalazinone hydrazone)

     RDKit          3D

 20 21  0  0  0  0  0  0  0  0999 V2000
    3.0450   -0.7028   -0.1550 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4244    0.1590    0.7644 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2402    0.8576    0.3648 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2632    2.2000    0.1717 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1777    2.8619   -0.2011 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9980    2.2436   -0.4095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1106    0.8708   -0.2351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3077    0.2273   -0.4499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3596   -1.1423   -0.2660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2294   -1.8464    0.1254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0468   -1.1615    0.3299 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0434    0.2084    0.1565 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6381   -0.5822   -1.0859 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1696   -1.6614    0.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8260    0.2757    1.6908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8805    2.7679   -0.7157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2137    0.7321   -0.7518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2759   -1.6942   -0.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2534   -2.9338    0.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8480   -1.6798    0.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  3  1  0
 12  7  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  6 16  1  0
  8 17  1  0
  9 18  1  0
 10 19  1  0
 11 20  1  0
M  END
Download

3D SDF for NP0146103 (1(2h)-phthalazinone hydrazone)

1275
  Mrv0541 02231215222D          

 12 13  0  0  0  0            999 V2000
    2.6954   -0.7582    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0094    0.4298    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0094    1.2219    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0094   -1.1543    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3813    0.4298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3813    1.2219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6954    0.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0893    0.0063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0893    1.6454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8070    0.4133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6954    1.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8070    1.2384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  2  7  2  0  0  0  0
  3 11  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  2  0  0  0  0
  6  9  2  0  0  0  0
  6 11  1  0  0  0  0
  8 10  1  0  0  0  0
  9 12  1  0  0  0  0
 10 12  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0146103

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NNC1=NN=CC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C8H8N4/c9-11-8-7-4-2-1-3-6(7)5-10-12-8/h1-5H,9H2,(H,11,12)

> <INCHI_KEY>
RPTUSVTUFVMDQK-UHFFFAOYSA-N

> <FORMULA>
C8H8N4

> <MOLECULAR_WEIGHT>
160.1759

> <EXACT_MASS>
160.074896276

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
16.061977722327377

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-hydrazinylphthalazine

> <ALOGPS_LOGP>
0.66

> <JCHEM_LOGP>
0.7513803336666666

> <ALOGPS_LOGS>
-1.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.69177277365625

> <JCHEM_PKA_STRONGEST_BASIC>
6.401050541238753

> <JCHEM_POLAR_SURFACE_AREA>
63.83

> <JCHEM_REFRACTIVITY>
50.23480000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.61e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hydralazine

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0146103 (1(2h)-phthalazinone hydrazone)

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PDB for NP0146103 (1(2h)-phthalazinone hydrazone)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1275                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0       5.031  -1.415   0.000  0.00  0.00           N+0
HETATM    2  N   UNK     0       3.751   0.802   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       3.751   2.281   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       3.751  -2.155   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       6.312   0.802   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.312   2.281   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.031   0.063   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.633   0.012   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.633   3.071   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.973   0.772   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.031   3.020   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.973   2.312   0.000  0.00  0.00           C+0
CONECT    1    4    7                                                       
CONECT    2    3    7                                                       
CONECT    3    2   11                                                       
CONECT    4    1                                                            
CONECT    5    6    7    8                                                  
CONECT    6    5    9   11                                                  
CONECT    7    1    2    5                                                  
CONECT    8    5   10                                                       
CONECT    9    6   12                                                       
CONECT   10    8   12                                                       
CONECT   11    3    6                                                       
CONECT   12    9   10                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

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3D PDB for NP0146103 (1(2h)-phthalazinone hydrazone)
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SMILES for NP0146103 (1(2h)-phthalazinone hydrazone)
NNC1=NN=CC2=CC=CC=C12
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INCHI for NP0146103 (1(2h)-phthalazinone hydrazone)
InChI=1S/C8H8N4/c9-11-8-7-4-2-1-3-6(7)5-10-12-8/h1-5H,9H2,(H,11,12)
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Synonyms
ValueSource
(1Z)-1(2H)-Phthalazinone hydrazoneChEBI
(2H)-Phthalazinone hydrazoneChEBI
1-HydrazinophthalazineChEBI
1-PhthalazinylhydrazineChEBI
6-HydralazineChEBI
HidralazinaChEBI
HydralazinChEBI
HydralazinumChEBI
HydrallazineChEBI
HydrazinophthalazineChEBI
Hydrazone 1(2H)-phthalazinoneChEBI
HypophthalinChEBI
IdralazinaChEBI
Phthalazin-1-ylhydrazineChEBI
HidralKegg
Hydralazine hydrochlorideHMDB
NepresolHMDB
ApressinHMDB
ApressolineHMDB
Hydralazine mono hydrochlorideHMDB
Hydralazine mono-hydrochlorideHMDB
HydrallazinHMDB
Hydrochloride, hydralazineHMDB
mono-Hydrochloride, hydralazineHMDB
ApresolineHMDB
Chemical FormulaC8H8N4
Average Mass160.1759 Da
Monoisotopic Mass160.07490 Da
IUPAC Name1-hydrazinylphthalazine
Traditional Namehydralazine
CAS Registry NumberNot Available
SMILES
NNC1=NN=CC2=CC=CC=C12
InChI Identifier
InChI=1S/C8H8N4/c9-11-8-7-4-2-1-3-6(7)5-10-12-8/h1-5H,9H2,(H,11,12)
InChI KeyRPTUSVTUFVMDQK-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
Achillea nobilisLOTUS Database
Achillea pseudopectinataLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phthalazines. Phthalazines are compounds containing a phthalazine moiety, which consists of a benzene ring fused to a pyridazine, forming a 2,3-benzodiazine skeleton.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassDiazanaphthalenes  
Sub ClassBenzodiazines  
Direct ParentPhthalazines  
Alternative Parents
Substituents
  • Phthalazine
    • 

  • Imidolactam
    • 

  • Benzenoid
    • 

  • Pyridazine
    • 

  • Heteroaromatic compound
    • 

  • Carboxylic acid amidrazone
    • 

  • Azacycle
    • 

  • Hydrazone
    • 

  • Organic nitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organonitrogen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic 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
logP0.66ALOGPS
logP0.75ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)17.69ChemAxon
pKa (Strongest Basic)6.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.83 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity50.23 m³·mol⁻¹ChemAxon
Polarizability16.06 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0015400  
DrugBank IDDB01275  
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3511  
KEGG Compound IDC07040  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHydralazine  
METLIN IDNot Available
PubChem Compound3637  
PDB IDNot Available
ChEBI ID5775  
Good Scents IDNot Available
References
General References
  1. Kandler MR, Mah GT, Tejani AM, Stabler SN: Hydralazine for essential hypertension. Cochrane Database Syst Rev. 2010 Aug 4;(8):CD004934. doi:  10.1002/14651858.CD004934.pub3. [PubMed:20687078  ] 
  2. Yamauchi Y, Litwin A, Adams L, Zimmer H, Hess EV: Induction of antibodies to nuclear antigens in rabbits by immunization with hydralazine-human serum albumin conjugates. J Clin Invest. 1975 Oct;56(4):958-69. doi: 10.1172/JCI108176. [PubMed:808562  ] 
  3. LOTUS database [Link]